Myristicin_properties by Asch

Query Query

Results

Date

9 substances in Reaxys

2017-11-15 01h:26m:53s (EST)

1. Query

O O

1/81

2017-11-15 01:27:11

Reaxys ID 166218 View in Reaxys

1/9 CAS Registry Number: 607-91-0 Chemical Name: myristicin; Myristicin; 4-methoxy-6-(prop-2en-1-yl)-1,3-benzodioxole; 1-allyl-4,5-methylenedioxy-3-methoxybenzene; 1-allyl-5-methoxy-3,4-methylenedioxybenzene; 3-methoxy-4,5-methylenedioxy-allylbenzene; 4-methoxy-6-(2propenyl)-1,3-benzodioxole Linear Structure Formula: CH2CHCH2C7H4O3CH3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: BNWJOHGLIBDBOB-UHFFFAOYSA-N Note:

O O O

Substance Label (15) Label References 3

Benevides, Paulo J.C.; Sartorelli, Patricia; Kato, Massuo J.; Phytochemistry; vol. 52; nb. 2; (1999); p. 339 - 343, View in Reaxys; Martins, Roberto C.C.; Latorre, Leandro R.; Sartorelli, Patricia; Kato, Massuo J.; Phytochemistry; vol. 55; nb. 7; (2000); p. 843 - 846, View in Reaxys; Yoshikawa, Masayuki; Uemura, Toshiaki; Shimoda, Hiroshi; Kishi, Akinobu; Kawahara, Yuzo; Matsuda, Hisashi; Chemical and Pharmaceutical Bulletin; vol. 48; nb. 7; (2000); p. 1039 - 1044, View in Reaxys; Srivastava; Gupta; Tripathi; Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 39; nb. 12; (2000); p. 946 949, View in Reaxys; Park, Ji-Young; Hwan Lim, Su; Ram Kim, Bo; Jae Jeong, Hyung; Kwon, HyungJun; Song, Gyu-Yong; Bae Ryu, Young; Song Lee, Woo; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 14; (2017); p. 3060 - 3064, View in Reaxys

Obst, Katja; Lieder, Barbara; Reichelt, Katharina V.; Backes, Michael; Paetz, Susanne; Geißler, Katrin; Krammer, Gerhard; Somoza, Veronika; Ley, Jakob P.; Engel, Karl-Heinz; Phytochemistry; vol. 135; (2017); p. 181 - 190, View in Reaxys

Wang, Cuizhu; Zhang, Nanqi; Wang, Zhenzhou; Qi, Zeng; Zhu, Hailin; Zheng, Bingzhen; Li, Pingya; Liu, Jinping; Molecules; vol. 22; nb. 8; (2017); Art.No: 1280, View in Reaxys

Nam, Bomi; So, Yangkang; Kim, Hyo-Young; Kim, Jin-Baek; Jin, Chang Hyun; Han, Ah-Reum; Molecules; vol. 22; nb. 9; (2017), View in Reaxys

Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Karmanova, Irina B.; Firgang, Sergei I.; Strelenko, Yuri A.; Semenova, Marina N.; Kiselyov, Alex S.; Semenov, Victor V.; Journal of Natural Products; vol. 76; nb. 8; (2013); p. 1485 - 1491, View in Reaxys; Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Semenova, Marina N.; Semenov, Victor V.; Mendeleev Communications; vol. 26; nb. 4; (2016); p. 285 - 287, View in Reaxys

Tsyganov, Dmitry V.; Krayushkin, Mikhail M.; Konyushkin, Leonid D.; Strelenko, Yuri A.; Semenova, Marina N.; Semenov, Victor V.; Journal of Natural Products; vol. 79; nb. 4; (2016); p. 923 - 928, View in Reaxys

Semenov, Victor V.; Tsyganov, Dmitry V.; Semenova, Marina N.; Chuprov-Netochin, Roman N.; Raihstat, Mikhail M.; Konyushkin, Leonid D.; Volynchuk, Polina B.; Marusich, Elena I.; Nazarenko, Vera V.; Leonov, Sergey V.; Kiselyov, Alex S.; Journal of Natural Products; vol. 79; nb. 5; (2016); p. 1429 - 1438, View in Reaxys

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys

Morikawa, Toshio; Hachiman, Ikuko; Matsuo, Kazuhiko; Nishida, Eriko; Ninomiya, Kiyofumi; Hayakawa, Takao; Yoshie, Osamu; Muraoka, Osamu; Nakayama, Takashi; Journal of Natural Products; vol. 79; nb. 8; (2016); p. 2005 - 2013, View in Reaxys

Zacchino, Susana A.; Lopez, Silvia N.; Pezzenati, German D.; Furlan, Ricardo L.; Santecchia, Carina B.; Munoz, Lorena; Giannini, Fernando A.; Rodriguez, Ana M.; Enriz, Ricardo D.; Journal of Natural Products; vol. 62; nb. 10; (1999); p. 1353 - 1357, View in Reaxys; Woo, Kyeong Wan; Han, Ji Young; Suh, Won Se; Lee, Jei Hyun; Lee, Kang Ro; Bulletin of the Korean Chemical Society; vol. 35; nb. 7; (2014); p. 2151 - 2154, View in Reaxys

Dang, Phu Hoang; Nguyen, Hai Xuan; Nguyen, Nhan Trung; Le, Hanh Ngoc Thi; Nguyen, Mai Thanh Thi; Phytotherapy Research; vol. 28; nb. 11; (2014); p. 1632 - 1636, View in Reaxys

Du, Shu-Shan; Yang, Kai; Wang, Cheng-Fang; You, Chun-Xue; Geng, Zhu-Feng; Guo, Shan-Shan; Deng, Zhi-Wei; Liu, Zhi-Long; Chemistry and Biodiversity; vol. 11; nb. 9; (2014); p. 1449 - 1456, View in Reaxys

Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys

2/81

2017-11-15 01:27:11

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys

Kojima, Keisuke; Isaka, Kimio; Purev, Ondognii; Jargalsaikhan, Gonbovanjilin; Suran, Dagdangin; Mizukami, Hajime; Ogihara, Yukio; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 11; (1998); p. 1781 1784, View in Reaxys

Patent-Specific Data (2) Prophetic ComLocation in Patent References pound Claim

prophetic product

Patent; Scaramuzzino, Giovanni; EP1336602; (2003); (A1) English, View in Reaxys; Patent; Procter and Gamble; US6495172; (2002); (B1) English, View in Reaxys; Patent; Unilever Home and Personal Care USA, Division of Conopco, Inc.; US2003/166498; (2003); (A1) English, View in Reaxys; Patent; Unilever Home and Personal Care USA, Division of Conopco, Inc.; US2003/166499; (2003); (A1) English, View in Reaxys; Patent; INTERNATIONAL FLAVORS and FRAGRANCES INC.; YALE UNIVERSITY; EP183436; (1991); (B1) English, View in Reaxys; Patent; The Proctor and Gamble Company; US5833999; (1998); (A1) English, View in Reaxys; Patent; Unilever Home and Personal Care USA, Division of Conopco, Inc.; US2003/166497; (2003); (A1) English, View in Reaxys Patent; International Flavors and Fragrances Inc.; Yale University; US4670264; (1987); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.719

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Derivative (4) Comment (Derivative)

References

Dibromderivatbromid: F: 130grad

Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys

Dibrommyristicindibromid: F: 129-130grad

Hayashi,S. et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 1465 - 1466, View in Reaxys

Bromid: F: 128grad

Privett et al.; Journal of the American Oil Chemists' Society; vol. 40; (1963); p. 28,29, View in Reaxys

Tetrabromderivat: F: 129grad (aus A.)

Rajkowski; Acta Poloniae Pharmaceutica; vol. 19; (1962); p. 383,391; Chem.Abstr.; vol. 60; nb. 13091; (1964), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

-30

Shulgin; Nature (London, United Kingdom); vol. 210; (1966); p. 380,381, View in Reaxys Boiling Point (16) Boiling Point [°C] Pressure (Boiling Point) [Torr] 138

106 - 107

1.50015 - 1.9502

Location

Comment (Boiling References Point)

Page/Page column 19

Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys Semenov; Rusak; Chartov; Zaretskii; Konyushkin; Firgang; Chizhov; Elkin; Latin; Bonashek; Stas'Eva; Russian Chemical Bulletin; vol. 56; nb. 12; (2007); p. 2448 - 2455, View in Reaxys

3/81

2017-11-15 01:27:11

276

Patent; Uchiyama, Hirotaka; Woo, Ricky AhMan; DuVal, Dean Larry; Reece, Steven; US2005/148544; (2005); (A1) English, View in Reaxys

198

Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys

149 - 149.6

Fujita; Yamashita; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3553, View in Reaxys

148 - 150

Moltrasio et al.; Organic Preparations and Procedures International; vol. 4; (1972); p. 13, View in Reaxys

94 - 95

0.4

Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys

115 - 116

Hayashi,S. et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 1465 - 1466, View in Reaxys

173

Shulgin; Nature (London, United Kingdom); vol. 210; (1966); p. 380,381, View in Reaxys

126

Shulgin; Nature (London, United Kingdom); vol. 210; (1966); p. 380,381, View in Reaxys

118

Privett et al.; Journal of the American Oil Chemists' Society; vol. 40; (1963); p. 28,29, View in Reaxys

138

Rao et al.; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 30; (1949); p. 114,118, View in Reaxys

95 - 97

0.02

Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys

0.4

Surrey; Journal of the American Chemical Society; vol. 70; (1948); p. 2887,2889, View in Reaxys

276 - 277

149.5

Hilditch; Jones; Journal of the Society of Chemical Industry, London; vol. 46; (1927); p. 176 T; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 238, View in Reaxys 15

Fluessigkeit.

Thoms; Chemische Berichte; vol. 36; (1903); p. 3448, View in Reaxys

Refractive Index (14) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

Location

References

1.5343

589

Page/Page column 19

Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys

1.5412

589

Page/Page column 19

Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys

1.5385

589

Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys

1.5409

589

Fujita; Yamashita; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3553, View in Reaxys

4/81

2017-11-15 01:27:11

1.54

589

Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys

1.5407

589

Shulgin; Nature (London, United Kingdom); vol. 210; (1966); p. 380,381, View in Reaxys

Privett et al.; Journal of the American Oil Chemists' Society; vol. 40; (1963); p. 28,29, View in Reaxys

1.538

1.5398

589

Rajkowski; Acta Poloniae Pharmaceutica; vol. 19; (1962); p. 383,391; Chem.Abstr.; vol. 60; nb. 13091; (1964), View in Reaxys

1.5426

589

Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys

1.5412

589

Rao et al.; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 30; (1949); p. 114,118, View in Reaxys

1.5343

589

Rao et al.; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 30; (1949); p. 114,118, View in Reaxys

1.5395

589

Surrey; Journal of the American Chemical Society; vol. 70; (1948); p. 2887,2889, View in Reaxys

1.5403

589

Power; Salway; Journal of the Chemical Society; vol. 91; (1907); p. 2045,2049, View in Reaxys

1.5293

589

45.5

Power; Salway; Journal of the Chemical Society; vol. 91; (1907); p. 2045,2049, View in Reaxys

Density (6) 1 of 6

Density [g·cm-3]

1.1401

Reference Temperature [°C]

Measurement Temperature [°C]

Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys 2 of 6

Density [g·cm-3]

1.442

Measurement Temperature [°C]

Shulgin; Nature (London, United Kingdom); vol. 210; (1966); p. 380,381, View in Reaxys 3 of 6

Density [g·cm-3]

1.1411

Reference Temperature [°C]

Measurement Temperature [°C]

Rajkowski; Acta Poloniae Pharmaceutica; vol. 19; (1962); p. 383,391; Chem.Abstr.; vol. 60; nb. 13091; (1964), View in Reaxys 4 of 6

Density [g·cm-3]

1.1453

Measurement Temperature [°C]

Mitsuhashi et al.; Yakugaku Zasshi; vol. 79; (1959); p. 106; Chem.Abstr.; (1959); p. 10104, View in Reaxys 5 of 6

Density [g·cm-3]

1.1437

5/81

2017-11-15 01:27:11

Reference Temperature [°C]

Measurement Temperature [°C]

Power; Salway; Journal of the Chemical Society; vol. 91; (1907); p. 2045,2049, View in Reaxys 6 of 6

Density [g·cm-3]

1.1425

Measurement Temperature [°C]

Thoms; Chemische Berichte; vol. 36; (1903); p. 3448, View in Reaxys Chromatographic Data (4) Chromatographic Location data

References

GC (Gas chroma- supporting infortography) mation

Wang, Guan-Jie; Qi, Mei-Ling; Chinese Chemical Letters; vol. 24; nb. 6; (2013); p. 542 - 544, View in Reaxys; Nouri, Amrah; Shafaghatlonbar, Ali; Natural Product Research; vol. 30; nb. 9; (2016); p. 1093 - 1097, View in Reaxys; Alizadeh, Ardalan; Abdollahzadeh, Hamid; Natural Product Research; vol. 31; nb. 17; (2017); p. 2081 - 2084, View in Reaxys

GC (Gas chromatography)

