5-Pentyl-1,3-benzenediol (Olivetol) [C11H16O2] by Asch

Query Query

Results

Date

7 substances in Reaxys

2018-02-18 00h:25m:16s (EST)

5 substances in Reaxys

2018-02-18 00h:27m:47s (EST)

1. Query OH

Search as: As drawn 2. Query

(1. Query) AND NOT itemno in (6,7)

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Reaxys ID 908277 View in Reaxys

1/5 CAS Registry Number: 500-66-3 Chemical Name: Olivetol Linear Structure Formula: C6H3OHOHC5H11 Molecular Formula: C11H16O2 Molecular Weight: 180.247 Type of Substance: isocyclic InChI Key: IRMPFYJSHJGOPE-UHFFFAOYSA-N Note:

Substance Label (28) Label References 3

Knoedler, Matthias; Conrad, Juergen; Wenzig, Eva M.; Bauer, Rudolf; Lacorn, Markus; Beifuss, Uwe; Carle, Reinhold; Schieber, Andreas; Phytochemistry; vol. 69; nb. 4; (2008); p. 988 - 993, View in Reaxys; Kumano, Takuto; Richard, Stephane B.; Noel, Joseph P.; Nishiyama, Makoto; Kuzuyama, Tomohisa; Bioorganic and Medicinal Chemistry; vol. 16; nb. 17; (2008); p. 8117 - 8126, View in Reaxys; Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys

Kozela, Ewa; Haj, Christeene; Hanuš, Lumir; Chourasia, Mukesh; Shurki, Avital; Juknat, Ana; Kaushansky, Nathali; Mechoulam, Raphael; Vogel, Zvi; Chemical Biology and Drug Design; vol. 87; nb. 1; (2016); p. 143 - 153, View in Reaxys

1-1

Kinney, William A.; McDonnell, Mark E.; Zhong, Hua Marlon; Liu, Chaomin; Yang, Lanyi; Ling, Wei; Qian, Tao; Chen, Yu; Cai, Zhijie; Petkanas, Dean; Brenneman, Douglas E.; ACS Medicinal Chemistry Letters; vol. 7; nb. 4; (2016); p. 424 - 428, View in Reaxys

Masuoka, Noriyoshi; Nihei, Ken-Ichi; Maeta, Ayami; Yamagiwa, Yoshiro; Kubo, Isao; Food Chemistry; vol. 166; (2015); p. 270 - 274, View in Reaxys

Dethe, Dattatraya H.; Erande, Rohan D.; Mahapatra, Samarpita; Das, Saikat; Kumar B., Vijay; Chemical Communications; vol. 51; nb. 14; (2015); p. 2871 - 2873, View in Reaxys

Luo, Guo-Ying; Wu, Hao; Tang, Yu; Li, Hui; Yeom, Hyun-Suk; Yang, Ka; Hsung, Richard P.; Synthesis (Germany); vol. 47; nb. 18; (2015); p. 2713 - 2720; Art.No: SS-2015-C0219-ST, View in Reaxys

Klotter, Felix; Studer, Armido; Angewandte Chemie - International Edition; vol. 54; nb. 29; (2015); p. 8547 8550; Angew. Chem.; vol. 127; nb. 54; (2015); p. 8667 - 8670,4, View in Reaxys

22a

Wuensch, Christiane; Gross, Johannes; Steinkellner, Georg; Lyskowski, Andrzej; Gruber, Karl; Glueck, Silvia M.; Faber, Kurt; RSC Advances; vol. 4; nb. 19; (2014); p. 9673 - 9679, View in Reaxys

Morales, Paula; Azofra, Luis Miguel; Cumella, Jose; Hernandez-Folgado, Laura; Roldan, Maria; Alkorta, Ibon; Jagerovic, Nadine; Arkivoc; vol. 2014; nb. 2; (2014); p. 319 - 332, View in Reaxys; Rosati, Ornelio; Messina, Federica; Pelosi, Azzurra; Curini, Massimo; Petrucci, Vanessa; Gertsch, Jürg; Chicca, Andrea; European Journal of Medicinal Chemistry; vol. 85; (2014); p. 77 - 86, View in Reaxys

1.1

Patent; NORTHEASTERN UNIVERSITY; MAKRIYANNIS, Alexandros; D'SOUZA, Marsha, R.; BAJAJ, Shama; NIKAS, Spyridon, P.; THAKUR, Ganeshsingh, A.; WO2014/62965; (2014); (A1) English, View in Reaxys

Yeom, Hyun-Suk; Li, Hui; Tang; Hsung, Richard P.; Organic Letters; vol. 15; nb. 12; (2013); p. 3130 3133, View in Reaxys

1; 8

Lin, Hao; Annamalai, Thirunavukkarasu; Bansod, Priyanka; Tse-Dinh, Yuk-Ching; Sun, Dianqing; MedChemComm; vol. 4; nb. 12; (2013); p. 1613 - 1618, View in Reaxys

S25

Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; FURUYA, Takeru; TANG, Pingping; WO2010/59943; (2010); (A2) English, View in Reaxys

36.2

Patent; NORTHEASTERN UNIVERSITY; WO2009/52319; (2009); (A1) English, View in Reaxys

Evans, David A.; Barnes, David M.; Johnson, Jeffrey S.; Lectka, Thomas; Von Matt, Peter; Miller, Scott J.; Murry, Jerry A.; Norcross, Roger D.; Shaughnessy, Eileen A.; Campos, Kevin R.; Journal of the American Chemical Society; vol. 121; nb. 33; (1999); p. 7582 - 7594, View in Reaxys; Lee, Yong Rok; Xia, Likai; Tetrahedron Letters; vol. 49; nb. 20; (2008); p. 3283 - 3287, View in Reaxys

Trost, Barry M.; Dogra, Kalindi; Organic Letters; vol. 9; nb. 5; (2007); p. 861 - 863, View in Reaxys

Brogan, Andrew P.; Eubanks, Lisa M.; Koob, George F.; Dickerson, Tobin J.; Janda, Kirn D.; Journal of the American Chemical Society; vol. 129; nb. 12; (2007); p. 3698 - 3702, View in Reaxys

14a

Nikas, Spyros P.; Thakur, Ganesh A.; Parrish, Damon; Alapafuja, Shakiru O.; Huestis, Marilyn A.; Makriyannis, Alexandros; Tetrahedron; vol. 63; nb. 34; (2007); p. 8112 - 8123, View in Reaxys

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phenol, R = npentyl

Brizzi, Antonella; Cascio, Maria Grazia; Brizzi, Vittorio; Bisogno, Tiziana; Dinatolo, Maria Teresa; Martinelli, Adriano; Tuccinardi, Tiziano; Di Marzo, Vincenzo; Bioorganic and Medicinal Chemistry; vol. 15; nb. 16; (2007); p. 5406 - 5416, View in Reaxys

Katz, Jeffrey L.; Geller, Bram J.; Conry, Rebecca R.; Organic Letters; vol. 8; nb. 13; (2006); p. 2755 2758, View in Reaxys

Patent; Souza, Fabio E.S.; Field, Jason E.; Pan, Ming; Ramjit, Navindra J.; Tharmanathan, Tharsika; Jende-Tindall, Tracey; US2006/74252; (2006); (A1) English, View in Reaxys

Patent; OAKVILLE HONG KONG COMPANY LIMITED; WO2006/29089; (2006); (A2) English, View in Reaxys

Katz, Jeffrey L.; Feldman, Michael B.; Conry, Rebecca R.; Organic Letters; vol. 7; nb. 1; (2005); p. 91 94, View in Reaxys

Lee, Yong Rok; Jung, Hyun Choi; Sang, Heum Yoon; Tetrahedron Letters; vol. 46; nb. 44; (2005); p. 7539 - 7543, View in Reaxys