Arun; Sudha; Brindha; Asian Journal of Chemistry; vol. 26; nb. 12; (2014); p. 3745 3748, View in Reaxys; Piras, Alessandra; Falconieri, Danilo; Porcedda, Silvia; Marongiu, Bruno; Gonçalves, Maria José; Cavaleiro, Carlos; Salgueiro, Ligia; Natural Product Research; vol. 28; nb. 21; (2014); p. 1819 - 1825, View in Reaxys; Hammami, Saoussen; Jmii, Habib; Mokni, Ridha El; Khmiri, Abdelbaki; Faidi, Khaled; Dhaouadi, Hatem; Aouni, Mohamed Hedi El; Aouni, Mahjoub; Joshi, Rajesh K.; Molecules; vol. 20; nb. 11; (2015); p. 20426 - 20433, View in Reaxys; Jia, Ruifang; Zhu, Jin; Zhai, Ruxia; Lai, Pengxiang; Asian Journal of Chemistry; vol. 28; nb. 2; (2016); p. 467 - 468, View in Reaxys; Wu, Yan; Zhang, Wen-Juan; Huang, Dong-Ye; Wang, Ying; Wei, Jian-Yu; Li, Zhi-Hua; Sun, Jian-Sheng; Bai, Jia-Feng; Tian, Zhao-Fu; Wang, PingJuan; Du, Shu-Shan; Molecules; vol. 20; nb. 12; (2015); p. 21939 - 21945, View in Reaxys; Nguir, Asma; Mabrouk, Hajer; Douki, Wahiba; Ben Ismail, Manel; Ben Jannet, Hichem; Flamini, Guido; Hamza, M'Hamed Ali; Medicinal Chemistry Research; vol. 25; nb. 3; (2016); p. 515 - 525, View in Reaxys; Papa, Fabrizio; Ricciutelli, Massimo; Cianfaglione, Kevin; Maggi, Filippo; Natural Product Research; vol. 30; nb. 3; (2016); p. 345 - 349, View in Reaxys; Zhao, Qipeng; Cheng, Xiuli; Wang, Xiaobo; Wang, Jing; Zhu, Yafei; Ma, Xueqin; Journal of Ethnopharmacology; vol. 192; (2016); p. 140 - 147, View in Reaxys; Santana, Ana I.; Vila, Roser; Cañigueral, Salvador; Gupta, Mahabir P.; Planta Medica; vol. 82; nb. 11-12; (2016); p. 986 - 991, View in Reaxys; Fitsiou, Eleni; Mitropoulou, Gregoria; Spyridopoulou, Katerina; Tiptiri-Kourpeti, Angeliki; Vamvakias, Manolis; Bardouki, Haido; Panayiotidis, Mihalis I.; Galanis, Alex; Kourkoutas, Yiannis; Chlichlia, Katerina; Pappa, Aglaia; Molecules; vol. 21; nb. 8; (2016); Art.No: 1069, View in Reaxys; Schepetkin, Igor A.; Kushnarenko, Svetlana V.; Özek, Gulmira; Kirpotina, Liliya N.; Sinharoy, Pritam; Utegenova, Gulzhakhan A.; Abidkulova, Karime T.; Özek, Temel; Başer, Kemal Hüsnü Can; Kovrizhina, Anastasia R.; Khlebnikov, Andrei I.; Damron, Derek S.; Quinn, Mark T.; Journal of Agricultural and Food Chemistry; vol. 64; nb. 38; (2016); p. 7156 - 7170, View in Reaxys; Hellali; Hadj Mahammed; Masrouk; Asian Journal of Chemistry; vol. 29; nb. 1; (2017); p. 181 - 186, View in Reaxys; Saleh-e-In, Md Moshfekus; Sultana, Nasim; Rahim, Md Matiur; Ahsan, Md Aminul; Bhuiyan, Md Nurul Huda; Hossain, Md Nur; Rahman, Md Mahbubar; Kumar Roy, Sudhangshu; Islam, Md Rabiul; BMC Complementary and Alternative Medicine; vol. 17; nb. 1; (2017); Art.No: 127, View in Reaxys; Zhang, Han-Yu; Gao, Yang; Lai, Peng-Xiang; Molecules; vol. 22; nb. 3; (2017); Art.No: 381, View in Reaxys; Garcia, Gabriel; Garcia, Adrien; Gibernau, Marc; Bighelli, Ange; Tomi, Félix; Natural Product Research; vol. 31; nb. 14; (2017); p. 1697 - 1703, View in Reaxys

HPLC (High performance liquid chromatography)

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 493, View in Reaxys; Nam, Bomi; So, Yangkang; Kim, Hyo-Young; Kim, Jin-Baek; Jin, Chang Hyun; Han, Ah-Reum; Molecules; vol. 22; nb. 9; (2017), View in Reaxys

UPLC (Ultra performance liquid chromatography)

Wang, Cuizhu; Zhang, Nanqi; Wang, Zhenzhou; Qi, Zeng; Zhu, Hailin; Zheng, Bingzhen; Li, Pingya; Liu, Jinping; Molecules; vol. 22; nb. 8; (2017); Art.No: 1280, View in Reaxys

Crystal Property Description (3) Colour & Other Location Properties

References

6/81

2017-11-15 01:27:11

colourless

supporting information

Park, Ji-Young; Hwan Lim, Su; Ram Kim, Bo; Jae Jeong, Hyung; Kwon, Hyung-Jun; Song, Gyu-Yong; Bae Ryu, Young; Song Lee, Woo; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 14; (2017); p. 3060 - 3064, View in Reaxys

colourless

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

11.31

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Hayashi,S. et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 1465 - 1466, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

0.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Rajkowski; Acta Poloniae Pharmaceutica; vol. 19; (1962); p. 383,391; Chem.Abstr.; vol. 60; nb. 13091; (1964), View in Reaxys Partition octan-1-ol/water (MCS) (1) 1 of 1

log POW

3.2

Patent; Uchiyama, Hirotaka; Woo, Ricky Ah-Man; DuVal, Dean Larry; Reece, Steven; US2005/148544; (2005); (A1) English, View in Reaxys NMR Spectroscopy (25) 1 of 25

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

Location

supporting information

7/81

2017-11-15 01:27:11

3 of 25

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys 7 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys 8 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

8/81

2017-11-15 01:27:11

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Du, Shu-Shan; Yang, Kai; Wang, Cheng-Fang; You, Chun-Xue; Geng, Zhu-Feng; Guo, Shan-Shan; Deng, ZhiWei; Liu, Zhi-Long; Chemistry and Biodiversity; vol. 11; nb. 9; (2014); p. 1449 - 1456, View in Reaxys 9 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys 11 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys 12 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Razzaghi-Abyaneh, Mehdi; Yoshinari, Tomoya; Shams-Ghahfarokhi, Masoomeh; Rezaee, Mohammad-Bagher; Nagasawa, Hiromichi; Sakuda, Shohei; Bioscience, Biotechnology and Biochemistry; vol. 71; nb. 9; (2007); p. 2329 - 2332, View in Reaxys 13 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy)

9/81

2017-11-15 01:27:11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500.1

Semenov; Rusak; Chartov; Zaretskii; Konyushkin; Firgang; Chizhov; Elkin; Latin; Bonashek; Stas'Eva; Russian Chemical Bulletin; vol. 56; nb. 12; (2007); p. 2448 - 2455, View in Reaxys 15 of 25

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Benevides, Paulo J.C.; Sartorelli, Patricia; Kato, Massuo J.; Phytochemistry; vol. 52; nb. 2; (1999); p. 339 - 343, View in Reaxys 16 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Benevides, Paulo J.C.; Sartorelli, Patricia; Kato, Massuo J.; Phytochemistry; vol. 52; nb. 2; (1999); p. 339 - 343, View in Reaxys 17 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Benevides, Paulo J.C.; Sartorelli, Patricia; Kato, Massuo J.; Phytochemistry; vol. 52; nb. 2; (1999); p. 339 - 343, View in Reaxys 18 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CCl4 scopy) Teresa, Joaquin de Pascual; Pascual, Marian de; Arias, Alicia; Hernandez, Jose M.; Moran, Joaquin R.; Grande, Manuel; Phytochemistry (Elsevier); vol. 24; nb. 8; (1985); p. 1773 - 1778, View in Reaxys 19 of 25

Description (NMR Spec- Spin-spin coupling constants troscopy)

10/81

2017-11-15 01:27:11

Solvents (NMR Spectro- CCl4 scopy) Comment (NMR Spectroscopy)

1H-1H

Teresa, Joaquin de Pascual; Pascual, Marian de; Arias, Alicia; Hernandez, Jose M.; Moran, Joaquin R.; Grande, Manuel; Phytochemistry (Elsevier); vol. 24; nb. 8; (1985); p. 1773 - 1778, View in Reaxys 20 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys 21 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys 22 of 25

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Bagirov, V. Yu.; Belyi, M. B.; Rasulov, F. A.; Ismailov, N. M.; Chemistry of Natural Compounds; vol. 18; nb. 1; (1982); p. 123 - 124; Khimiya Prirodnykh Soedinenii; vol. 18; nb. 1; (1982); p. 127 - 129, View in Reaxys 24 of 25

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- acetone-d6 scopy) Bagirov, V. Yu.; Belyi, M. B.; Rasulov, F. A.; Ismailov, N. M.; Chemistry of Natural Compounds; vol. 18; nb. 1; (1982); p. 123 - 124; Khimiya Prirodnykh Soedinenii; vol. 18; nb. 1; (1982); p. 127 - 129, View in Reaxys 25 of 25

Description (NMR Spec- NMR troscopy) Shibuya; Abe; Nakahashi; Kubota; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 9; (1978); p. 2671 - 2673, View in Reaxys; Moltrasio et al.; Organic Preparations and Procedures International; vol. 4; (1972); p. 13, View in Reaxys; Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys; Hayashi et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 1465, View in Reaxys; Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys; Bohannon; Kleiman; Lipids; vol. 12; nb. 3; (1977); p. 321 - 323, View in Reaxys; Isogai et al.; Agricultural and Biological Chemistry; vol. 37; (1973); p. 889,894, View in Reaxys

IR Spectroscopy (4)

11/81

2017-11-15 01:27:11

1 of 4

Description (IR Spectroscopy)

Bands

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3040 - 915 cm**(-1)

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1630 - 935 cm**(-1)

Description (IR Spectroscopy)

Shibuya; Abe; Nakahashi; Kubota; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 9; (1978); p. 2671 - 2673, View in Reaxys; Moltrasio et al.; Organic Preparations and Procedures International; vol. 4; (1972); p. 13, View in Reaxys; Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys; Privett et al.; Journal of the American Oil Chemists' Society; vol. 40; (1963); p. 28,29, View in Reaxys; Fujita; Yamashita; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3553, View in Reaxys; Buttery et al.; Journal of Agricultural and Food Chemistry; vol. 16; (1968); p. 1009,1014, View in Reaxys; Lichtenstein; Casida; Journal of Agricultural and Food Chemistry; vol. 11; (1963); p. 410,411, View in Reaxys; Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys; Isogai et al.; Agricultural and Biological Chemistry; vol. 37; (1973); p. 889,894, View in Reaxys Mass Spectrometry (5) Description (Mass Location Spectrometry)

References

gas chromatogra- supporting inforphy mass specmation trometry (GCMS); spectrum

time-of-flight mass spectra (TOFMS); high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 493, View in Reaxys

gas chromatography mass spectrometry (GCMS); electron impact (EI); spectrum

EI (Electron impact); Spectrum

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys Shibuya; Abe; Nakahashi; Kubota; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 9; (1978); p. 2671 - 2673, View in Reaxys; Buttery et al.; Journal of Agricultural and Food Chemistry; vol. 16; (1968); p. 1009,1014, View in Reaxys; Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys; Bohannon; Kleiman; Lipids; vol. 12; nb. 3; (1977); p. 321 - 323, View in Reaxys

UV/VIS Spectroscopy (3)

12/81

2017-11-15 01:27:11

1 of 3

Absorption Maxima (UV/ 225; 292 VIS) [nm] Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys

2 of 3

Description (UV/VIS Spectroscopy)

UV/VIS

Moltrasio et al.; Organic Preparations and Procedures International; vol. 4; (1972); p. 13, View in Reaxys; Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

hexane

Comment (UV/VIS Spectroscopy)

220 - 300 nm

Herzog; Hillmer; Chemische Berichte; vol. 64; (1931); p. 1288,1305, View in Reaxys; Kiss et al.; Acta Physica et Chemica; vol. 2; (1949); p. 192,193-196; Chem.Abstr.; nb. 5706; (1950), View in Reaxys Ecotoxicology (4) 1 of 4

Effect (Ecotoxicology)

fungal aflatoxin B1 production; effect on

Species or Test-System (Ecotoxicology)

Aspergillus parasiticus

Concentration (Ecotoxicology)

0.062 - 64 μmol/l

Method (Ecotoxicology)

microplate two-fold dilution method; title comp. incubated with test fungi in potato dextrose medium for 4 d; amount of aflatoxin B1 in culture filtrate determined; HPLC

Comment (Ecotoxicology)

No effect

Effect (Ecotoxicology)

aflatoxin G1 production; inhibition of

Species or Test-System (Ecotoxicology)

Aspergillus parasiticus

Concentration (Ecotoxicology)

0.062 - 64 μmol/l

Method (Ecotoxicology)

microplate two-fold dilution method; title comp. incubated with test fungi in potato dextrose medium for 4 d; amount of aflatoxin G1 in culture filtrate determined; HPLC

Type (Ecotoxicology)

IC50

Value of Type (Ecotoxicology)

3.5 μmol/l

Effect (Ecotoxicology)

growth; inhibition of

Endpoint of Effect (Ecotoxicology)

weight

Species or Test-System (Ecotoxicology)

Spilarctia obliqua larvae

Exposure Period (Ecotoxicology)

Method (Ecotoxicology)

freshly moulted 4th instar larvae; diet mix bioassay, the test comp. was mixed with diet, weight of each larvae was taken daily till the termination of the experiment

13/81

2017-11-15 01:27:11

Results

Log dose (1.2-2.4 ug/ml) - percent growth inhibition curve; less than 60 percent active

Srivastava; Gupta; Tripathi; Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 39; nb. 12; (2000); p. 946 - 949, View in Reaxys 4 of 4

Effect (Ecotoxicology)

antifeedant activity

Endpoint of Effect (Ecotoxicology)

faecal pellets produced

Species or Test-System (Ecotoxicology)

Spilarctia obliqua larvae

Exposure Period (Ecotoxicology)

24 h

Method (Ecotoxicology)

freshly moulted 4th instar larvae; diet mix bioassay, the test comp. was mixed with diet, number of faecal pellets produced were counted

Results

Log dose (1.2-2.4 ug/ml) - percent feeding deterrence curve; less than 60 percent active

Srivastava; Gupta; Tripathi; Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 39; nb. 12; (2000); p. 946 - 949, View in Reaxys Biodegradation (1) 1 of 1

Type (Biodegradation)

anaerobic

Inoculum

activated sewage sludge

Temperature (Biodegradation) [°C]

Method, Remarks (Biodegradation)

96/240 μl parsley seed oil component (29.8 percent); 5 ml 2,2,4,4,6,8,8-heptamethylnonane, 150 ml freshwater medium, nitrate (10 mM, refilled on depletion); in the dark; recovery after 4 months ( percent): 7 (96 μl) and 0 (240 μl); GC-FID analyses

Harder, Jens; Biodegradation; vol. 11; nb. 1; (2000); p. 55 - 63, View in Reaxys Use (8) Use Pattern

References

antioxidant

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys

Pungent constituent in a composition for damaged skin

Patent; FRANKE, Patrick; ROESSLING, Georg; WO2008/80980; (2008); (A1) English, View in Reaxys

Pungent constituent in a composition for wound healing

Patent; FRANKE, Patrick; ROESSLING, Georg; WO2008/80980; (2008); (A1) English, View in Reaxys

Pungent constituent in a composition for irritated skin

Patent; FRANKE, Patrick; ROESSLING, Georg; WO2008/80980; (2008); (A1) English, View in Reaxys

Pungent constituent in a composition for injured skin

Patent; FRANKE, Patrick; ROESSLING, Georg; WO2008/80980; (2008); (A1) English, View in Reaxys

Pungent constitu- Patent; FRANKE, Patrick; ROESSLING, Georg; WO2008/80980; (2008); (A1) English, View in Reaxys ent in a composition for excoriated skin increasing of farnesoid X-activated receptor (FXR)-mediated transcription or ecdysone receptor (EcR)-mediated transcription

Patent; Henrich, Vincent C.; Weinberger, Cary Alan; US2005/49230; (2005); (A1) English, View in Reaxys

14/81

2017-11-15 01:27:11

Component of insecticide composition

Patent; Henrich, Vincent C.; Weinberger, Cary Alan; US2005/49230; (2005); (A1) English, View in Reaxys

Isolation from Natural Product (60) Isolation from Location Natural Product

References

dried leaves of Macropiper excelsum obtained from D. M. Dunningham Ltd., Auckland, New Zealand

seeds of Myristica fragrans

leaves of gamma irradiated mutant cultivar of Perilla frutescens var. crispa; deposited at the Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute (Jeongeupsi, Jeollabuk-do, Korea)

Nam, Bomi; So, Yangkang; Kim, Hyo-Young; Kim, Jin-Baek; Jin, Chang Hyun; Han, Ah-Reum; Molecules; vol. 22; nb. 9; (2017), View in Reaxys

from full-ripe fruits of M. beddomei, M. fragrans, M. fatua and M. malabaricawere collected from Palode, Thiruvananthapuram, Kerala,India

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 493, View in Reaxys

arils of Myristica fragrans; purchased from Tochimoto Tenkaido Co., Ltd. (Osaka, Japan), cultivated in Indonesia

leaves of Perilla frutescens Britton var. acuta Kudo; collected from Namwon in Jeollanam-do, Korea

supporting information

Woo, Kyeong Wan; Han, Ji Young; Suh, Won Se; Lee, Jei Hyun; Lee, Kang Ro; Bulletin of the Korean Chemical Society; vol. 35; nb. 7; (2014); p. 2151 - 2154, View in Reaxys

stems of Embelia ribes (Myrsinaceae); collected at an Giang province, Vietnam, May 2011

Dang, Phu Hoang; Nguyen, Hai Xuan; Nguyen, Nhan Trung; Le, Hanh Ngoc Thi; Nguyen, Mai Thanh Thi; Phytotherapy Research; vol. 28; nb. 11; (2014); p. 1632 1636, View in Reaxys

dried seed kernels of Myristica fragrans Houtt; purchased from Anguo Chinese Medicinal Herbs Market (Anguo

15/81

2017-11-15 01:27:11

071200, Baoding, Hebei Province, P. R. China). aerial parts of Foeniculum vulgare Mill.; collected in Capoterra, Cagliari, Southern Sardinia, Italy, May 2013 parsley seeds

Piras, Alessandra; Falconieri, Danilo; Porcedda, Silvia; Marongiu, Bruno; Gonçalves, Maria José; Cavaleiro, Carlos; Salgueiro, Ligia; Natural Product Research; vol. 28; nb. 21; (2014); p. 1819 - 1825, View in Reaxys

supporting information

Chernysheva, Natalia B.; Tsyganov, Dmitry V.; Philchenkov, Alex A.; Zavelevich, Michael P.; Kiselyov, Alex S.; Semenov, Roman V.; Semenova, Marina N.; Semenov, Victor V.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 7; (2012); p. 2590 2593, View in Reaxys

roots of Ligusticum porteri Coult. & Rose (Apiaceae); collected in Basigochi, Chihuahua, Mexico, October 2003

Brindis, Fernando; Rodriguez, Rogelio; Bye, Robert; Gonzalez-Andrade, Martin; Mata, Rachel; Journal of Natural Products; vol. 74; nb. 3; (2011); p. 314 - 320, View in Reaxys

roots of Cinnamomum subavenium Miq.; collected in Wulai Hsiang, Taipei County, Taiwan

Chen, Chung-Yi; Wang, Yau-Der; Chemistry of Natural Compounds; vol. 47; nb. 3; (2011); p. 461 - 462, View in Reaxys

air-dried roots of Cinnamomum subavenium Miq. (Lauraceae); collected from Wulai Hsiang, Taipei County, Taiwan

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys

seeds of Petroselinum sativum Hoffm. var Astra, parsley; cultivated in Russia

Semenov, Victor V.; Kiselyov, Alex S.; Titov, Ilia Y.; Sagamanova, Irina K.; Ikizalp, Natalie N.; Chernysheva, Natalia B.; Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Firgang, Sergei I.; Semenov, Roman V.; Karmanova, Irina B.; Raihstat, Mikhail M.; Semenova, Marina N.; Journal of Natural Products; vol. 73; nb. 11; (2010); p. 1796 1802, View in Reaxys

stems of Cinnamomum tenuifolium Sugimoto form. nervosum (Meissn.) Hara. (Lauraceae); collected from Lanyu Island, Taiwan

Lin, Rong-Jyh; Cheng, Ming-Jen; Huang, Jin-Cherng; Lo, Wen-Li; Yeh, Yu-Ting; Yen, Chung-Min; Lu, Chin-Mei; Chen, Chung-Yi; Journal of Natural Products; vol. 72; nb. 10; (2009); p. 1816 - 1824, View in Reaxys

flower oil of Ridolfia segetum

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys

Piper aduncum, leaves, obtained from Isan village, Teptep in the Finnisterre mountain Ranges, Morobe Province, Papua New Guinea

Rali, Topul; Wossa, Stewart W.; Leach, David N.; Waterman, Peter G.; Molecules; vol. 12; nb. 3; (2007); p. 389 - 394, View in Reaxys

seed essential oil of Petroselinum crispum

16/81

2017-11-15 01:27:11

parsley var. universal'naya bogatyr'

Semenov; Rusak; Chartov; Zaretskii; Konyushkin; Firgang; Chizhov; Elkin; Latin; Bonashek; Stas'Eva; Russian Chemical Bulletin; vol. 56; nb. 12; (2007); p. 2448 - 2455, View in Reaxys

parsley var. kudryavaya slavyanovskaya

Semenov; Rusak; Chartov; Zaretskii; Konyushkin; Firgang; Chizhov; Elkin; Latin; Bonashek; Stas'Eva; Russian Chemical Bulletin; vol. 56; nb. 12; (2007); p. 2448 - 2455, View in Reaxys

parsley

Semenov; Rusak; Chartov; Zaretskii; Konyushkin; Firgang; Chizhov; Elkin; Latin; Bonashek; Stas'Eva; Russian Chemical Bulletin; vol. 56; nb. 12; (2007); p. 2448 - 2455, View in Reaxys

leaves and stems of Peperomia villipetiola collected from Chota-Cajamarca, Peru

Malquichagua Salazar, Karina J.; Delgado Paredes, Guillermo E.; Lluncor, Luis Ripalda; Young, Maria Claudia Max; Kato, Massuo Jorge; Phytochemistry; vol. 66; nb. 5; (2005); p. 573 - 579, View in Reaxys

nutmeg (Myristica fragrans)

Morita, Tatsuya; Jinno, Keiko; Kawagishi, Hirokazu; Arimoto, Yasushi; Suganuma, Hiroyuki; Inakuma, Takahiro; Sugiyama, Kimio; Journal of Agricultural and Food Chemistry; vol. 51; nb. 6; (2003); p. 1560 - 1565, View in Reaxys

Piper solmsianum

Martins, Roberto C.C.; Latorre, Leandro R.; Sartorelli, Patricia; Kato, Massuo J.; Phytochemistry; vol. 55; nb. 7; (2000); p. 843 - 846, View in Reaxys

Petroselinum crispum Mill. (American parsley)

Yoshikawa, Masayuki; Uemura, Toshiaki; Shimoda, Hiroshi; Kishi, Akinobu; Kawahara, Yuzo; Matsuda, Hisashi; Chemical and Pharmaceutical Bulletin; vol. 48; nb. 7; (2000); p. 1039 - 1044, View in Reaxys

Piper mullesua

Srivastava; Gupta; Tripathi; Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 39; nb. 12; (2000); p. 946 - 949, View in Reaxys

Piper regnellii, roots

Benevides, Paulo J.C.; Sartorelli, Patricia; Kato, Massuo J.; Phytochemistry; vol. 52; nb. 2; (1999); p. 339 - 343, View in Reaxys

leaves of Piper aduncum

Parmar, Virinder S.; Jain, Subhash C.; Gupta, Sangita; Talwar, Sangeeta; Rajwanshi, Vivek K.; Kumar, Rajesh; Azim, Abul; Malhotra, Sanjay; Kumar, Naresh; Jain, Rajni; Sharma, Nawal K.; Tyagi, Om D.; Lawrie, Stephen J.; Errington, William; Howarth, Oliwer W.; Olsen, Carl E.; Singh, Sanjay K.; Wengel, Jesper; Phytochemistry; vol. 49; nb. 4; (1998); p. 1069 - 1078, View in Reaxys

roots of Ferula ferulioides (Steud.) Korovin (Umbelliferae)

Piper aduncum

Parmar, Virinder S.; Jain, Subhash C.; Bisht, Kirpal S.; Jain, Rajni; Taneja, Poonam; Jha, Amitabh; Tyagi, Om D.; Prasad, Ashok K.; Wengel, Jesper; Olsen, Carl E.; Boll, Per M.; Phytochemistry; vol. 46; nb. 4; (1997); p. 597 - 673, View in Reaxys

aerial parts of Cassia grandis, Caesalpiniaceae

Gonzalez; Bermejo; Valencia; Planta Medica; vol. 62; nb. 2; (1996); p. 176 - 177, View in Reaxys

Oenanthe javanica

Fujita; Kadoya; Aota; Nakayama; Bioscience, biotechnology, and biochemistry; vol. 59; nb. 3; (1995); p. 526 - 528, View in Reaxys

Perilla fructescens

Honda; Koezuka; Tabata; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 8; (1988); p. 3153 - 3155, View in Reaxys

mace essential oil

Teresa, Joaquin de Pascual; Pascual, Marian de; Arias, Alicia; Hernandez, Jose M.; Moran, Joaquin R.; Grande, Manuel; Phytochemistry (Elsevier); vol. 24; nb. 8; (1985); p. 1773 - 1778, View in Reaxys

timber of I. anisatum L., collected on Mie Prefectur (Japan), and from leaves of I. anisatum L., collected on Mie Prefectur (Japan)

Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, ShengTen; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys

dried roots of Guillonea scabra

Pinar, Mariano; Rico, Manuel; Rodriguez, Benjamin; Phytochemistry (Elsevier); vol. 21; nb. 3; (1982); p. 735 - 738, View in Reaxys

17/81

2017-11-15 01:27:11

aus Illicium anisatum L.

Shibuya; Abe; Nakahashi; Kubota; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 9; (1978); p. 2671 - 2673, View in Reaxys

aus Portenschlagia ramosissima

Bohannon; Kleiman; Lipids; vol. 12; nb. 3; (1977); p. 321 - 323, View in Reaxys

aus Ferula equisetaca

Borisov et al.; Chemistry of Natural Compounds; vol. 9; (1973); p. 266; Khimiya Prirodnykh Soedinenii; vol. 9; (1973); p. 275, View in Reaxys

Myristica fragrans (Samen)

Isogai et al.; Agricultural and Biological Chemistry; vol. 37; (1973); p. 889,894, View in Reaxys

Petroselinum sativum Hoffm.

Alimukhamedov et al.; Pharmaceutical Chemistry Journal; vol. 6; nb. 9; (1972); p. 572; Khimiko-Farmatsevticheskii Zhurnal; vol. 6; nb. 9; (1972); p. 15, View in Reaxys

aus Myristica

Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys

Vork. im aether.Oel aus den Wurzeln v. Foeniculum vulgare Mill.

Trenkle; Die Pharmazie; vol. 24; nb. 12; (1969); p. 782 - 782, View in Reaxys

aus Cinnamomum Camphora Sieb.

Hayashi,S. et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 1465 1466, View in Reaxys

aus Daucus carota L., var. Sativa

Buttery et al.; Journal of Agricultural and Food Chemistry; vol. 16; (1968); p. 1009,1014, View in Reaxys

aus Petersilie

Shulgin; Nature (London, United Kingdom); vol. 210; (1966); p. 380,381, View in Reaxys

im aetherischen Oel aus Fruechten verschiedener Rassen v. Petroseticum hortense Hoffm.

Stahl; Jork; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 297; (1964); p. 273,279, View in Reaxys

aus parsley seed oil

Privett et al.; Journal of the American Oil Chemists' Society; vol. 40; (1963); p. 28,29, View in Reaxys

aus Pastinaca sativa L.

Lichtenstein; Casida; Journal of Agricultural and Food Chemistry; vol. 11; (1963); p. 410,411, View in Reaxys

aus Petersilienoel

Rajkowski; Acta Poloniae Pharmaceutica; vol. 19; (1962); p. 383,391; Chem.Abstr.; vol. 60; nb. 13091; (1964), View in Reaxys

Isolierung aus den aetherischen Oelen der Rhizome von Ligusticum scoticum

Mitsuhashi et al.; Yakugaku Zasshi; vol. 79; (1959); p. 106; Chem.Abstr.; (1959); p. 10104, View in Reaxys

Isolierung aus den aetherischen Oelen der Samen von Myristica fragrans:

Rao; Seshadri; Proceedings - Indian Academy of Sciences, Section A; vol. 23; (1946); p. 147,149, View in Reaxys

Isolierung aus Ridolfia (Carum) segetum:

Gattefosse; Igolen; Bulletin de la Societe Chimique de France; (1946); p. 361; Ind. Parfum.; vol. 6; (1951); p. 305, View in Reaxys

Isolierung aus den aetherischen Oelen der Blaetter von Macropiper excelsum:

Briggs; Journal of the Society of Chemical Industry, London; vol. 60; (1941); p. 210, View in Reaxys

Im Dillkrautoel

Schimmel and Co; Ber. Schimmel; (1927); p. 26; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 1518, View in Reaxys

18/81

2017-11-15 01:27:11

Zum Vorkommen im Petersilienoel

van Loon; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 496, View in Reaxys; Hilditch; Jones; Journal of the Society of Chemical Industry, London; vol. 46; (1927); p. 176 T; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 238, View in Reaxys

Im aether. Oel des Holzes von Cinnamomum glanduliferium Meissn.