Patent; CEDARBURG PHARMACEUTICALS, INC.; WO2005/100333; (2005); (A1) English, View in Reaxys

13c

Shindo, Takeyuki; Fukuyama, Yasuaki; Sugai, Takeshi; Synthesis; nb. 5; (2004); p. 692 - 700, View in Reaxys

Malkov, Andrei V.; Kocovsky, Pavel; Collection of Czechoslovak Chemical Communications; vol. 66; nb. 8; (2001); p. 1257 - 1268, View in Reaxys

Reek, Joost N. H.; Priem, Alex H.; Engelkamp, Hans; Rowan, Alan E.; Elemans, Johannes A. A. W.; Nolte, Roeland J. M.; Journal of the American Chemical Society; vol. 119; nb. 42; (1997); p. 9956 - 9964, View in Reaxys

Patent-Specific Data (4) Location in Patent References Patent; KAO CORPORATION; SUGIYAMA, MITSURU; TAKIGAWA, HIROFUMI; SASAKI, KENJI; CHIBA, MASASHI; KUMAGAI, AKIRA; (14 pag.); JP2017/218389; (2017); (A) Japanese, View in Reaxys Patent; FULL SPECTRUM LABORATORIES LIMITED; WINNICKI, Robert; DONSKY, Marc; WO2014/134281; (2014); (A1) English, View in Reaxys Patent; MALLINCKRODT INC.; WO2009/99868; (2009); (A1) English, View in Reaxys Claim

Patent; The University of Mississippi; US4315862; (1982); (A1) English, View in Reaxys; Patent; Rutgers, The State University of New Jersey; US6328988; (2001); (B1) English, View in Reaxys; Patent; The John C. Sheehan Institute for Research, Inc.; US4025516; (1977); (A1) English, View in Reaxys; Patent; Schering-Plough HealthCare Products, Inc.; US5702694; (1997); (A1) English, View in Reaxys; Patent; AerojetGeneral Corporation; US4381399; (1983); (A1) English, View in Reaxys; Patent; Heinrich Mack Nachf.; US5227537; (1993); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.818

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.46

Lipinski Number

Veber Number

Derivative (1) Comment (Derivative) bis-<3.5-dinitrobenzoyl>-derivative (mp: 127-128 degree )

References Adams; Hunt; Clark; Journal of the American Chemical Society; vol. 62; (1940); p. 735,737, View in Reaxys

Melting Point (8) 1 of 8

Melting Point [°C]

47 - 49

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys

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2 of 8

Melting Point [°C]

44 - 45

Jaxa-Chamiec, Albert A.; Sammes, Peter G.; Kennewell, Peter D.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 170 - 175, View in Reaxys 3 of 8

Melting Point [°C]

85 - 86

Focella; Teitel; Brossi; Journal of Organic Chemistry; vol. 42; nb. 21; (1977); p. 3456 - 3457, View in Reaxys 4 of 8

Melting Point [°C]

39 - 41

Krishnamurty; Prasad; Tetrahedron Letters; (1975); p. 2511, View in Reaxys 5 of 8

Melting Point [°C]

44 - 46

Marmor,R.S.; Journal of Organic Chemistry; vol. 37; nb. 18; (1972); p. 2901 - 2904, View in Reaxys 6 of 8

Melting Point [°C]

Korte,F.; Sieper,H.; Justus Liebigs Annalen der Chemie; vol. 630; (1960); p. 71 - 83, View in Reaxys; Anker; Cook; Journal of the Chemical Society; (1945); p. 311, View in Reaxys; Asahina; Asano; Chemische Berichte; vol. 65; (1932); p. 475,581; Yakugaku Zasshi; vol. 52; (1932); p. 417,428, View in Reaxys 7 of 8

Melting Point [°C]

Solvent (Melting Point)

H2O

Comment (Melting Point)

with:1 Mol.H2O (solvent).

Anker; Cook; Journal of the Chemical Society; (1945); p. 311, View in Reaxys; Asahina; Asano; Chemische Berichte; vol. 65; (1932); p. 475,581; Yakugaku Zasshi; vol. 52; (1932); p. 417,428, View in Reaxys; Asahina; Chemische Berichte; vol. 69; (1936); p. 1643,1644, View in Reaxys; Adams; Hunt; Clark; Journal of the American Chemical Society; vol. 62; (1940); p. 735,737, View in Reaxys; Asahina; Fujikawa; Chemische Berichte; vol. 68; (1935); p. 634,636, 638, View in Reaxys 8 of 8

Melting Point [°C]

40 - 41

Solvent (Melting Point)

H2O

Comment (Melting Point)

with:1 Mol.H2O (solvent).

Pressure (Boiling Point) [Torr]

References

145

0.6

Barker; Settine; Organic Preparations and Procedures International; vol. 11; (1979); p. 87,90, View in Reaxys

170 - 175

0.3

Chandrasekharan,V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 16; (1978); p. 970 - 972, View in Reaxys

126 - 129

Kato,T.; Hozumi,T.; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 1574 1578, View in Reaxys

132

0.05

Marmor,R.S.; Journal of Organic Chemistry; vol. 37; nb. 18; (1972); p. 2901 - 2904, View in Reaxys

160 - 170

3-4

Baeckstroem; Sundstroem; Acta Chemica Scandinavica (1947-1973); vol. 24; (1970); p. 716, View in Reaxys

123

0.01

Korte,F.; Sieper,H.; Justus Liebigs Annalen der Chemie; vol. 630; (1960); p. 71 - 83, View in Reaxys

162 - 164

Suter; Weston; Journal of the American Chemical Society; vol. 61; (1939); p. 232,235, View in Reaxys

164

Asahina; Chemische Berichte; vol. 69; (1936); p. 1643,1644, View in Reaxys

Association (MCS) (33) 1 of 33

Description (Association Further physical properties of the complex (MCS))

4/40

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Partner (Association (MCS))

C86H92N14O10

Sprakel, Vera S. I.; Elemans, Johannes A. A. W.; Feiters, Martin C.; Lucchese, Baldo; Karlin, Kenneth D.; Nolte, Roeland J. M.; European Journal of Organic Chemistry; nb. 10; (2006); p. 2281 - 2295, View in Reaxys 2 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.85

Partner (Association (MCS))

C148H132N14O12(4-)*2Zn(2+); 5,15-di(4-methylphenyl)-10,20-di(4-pyridyl)-porphyrin

Elemans, Johannes A.A.W.; Slagt, Vincent F.; Rowan, Alan E.; Nolte, Roeland J.M.; Israel Journal of Chemistry; vol. 45; nb. 3; (2005); p. 271 - 279, View in Reaxys 3 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.85

Partner (Association (MCS))

C148H132N14O12(4-)*2Zn(2+); 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine

Elemans, Johannes A.A.W.; Slagt, Vincent F.; Rowan, Alan E.; Nolte, Roeland J.M.; Israel Journal of Chemistry; vol. 45; nb. 3; (2005); p. 271 - 279, View in Reaxys 4 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.85

Partner (Association (MCS))

C148H136N14O12

Elemans, Johannes A.A.W.; Slagt, Vincent F.; Rowan, Alan E.; Nolte, Roeland J.M.; Israel Journal of Chemistry; vol. 45; nb. 3; (2005); p. 271 - 279, View in Reaxys 5 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.85

Partner (Association (MCS))

C148H132N14O12(4-)*2Zn(2+)

Elemans, Johannes A.A.W.; Slagt, Vincent F.; Rowan, Alan E.; Nolte, Roeland J.M.; Israel Journal of Chemistry; vol. 45; nb. 3; (2005); p. 271 - 279, View in Reaxys 6 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Partner (Association (MCS))

C80H60N10O6

Reek, Joost N. H.; Rowan, Alan E.; Crossley, Maxwell J.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6653 - 6663, View in Reaxys