Pickles; Journal of the Chemical Society; vol. 101; (1912); p. 1437, View in Reaxys

im aether. Muskatnussoel

Thoms; Chemische Berichte; vol. 36; (1903); p. 3448, View in Reaxys; Power; Salway; Journal of the Chemical Society; vol. 91; (1907); p. 2045,2049, View in Reaxys

im franzoesischen Petersilienoel

Thoms; Chemische Berichte; vol. 36; (1903); p. 3448, View in Reaxys

im Muskatbluetenoel

Semmler; Chemische Berichte; vol. 23; (1890); p. 1809, View in Reaxys; Thoms; Chemische Berichte; vol. 36; (1903); p. 3448, View in Reaxys

Medchem (113) 1 of 113

Substance Effect

Estrogen

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Bioassay : cell proliferation assessed by MTT assay in vitro; estrogenic activity evaluated as proliferative activities in estrogen-sensitive cells; 2000 cells/100 μl; phenol red-free DMEM containing 5 percent estrogen free FCS; after 24 h culture title comp. added and incubated for 4 d

Cells/Cell Lines

MCF-7

Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

0.100000 µM

Qualitative Results

at 0.1/1/10 μmol/l title comp. enhanced cell proliferation to 94.4/102.4/92.7 percent of control

Measurement Parameter

Qualitative

Yoshikawa, Masayuki; Uemura, Toshiaki; Shimoda, Hiroshi; Kishi, Akinobu; Kawahara, Yuzo; Matsuda, Hisashi; Chemical and Pharmaceutical Bulletin; vol. 48; nb. 7; (2000); p. 1039 - 1044, View in Reaxys 2 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : basophilic leukemia RBL-2H3 cells of ratBioassay : reference comp.: epigallocathechin gallate (50 μmol/l) cells were pretreated with title comp. for 30 min at 37 deg C and stimulated with A23187 (2 μmol/l); effect of title comp. on the inhibition of histamine release was assayed

Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

50 µM

Qualitative Results

title comp. showed ca. 10% inhibition of histamine release (vs. 28.6% inhibition by reference comp.); figure

Measurement Parameter

Qualitative

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys 3 of 113

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

19/81

2017-11-15 01:27:11

Bioassay Details

Effect : free radical scavengingTarget : DPPH Bioassay : DPPH

Substance RN

166218View in Reaxys

Substance Name

Substance Dose

100 µM

Qualitative Results

DPPH inhibition 19

Measurement Parameter

Qualitative

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys 4 of 113

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : metal chelating activityTarget : ferrous ion-ferrozine complex Bioassay : ferrous ion-ferrozine complex

Substance RN

166218View in Reaxys

Substance Name

Substance Dose

100 µM

Qualitative Results

metal chelating inhibition 10

Measurement Parameter

Qualitative

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys 5 of 113

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : reducing powerTarget : potassium ferricyanide Bioassay : potassium ferricyanide

Substance RN

166218View in Reaxys

Substance Name

Substance Dose

100 µM

Qualitative Results

reducing power 10

Measurement Parameter

Qualitative

Chen; Wang; Chung; Lo; Yang; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 474 - 477, View in Reaxys 6 of 113

Substance Effect

Cell Viability

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : cell viabilitySpecies : mouse macrophages mouse macrophagesmouseMTS assay

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

<= 50 µM

Measurement Parameter

Qualitative

20/81

2017-11-15 01:27:11

Qualitative value

Lee, Ji Young; Park, Wansu; Molecules; vol. 16; nb. 8; (2011); p. 7132 - 7142, View in Reaxys 7 of 113

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

166218View in Reaxys

Substance Name

273290

Qualitative Results

effect on hexobarbital-induced sleep in mice

Measurement Parameter

Qualitative

Honda; Koezuka; Tabata; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 8; (1988); p. 3153 - 3155, View in Reaxys 8 of 113

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

166218View in Reaxys

Substance Name

273290

Qualitative Results

MIC >200 μg/ml (against Streptococcus mutans)

Measurement Parameter

Qualitative

Hattori; Hada; Watahiki; Ihara; Shu; Kakiuchi; Mizuno; Namba; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3885 - 3893, View in Reaxys 9 of 113

Target Name

Ecdysone receptor; Retinoic acid receptor RXR-alpha [Mus musculus]; bile acid receptor

Target Synonyms

20-hydroxy-ecdysone receptor (ecdysone receptor); 20e receptor; aaecr; aael009600; ecdysone receptor; ecdysteroid receptor (ecdysone receptor); ecr (ecdysone receptor); ecrh (ecdysone receptor); hvecr; nr1h1 (ecdysone receptor); nuclear receptor subfamily 1 group h member 1 (ecdysone receptor) + nr2b1; nuclear receptor subfamily 2 group b member 1; retinoic acid receptor rxr-alpha; retinoid x receptor alpha; rxra + bar (bile acid receptor); bile acid receptor; farnesoid x-activated receptor; farnesol receptor hrr-1; fxr (bile acid receptor); hrr1 (bile acid receptor); nr1h4; nuclear receptor subfamily 1 group h member 4; retinoid x receptor-interacting protein 14; rip14; rxr-interacting protein 14

Target Uniprot ID

p28700

Target PDB ID

1dkf; 1xdk; 3a9e

Target, Subunit, Species Ecdysone receptor; Retinoic acid receptor RXR-alpha [Mus musculus]; bile acid receptor Target Mutant/Chimera Details

Ecdysone receptor:Wild; Retinoic acid receptor RXR-alpha [Mus musculus]:Wild; bile acid receptor:Wild

Target Species (Bioactivity)

Mus musculus

Target Transfection

Transfected; Transfected; Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Transactivation assay

Cells/Cell Lines

CHO

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

250 µM

Measurement Parameter

Fold-increase

Quantitative value

21/81

2017-11-15 01:27:11

10 of 113

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : fungal aflatoxin B1 production; effect onBioassay : microplate two-fold dilution method; title comp. incubated with test fungi in potato dextrose medium for 4 d; amount of aflatoxin B1 in culture filtrate determined; HPLC

Biological Species/NCBI Aspergillus parasiticus ID Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

0.0620000 µM

Measurement Parameter

Qualitative

Qualitative value

Measurement pX

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : aflatoxin G1 production; inhibition ofBioassay : microplate two-fold dilution method; title comp. incubated with test fungi in potato dextrose medium for 4 d; amount of aflatoxin G1 in culture filtrate determined; HPLC

Biological Species/NCBI Aspergillus parasiticus ID Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

0.0620000 µM

Measurement Parameter

IC50

Unit

µM

Quantitative value

3.5

Measurement pX

5.46

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : bactericidalclinically isolated strain

Biological Species/NCBI Salmonella enterica subsp. enterica serovar Typhimurium ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Quantitative value

2.5

Measurement pX

1.89

22/81

2017-11-15 01:27:11

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 13 of 113

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antibacterialclinically isolated strain

Biological Species/NCBI Salmonella enterica subsp. enterica serovar Typhimurium ID Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

Unit

mg/mL

Quantitative value

0.62

Measurement pX

2.49

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 14 of 113

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : bactericidalenvironmentally isolated strain

Biological Species/NCBI Staphylococcus aureus ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Quantitative value

2.5

Measurement pX

1.89

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 15 of 113

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antibacterialenvironmentally isolated strain

Biological Species/NCBI Staphylococcus aureus ID Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

Unit

mg/mL

Quantitative value

0.62

23/81

2017-11-15 01:27:11

Measurement pX

2.49

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 16 of 113

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : bactericidalenvironmentally isolated strain

Biological Species/NCBI Pseudomonas aeruginosa ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Quantitative value

Measurement pX

1.59

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 17 of 113

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antibacterialenvironmentally isolated strain

Biological Species/NCBI Pseudomonas aeruginosa ID Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

Unit

mg/mL

Quantitative value

1.25

Measurement pX

2.19

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 18 of 113

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : bactericidalSpecies : Shigella spp. clinically isolated strain

Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Quantitative value

2.5

Measurement pX

1.89

24/81

2017-11-15 01:27:11

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 19 of 113

Substance Effect

Antimicrobial

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : antibacterialSpecies : Shigella spp. clinically isolated strain

Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

Unit

mg/mL

Quantitative value

1.25

Measurement pX

2.19

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 20 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : bactericidal

Biological Species/NCBI Escherichia coli ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Quantitative value

Measurement pX

1.59

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 21 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : antibacterial

Biological Species/NCBI Escherichia coli ID Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

Unit

mg/mL

Quantitative value

2.5

Measurement pX

1.89

25/81

2017-11-15 01:27:11

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 22 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : bactericidal

Biological Species/NCBI Staphylococcus aureus ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Qualitative value

Quantitative value

Measurement pX

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 23 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : antibacterial

Biological Species/NCBI Staphylococcus aureus ID Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

Unit

mg/mL

Quantitative value

Measurement pX

1.59

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 24 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : bactericidal

Biological Species/NCBI Enterococcus faecalis ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Qualitative value

26/81

2017-11-15 01:27:11

Quantitative value

Measurement pX

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 25 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : antibacterial

Biological Species/NCBI Enterococcus faecalis ID Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

Unit

mg/mL

Quantitative value

Measurement pX

1.59

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 26 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : bactericidal

Biological Species/NCBI Pseudomonas aeruginosa ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

MBC

Unit

mg/mL

Quantitative value

Measurement pX

1.59

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 27 of 113

Substance Effect

Antimicrobial

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : antibacterial

Biological Species/NCBI Pseudomonas aeruginosa ID Substance RN

166218View in Reaxys

Substance Name

Substance Dose

0.0775000 mg/mL

Measurement Parameter

MIC

27/81

2017-11-15 01:27:11

Unit

mg/mL

Quantitative value

2.5

Measurement pX

1.89

Jabrane, Aymen; Jannet, Hichem Ben; Harzallah-Skhiri, Fethia; Mastouri, Maha; Casanova, Joseph; Mighri, Zine; Chemistry and Biodiversity; vol. 6; nb. 6; (2009); p. 881 - 889, View in Reaxys 28 of 113

Target Name

Cytochrome P450 3A4 [human]

Target Synonyms

1,8-cineole 2-exo-monooxygenase; albendazole monooxygenase; albendazole sulfoxidase; cyp3a3; cyp3a4; cypiiia3; cypiiia4; cytochrome p450 3a3; cytochrome p450 3a4; cytochrome p450 hlp; cytochrome p450 nf-25; cytochrome p450-pcn1; nifedipine oxidase; quinine 3-monooxygenase; taurochenodeoxycholate 6-alpha-hydroxylase

Target Uniprot ID

p08684

Target PDB ID

1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

Target, Subunit, Species Cytochrome P450 3A4 [human]

29 of 113

Target Mutant/Chimera Details

Cytochrome P450 3A4 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

43.2

Measurement pX

4.36

Metabolite RN

2625776

Metabolite name

6beta-Hydroxytestosterone

Concomitants: Compound RN

24140787; 1915399; 506008; 77911

Concomitants: Compound name

Glucose-6-phosphate; Testosterone; DMSO; NADPH

Concomitants: Compound role

COM; SUB; SLV; COE

Target Name

Cytochrome P450 2C9 [human]

Target Synonyms

(r)-limonene 6-monooxygenase (cytochrome p450 2c9); (s)-limonene 6-monooxygenase (cytochrome p450 2c9); (s)-limonene 7-monooxygenase (cytochrome p450 2c9); cyp2c10; cyp2c9; cypiic9; cytochrome p-450mp; cytochrome p450 2c9; cytochrome p450 mp-4; cytochrome p450 mp-8; cytochrome p450 pb-1; s-mephenytoin 4-hydroxylase (cytochrome p450 2c9)

Target Uniprot ID

p11712

Target PDB ID

1og2; 1og5; 1r9o; 4nz2

Target, Subunit, Species Cytochrome P450 2C9 [human] Target Mutant/Chimera Details

Cytochrome P450 2C9 [human]:Wild

28/81

2017-11-15 01:27:11

30 of 113

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Metabolite RN

4198042

Metabolite name

4'-Hydroxydiclofenac

Concomitants: Compound RN

2146636; 2146636; 24140787; 506008; 77911

Concomitants: Compound name

Diclofenac; Diclofenac; Glucose-6-phosphate; DMSO; NADPH

Concomitants: Compound role

SUB; SUB; COM; SLV; COE

Target Name

Cytochrome P450 3A4 [human]

Target Synonyms

Target Uniprot ID

p08684

Target PDB ID

1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

Target, Subunit, Species Cytochrome P450 3A4 [human] Target Mutant/Chimera Details

Cytochrome P450 3A4 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

166218View in Reaxys

Substance Name

Substance Dose

10 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

29/81

2017-11-15 01:27:11

31 of 113

Metabolite RN

2625776

Metabolite name

6beta-Hydroxytestosterone

Concomitants: Compound RN

24140787; 1915399; 506008; 77911

Concomitants: Compound name

Glucose-6-phosphate; Testosterone; DMSO; NADPH

Concomitants: Compound role

COM; SUB; SLV; COE

Target Name

Cytochrome P450 2C9 [human]

Target Synonyms

Target Uniprot ID

p11712

Target PDB ID

1og2; 1og5; 1r9o; 4nz2

Target, Subunit, Species Cytochrome P450 2C9 [human]

32 of 113

Target Mutant/Chimera Details

Cytochrome P450 2C9 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

166218View in Reaxys

Substance Name

Substance Dose

10 µM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

4.82

Metabolite RN

4198042

Metabolite name

4'-Hydroxydiclofenac

Concomitants: Compound RN

2146636; 2146636; 24140787; 506008; 77911

Concomitants: Compound name

Diclofenac; Diclofenac; Glucose-6-phosphate; DMSO; NADPH

Concomitants: Compound role

SUB; SUB; COM; SLV; COE

Substance Effect

Hepatoprotective

Bioassay Category

In Vivo (Animal models)

Bioassay Name

In vivo Measurement

Bioassay Details

Bioassay : at 8 h after intoxication killed and blood samples obtained; activities of serum ALT and AST measured colorimetrically effect on serum ALT and AST activities assessed in mice with Escherichia coli lipopolysaccharide (LPS)/D-galactosamine (D-GalN)-induced liver injury; 10 mice (30-36 g)/group administered iv with 10 μg/kg LPS plus 700 mg/kg DGalN

30/81

2017-11-15 01:27:11

Biological Species/NCBI Mus musculus ID Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

50 mg/kg

Substance Route of Adm.

oral administration

Qualitative Results

title comp. administration dose-dependently prohibited elevations of serum ALT and AST activities in mice with LPS-(D-GalN)-induced liver injury

Measurement Parameter

Qualitative

Substance Effect

Hepatoprotective

Bioassay Category

In Vivo (Animal models)

Bioassay Name

In vivo Measurement

Bioassay Details

Bioassay : at 8 h after intoxication killed and blood samples obtained; serum levels of TNF-α measured by ELISA effect on Escherichia coli lipopolysaccharide (LPS)/D-galactosamine (D-GalN)-induced enhancement of serum TNF-α levels evaluated; 5 mice (30-36 g)/group administered iv with 10 μg/kg LPS plus 700 mg/kg D-GalN

Biological Species/NCBI Mus musculus ID Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

200 mg/kg

Substance Route of Adm.

oral administration

Qualitative Results

title comp. markedly inhibited elevation of serum TNF-α levels

Measurement Parameter

Qualitative

Substance Effect

Hepatoprotective

Bioassay Category

In Vivo (Animal models)

Bioassay Name

In vivo Measurement

Bioassay Details

Bioassay : at 8 h after intoxication killed and livers obtained; hepatic DNA fragmentation detected and quantified by 1.8 percent agarose gel electrophoresis and DNA ELISA, resp. effect on DNA ladder and DNA fragmentation assessed in mice with Escherichia coli lipopolysaccharide (LPS)/D-galactosamine (D-GalN)-induced liver injury; 10 mice (30-36 g)/ group administered iv with 10 μg/kg LPS plus 700 mg/kg D-GalN

Biological Species/NCBI Mus musculus ID Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

100 mg/kg

Substance Route of Adm.

oral administration

Qualitative Results

at 200 mg/kg title comp. markedly suppressed LPS-(D-GalN)-induced enhancement of hepatic DNA fragmentation

31/81

2017-11-15 01:27:11

Measurement Parameter

Qualitative

Substance Effect

Antifeedant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : faecal pellets producedTarget : Spilarctia obliqua larvaeBioassay : freshly moulted 4th instar larvae; diet mix bioassay, the test comp. was mixed with diet, number of faecal pellets produced were counted

Substance RN

166218View in Reaxys

Substance Name

273290

Qualitative Results

Log dose (1.2-2.4 ug/ml) - percent feeding deterrence curve; less than 60 percent active

Measurement Parameter

Qualitative

Srivastava; Gupta; Tripathi; Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 39; nb. 12; (2000); p. 946 - 949, View in Reaxys 36 of 113

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : weightTarget : Spilarctia obliqua larvaeBioassay : freshly moulted 4th instar larvae; diet mix bioassay, the test comp. was mixed with diet, weight of each larvae was taken daily till the termination of the experiment

Substance RN

166218View in Reaxys

Substance Name

273290

Qualitative Results

Log dose (1.2-2.4 ug/ml) - percent growth inhibition curve; less than 60 percent active

Measurement Parameter

Qualitative

Srivastava; Gupta; Tripathi; Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 39; nb. 12; (2000); p. 946 - 949, View in Reaxys 37 of 113

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : DNA adducts; formation ofBioassay : cells incubated with title comp. for 24 h; DNA adducts formation analyzed by dinucleotide/monophosphate version of <32P>-postlabeling assay and multidirectional ion-exchanged thin-layer chromatography

Biological Species/NCBI Human ID Cells/Cell Lines

HepG 2

Substance RN

166218View in Reaxys

Substance Name

273290

Substance Dose

50 µM

Qualitative Results

title comp. dose-dependently leads to DNA adduct formation; two types of DNA adducts were detected: major and minor (3' or 1'-carbons of side chain of title comp. binds to guanine, resp.) in the ratio of 4.7

Measurement Parameter

Qualitative

Zhou, Guo-Dong; Moorthy, Bhagavatula; Bi, Jia; Donnelly, Kirby C.; Randerath, Kurt; Environmental and Molecular Mutagenesis; vol. 48; nb. 9; (2007); p. 715 - 721, View in Reaxys 38 of 113

Substance Effect

Acaricidal

32/81

2017-11-15 01:27:11

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : miticidalimpregnated fabric disk assay

Biological Species/NCBI Dermatophagoides pteronyssinus ID Substance RN

166218View in Reaxys

Substance Name

Qualitative Results

mortality rate 74 - 100 percent

Measurement Parameter

Qualitative

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 39 of 113

Substance Effect

Acaricidal

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : miticidalimpregnated fabric disk assay

Biological Species/NCBI Dermatophagoides pteronyssinus ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

LC50

Unit

µg/cm2

Quantitative value

4.75

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 40 of 113

Substance Effect

Acaricidal

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : miticidalimpregnated fabric disk assay

Biological Species/NCBI Dermatophagoides farinae ID Substance RN

166218View in Reaxys

Substance Name

Qualitative Results

mortality rate 91.2 - 100 percent

Measurement Parameter

Qualitative

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 41 of 113

Substance Effect

Acaricidal

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : miticidalimpregnated fabric disk assay

Biological Species/NCBI Dermatophagoides farinae ID Substance RN

166218View in Reaxys

33/81

2017-11-15 01:27:11

Substance Name

Measurement Parameter

LC50

Unit

µg/cm2

Quantitative value

2.75

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 42 of 113

Substance Effect

Acaricidal

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : miticidalimpregnated fabric disk assay

Biological Species/NCBI Tyrophagus putrescentiae ID Substance RN

166218View in Reaxys

Substance Name

Measurement Parameter

Qualitative

Qualitative value

Measurement pX

Song, Ha Yun; Yang, Ji Yeon; Suh, Joo Won; Lee, Hoi Seon; Journal of Agricultural and Food Chemistry; vol. 59; nb. 14; (2011); p. 7759 - 7764, View in Reaxys 43 of 113

Target Name

Cytochrome P450 1A2 [human]; Cytochrome P450 3A4 [human]

Target Synonyms

cyp1a2; cypia2; cytochrome p(3)450; cytochrome p450 1a2; cytochrome p450 4; cytochrome p450-p3 + 1,8-cineole 2-exo-monooxygenase; albendazole monooxygenase; albendazole sulfoxidase; cyp3a3; cyp3a4; cypiiia3; cypiiia4; cytochrome p450 3a3; cytochrome p450 3a4; cytochrome p450 hlp; cytochrome p450 nf-25; cytochrome p450-pcn1; nifedipine oxidase; quinine 3-monooxygenase; taurochenodeoxycholate 6-alpha-hydroxylase

Target Uniprot ID

p05177 + p08684

Target PDB ID

2hi4 + 1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

Target, Subunit, Species Cytochrome P450 1A2 [human]; Cytochrome P450 3A4 [human] Target Mutant/Chimera Details

Cytochrome P450 1A2 [human]:Wild; Cytochrome P450 3A4 [human]:Wild

Target Species (Bioactivity)

human; human

Target Transfection

Non Transfected; Non Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology substrate

Biological Species/NCBI Human ID Organs/Tissues

Liver

Cell Fraction

Microsome

Substance RN

166218View in Reaxys

Substance Name

Myristicin

Substance Dose

100 µM

Measurement Parameter

Rate

34/81

2017-11-15 01:27:11

44 of 113

Unit

nmol/min/nmol P450 all

Quantitative value

0.176

Metabolite RN

2261529

Metabolite name

Concomitants: Compound RN

19279336

Concomitants: Compound name

NADPH regenerating System

Concomitants: Compound role

COM

Target Name

Cytochrome P450 1A2 [human]

Target Synonyms

cyp1a2; cypia2; cytochrome p(3)450; cytochrome p450 1a2; cytochrome p450 4; cytochrome p450-p3

Target Uniprot ID

p05177

Target PDB ID

2hi4

Target, Subunit, Species Cytochrome P450 1A2 [human] Target Mutant/Chimera Details

Cytochrome P450 1A2 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology substrate

Biological Species/NCBI Escherichia coli ID

45 of 113

Substance RN

166218View in Reaxys

Substance Name

Myristicin

Substance Dose

100 µM

Measurement Parameter

Rate

Unit

nmol/min/nmol target

Quantitative value

0.01

Metabolite RN

2261529

Metabolite name

Concomitants: Compound RN

19279336

Concomitants: Compound name

NADPH regenerating System; L-alpha-Dilauroyl phosphatidylcholine

Concomitants: Compound role

COM; COM

Target Name

Cytochrome P450 3A4 [human]

Target Synonyms

Target Uniprot ID

p08684

Target PDB ID

1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

35/81

2017-11-15 01:27:11

Target, Subunit, Species Cytochrome P450 3A4 [human] Target Mutant/Chimera Details

Cytochrome P450 3A4 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology substrate

Biological Species/NCBI Escherichia coli ID

46 of 113

Substance RN

166218View in Reaxys

Substance Name

Myristicin

Substance Dose

100 µM

Measurement Parameter

Rate

Unit

nmol/min/nmol target

Quantitative value

0.037

Metabolite RN

2261529

Metabolite name

Concomitants: Compound RN

19279336

Concomitants: Compound name

NADPH regenerating System; L-alpha-Dilauroyl phosphatidylcholine

Concomitants: Compound role

COM; COM

Target Name

Cytochrome P450 2C18 [human]

Target Synonyms

cyp2c18; cypiic18; cytochrome p450 2c18; cytochrome p450-6b/29c

Target Uniprot ID

p33260

Target PDB ID

2cik; 2h6p

Target, Subunit, Species Cytochrome P450 2C18 [human] Target Mutant/Chimera Details

Cytochrome P450 2C18 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology substrate

Biological Species/NCBI Escherichia coli ID Substance RN

166218View in Reaxys

Substance Name

Myristicin

Substance Dose

100 µM

Measurement Parameter

Rate

Unit

nmol/min/nmol target

Qualitative value

Quantitative value

0.001

36/81

2017-11-15 01:27:11

47 of 113

Metabolite RN

2261529

Metabolite name

Concomitants: Compound RN

19279336

Concomitants: Compound name

NADPH regenerating System; L-alpha-Dilauroyl phosphatidylcholine

Concomitants: Compound role

COM; COM

Target Name

Cytochrome P450 2A6 [human]

Target Synonyms

1,4-cineole 2-exo-monooxygenase (cytochrome p450 2a6); coumarin 7-hydroxylase; cyp2a3; cyp2a6; cypiia6; cytochrome p450 2a6; cytochrome p450 iia3; cytochrome p450(i)

Target Uniprot ID

p11509

Target PDB ID

1z10; 1z11; 2fdu; 2fdv; 2fdw; 2fdy; 3ebs; 3t3q; 3t3r; 4ejj; 4rui

Target, Subunit, Species Cytochrome P450 2A6 [human] Target Mutant/Chimera Details

Cytochrome P450 2A6 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology substrate

Biological Species/NCBI Escherichia coli ID

48 of 113

Substance RN

166218View in Reaxys

Substance Name

Myristicin

Substance Dose

100 µM

Measurement Parameter

Rate

Unit

nmol/min/nmol target

Qualitative value

Quantitative value

0.001

Metabolite RN

2261529

Metabolite name

Concomitants: Compound RN

19279336

Concomitants: Compound name

NADPH regenerating System; L-alpha-Dilauroyl phosphatidylcholine

Concomitants: Compound role

COM; COM

Target Name

Cytochrome P450 2E1 [human]

Target Synonyms

4-nitrophenol 2-hydroxylase; cyp2e; cyp2e1 (cytochrome p450 2e1); cypiie1; cytochrome p450 2e1; cytochrome p450-j

Target Uniprot ID

p05181

Target PDB ID

3e4e; 3e6i; 3gph; 3koh; 3lc4; 3t3z

Target, Subunit, Species Cytochrome P450 2E1 [human] Target Mutant/Chimera Details

Cytochrome P450 2E1 [human]:Wild

37/81

2017-11-15 01:27:11

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology substrate

Biological Species/NCBI Escherichia coli ID

49 of 113

Substance RN

166218View in Reaxys

Substance Name

Myristicin

Substance Dose

100 µM

Measurement Parameter

Rate

Unit

nmol/min/nmol target

Qualitative value

Quantitative value

0.001

Metabolite RN

2261529

Metabolite name

Concomitants: Compound RN

19279336

Concomitants: Compound name

NADPH regenerating System; L-alpha-Dilauroyl phosphatidylcholine

Concomitants: Compound role

COM; COM

Target Name

Cytochrome P450 2D6 [human]

Target Synonyms

cyp2d6 (cytochrome p450 2d6); cyp2dl1; cypiid6; cytochrome p450 2d6; cytochrome p450-db1; debrisoquine 4-hydroxylase

Target Uniprot ID

p10635

Target PDB ID

2f9q; 3qm4; 3tbg; 3tda; 4wnt; 4wnu; 4wnv; 4wnw; 4xry; 4xrz

Target, Subunit, Species Cytochrome P450 2D6 [human] Target Mutant/Chimera Details

Cytochrome P450 2D6 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology substrate

Biological Species/NCBI Escherichia coli ID Substance RN

166218View in Reaxys

Substance Name

Myristicin

Substance Dose

100 µM

Measurement Parameter

Rate

Unit

nmol/min/nmol target

Qualitative value

Quantitative value

0.001

Metabolite RN

2261529

38/81

2017-11-15 01:27:11

50 of 113

Metabolite name

Concomitants: Compound RN

19279336

Concomitants: Compound name

NADPH regenerating System; L-alpha-Dilauroyl phosphatidylcholine

Concomitants: Compound role

COM; COM

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

166218View in Reaxys

Substance Name

273290

Qualitative Results

no antimicrobial activity at 100 μg/disk against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Saccharomyces cerevisiae, Aspergillus niger and Penicillium chrysogenum

Measurement Parameter

Qualitative

Fujita; Kadoya; Aota; Nakayama; Bioscience, biotechnology, and biochemistry; vol. 59; nb. 3; (1995); p. 526 - 528, View in Reaxys 51 of 113

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal dose of the compound against Aedes aegypti larvae measured after 24 h

Biological Species/NCBI Aedes aegypti ID Substance RN

166218View in Reaxys

Measurement Parameter

LD100

Unit

ppm

Qualitative value

Quantitative value

Marston; Hostettmann; Msonthi; Journal of Natural Products (Lloydia); vol. 58; nb. 1; (1995); p. 128 - 130, View in Reaxys 52 of 113

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Antifungal activity evaluated as minimum quantity required to inhibit growth of Cladosporium cucumerinum spore on tlc plate

Biological Species/NCBI Cladosporium cucumerinum ID Substance RN

166218View in Reaxys

Measurement Parameter

Activity

Unit

µg

Measurement Object

Inhibit growth of Cladosporium cucumerinum spore on tlc plate

Qualitative value

Quantitative value

Marston; Hostettmann; Msonthi; Journal of Natural Products (Lloydia); vol. 58; nb. 1; (1995); p. 128 - 130, View in Reaxys 53 of 113

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro antifungal activity against Microsporum canis C 112 upon incubation at 30 degree C for 72 h with the compound dissolved in DMSO

Biological Species/NCBI Arthroderma otae C 112 ID

39/81

2017-11-15 01:27:11

Substance RN

166218View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Qualitative value

Quantitative value

Measurement pX

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro antifungal activity against Epidermophyton floccosum C 114 upon incubation at 30 degree C for 72 h with the compound dissolved in DMSO

Biological Species/NCBI Epidermophyton floccosum C114 ID Substance RN

166218View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Qualitative value

Quantitative value

Measurement pX

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro antifungal activity against Microsporum gypseum C 115 upon incubation at 30 degree C for 72 h with the compound dissolved in DMSO

Biological Species/NCBI Arthroderma gypseum C 115 ID Substance RN

166218View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Qualitative value

Quantitative value

Measurement pX

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro antifungal activity against Trichophyton mentagrophytes ATCC 9972 upon incubation at 30 degree C for 72 h with the compound dissolved in DMSO

Biological Species/NCBI Trichophyton mentagrophytes ATCC 9972 ID Substance RN

166218View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

40/81

2017-11-15 01:27:11

Qualitative value

Quantitative value

Measurement pX

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro antifungal activity against Trichophyton rubrum C 113 upon incubation at 30 degree C for 72 h with the compound dissolved in DMSO

Biological Species/NCBI Trichophyton rubrum C 113 ID Substance RN

166218View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Qualitative value

Quantitative value

Measurement pX

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of mammary alveolar lesions (MAL) development in mouse mammary gland organ culture (MMOC) model upon incubation for 10 days at 37 degree C at a compound concentration of 1E-6 M in presence of growth promoting hormones