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7 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.9

Partner (Association (MCS))

bis(o-xylene)bipyridine glycoluril

Elemans, Johannes A. A. W.; De Gelder, Rene; Rowan, Alan E.; Nolte, Roeland J. M.; Chemical Communications; nb. 15; (1998); p. 1553 - 1554, View in Reaxys 8 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.9

Partner (Association (MCS))

C5H3NC2C5H3NN2(CO)2(CH2C10H6CH2)2N2

Elemans, Johannes A. A. W.; De Gelder, Rene; Rowan, Alan E.; Nolte, Roeland J. M.; Chemical Communications; nb. 15; (1998); p. 1553 - 1554, View in Reaxys 9 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.9

Partner (Association (MCS))

17b,17c-dihydro-17b,17c-diphenyl-7H,8H,9H,16H,17H,18H-7a,8a,16a,17a-tetraazapentaleno[1'',6'':5,6,7;3'',4'':5',6',7']dicycloocta(1,2,3-de:1',2',3'd'e')dinaphthalene-8,17-dione

Reek, Joost N. H.; Engelkamp, Hans; Rowan, Alan E.; Elemans, Johannes A. A. W.; Nolte, Roeland J. M.; Chemistry - A European Journal; vol. 4; nb. 4; (1998); p. 716 - 722, View in Reaxys 10 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.9

Partner (Association (MCS))

17b,17c-dihydro-1,6,10,15-tetramethoxy-17b,17c-diphenyl-7H,8H,9H,16H,17H,18H-7a,8a, 16a,17a-tetrazapentaleno[1'',6'':5,6,7:3'',4'':5',6',7']dicycloocta(1,2,3-de:1',2',3'-d'e')dinaphthalene-8,17-dione

Reek, Joost N. H.; Engelkamp, Hans; Rowan, Alan E.; Elemans, Johannes A. A. W.; Nolte, Roeland J. M.; Chemistry - A European Journal; vol. 4; nb. 4; (1998); p. 716 - 722, View in Reaxys 11 of 33

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

24.9

Partner (Association (MCS))

C32H28N4O5

Reek, Joost N. H.; Engelkamp, Hans; Rowan, Alan E.; Elemans, Johannes A. A. W.; Nolte, Roeland J. M.; Chemistry - A European Journal; vol. 4; nb. 4; (1998); p. 716 - 722, View in Reaxys 12 of 33

Description (Association IR spectrum of the complex (MCS))

6/40

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Solvent (Association (MCS))

CH2Cl2

Partner (Association (MCS))

diphenylglycoluril-ferrocene

Dol, Georg C.; Kamer, Paul C. J.; Hartl, Frantisek; Van Leeuwen, Piet W. N. M.; Nolte, Roeland J. M.; Journal of the Chemical Society - Dalton Transactions; nb. 12; (1998); p. 2083 - 2089, View in Reaxys 13 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

8b,8c-diphenylperhydro-2,6-dioxa-3a,4a,7a,8a-tetraazacyclopenta[def]fluorene-4,8-dione

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 14 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C28H26N4O5

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 15 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

5,7,12,13b,13c,14-Hexahydro-1,4,8,11-tetramethoxy-13b,13c-diphenyl-6H,13H-5a,6a,12a, 13a-tetraazabenzlt;5,6gt;azulenolt;2,1,8-ijagt;benzlt;fgt;azulene-6,13-dione

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 16 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C32H28N4O5

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 17 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C40H36N4O6

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 18 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C40H30N8O5

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 19 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C60H42N12O6

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 20 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C48H38N8O6

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Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 21 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C48H40N8O6

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 22 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

C80H60N10O6

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 23 of 33

Description (Association Stability constant of the complex with ... (MCS)) Partner (Association (MCS))

6,8,15,16b,16c,17-Hexahydro-5,9,14,18-tetramethoxy-16b,16c-diphenyl-7H,16H-6a,7a, 15a,16a-tetraazanaphtholt;5,6gt;azulenolt;2,1,8-ijagt;naphtholt;fgt;-azulene-7,16-dione

Reek, Joost N. H.; Elemans, Johannes A.A.W.; Nolte, Roeland J. M.; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2234 - 2243, View in Reaxys 24 of 33

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

5,7,12,13b,13c,14-hexahydro-1,4,8,11-tetrakis[(3,4,5-trihexyloxy)benzoyloxy]-13b,13c-diphenyl-6H,13H-5a,6a,12a,13a-tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13-dione

Van Nunen, Johanna L. M.; Nolte, Roeland J. M.; Journal of the Chemical Society. Perkin Transactions 2; nb. 8; (1997); p. 1473 - 1478, View in Reaxys 25 of 33

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

5,7,12,13b,13c,14-hexahydro-1,4,8,11-tetrakis[(3,4,5-tridodecyloxy)benzoyloxy]-13b,13cdiphenyl-6H,13H-5a,6a,12a,13a-tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13dione

Van Nunen, Johanna L. M.; Nolte, Roeland J. M.; Journal of the Chemical Society. Perkin Transactions 2; nb. 8; (1997); p. 1473 - 1478, View in Reaxys 26 of 33

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C36H34N4O4S2

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C44H38N4O6

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Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C28H26N4O5

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C20H18N4O2(C6H2HH)2(CH2O)4

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C44H38N4O6

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C32H28N4O5

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C32H28N4O5

Description (Association Association with compound (MCS)) Solvent (Association (MCS))

CHCl3

Partner (Association (MCS))

C44H38N4O6

Location

References

9/40

2018-02-18 00:37:05

TLC (Thin layer chromatography) HPLC (High performance liquid chromatography)

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys HPLC-Analysis: 2.8 min

Page/Page column 26

Patent; SYMRISE AG; ERFURT, Harry; WEBER, Maria; NIEMEYER, Hans-Jürgen; GÖTZ, Marcus Rudolf; WINKLER, Matthias; (44 pag.); WO2017/194173; (2017); (A1) English, View in Reaxys

GC (Gas chroma- GC-EI-MS: AR5:0 Page/Page coltography) —R&t %5.40 min umn 24

Patent; The United States of America, as represented by The Secretary of Agriculture; Baerson, Scott R.; Pan, Zhiqiang; Rimando, Agnes M.; Dayan, Franck E.; Cook, Daniel; (56 pag.); US9248145; (2016); (B2) English, View in Reaxys

HPLC (High performance liquid chromatography)

Wang, Wen-Jing; Yang, Hong-Mei; Chen, Ye-Gao; Chemistry of Natural Compounds; vol. 49; nb. 2; (2013); p. 356 - 357; Khim. Prir. Soedin.; vol. 49; nb. 2; (2013); p. 300 - 301,2, View in Reaxys; Studzińska-Sroka, Elzbieta; Hołderna-Kędzia, Elzbieta; Galanty, Agnieszka; Bylka, Wiesława; Kacprzak, Karol; Ćwiklińska, Karolina; Natural Product Research; vol. 29; nb. 24; (2015); p. 2302 - 2307, View in Reaxys

UPLC (Ultra performance liquid chromatography)

Bian, Yuan-Yuan; Guo, Jia; Zhu, Ke-Xue; Guo, Xiao-Na; Peng, Wei; Zhou, Hui-Ming; RSC Advances; vol. 5; nb. 21; (2015); p. 16116 - 16124, View in Reaxys

GC (Gas chromatography)

Abdelshafeek, Khalid A.; Abdelmohsen, Mona M.; Hamed, Ahmed; Shahat, Abdelaaty A.; Chemistry of Natural Compounds; vol. 49; nb. 3; (2013); p. 539 - 543; Khim. Prir. Soedin.; nb. 3; (2013); p. 459 - 462, View in Reaxys