Biological Species/NCBI Mus musculus ID Substance RN

166218View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

Concomitants: Compound name

Growth promoting hormones

Concomitants: Compound role

COM

Mehta, Rajendra G; Naithani, Rajesh; Huma, Loredana; Hawthorne, Michael; Moriarty, Robert M; McCormick, David L; Steele, Vernon E; Kopelovich, Levy; Current medicinal chemistry; vol. 15; nb. 27; (2008); p. 2785 - 2825, View in Reaxys 59 of 113

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Oral lowest lethal dose in cat;Oral

Biological Species/NCBI domestic cat ID Substance RN

166218View in Reaxys

Substance Route of Adm.

oral administration

Unit

mg/kg

41/81

2017-11-15 01:27:11

Qualitative value

Quantitative value

400

The American journal of pharmacy; vol. 80; (1909); p. 563, View in Reaxys 60 of 113

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Oral Lowest toxic dose in human

Biological Species/NCBI Human ID Substance RN

166218View in Reaxys

Measurement Parameter

TDLo

Unit

mg/kg

Qualitative value

Quantitative value

5.7

The American journal of pharmacy; vol. 80; (1909); p. 563, View in Reaxys 61 of 113

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal dose in rat; >1.00 mg/kg;Intraperitoneal

Biological Species/NCBI Rattus norvegicus ID Substance RN

166218View in Reaxys

Substance Route of Adm.

intraperitoneal administration

Measurement Parameter

LD50

Unit

mg/kg

Qualitative value

Quantitative value

Hallstrom; Thuvander; Natural Toxins; vol. 5; nb. 5; (1997); p. 186 - 192, View in Reaxys 62 of 113

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Oral lethal dose in rat

Biological Species/NCBI Rattus norvegicus ID Substance RN

166218View in Reaxys

Substance Route of Adm.

oral administration

Measurement Parameter

LD50

Unit

mg/kg

Qualitative value

Quantitative value

4260

Marcus; Lichtenstein; Journal of agricultural and food chemistry; vol. 30; nb. 3; (1982); p. 563 - 568, View in Reaxys 63 of 113

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of benzo[a]pyrene-induced tumorigenesis in forestomach of female A/J mice

Biological Species/NCBI Mus musculus ID

42/81

2017-11-15 01:27:11

Substance RN

166218View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

Benzo[a]pyrene-induced tumorigenesis in forestomach

Qualitative value

Quantitative value

Zheng -q.; Kenney; Zhang; Lam; Carcinogenesis; vol. 13; nb. 10; (1992); p. 1921 - 1923, View in Reaxys 64 of 113

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Subcutaneous lowest lethal dose in rabbit

Biological Species/NCBI rabbit ID Substance RN

166218View in Reaxys

Substance Route of Adm.

subcutaneous administration

Unit

mg/kg

Measurement Object

Lowest lethal dose

Qualitative value

Quantitative value

900

Marcus; Lichtenstein; Journal of agricultural and food chemistry; vol. 30; nb. 3; (1982); p. 563 - 568, View in Reaxys 65 of 113

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of benzo[a]pyrene-induced tumorigenesis in lung of female A/J mice

Biological Species/NCBI Mus musculus ID Substance RN

166218View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

Benzo[a]pyrene-induced tumorigenesis in lung

Qualitative value

Quantitative value

Zheng -q.; Kenney; Zhang; Lam; Carcinogenesis; vol. 13; nb. 10; (1992); p. 1921 - 1923, View in Reaxys 66 of 113

Target Name

alpha-glucosidase

Target Synonyms

agda; agl; agl1 (alpha-glucosidase); agla (alpha-glucosidase); alpha-glucosidase; ao090003001209; c23_036; mal1 (alpha-glucosidase); mal2 (alpha-glucosidase); mala (alpha-glucosidase); maltase (alpha-glucosidase); palh (alpha-glucosidase); spapb24d3.10c; spbc1683.07; sso3051; ssol_0793; tm_1834

Target, Subunit, Species alpha-glucosidase Target Mutant/Chimera Details

alpha-glucosidase:Wild

Substance Action on Target

Inhibitor

Substance Effect

Antidiabetic

Bioassay Category

In Vitro (Efficacy)

43/81

2017-11-15 01:27:11

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

100 μM

Measurement Parameter

% Inhibition

Unit

Quantitative value

30.7

Measurement pX

3.65

Dang, Phu Hoang; Nguyen, Hai Xuan; Nguyen, Nhan Trung; Le, Hanh Ngoc Thi; Nguyen, Mai Thanh Thi; Phytotherapy Research; vol. 28; nb. 11; (2014); p. 1632 - 1636, View in Reaxys 67 of 113

Target Name

alpha-glucosidase

Target Synonyms

Target, Subunit, Species alpha-glucosidase Target Mutant/Chimera Details

alpha-glucosidase:Wild

Substance Action on Target

Inhibitor

Substance Effect

Antidiabetic

Bioassay Category

In Vitro (Efficacy)

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Unit

Quantitative value

20.4

Measurement pX

Dang, Phu Hoang; Nguyen, Hai Xuan; Nguyen, Nhan Trung; Le, Hanh Ngoc Thi; Nguyen, Mai Thanh Thi; Phytotherapy Research; vol. 28; nb. 11; (2014); p. 1632 - 1636, View in Reaxys 68 of 113

Target Name

alpha-glucosidase

Target Synonyms

Target, Subunit, Species alpha-glucosidase Target Mutant/Chimera Details

alpha-glucosidase:Wild

Substance Action on Target

Inhibitor

Substance Effect

Antidiabetic

Bioassay Category

In Vitro (Efficacy)

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

25 μM

44/81

2017-11-15 01:27:11

Measurement Parameter

% Inhibition

Unit

Quantitative value

14.3

Measurement pX

Dang, Phu Hoang; Nguyen, Hai Xuan; Nguyen, Nhan Trung; Le, Hanh Ngoc Thi; Nguyen, Mai Thanh Thi; Phytotherapy Research; vol. 28; nb. 11; (2014); p. 1632 - 1636, View in Reaxys 69 of 113

Target Name

alpha-glucosidase

Target Synonyms

Target, Subunit, Species alpha-glucosidase Target Mutant/Chimera Details

alpha-glucosidase:Wild

Substance Action on Target

Inhibitor

Substance Effect

Antidiabetic

Bioassay Category

In Vitro (Efficacy)

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

250 μM

Measurement Parameter

% Inhibition

Unit

Quantitative value

53.7

Measurement pX

3.67

Dang, Phu Hoang; Nguyen, Hai Xuan; Nguyen, Nhan Trung; Le, Hanh Ngoc Thi; Nguyen, Mai Thanh Thi; Phytotherapy Research; vol. 28; nb. 11; (2014); p. 1632 - 1636, View in Reaxys 70 of 113

Target Name

alpha-glucosidase

Target Synonyms

Target, Subunit, Species alpha-glucosidase Target Mutant/Chimera Details

alpha-glucosidase:Wild

Substance Action on Target

Inhibitor

Substance Effect

Antidiabetic

Bioassay Category

In Vitro (Efficacy)

Substance RN

166218View in Reaxys

Substance Name

myristicin

Measurement Parameter

IC50

Unit

μM

Quantitative value

224.4

Measurement pX

3.65

45/81

2017-11-15 01:27:11

Dang, Phu Hoang; Nguyen, Hai Xuan; Nguyen, Nhan Trung; Le, Hanh Ngoc Thi; Nguyen, Mai Thanh Thi; Phytotherapy Research; vol. 28; nb. 11; (2014); p. 1632 - 1636, View in Reaxys 71 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

100 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

35.89

Measurement pX

3.03

Concomitants: Compound RN

8188194

Concomitants: Compound name

LPS

Concomitants: Compound role

IND

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 72 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

100 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

75.54

Measurement pX

3.77

Concomitants: Compound RN

8188194

Concomitants: Compound name

LPS

Concomitants: Compound role

IND

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 73 of 113

Substance Effect

Antiallergic

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

rbl-2h3

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

1 μg/ml

46/81

2017-11-15 01:27:11

Measurement Parameter

% Inhibition

Unit

Quantitative value

-45.83

Measurement pX

Concomitants: Compound RN

31083518; 25358208

Concomitants: Compound name

DNP-BAS; PNAG

Concomitants: Compound role

IND; SUB

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 74 of 113

Substance Effect

Antiallergic

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

rbl-2h3

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

10 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

0.34

Measurement pX

Concomitants: Compound RN

31083518; 25358208

Concomitants: Compound name

DNP-BAS; PNAG

Concomitants: Compound role

IND; SUB

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 75 of 113

Substance Effect

Antiallergic

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

rbl-2h3

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

50 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

31.82

Measurement pX

3.25

Concomitants: Compound RN

31083518; 25358208

Concomitants: Compound name

DNP-BAS; PNAG

47/81

2017-11-15 01:27:11

Concomitants: Compound role

IND; SUB

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 76 of 113

Substance Effect

Antiallergic

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

rbl-2h3

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

100 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

75.29

Measurement pX

3.77

Concomitants: Compound RN

31083518; 25358208

Concomitants: Compound name

DNP-BAS; PNAG

Concomitants: Compound role

IND; SUB

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 77 of 113

Substance Effect

Antiallergic

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

rbl-2h3

Substance RN

166218View in Reaxys

Substance Name

myristicin

Measurement Parameter

IC50

Unit

μM

Quantitative value

420.37

Measurement pX

3.38

Concomitants: Compound RN

31083518; 25358208

Concomitants: Compound name

DNP-BAS; PNAG

Concomitants: Compound role

IND; SUB

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 78 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

myristicin

Measurement Parameter

IC50

48/81

2017-11-15 01:27:11

Unit

μM

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

8188194

Concomitants: Compound name

LPS

Concomitants: Compound role

IND

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 79 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

1 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

-22.08

Measurement pX

Concomitants: Compound RN

8188194

Concomitants: Compound name

LPS

Concomitants: Compound role

IND

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 80 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

10 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

-6.2

Measurement pX

Concomitants: Compound RN

8188194

Concomitants: Compound name

LPS

Concomitants: Compound role

IND

49/81

2017-11-15 01:27:11

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 81 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

50 μg/ml

Measurement Parameter

% Inhibition

Unit

Quantitative value

52.31

Measurement pX

3.63

Concomitants: Compound RN

8188194

Concomitants: Compound name

LPS

Concomitants: Compound role

IND

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 82 of 113

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

RAW 264.7

Substance RN

166218View in Reaxys

Substance Name

myristicin

Measurement Parameter

IC50

Unit

μM

Quantitative value

248.74

Measurement pX

3.6

Concomitants: Compound RN

8188194

Concomitants: Compound name

LPS

Concomitants: Compound role

IND

Makchuchit, Sunita; Rattarom, Ruchilak; Itharat, Arunporn; Biomedicine and Pharmacotherapy; vol. 89; (2017); p. 1018 - 1026, View in Reaxys 83 of 113

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

50/81

2017-11-15 01:27:11

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

27.5

Metabolite RN

204217

Al-Malahmeh, Amer J.; Al-Ajlouni, Abdelmajeed; Wesseling, Sebastiaan; Soffers, Ans E. M. F.; Al-Subeihi, Ala’.; Kiwamoto, Reiko; Vervoort, Jacques; Rietjens, Ivonne M. C. M.; Archives of Toxicology; vol. 91; nb. 2; (2017); p. 713 - 734, View in Reaxys 84 of 113

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

5.663

Metabolite RN

4447987

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

8.431

Metabolite RN

19377590

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

51/81

2017-11-15 01:27:11

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

39.394

Metabolite RN

2261529

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

Quantitative value

Measurement pX

4.8

Metabolite RN

204217

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

Quantitative value

Measurement pX

4.48

Metabolite RN

204217

52/81

2017-11-15 01:27:11

89 of 113

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

0.08

Metabolite RN

204217

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

Quantitative value

1629

Measurement pX

2.79

Metabolite RN

4447987

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

0.29

Metabolite RN

4447987

53/81

2017-11-15 01:27:11

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

Quantitative value

234

Measurement pX

3.63

Metabolite RN

19377590

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

0.17

Metabolite RN

19377590

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

54/81

2017-11-15 01:27:11

Quantitative value

118

Measurement pX

3.93

Metabolite RN

2261529

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

0.93

Metabolite RN

2261529

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

0.44

Metabolite RN

204217

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

55/81

2017-11-15 01:27:11

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

2.424

Metabolite RN

204217

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

Quantitative value

Measurement pX

4.08

Metabolite RN

4447987

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

0.178

Metabolite RN

4447987

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

56/81

2017-11-15 01:27:11

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

0.726

Metabolite RN

19377590

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Clint

Unit

μl/min

Measurement Object

Catalytic efficiency

Quantitative value

7.881

Metabolite RN

2261529

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

0.47

Metabolite RN

4447987

Bioassay Category

Metabolism/Transport

57/81

2017-11-15 01:27:11

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

Quantitative value

102

Measurement pX

3.99

Metabolite RN

19377590

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

0.86

Metabolite RN

19377590

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Unit

μM

Quantitative value

Measurement pX

4.48

Metabolite RN

2261529

58/81

2017-11-15 01:27:11

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

liver

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

25 - 1000 μM

Measurement Parameter

Vmax

Unit

nmol/min

Quantitative value

1.3

Metabolite RN

2261529

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Cells/Cell Lines

lung alveolus cell

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

1000 μM

Measurement Parameter

Qualitative

Measurement Object

metabolism

Qualitative value

Not active

Measurement pX

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Cells/Cell Lines

kidney cell

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

1000 μM

Measurement Parameter

Qualitative

Measurement Object

metabolism

Qualitative value

Not active

59/81

2017-11-15 01:27:11

Measurement pX

Bioassay Category

Metabolism/Transport

Biological Species/NCBI Sprague Dawley rat ID Organs/Tissues

small intestine

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

1000 μM

Measurement Parameter

Qualitative

Measurement Object

metabolism

Qualitative value

Not active

Measurement pX

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cells/Cell Lines

kidney cell

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

1000 μM

Measurement Parameter

Qualitative

Measurement Object

metabolism

Qualitative value

Not active

Measurement pX

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

liver

Cells/Cell Lines

lung alveolus cell

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

1000 μM

60/81

2017-11-15 01:27:11

Measurement Parameter

Qualitative

Measurement Object

metabolism

Qualitative value

Not active

Measurement pX

Bioassay Category

Metabolism/Transport

Biological Species/NCBI human ID Organs/Tissues

small intestine

Cell Fraction

Microsome (pooled)

Substance RN

166218View in Reaxys

Substance Name

1-allyl-5-methoxy-3,4-methylenedioxybenzene

Substance Dose

1000 μM

Measurement Parameter

Qualitative

Measurement Object

metabolism

Qualitative value

Not active

Measurement pX

Target Name

Sialidase A [Streptococcus pneumoniae]

Target Synonyms

nana; neuraminidase a; sialidase a

Target Uniprot ID

p62575

Target PDB ID

2vvz; 2ya4; 2ya5; 2ya6; 2ya7; 2ya8; 4c1x; 4zxk

Target, Subunit, Species Sialidase A [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase A [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

166218View in Reaxys

Substance Name

myristicin

Substance Dose

<= 200 μM

Measurement Parameter

IC50

Unit

μM

Quantitative value

196.9

Measurement pX

3.71

Concomitants: Compound RN

25467977

61/81

2017-11-15 01:27:11

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Reaxys ID 174425 View in Reaxys

2/9 CAS Registry Number: 18607-93-7 Chemical Name: 1-allyl-2-methoxy-4,5-methylenedioxybenzene; asaricin; sarisan; 5-allyl-6-methoxy-benzo[1,3]dioxole; 5Allyl-6-methoxy-benzo[1,3]dioxol Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: FYRHTIWFKXZWAD-UHFFFAOYSA-N Note:

O O

Substance Label (9) Label References 1

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys; Seo, Chang-Seob; Lee, Yeun-Kyung; Kim, Young-Jin; Jung, Jun-Sub; Jahng, Yurngdong; Chang, Hyun-Wook; Song, Dong-Keun; Son, Jong-Keun; Biological and Pharmaceutical Bulletin; vol. 31; nb. 3; (2008); p. 523 - 526, View in Reaxys; Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys

Guo, Yong; Qu, Lailiang; Wang, Xiaoguang; Huang, Mengxing; Jia, Lu; Zhang, Yanbing; RSC Advances; vol. 6; nb. 96; (2016); p. 93505 - 93510, View in Reaxys

G24

Li, Chen; Xu, Feng; Xie, De-Mei; Jing, Yu; Shang, Ming-Ying; Liu, Guang-Xue; Wang, Xuan; Cai, ShaoQing; Molecules; vol. 19; nb. 4; (2014); p. 4857 - 4879, View in Reaxys

Patent; HER MAJESTY THE QUEEN IN RIGHT OF CANADA AS REPRESENTED BY THE MINISTER OF HEALTH; UNIVERSITY OF OTTAWA; Arnason, John Thor; Durst, Tony; Foster, Brian; US2013/12477; (2013); (A1) English, View in Reaxys

Damsud, Thanakorn; Adisakwattana, Sirichai; Phuwapraisirisan, Preecha; Phytochemistry Letters; vol. 6; nb. 3; (2013); p. 350 - 354, View in Reaxys

Tuntiwachwuttikul, Pittaya; Phansa, Photchana; Pootaeng-on, Yupa; Taylor, Walter Charles; Chemical and Pharmaceutical Bulletin; vol. 54; nb. 2; (2006); p. 149 - 151, View in Reaxys

Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; Organic and Biomolecular Chemistry; vol. 3; nb. 15; (2005); p. 2868 - 2871, View in Reaxys

Spitaler, Renate; Ellmerer-Mueller, Ernst-Peter; Zidorn, Christian; Stuppner, Hermann; Scientia Pharmaceutica; vol. 70; nb. 1; (2002); p. 101 - 109, View in Reaxys

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys

Patent-Specific Data (1) References Patent; HER MAJESTY THE QUEEN IN RIGHT OF CANADA AS REPRESENTED BY THE MINISTER OF HEALTH; UNIVERSITY OF OTTAWA; Arnason, John Thor; Durst, Tony; Foster, Brian; US2013/12477; (2013); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.508

H Bond Donors

H Bond Acceptors

Rotatable Bonds

62/81

2017-11-15 01:27:11

TPSA

27.69

Lipinski Number

Veber Number

Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

86 - 87

0.5

Devakumar, C.; Mukerjee, S. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 368 - 372, View in Reaxys

119 - 124

2.5

Alexander et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1504,1507, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5412

Alexander et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 1504,1507, View in Reaxys

589

Chromatographic Data (2) Chromatographic References data TLC (Thin layer chromatography)

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys; Xiang, Cai-Peng; Han, Jia-Xin; Li, Xing-Cong; Li, Yun-Hui; Zhang, Yi; Chen, Lin; Qu, Yan; Hao, Chao-Yun; Li, Hai-Zhou; Yang, Chong-Ren; Zhao, San-Jun; Xu, Min; Journal of Agricultural and Food Chemistry; vol. 65; nb. 18; (2017); p. 3702 - 3710, View in Reaxys

GC (Gas chroma- Li, Chen; Xu, Feng; Xie, De-Mei; Jing, Yu; Shang, Ming-Ying; Liu, Guang-Xue; Wang, Xuan; Cai, Shaotography) Qing; Molecules; vol. 19; nb. 4; (2014); p. 4857 - 4879, View in Reaxys; Linde, Johan; Combrinck, Sandra; Van Vuuren, Sandy; Van Rooy, Jacques; Ludwiczuk, Agnieszka; Mokgalaka, Ntebogeng; Phytochemistry Letters; vol. 16; (2016); p. 61 - 69, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys

Partition octan-1-ol/water (MCS) (1) 1 of 1

log POW

2.74

Location

Page/Page column 17

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

800

Xiang, Cai-Peng; Han, Jia-Xin; Li, Xing-Cong; Li, Yun-Hui; Zhang, Yi; Chen, Lin; Qu, Yan; Hao, Chao-Yun; Li, Hai-Zhou; Yang, Chong-Ren; Zhao, San-Jun; Xu, Min; Journal of Agricultural and Food Chemistry; vol. 65; nb. 18; (2017); p. 3702 - 3710, View in Reaxys 2 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

63/81

2017-11-15 01:27:11

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys 4 of 13

Description (NMR Spec- COSY (Correlation Spectroscopy) troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys 5 of 13

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence) troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys 6 of 13

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence) troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys 7 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys 8 of 13

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

300

Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; Organic and Biomolecular Chemistry; vol. 3; nb. 15; (2005); p. 2868 - 2871, View in Reaxys

64/81

2017-11-15 01:27:11

9 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Masuda, Toshiya; Inazumi, Aya; Yamada, Yasumasa; Padolina, William G.; Kikuzaki, Hiroe; Nakatani, Nobuji; Phytochemistry (Elsevier); vol. 30; nb. 10; (1991); p. 3227 - 3228, View in Reaxys; Schuda, Paul Francis; Price, William A.; Journal of Organic Chemistry; vol. 52; nb. 10; (1987); p. 1972 - 1979, View in Reaxys; Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys 10 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Masuda, Toshiya; Inazumi, Aya; Yamada, Yasumasa; Padolina, William G.; Kikuzaki, Hiroe; Nakatani, Nobuji; Phytochemistry (Elsevier); vol. 30; nb. 10; (1991); p. 3227 - 3228, View in Reaxys; Schuda, Paul Francis; Price, William A.; Journal of Organic Chemistry; vol. 52; nb. 10; (1987); p. 1972 - 1979, View in Reaxys; Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys 12 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- NMR troscopy) Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys

IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3010 - 1040 cm**(-1)

Schuda, Paul Francis; Price, William A.; Journal of Organic Chemistry; vol. 52; nb. 10; (1987); p. 1972 - 1979, View in Reaxys 3 of 4

Description (IR Spectroscopy)

Bands

65/81

2017-11-15 01:27:11

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1635 - 932 cm**(-1)

Description (IR Spectroscopy)

Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys Mass Spectrometry (4) Description (Mass References Spectrometry) electrospray ioni- Xiang, Cai-Peng; Han, Jia-Xin; Li, Xing-Cong; Li, Yun-Hui; Zhang, Yi; Chen, Lin; Qu, Yan; Hao, Chaosation (ESI); time- Yun; Li, Hai-Zhou; Yang, Chong-Ren; Zhao, San-Jun; Xu, Min; Journal of Agricultural and Food Chemisof-flight mass try; vol. 65; nb. 18; (2017); p. 3702 - 3710, View in Reaxys spectra (TOFMS); spectrum liquid chromatog- Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; raphy mass spec- Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys trometry (LCMS); IT (ion trap); timeof-flight mass spectra (TOFMS); spectrum electron impact (EI); spectrum

Isolation from Natural Product (12) Isolation from References Natural Product essential oil from Xiang, Cai-Peng; Han, Jia-Xin; Li, Xing-Cong; Li, Yun-Hui; Zhang, Yi; Chen, Lin; Qu, Yan; Hao, Chaoleaves and stems Yun; Li, Hai-Zhou; Yang, Chong-Ren; Zhao, San-Jun; Xu, Min; Journal of Agricultural and Food Chemisof Piper hispiditry; vol. 65; nb. 18; (2017); p. 3702 - 3710, View in Reaxys mervium C. DC.; collected in Guangzhou province, People’s Republic of China roots of Piper sar- Hematpoor, Arshia; Liew, Sook Yee; Chong, Wei Lim; Azirun, Mohd Sofian; Lee, Vannajan Sanghiran; mentosum (Piper- Awang, Khalijah; PLoS ONE; vol. 11; nb. 5; (2016); Art.No: E0155265, View in Reaxys aceae); collected in the vicinity of University of Malaya leaves of Piper sarmentosum Roxb.(Piperales: Piperaceae); collected in Samutprakan, in February 2011

Damsud, Thanakorn; Adisakwattana, Sirichai; Phuwapraisirisan, Preecha; Phytochemistry Letters; vol. 6; nb. 3; (2013); p. 350 - 354, View in Reaxys

dried roots of Seo, Chang-Seob; Lee, Yeun-Kyung; Kim, Young-Jin; Jung, Jun-Sub; Jahng, Yurngdong; Chang, HySaururus chinen- un-Wook; Song, Dong-Keun; Son, Jong-Keun; Biological and Pharmaceutical Bulletin; vol. 31; nb. 3; sis (Saururaceae) (2008); p. 523 - 526, View in Reaxys fresh roots of Pip- Tuntiwachwuttikul, Pittaya; Phansa, Photchana; Pootaeng-on, Yupa; Taylor, Walter Charles; Chemical er sarmentosum and Pharmaceutical Bulletin; vol. 54; nb. 2; (2006); p. 149 - 151, View in Reaxys Roxb., known as "cha-plu" in Thailand

66/81

2017-11-15 01:27:11

roots of LigustiSpitaler, Renate; Ellmerer-Mueller, Ernst-Peter; Zidorn, Christian; Stuppner, Hermann; Scientia Pharcum mutellina (L.) maceutica; vol. 70; nb. 1; (2002); p. 101 - 109, View in Reaxys CRANTZ leaves of Piper aduncum

Piper aduncum

Piper sarmentosum

Masuda, Toshiya; Inazumi, Aya; Yamada, Yasumasa; Padolina, William G.; Kikuzaki, Hiroe; Nakatani, Nobuji; Phytochemistry (Elsevier); vol. 30; nb. 10; (1991); p. 3227 - 3228, View in Reaxys

leaves of I. anisa- Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, tum L., collected Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys on Mie Prefecture (Japan), and from timber of I. anisatum L., collected on Nanjenshan, Pingtung (Taiwan) aus Beilschmiedia Kumamoto; Scora; Journal of Agricultural and Food Chemistry; vol. 18; (1970); p. 544, View in Reaxys miersii aus den Wurzeln von Asiasarum heterotropoides var. Seoulensis

Saiki et al.; Yakugaku Zasshi; vol. 87; (1967); p. 1524,1528; Chem.Abstr.; vol. 68; nb. 81440; (1968), View in Reaxys

Medchem (10) 1 of 10

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Target : Mycobacterium tuberculosis H37RaBioassay : isoniazide and kanamycin sulphate used as reference comp. (MIC: 0.04-0.09 and 2.0-5.0 μg/ml, respectively) Microplate Alamar Blue Assay

Substance RN

174425View in Reaxys

Substance Name

1422184

Measurement Parameter

MIC

Unit

mg/L

Quantitative value

200

Measurement pX

2.98

Tuntiwachwuttikul, Pittaya; Phansa, Photchana; Pootaeng-on, Yupa; Taylor, Walter Charles; Chemical and Pharmaceutical Bulletin; vol. 54; nb. 2; (2006); p. 149 - 151, View in Reaxys 2 of 10

Substance Effect

Antiparasitic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : P;asmodium falciparum K1Bioassay : chloroquine diphosphate used as reference comp. (IC50: 0.16 μg/ml, 0.31 μmol/l) microculture radioisotope technique; multidrug resistant strain

Substance RN

174425View in Reaxys

Substance Name

1422184

Measurement Parameter

EC50

Unit

mg/L

67/81

2017-11-15 01:27:11

Quantitative value

Measurement pX

3.98

Tuntiwachwuttikul, Pittaya; Phansa, Photchana; Pootaeng-on, Yupa; Taylor, Walter Charles; Chemical and Pharmaceutical Bulletin; vol. 54; nb. 2; (2006); p. 149 - 151, View in Reaxys 3 of 10

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : amphotericin B used as reference comp. (IC50: 0.01 μg/ml) 2E6 CFU/ml of clinical isolate; RPMI 1640 medium; 37 deg C; incubated for 4 h; number of living cells determined using 2,3-bis(2-methoxy-4-nitro-5-sulfonylphenyl)-5-<(phenylamino)carbonyl>-2H-tetrazolium hydroxide/N-methylphenazolium methosulfate assay

Biological Species/NCBI Candida albicans ID Substance RN

174425View in Reaxys

Substance Name

1422184

Measurement Parameter

IC50

Unit

mg/L

Quantitative value

Measurement pX

3.59

Tuntiwachwuttikul, Pittaya; Phansa, Photchana; Pootaeng-on, Yupa; Taylor, Walter Charles; Chemical and Pharmaceutical Bulletin; vol. 54; nb. 2; (2006); p. 149 - 151, View in Reaxys 4 of 10

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Substance RN

174425View in Reaxys

Substance Name

1422184

Substance Dose

50 µM

Qualitative Results

title comp. showed ca. 10% inhibition of histamine release (vs. 28.6% inhibition by reference comp.); figure

Measurement Parameter

Qualitative

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys 5 of 10

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

174425View in Reaxys

Substance Name

1422184

Qualitative Results

activities against Escherichia coli and Bacillus subtilis: MIC not under 100 ppm at 37 deg

Measurement Parameter

Qualitative

Masuda, Toshiya; Inazumi, Aya; Yamada, Yasumasa; Padolina, William G.; Kikuzaki, Hiroe; Nakatani, Nobuji; Phytochemistry (Elsevier); vol. 30; nb. 10; (1991); p. 3227 - 3228, View in Reaxys 6 of 10

Bioassay Category

Toxicity/Safety Pharmacology

68/81

2017-11-15 01:27:11

Bioassay Details

Effect of the compound (10 mg/kg, i.p.) on LPS/D-GalN-induced lethality in mice at day 1; n=5, Control = 2 out of 5

Biological Species/NCBI Mus musculus ID Substance RN

174425View in Reaxys

Substance Route of Adm.

intraperitoneal administration

Qualitative Results

Number of live mice/number of total mice = 3/5

Measurement Parameter

Qualitative

Measurement Object

Survival rate

Concomitants: Compound name

LPS/D-GalN

Concomitants: Compound role

COM

Seo, Chang-Seob; Lee, Yeun-Kyung; Kim, Young-Jin; Jung, Jun-Sub; Jahng, Yurngdong; Chang, HyunWook; Song, Dong-Keun; Son, Jong-Keun; Biological and Pharmaceutical Bulletin; vol. 31; nb. 3; (2008); p. 523 526, View in Reaxys 7 of 10