Crystal Property Description (5) Colour & Other References Properties yellow

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys

colourless

Wu, Li-Qiang; Yang, Chun-Guang; Yang, Li-Ming; Yang, Li-Juan; Journal of Chemical Research; nb. 3; (2009); p. 183 - 185, View in Reaxys

Prismen oder Blaetter

Blaetter oder Pris- Anker; Cook; Journal of the Chemical Society; (1945); p. 311, View in Reaxys; Asahina; Asano; Chemische men Berichte; vol. 65; (1932); p. 475,581; Yakugaku Zasshi; vol. 52; (1932); p. 417,428, View in Reaxys; Asahina; Chemische Berichte; vol. 69; (1936); p. 1643,1644, View in Reaxys; Adams; Hunt; Clark; Journal of the American Chemical Society; vol. 62; (1940); p. 735,737, View in Reaxys; Asahina; Fujikawa; Chemische Berichte; vol. 68; (1935); p. 634,636, 638, View in Reaxys wasserfrei

Further Information (3) Description (Fur- References ther Information) Further information

Kueppers et al.; Journal of Chromatography; vol. 108; (1975); p. 375,377,378, View in Reaxys

Further information

Brodskii et al.; Journal of Organic Chemistry USSR (English Translation); vol. 6; (1970); p. 2102; Zhurnal Organicheskoi Khimii; vol. 6; (1970); p. 2096, View in Reaxys

Further information

Gaoni; Mechoulam; Proceedings of the Chemical Society, London; (1964); p. 82, View in Reaxys

NMR Spectroscopy (12) 1 of 12

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

Solvents (NMR Spectro- chloroform-d1 scopy)

10/40

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Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys 2 of 12

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

13C

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

400

Location

supporting information

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys 3 of 12

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

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

400

Wu, Li-Qiang; Yang, Chun-Guang; Yang, Li-Ming; Yang, Li-Juan; Journal of Chemical Research; nb. 3; (2009); p. 183 - 185, View in Reaxys 4 of 12

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

13C

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

100

Wu, Li-Qiang; Yang, Chun-Guang; Yang, Li-Ming; Yang, Li-Juan; Journal of Chemical Research; nb. 3; (2009); p. 183 - 185, View in Reaxys 5 of 12

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

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

270

Comment (NMR Spectroscopy)

ambient temperature

Shindo, Takeyuki; Fukuyama, Yasuaki; Sugai, Takeshi; Synthesis; nb. 5; (2004); p. 692 - 700, View in Reaxys 6 of 12

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy)

11/40

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Frequency (NMR Spectroscopy) [MHz]

270

Comment (NMR Spectroscopy)

ambient temperature

Shindo, Takeyuki; Fukuyama, Yasuaki; Sugai, Takeshi; Synthesis; nb. 5; (2004); p. 692 - 700, View in Reaxys 7 of 12

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

Solvents (NMR Spectro- CDCl3 scopy) Durrani, Aziz A.; Tyman, John H. P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1658 - 1666, View in Reaxys; Huneck, Siegfried; Schmidt, Juergen; Tabacchi, Raffaele; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 44; nb. 10; (1989); p. 1283 - 1289, View in Reaxys 8 of 12

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

1H-1H

Huneck, Siegfried; Schmidt, Juergen; Tabacchi, Raffaele; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 44; nb. 10; (1989); p. 1283 - 1289, View in Reaxys 9 of 12

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

Solvents (NMR Spectro- acetone-d6 scopy) Jaxa-Chamiec, Albert A.; Sammes, Peter G.; Kennewell, Peter D.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 170 - 175, View in Reaxys 10 of 12

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Comment (NMR Spectroscopy)

1H-1H

Description (NMR Spec- NMR troscopy) Focella; Teitel; Brossi; Journal of Organic Chemistry; vol. 42; nb. 21; (1977); p. 3456 - 3457, View in Reaxys; Barker; Settine; Organic Preparations and Procedures International; vol. 11; (1979); p. 87,90, View in Reaxys

12 of 12

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

Petrzilka,T. et al.; Helvetica Chimica Acta; vol. 52; nb. 4; (1969); p. 1102 - 1134, View in Reaxys; Marmor,R.S.; Journal of Organic Chemistry; vol. 37; nb. 18; (1972); p. 2901 - 2904, View in Reaxys IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

potassium bromide

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands; Spectrum

Solvent (IR Spectroscopy)

potassium bromide

Jin, Ya-Feng; Chen, Na; Liu, Run-Qiang; Zhang, Yu-Ping; Bai, Lian-Yang; Chen, Jun; Journal of the Chinese Chemical Society; vol. 60; nb. 8; (2013); p. 1043 - 1049, View in Reaxys 3 of 4

Description (IR Spectroscopy)

Bands

Chandrasekharan,V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 16; (1978); p. 970 - 972, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Focella; Teitel; Brossi; Journal of Organic Chemistry; vol. 42; nb. 21; (1977); p. 3456 - 3457, View in Reaxys Mass Spectrometry (7) Description (Mass Location Spectrometry)

References

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas; Tetrahedron; vol. 73; nb. 35; (2017); p. 5297 - 5301, View in Reaxys

gas chromatogra- Page/Page colphy mass specumn 24 trometry (GCMS); electron impact (EI); spectrum

liquid chromatography mass spectrometry (LCMS); tandem mass spectrometry; electrospray ionisation (ESI); spectrum

Bian, Yuan-Yuan; Guo, Jia; Zhu, Ke-Xue; Guo, Xiao-Na; Peng, Wei; Zhou, Hui-Ming; RSC Advances; vol. 5; nb. 21; (2015); p. 16116 - 16124, View in Reaxys

liquid chromatography mass spectrometry (LCMS); electrospray ionisation (ESI); spectrum

Bian, Yuan-Yuan; Guo, Jia; Zhu, Ke-Xue; Guo, Xiao-Na; Peng, Wei; Zhou, Hui-Ming; RSC Advances; vol. 5; nb. 21; (2015); p. 16116 - 16124, View in Reaxys

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

spectrum

Petrzilka,T. et al.; Helvetica Chimica Acta; vol. 52; nb. 4; (1969); p. 1102 - 1134, View in Reaxys; Vree; Journal of Pharmaceutical Sciences; vol. 66; nb. 10; (1977); p. 1444 - 1450, View in Reaxys Kueppers et al.; Journal of Chromatography; vol. 108; (1975); p. 375,377,378, View in Reaxys; Brodskii et al.; Journal of Organic Chemistry USSR (English Translation); vol. 6; (1970); p. 2102; Zhurnal Organicheskoi Khimii; vol. 6; (1970); p. 2096, View in Reaxys

UV/VIS Spectroscopy (1)

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1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Korte,F.; Sieper,H.; Justus Liebigs Annalen der Chemie; vol. 630; (1960); p. 71 - 83, View in Reaxys Ecotoxicology (1) 1 of 1

Effect (Ecotoxicology)

growth; inhibition of

Species or Test-System (Ecotoxicology)

Tetrahymena pyriformis GL-C, protozoa

Method (Ecotoxicology)

population growth impairment testing; 40-h TETRATOX assay; population density quantitated spectrophotometrically at 540 nm

Further Details (Ecotoxi- controls: 1) no title comp., no T. pyriformis; 2) inoculated with T. pyriformis without title cology) comp. Type (Ecotoxicology)

log(1/IGC50)

Value of Type (Ecotoxicology)

1.31 dimensionless

Schultz, T. Wayne; Chemical Research in Toxicology; vol. 12; nb. 12; (1999); p. 1262 - 1267, View in Reaxys Use (7) Use Pattern

References

Multiple sclerosis (MS)

Patent; University of Plymouth; US2008/175902; (2008); (A1) English, View in Reaxys