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Effect of the compound (10 mg/kg, i.p.) on LPS/D-GalN-induced lethality in mice at day 2; n=5, Control = 2 out of 5

Biological Species/NCBI Mus musculus ID Substance RN

174425View in Reaxys

Substance Route of Adm.

intraperitoneal administration

Qualitative Results

Number of live mice/number of total mice = 3/5

Measurement Parameter

Qualitative

Measurement Object

Survival rate

Concomitants: Compound name

LPS/D-GalN

Concomitants: Compound role

COM

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Effect of the compound (10 mg/kg, i.p.) on LPS/D-GalN-induced lethality in mice at day 3; n=5, Control = 2 out of 5

Biological Species/NCBI Mus musculus ID Substance RN

174425View in Reaxys

Substance Route of Adm.

intraperitoneal administration

Qualitative Results

Number of live mice/number of total mice = 3/5

Measurement Parameter

Qualitative

Measurement Object

Survival rate

Concomitants: Compound name

LPS/D-GalN

69/81

2017-11-15 01:27:11

Concomitants: Compound role

COM

Target Name

Cytochrome P450 3A4 [human]

Target Synonyms

Target Uniprot ID

p08684

Target PDB ID

1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

Target, Subunit, Species Cytochrome P450 3A4 [human] Target Mutant/Chimera Details

Cytochrome P450 3A4 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration of the compound against human liver microsomes cytochrome P450 3A4 metabolism of 1 uM/well Dibenzylfluorescein substrate upon incubation in 0.5 M PBS, pH 7.4 by microtiter plate-based fluorimetric assay

Biological Species/NCBI Human ID Substance RN

174425View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

METABOLIC ACTIVATION

Qualitative value

Quantitative value

Measurement pX

Concomitants: Compound name

DIBENZYLFLUORESCEIN

Concomitants: Compound role

SUB

Target Name

Cytochrome P450 3A4 [human]

Target Synonyms

Target Uniprot ID

p08684

Target PDB ID

1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

Target, Subunit, Species Cytochrome P450 3A4 [human] Target Mutant/Chimera Details

Cytochrome P450 3A4 [human]:Wild

70/81

2017-11-15 01:27:11

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Biological Species/NCBI Human ID Substance RN

174425View in Reaxys

Measurement Parameter

IC50

Unit

µg/mL

Measurement Object

METABOLIC ACTIVATION

Qualitative value

Quantitative value

Measurement pX

Concomitants: Compound name

DIBENZYLFLUORESCEIN

Concomitants: Compound role

SUB

Reaxys ID 165434 View in Reaxys

3/9 CAS Registry Number: 484-34-4 Chemical Name: croweacin; 5-allyl-4-methoxy-benzo[1,3]dioxole; 5-Allyl-4-methoxy-benzo[1,3]dioxol Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: VGXJTTXSNPYTSK-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References 92

Dinan; Bourne; Meng; Sarker; Tolentino; Whiting; Cellular and Molecular Life Sciences; vol. 58; nb. 2; (2001); p. 321 - 342, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.508

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Related Structure (1) Related Structure References Konstitution.

Baker et al.; Journal of the Chemical Society; (1939); p. 439,441, View in Reaxys

71/81

2017-11-15 01:27:11

Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

129 - 131

Penfold et al.; Journal of the Chemical Society; (1938); p. 756, View in Reaxys; Baker et al.; Journal of the Chemical Society; (1939); p. 439,441, View in Reaxys

256 - 258

766

Penfold; Morrison; Journal and Proceedings of the Royal Society of New South Wales; vol. 56; (1922); p. 227,229, View in Reaxys

Refractive Index (2) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5346

589

19.5

Baker et al.; Journal of the Chemical Society; (1939); p. 439,441, View in Reaxys

1.5339

589

Penfold et al.; Journal of the Chemical Society; (1938); p. 756, View in Reaxys

Density (2) 1 of 2

Density [g·cm-3]

1.1346

Reference Temperature [°C]

Measurement Temperature [°C]

Baker et al.; Journal of the Chemical Society; (1939); p. 439,441, View in Reaxys 2 of 2

Density [g·cm-3]

1.1324

Reference Temperature [°C]

Measurement Temperature [°C]

Penfold et al.; Journal of the Chemical Society; (1938); p. 756, View in Reaxys Ecotoxicology (3) 1 of 3

Effect (Ecotoxicology)

cytotoxicity

Species or Test-System (Ecotoxicology)

Drosophila melanogaster BII cells

Concentration (Ecotoxicology)

1E-08 - 0.001 mol/l

Method (Ecotoxicology)

in vitro

Comment (Ecotoxicology)

No effect

Dinan; Bourne; Meng; Sarker; Tolentino; Whiting; Cellular and Molecular Life Sciences; vol. 58; nb. 2; (2001); p. 321 - 342, View in Reaxys 2 of 3

Effect (Ecotoxicology)

antagonist

Species or Test-System (Ecotoxicology)

Drosophila melanogaster BII cells

Concentration (Ecotoxicology)

1E-08 - 0.001 mol/l

Method (Ecotoxicology)

in vitro; ecdysteroid antagonist activity evaluated; 1E-8 mol/l 20-hydroxyecdysone used as agonist

Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

7.3E-4 mol/l

Dinan; Bourne; Meng; Sarker; Tolentino; Whiting; Cellular and Molecular Life Sciences; vol. 58; nb. 2; (2001); p. 321 - 342, View in Reaxys 3 of 3

Effect (Ecotoxicology)

agonist

72/81

2017-11-15 01:27:11

Species or Test-System (Ecotoxicology)

Drosophila melanogaster BII cells

Concentration (Ecotoxicology)

1E-08 - 0.001 mol/l

Method (Ecotoxicology)

in vitro; ecdysteroid agonist activity evaluated

Comment (Ecotoxicology)

No effect

Dinan; Bourne; Meng; Sarker; Tolentino; Whiting; Cellular and Molecular Life Sciences; vol. 58; nb. 2; (2001); p. 321 - 342, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Isolierung aus Eriostemon crowei (Crowea saligna):

Penfold; Morrison; Journal and Proceedings of the Royal Society of New South Wales; vol. 56; (1922); p. 227,229, View in Reaxys

Medchem (3) 1 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : |agonist Target : Drosophila melanogaster BII cellsBioassay : in vitro; ecdysteroid agonist activity evaluated

Substance RN

165434View in Reaxys

Substance Name

Substance Dose

1.00000E-08 M

Measurement Parameter

Qualitative

Qualitative value

Measurement pX

Dinan; Bourne; Meng; Sarker; Tolentino; Whiting; Cellular and Molecular Life Sciences; vol. 58; nb. 2; (2001); p. 321 - 342, View in Reaxys 2 of 3

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : |antagonist Target : Drosophila melanogaster BII cellsBioassay : in vitro; ecdysteroid antagonist activity evaluated; 1E-8 mol/l 20-hydroxyecdysone used as agonist

Substance RN

165434View in Reaxys

Substance Name

Substance Dose

1.00000E-08 M

Measurement Parameter

EC50

Unit

Quantitative value

0.00073

Measurement pX

3.14

Dinan; Bourne; Meng; Sarker; Tolentino; Whiting; Cellular and Molecular Life Sciences; vol. 58; nb. 2; (2001); p. 321 - 342, View in Reaxys 3 of 3

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : Drosophila melanogaster BII cellsBioassay : in vitro

Substance RN

165434View in Reaxys

73/81

2017-11-15 01:27:11

Substance Name

Substance Dose

1.00000E-08 M

Measurement Parameter

Qualitative

Qualitative value

Measurement pX

Dinan; Bourne; Meng; Sarker; Tolentino; Whiting; Cellular and Molecular Life Sciences; vol. 58; nb. 2; (2001); p. 321 - 342, View in Reaxys

Reaxys ID 6861409 View in Reaxys

4/9 Chemical Name: 1-allyl-2,3-(methylenedioxy)-5-methoxybenzene Linear Structure Formula: C11H12O3 Molecular Formula: C11H12O3 Molecular Weight: 192.214 Type of Substance: heterocyclic InChI Key: HFGSPIVAGONERP-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 1

Nair, Muraleedharan G.; Sommerville, John; Burke, Basil A.; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 654 - 655, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.508

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Nair, Muraleedharan G.; Sommerville, John; Burke, Basil A.; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 654 - 655, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Nair, Muraleedharan G.; Sommerville, John; Burke, Basil A.; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 654 - 655, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy)

74/81

2017-11-15 01:27:11

Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Nair, Muraleedharan G.; Sommerville, John; Burke, Basil A.; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 654 - 655, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Nair, Muraleedharan G.; Sommerville, John; Burke, Basil A.; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 654 - 655, View in Reaxys

Isolation from Natural Product (2) Isolation from References Natural Product fruits of Illicium Lin, Ya-Xu; Fazary, Ahmed Eid; Chen, Shun-Ying; Chien, Ching-Te; Kuo, Yao-Haur; Sheu, Shiow-Yunn; arborescens Hay- Shen, Ya-Ching; Food Chemistry; vol. 123; nb. 4; (2010); p. 1105 - 1111, View in Reaxys ata; collected in Ping-tong country, Taiwan Piper auritum

Nair, Muraleedharan G.; Sommerville, John; Burke, Basil A.; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 654 - 655, View in Reaxys

Reaxys ID 1245686 View in Reaxys

5/9 Chemical Name: 1-Vinyl-3,4-methylendioxy-5-methoxy-6methyl-benzol Linear Structure Formula: C12H14O3 Molecular Formula: C12H14O3 Molecular Weight: 206.241 Type of Substance: heterocyclic InChI Key: XYGVEPJEKZGKLG-UHFFFAOYSA-N Note:

O O O

Druglikeness (1) 1 of 1

LogP

2.945

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Awe; Wiegrebe; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 296; (1963); p. 370,373, View in Reaxys

Boiling Point (1) Boiling Point [°C] 80 - 82

Pressure (Boiling Point) [Torr]

References

1-2

Awe; Wiegrebe; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 296; (1963); p. 370,373, View in Reaxys

Reaxys ID 19720579 View in Reaxys

6/9

75/81

2017-11-15 01:27:11

CAS Registry Number: 1192659-03-2 Chemical Name: 6-allyl-5-bromo-4-methoxybenzo[1,3]dioxole Linear Structure Formula: C11H11BrO3 Molecular Formula: C11H11BrO3 Molecular Weight: 271.111 InChI Key: UBLMABOUWLSEJS-UHFFFAOYSA-N Note:

O O

Br O

Druglikeness (1) 1 of 1

LogP

3.306

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Takaoka, Shigeki; Takaoka, Noriko; Minoshima, Yuka; Huang, Jian-Mei; Kubo, Miwa; Harada, Kenichi; Hioki, Hideaki; Fukuyama, Yoshiyasu; Tetrahedron; vol. 65; nb. 40; (2009); p. 8354 - 8361, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); EI (Electron impact); Spectrum

EI (Electron impact); Spectrum

Reaxys ID 19720588 View in Reaxys

7/9 CAS Registry Number: 1192659-17-8 Chemical Name: 5-allyl-7-methoxy-4-(3-methylbut-2-enyl)benzo[1,3]dioxole Linear Structure Formula: C16H20O3 Molecular Formula: C16H20O3 Molecular Weight: 260.333 InChI Key: AYHXTLXWOYUNFW-UHFFFAOYSA-N Note:

O O O

Druglikeness (1) 1 of 1

LogP

4.387

76/81

2017-11-15 01:27:11

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

EI (Electron impact); Spectrum

Medchem (1) 1 of 1

Substance Effect

Neurotrophic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : neurite outgrowthSpecies : SD ratBioassay : primary cultured fetal cortical neuronsneurite length = 249 μm in control (0.5 % ethanol)

Biological Species/NCBI Rattus norvegicus ID Substance RN

19720588View in Reaxys

Substance Name

77/81

2017-11-15 01:27:11

Substance Dose

1 µM

Qualitative Results

neurite length 320 μm

Measurement Parameter

Qualitative

Reaxys ID 19720591 View in Reaxys

8/9 CAS Registry Number: 1193499-36-3 Chemical Name: illicinin A; 1,2-methylenedioxy-3-methoxy-4prenyl-5-allylbenzene Linear Structure Formula: C16H20O3 Molecular Formula: C16H20O3 Molecular Weight: 260.333 InChI Key: KDIYCHFLYMQXBV-UHFFFAOYSA-N Note:

O O O

Druglikeness (1) 1 of 1

LogP

4.387

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties colourless

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- benzene-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- benzene-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

100

78/81

2017-11-15 01:27:11

3 of 4

Description (NMR Spec- NOESY (Nuclear Overhauser Enhanced Spectroscopy); Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

Solvents (NMR Spectro- benzene-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Solvents (NMR Spectro- benzene-d6 scopy) Takaoka, Shigeki; Takaoka, Noriko; Minoshima, Yuka; Huang, Jian-Mei; Kubo, Miwa; Harada, Kenichi; Hioki, Hideaki; Fukuyama, Yoshiyasu; Tetrahedron; vol. 65; nb. 40; (2009); p. 8354 - 8361, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

EI (Electron impact); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 287; 225 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

2900; 11400

Takaoka, Shigeki; Takaoka, Noriko; Minoshima, Yuka; Huang, Jian-Mei; Kubo, Miwa; Harada, Kenichi; Hioki, Hideaki; Fukuyama, Yoshiyasu; Tetrahedron; vol. 65; nb. 40; (2009); p. 8354 - 8361, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product flowers of Illicium anisatum; collected in Tokushima, Japan

Medchem (1) 1 of 1

Substance Effect

Neurotrophic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

79/81

2017-11-15 01:27:11

Bioassay Details

Effect : neurite outgrowthSpecies : SD ratBioassay : primary cultured fetal cortical neuronsPDP value was concentration-dependent; neurite length = 249-251 μm in control (0.5 % ethanol)

Biological Species/NCBI Rattus norvegicus ID Substance RN

19720591View in Reaxys

Substance Name

Substance Dose

0.0100000 µM

Qualitative Results

neurite length 255 - 347 μm

Measurement Parameter

Qualitative

Reaxys ID 19720596 View in Reaxys

9/9 CAS Registry Number: 1192659-10-1 Chemical Name: 6-allyl-4-methoxy-5-(3-methylbut-2-enyl)-2,2diphenylbenzo[1,3]dioxole Linear Structure Formula: C28H28O3 Molecular Formula: C28H28O3 Molecular Weight: 412.529 InChI Key: DCJIOLLVBXLIRA-UHFFFAOYSA-N Note:

O O O

Druglikeness (1) 1 of 1

LogP

7.763

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy)

80/81

2017-11-15 01:27:11

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

EI (Electron impact); Spectrum

81/81

2017-11-15 01:27:11