Symptoms of mul- Patent; University of Plymouth; US2008/175902; (2008); (A1) English, View in Reaxys tiple sclerosis (MS) Pain

Patent; University of Plymouth; US2008/175902; (2008); (A1) English, View in Reaxys

Spasms

Patent; University of Plymouth; US2008/175902; (2008); (A1) English, View in Reaxys

Spasticity

Patent; University of Plymouth; US2008/175902; (2008); (A1) English, View in Reaxys

Schizophrenia

Patent; NORTHERN SYDNEY AND CENTRAL COAST AREA HEALTH SERVICE; WO2006/17892; (2006); (A1) English, View in Reaxys

Schizoaffective Disorder

Patent; NORTHERN SYDNEY AND CENTRAL COAST AREA HEALTH SERVICE; WO2006/17892; (2006); (A1) English, View in Reaxys

Isolation from Natural Product (2) Isolation from References Natural Product herb of Matthiola Abdelshafeek, Khalid A.; Abdelmohsen, Mona M.; Hamed, Ahmed; Shahat, Abdelaaty A.; Chemistry of longipetala subsp. Natural Compounds; vol. 49; nb. 3; (2013); p. 539 - 543; Khim. Prir. Soedin.; nb. 3; (2013); p. 459 - 462, longipetala; colView in Reaxys lected from the Sirt region, Libya in March 2009 roots and stems Chang, Hsun-Shuo; Lin, Yi-Ju; Lee, Shiow-Ju; Yang, Cheng-Wei; Lin, Wei-Yu; Tsai, Ian-Lih; Chen, Ihof Ardisia virens Sheng; Phytochemistry; vol. 70; nb. 17-18; (2009); p. 2064 - 2071, View in Reaxys Kurz; collected in Meinon, Kaohsiung County, Taiwan Medchem (64) 1 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

SNB-75

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µg/mL

14/40

2018-02-18 00:37:05

Quantitative value

Measurement pX

3.65

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 2 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

DLD I

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µg/mL

Quantitative value

Measurement pX

3.63

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 3 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

NCI H23

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µg/mL

Quantitative value

Measurement pX

3.74

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 4 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

ZR 75.1

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µg/mL

Quantitative value

Measurement pX

3.7

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 5 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

LOXIMVI

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µg/mL

15/40

2018-02-18 00:37:05

Quantitative value

Measurement pX

3.61

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 6 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

PC-3

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µg/mL

Quantitative value

Measurement pX

3.69

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 7 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Cells/Cell Lines

caki I

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µg/mL

Quantitative value

Measurement pX

3.65

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 8 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Viral infection

Biological Species/NCBI human ID Cells/Cell Lines

monocyte

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µM

Quantitative value

63.7

Measurement pX

4.2

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 9 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Viral infection

Biological Species/NCBI human ID Cells/Cell Lines

monocyte

Substance RN

908277View in Reaxys

16/40

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Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µM

Quantitative value

75.9

Measurement pX

4.12

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 10 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Viral infection

Biological Species/NCBI human ID Cells/Cell Lines

peripheral blood mononuclear cell

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µM

Quantitative value

16.9

Measurement pX

4.77

Concomitants: Compound RN

24140623; 12471441; 1723797; 9186271

Concomitants: Compound name

Gentamycin; Streptomycin; Glutamine; Penicillin; Fetal calf serum

Concomitants: Compound role

COM; COM; COM; COM; COM

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 11 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Viral infection

Biological Species/NCBI human ID Cells/Cell Lines

peripheral blood mononuclear cell

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

100

Measurement pX

Concomitants: Compound RN

24140623; 12471441; 1723797; 9186271

Concomitants: Compound name

Gentamycin; Streptomycin; Glutamine; Penicillin; Fetal calf serum

Concomitants: Compound role

COM; COM; COM; COM; COM

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 12 of 64

Bioassay Category

Toxicity/Safety Pharmacology

17/40

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Bioassay Name

Viral infection

Biological Species/NCBI human ID Cells/Cell Lines

U-1

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µM

Quantitative value

22.5

Measurement pX

4.65

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 13 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Viral infection

Biological Species/NCBI human ID Cells/Cell Lines

U-1

Substance RN

908277View in Reaxys

Substance Name

Olivetol

Measurement Parameter

IC50

Unit

µM

Quantitative value

77.5

Measurement pX

4.11

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 14 of 64

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : cell growth

Biological Species/NCBI Staphylococcus aureus ID Substance RN

908277View in Reaxys

Substance Name

Measurement Parameter

MIC

Unit

µg/mL

Quantitative value

128

Measurement pX

3.15

Appendino, Giovanni; Gibbons, Simon; Giana, Anna; Pagani, Alberto; Grassi, Gianpaolo; Stavri, Michael; Smith, Eileen; Rahman, M. Mukhlesur; Journal of Natural Products; vol. 71; nb. 8; (2008); p. 1427 - 1430, View in Reaxys 15 of 64

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : cell growthSpecies : Staphylococcus aureus EMRSA-15methicillin-resistant strain used

18/40

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Biological Species/NCBI Staphylococcus aureus ID Substance RN

908277View in Reaxys

Substance Name

Measurement Parameter

MIC

Unit

µg/mL

Quantitative value

Measurement pX

3.45

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : cell growthSpecies : Staphylococcus aureus EMRSA-16methicillin-resistant strain used

Biological Species/NCBI Staphylococcus aureus ID Substance RN

908277View in Reaxys

Substance Name

Measurement Parameter

MIC

Unit

µg/mL

Quantitative value

Measurement pX

3.45

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : cell growthSpecies : Staphylococcus aureus RN-4220macrolide-resistant strain with MsrA macrolide efflux pump used

Biological Species/NCBI Staphylococcus aureus ID Substance RN

908277View in Reaxys

Substance Name

Measurement Parameter

MIC

Unit

µg/mL

Quantitative value

Measurement pX

3.45

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

19/40

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Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : cell growthSpecies : Staphylococcus aureus SA-1199Bmultidrug resistant strain with gyrase mutation and overexpression of NorA MDR efflux pump used

Biological Species/NCBI Staphylococcus aureus ID Substance RN

908277View in Reaxys

Substance Name

Measurement Parameter

MIC

Unit

µg/mL

Quantitative value

Measurement pX

3.45

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : cell growthSpecies : Staphylococcus aureus XU212tetracycline-resistant strain with TetK efflux pump used

Biological Species/NCBI Staphylococcus aureus ID Substance RN

908277View in Reaxys

Substance Name

Measurement Parameter

MIC

Unit

µg/mL

Quantitative value

Measurement pX

3.45

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

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

908277View in Reaxys

Substance Name

olivetol

20/40

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21 of 64

Measurement Parameter

IC50

Unit

µM

Quantitative value

7.21

Measurement pX

5.14

Metabolite RN

22541978

Metabolite name

AHMC

Concomitants: Compound RN

11841397; 11841397; 24140787; 3885115

Concomitants: Compound name

3-[2-(N,N-diethyl-N-methylamino]-ethyl)-7-Methoxy-4-methylcoumarin; 3-[2-(N,N-diethylN-methylamino]-ethyl)-7-Methoxy-4-methylcoumarin; Glucose-6-phosphate; NADP

Concomitants: Compound role

SUB; SUB; COM; COE

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]

22 of 64

Target Mutant/Chimera Details

Cytochrome P450 2D6 [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

908277View in Reaxys

Substance Name

olivetol

Substance Dose

0 µM

Measurement Parameter

Unit

µM

Quantitative value

2.87

Measurement pX

5.54

Metabolite RN

22541978

Metabolite name

AHMC

Concomitants: Compound RN

11841397; 11841397; 24140787; 3885115

Concomitants: Compound name

3-[2-(N,N-diethyl-N-methylamino]-ethyl)-7-Methoxy-4-methylcoumarin; 3-[2-(N,N-diethylN-methylamino]-ethyl)-7-Methoxy-4-methylcoumarin; Glucose-6-phosphate; NADP

Concomitants: Compound role

SUB; SUB; COM; COE

Target Name

estrogen receptor [human]

Target Synonyms

er; er-alpha; esr; esr1; estradiol receptor; estrogen receptor; nr3a1; nuclear receptor subfamily 3 group a member 1

Target Uniprot ID

p03372

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2018-02-18 00:37:05

Target PDB ID

1a52; 1ere; 1err; 1g50; 1gwq; 1gwr; 1hcq; 1l2i; 1pcg; 1qkt; 1qku; 1r5k; 1sj0; 1uom; 1x7e; 1x7r; 1xp1; 1xp6; 1xp9; 1xpc; 1xqc; 1yim; 1yin; 1zky; 2ayr; 2b1v; 2b1z; 2b23; 2bj4; 2fai; 2g44; 2g5o; 2i0j; 2iog; 2iok; 2jf9; 2jfa; 2ocf; 2ouz; 2p15; 2pog; 2q6j; 2q70; 2qa6; 2qa8; 2qab; 2qe4; 2qgt; 2qgw; 2qh6; 2qr9; 2qse; 2qxm; 2qxs; 2qzo; 2r6w; 2r6y; 2yat; 2yja; 3cbm; 3cbo; 3cbp; 3dt3; 3erd; 3ert; 3hlv; 3hm1; 3l03; 3os8; 3os9; 3osa; 3q95; 3q97; 3uu7; 3uua; 3uuc; 3uud; 4aa6; 4dma; 4iu7; 4iui; 4iv2; 4iv4; 4ivw; 4ivy; 4iw6; 4iw8; 4iwc; 4iwf; 4jc3; 4jdd; 4mg5; 4mg6; 4mg7; 4mg8; 4mg9; 4mga; 4mgb; 4mgc; 4mgd; 4o6f; 4pp6; 4ppp; 4pps; 4pxm; 4q13; 4q50; 4tuz; 4tv1; 5ak2

Target, Subunit, Species estrogen receptor [human] Target Mutant/Chimera Details

estrogen receptor [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Transactivation assay

Biological Species/NCBI Saccharomyces cerevisiae ID

23 of 64

Substance RN

908277View in Reaxys

Substance Name

106

Measurement Parameter

% Stimulation

Qualitative value

Measurement pX

Target Name

enzyme

Target Synonyms

catalytic; enzyme

Target, Subunit, Species enzyme Target Mutant/Chimera Details

enzyme:Wild

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : enzyme activity; inhibition ofBioassay : zileuton as control leukotriene inhibition assay; test cells had 5-LOX activity; test cell suspension incubated with title comp., CaCl2, calcimycin A23187 and arachidonic acid as substrate at 37 deg C for 10 min.; concn. of LTB4 determined by competitive LTB4 EIA kit

Substance RN

908277View in Reaxys

Substance Name

79663

Qualitative Results

IC50 = 39.3 μM for title comp. compared with IC50 = 5.0 μM for zileuton

Measurement Parameter

Qualitative

Target Name

enzyme

Target Synonyms

catalytic; enzyme

Target, Subunit, Species enzyme Target Mutant/Chimera Details

enzyme:Wild

22/40

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Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : enzyme activity; inhibition ofBioassay : COX-1: cyclooxygenase-1; control: indomethacin with IC50 0.9 μM arachidonic acid as substrate; title comp. added to test enzyme; concentration of PGE2 determined by competitive PGE2 EIA kit; inhibition of COX-1 referred to reduction of PGE2 formation

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

IC50

Unit

µM

Quantitative value

13.1

Measurement pX

4.88

Target Name

enzyme

Target Synonyms

catalytic; enzyme

Target, Subunit, Species enzyme Target Mutant/Chimera Details

enzyme:Wild

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : enzyme activity; inhibition ofBioassay : COX-2: cyclooxygenase-2; control: NS-398 with IC50 2.6 μM arachidonic acid as substrate; title comp. added to test enzyme; concentration of PGE2 determined by competitive PGE2 EIA kit; inhibition of COX-2 referred to reduction of PGE2 formation

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

IC50

Unit

µM

Quantitative value

46.4

Measurement pX

4.33

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

908277View in Reaxys

Substance Name

79663

Qualitative Results

antibiotic screening: acitivity against Candida albicans, Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Salmonella typhimurium, Staphylococcus aureus and S. epidermis

Measurement Parameter

Qualitative

Ayer, William A.; Browne, Lois M.; Lovell, Sarah H.; Phytochemistry (Elsevier); vol. 22; nb. 10; (1983); p. 2267 2272, View in Reaxys

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27 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

908277View in Reaxys

Substance Name

79663

Qualitative Results

It produced a maximal inhibitory effect of about 40 percent at a dose of 2.8 E-3 M upon TPA-induced aggregation of human platelets.

Measurement Parameter

Qualitative

Formukong; Evans; Journal of Pharmacy and Pharmacology; vol. 41; nb. 10; (1989); p. 705 - 709, View in Reaxys 28 of 64

Substance Effect

Antiproliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : Tetrahymena pyriformis GL-C, protozoaBioassay : controls: 1) no title comp., no T. pyriformis; 2) inoculated with T. pyriformis without title comp. population growth impairment testing; 40-h TETRATOX assay; population density quantitated spectrophotometrically at 540 nm

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

pGI50

Quantitative value

1.31

Measurement pX

1.31

Schultz, T. Wayne; Chemical Research in Toxicology; vol. 12; nb. 12; (1999); p. 1262 - 1267, View in Reaxys 29 of 64

Substance Effect

Antiviral

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : human peripheral blood monocytes (PBM) infected with human immunodeficiency virus 1 (HIV-1)Bioassay : Example 6 This example demonstrates the antiviral activity of several compounds according to the invention. Compounds. Compounds indicated in Table 1 were prepared as varying concentrations in SDMSA and used fresh. Latently Infected Cells. 5&times;103 U1 cells (obtained from the AIDS Research

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

IC50

Unit

µM

Quantitative value

63.7

Measurement pX

4.2

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 30 of 64

Substance Effect

Antiviral

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : human peripheral blood mononuclear cells (PBMC) infected with human immunodeficiency virus 1 (HIV-1)Bioassay : Example 6 This example demonstrates the antiviral activity of several compounds according to the invention. Compounds. Compounds indicated in Table 1 were prepared as varying concentrations in SDMSA and used fresh. Latently Infected Cells. 5&times;103 U1 cells (obtained from the AIDS Research

Substance RN

908277View in Reaxys

24/40

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Substance Name

79663

Measurement Parameter

IC50

Unit

µM

Quantitative value

16.9

Measurement pX

4.77

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 31 of 64

Substance Effect

Antiviral

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : tumor necrosis factor α (TNFα) induced U1 cellsBioassay : Example 6 This example demonstrates the antiviral activity of several compounds according to the invention. Compounds. Compounds indicated in Table 1 were prepared as varying concentrations in SDMSA and used fresh. Latently Infected Cells. 5&times;103 U1 cells (obtained from the AIDS Research

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

IC50

Unit

µM

Quantitative value

22.5

Measurement pX

4.65

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 32 of 64

Substance Effect

Antineoplastic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : CAKI-1 renal cellsBioassay : Example 7 This example demonstrates the antineoplastic activity of compounds according to Formula 1. Cell Lines. Cell lines indicated in table 2 were propagated under sterile conditions in RPMI 1640 or DMEM with 10% fetal calf serum, 2 mM L-glutamine, and sodium bicarbonate (&ldquo;complete medium&rdquo;)

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

IC50

Unit

Quantitative value

0.00022

Measurement pX

3.66

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 33 of 64

Substance Effect

Antineoplastic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : DLO-1 colon cellsBioassay : Example 7 This example demonstrates the antineoplastic activity of compounds according to Formula 1. Cell Lines. Cell lines indicated in table 2 were propagated under sterile conditions in RPMI 1640 or DMEM with 10% fetal calf serum, 2 mM L-glutamine, and sodium bicarbonate (&ldquo;complete medium&rdquo;)

Substance RN

908277View in Reaxys

Substance Name

79663

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Measurement Parameter

IC50

Unit

Quantitative value

0.00023

Measurement pX

3.64

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 34 of 64

Substance Effect

Antineoplastic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : SNB-7 CNS cellsBioassay : Example 7 This example demonstrates the antineoplastic activity of compounds according to Formula 1. Cell Lines. Cell lines indicated in table 2 were propagated under sterile conditions in RPMI 1640 or DMEM with 10% fetal calf serum, 2 mM L-glutamine, and sodium bicarbonate (&ldquo;complete medium&rdquo;)

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

IC50

Unit

Quantitative value

0.00022

Measurement pX

3.66

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 35 of 64

Substance Effect

Antineoplastic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : ZR-75-1 mammary cellsBioassay : Example 7 This example demonstrates the antineoplastic activity of compounds according to Formula 1. Cell Lines. Cell lines indicated in table 2 were propagated under sterile conditions in RPMI 1640 or DMEM with 10% fetal calf serum, 2 mM L-glutamine, and sodium bicarbonate (&ldquo;complete medium&rdquo;)

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

IC50

Unit

Quantitative value

0.0002

Measurement pX

3.7

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 36 of 64

Substance Effect

Antineoplastic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : Example 7 This example demonstrates the antineoplastic activity of compounds according to Formula 1. Cell Lines. Cell lines indicated in table 2 were propagated under sterile conditions in RPMI 1640 or DMEM with 10% fetal calf serum, 2 mM L-glutamine, and sodium bicarbonate (&ldquo;complete medium&rdquo;)

Cells/Cell Lines

PC-3

Substance RN

908277View in Reaxys

Substance Name

79663

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Measurement Parameter

IC50

Unit

Quantitative value

0.0002

Measurement pX

3.7

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 37 of 64

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : peripheral blood monocytes (PBM) of humanBioassay : Example 6 This example demonstrates the antiviral activity of several compounds according to the invention. Compounds. Compounds indicated in Table 1 were prepared as varying concentrations in SDMSA and used fresh. Latently Infected Cells. 5&times;103 U1 cells (obtained from the AIDS Research

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

TC50

Unit

µM

Quantitative value

75.9

Measurement pX

4.12

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 38 of 64

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : peripheral blood mononuclear cells (PBMC) of humanBioassay : Example 6 This example demonstrates the antiviral activity of several compounds according to the invention. Compounds. Compounds indicated in Table 1 were prepared as varying concentrations in SDMSA and used fresh. Latently Infected Cells. 5&times;103 U1 cells (obtained from the AIDS Research

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

TC50

Unit

µM

Quantitative value

100

Measurement pX

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 39 of 64

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Substance RN

908277View in Reaxys

Substance Name

79663

27/40

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Measurement Parameter

TC50

Unit

µM

Quantitative value

77.5

Measurement pX

4.11

Patent; Travis, Craig Rick; US2007/179135; (2007); (A1) English, View in Reaxys 40 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

Qualitative

Qualitative value

Measurement pX

Formukong; Evans; Journal of Pharmacy and Pharmacology; vol. 40; nb. 2; (1988); p. 132 - 134, View in Reaxys 41 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : |metabolic Target : mouse hepatic microsomesBioassay : generated CO (reduced to CH4 or oxidized to CO2) determined by GC in vitro; microsomes from ddN mice (25 35 g) pretreated with phenobarbital; aerobic; 25 deg C; NADPH generating system

Substance RN

908277View in Reaxys

Substance Name

79663

Substance Dose

191 µM

Qualitative Results

amount of generated CO : 2.6 ppm/nmol P450

Measurement Parameter

Qualitative

Usami; Tateoka; Watanabe; Yamamoto; Yoshimura; Biological and Pharmaceutical Bulletin; vol. 18; nb. 4; (1995); p. 529 - 535, View in Reaxys 42 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

908277View in Reaxys

Substance Name

79663

Qualitative Results

cytotoxicity against KB cell ED 50 (μg/ml): 19

Measurement Parameter

Qualitative

Arisawa; Ohmura; Kobayashi; Morita; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 9; (1989); p. 2431 2434, View in Reaxys 43 of 64

Substance Effect

Estrogen

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : 17β-estradiol as positive control; ethanol as negative control in vitro Lac-Z reporter assay; seeded assay medium (ca. 5E3 yeast/ml) contain. chlorophenol red-β-D-galactopyranoside was added to 96-well microtitre plate contain. title comp.; incub. at 30 deg C for 5 d; agitated daily; absorbency at 450 nm meas.

Biological Species/NCBI Saccharomyces cerevisiae ID Substance RN

908277View in Reaxys

28/40

2018-02-18 00:37:05

Substance Name

79663

Measurement Parameter

Qualitative

Qualitative value

Measurement pX

Schultz, T. Wayne; Sinks, Glendon D.; Cronin, Mark T. D.; Environmental Toxicology; vol. 17; nb. 1; (2002); p. 14 - 23, View in Reaxys 44 of 64

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : in vitro; seeded assay medium was added to 96-well microtitre plate contain. title comp.; incub. at 30 deg C for 5 d; agitated daily

Biological Species/NCBI Saccharomyces cerevisiae ID Substance RN

908277View in Reaxys

Substance Name

79663

Measurement Parameter

LC50

Unit

Quantitative value

6.93E-05

Measurement pX

4.16

Schultz, T. Wayne; Sinks, Glendon D.; Cronin, Mark T. D.; Environmental Toxicology; vol. 17; nb. 1; (2002); p. 14 - 23, View in Reaxys 45 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Bioassay Details

Effect : enzyme activity Target : human hepatic cytochrome P450 A4 Bioassay : recombinant hepatic cytochrome P450 A4

Biological Species/NCBI human ID Substance RN

908277View in Reaxys

Substance Name

79663

Substance Dose

<= 50 µM

Measurement Parameter

Qualitative

Qualitative value

Yamaori, Satoshi; Ebisawa, Juri; Okushima, Yoshimi; Yamamoto, Ikuo; Watanabe, Kazuhito; Life Sciences; vol. 88; nb. 15-16; (2011); p. 730 - 736, View in Reaxys 46 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Bioassay Details

Effect : enzyme activity Target : human hepatic cytochrome P450 A5 Bioassay : recombinant hepatic cytochrome P450 A5

Biological Species/NCBI human ID Substance RN

908277View in Reaxys

Substance Name

79663

Substance Dose

<= 50 µM

Measurement Parameter

Qualitative

29/40

2018-02-18 00:37:05

Qualitative value

Yamaori, Satoshi; Ebisawa, Juri; Okushima, Yoshimi; Yamamoto, Ikuo; Watanabe, Kazuhito; Life Sciences; vol. 88; nb. 15-16; (2011); p. 730 - 736, View in Reaxys 47 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Bioassay Details

Effect : enzyme activity Target : human hepatic cytochrome P450 A7 Bioassay : recombinant hepatic cytochrome P450 A7

Biological Species/NCBI human ID Substance RN

908277View in Reaxys

Substance Name

79663

Substance Dose

<= 50 µM

Measurement Parameter

Qualitative

Qualitative value

Yamaori, Satoshi; Ebisawa, Juri; Okushima, Yoshimi; Yamamoto, Ikuo; Watanabe, Kazuhito; Life Sciences; vol. 88; nb. 15-16; (2011); p. 730 - 736, View in Reaxys 48 of 64

Target Name

Cis-Prenyltransferase [Streptomyces]

Target Synonyms

cis-prenyltransferase

Target, Subunit, Species Cis-Prenyltransferase [Streptomyces] Target Mutant/Chimera Details

Cis-Prenyltransferase [Streptomyces]:Wild

Target Species (Bioactivity)

Streptomyces

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Michealis menten's constant of the compound towards Prenyltransferase was determined

Biological Species/NCBI Streptomyces CL190 ID Substance RN

908277View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

0.52

Deviation

0.03

Measurement pX

3.28

Kumano, Takuto; Richard, Stephane B.; Noel, Joseph P.; Nishiyama, Makoto; Kuzuyama, Tomohisa; Bioorganic and Medicinal Chemistry; vol. 16; nb. 17; (2008); p. 8117 - 8126, View in Reaxys 49 of 64

Target Name

Cis-Prenyltransferase [Streptomyces]

Target Synonyms

cis-prenyltransferase

Target, Subunit, Species Cis-Prenyltransferase [Streptomyces] Target Mutant/Chimera Details

Cis-Prenyltransferase [Streptomyces]:Wild

Target Species (Bioactivity)

Streptomyces

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Michealis menten's constant of the compound towards Prenyltransferase was determined

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Biological Species/NCBI Streptomyces CL190 ID Substance RN

908277View in Reaxys

Measurement Parameter

Unit

Qualitative value

Quantitative value

0.64

Deviation

0.16

Measurement pX

3.19

Kumano, Takuto; Richard, Stephane B.; Noel, Joseph P.; Nishiyama, Makoto; Kuzuyama, Tomohisa; Bioorganic and Medicinal Chemistry; vol. 16; nb. 17; (2008); p. 8117 - 8126, View in Reaxys 50 of 64

Target Name

Cannabinoid receptor 2

Target Synonyms

cannabinoid receptor 2; cb-2; cb2; cb2a; cb2b; cnr2 (cannabinoid receptor 2); cx5; hcb2; mcb2; rcb2

Target, Subunit, Species Cannabinoid receptor 2 Target Mutant/Chimera Details

Cannabinoid receptor 2:Wild

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Agonistic activity of the compound towards cannabinoid receptor 2

Substance RN

908277View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; Immugen Pharmaceuticals Inc.; US6274635; (2001); (B1) English, View in Reaxys 51 of 64

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Relative potency of the compound to induce convulsions in THC-SS rabbit with respect to delta 9-THC (=100)

Biological Species/NCBI rabbit ID Substance RN

908277View in Reaxys

Measurement Parameter

Qualitative

Measurement Object

Relative potency

Qualitative value

Not Published

Consroe; Martin; Schneiderman Fish; Journal of Medicinal Chemistry; vol. 25; nb. 5; (1982); p. 596 - 599, View in Reaxys 52 of 64

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Number of rabbits convulsed at 20 mg/kg dose administered intravenously out of 4 rabbits tested

Biological Species/NCBI rabbit ID Substance RN

908277View in Reaxys

Substance Route of Adm.

intravenous administration

Qualitative Results

Number of rabbits convulsed = 0/4

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Measurement Parameter

Number

Measurement Object

Number of rabbits convulsed

Consroe; Martin; Schneiderman Fish; Journal of Medicinal Chemistry; vol. 25; nb. 5; (1982); p. 596 - 599, View in Reaxys 53 of 64

Bioassay Category

In Vivo (Animal models)

Bioassay Details

Number of rabbits convulsed at 20 mg/kg dose administered intravenously out of 4 rabbits tested

Biological Species/NCBI rabbit ID Substance RN

908277View in Reaxys

Substance Route of Adm.

intravenous administration

Measurement Parameter

Number

Measurement Object

Number of rabbits convulsed

Quantitative value

Consroe; Martin; Schneiderman Fish; Journal of Medicinal Chemistry; vol. 25; nb. 5; (1982); p. 596 - 599, View in Reaxys 54 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Toxicity was measured as population growth impairment to Tetrahymena pyriformis

Biological Species/NCBI Tetrahymena pyriformis ID Substance RN

908277View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Schultz, T. Wayne; Chemical Research in Toxicology; vol. 12; nb. 12; (1999); p. 1262 - 1267, View in Reaxys 55 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Ciliate toxicity of the compound in Tetrahymena pyriformis

Biological Species/NCBI Tetrahymena pyriformis ID Substance RN

908277View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Schueuermann, Gerrit; Aptula, Aynur O.; Kuehne, Ralph; Ebert, Ralf-Uwe; Chemical Research in Toxicology; vol. 16; nb. 8; (2003); p. 974 - 987, View in Reaxys 56 of 64

Target Name

Cytochrome P450 1A1 [human]

Target Synonyms

cyp1a1 (cytochrome p450 1a1); cypia1; cytochrome p450 1a1; cytochrome p450 form 6; cytochrome p450-c; cytochrome p450-p1

Target Uniprot ID

p04798

Target PDB ID

4i8v

Target, Subunit, Species Cytochrome P450 1A1 [human] Target Mutant/Chimera Details

Cytochrome P450 1A1 [human]:Wild

Target Species (Bioactivity)

human

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57 of 64

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

908277View in Reaxys

Substance Name

table 1, entry 2

Substance Dose

0 µM

Measurement Parameter

Unit

µM

Measurement Object

Apparent

Quantitative value

3.04

Statistical sgnificance (p-value)

0.0001

Measurement pX

5.52

Concomitants: Compound RN

225973; 77911

Concomitants: Compound name

Ethoxyresorufin; NADPH

Concomitants: Compound role

SUB; COE

Target Name

Cytochrome P450 1A1 [human]

Target Synonyms

cyp1a1 (cytochrome p450 1a1); cypia1; cytochrome p450 1a1; cytochrome p450 form 6; cytochrome p450-c; cytochrome p450-p1

Target Uniprot ID

p04798

Target PDB ID

4i8v

Target, Subunit, Species Cytochrome P450 1A1 [human] Target Mutant/Chimera Details

Cytochrome P450 1A1 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

908277View in Reaxys

Substance Name

table 1, entry 2

Substance Dose

0 µM

Measurement Parameter

IC50

Unit

µM

Quantitative value

13.8

Measurement pX

4.86

33/40

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58 of 64

Concomitants: Compound RN

225973; 77911

Concomitants: Compound name

Ethoxyresorufin; NADPH

Concomitants: Compound role

SUB; COE

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal concentration was measured in brine shrimp upon treatment with the compound dissolved in DMSO

Biological Species/NCBI Artemia salina ID Substance RN

908277View in Reaxys

Measurement Parameter

LC50

Unit

µM

Measurement Object

Lethal concentration against brine shrimp with the compound dissolved in DMSO

Qualitative value

Quantitative value

100

Measurement pX

Patent; Basil Don Roufogalis; Colin Charles Duke; Qian Li; US5859067; (A); (1999), View in Reaxys 59 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal concentration was measured in brine shrimp upon treatment with the compound dissolved in DMSO

Biological Species/NCBI Artemia salina ID Substance RN

908277View in Reaxys

Measurement Parameter

LC50

Unit

µg/mL

Measurement Object

Lethal concentration against brine shrimp with the compound dissolved in DMSO

Qualitative value

Quantitative value

Measurement pX

Patent; Basil Don Roufogalis; Colin Charles Duke; Qian Li; US5859067; (A); (1999), View in Reaxys 60 of 64

Target Name

Calcium ATPase [human]

Target Synonyms

calcium atpase

Target, Subunit, Species Calcium ATPase [human] Target Mutant/Chimera Details

Calcium ATPase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibition of Ca++ transporting ATPase from human erythrocyte plasma membrane upon incubation for 1 h at 37 degree C, pH 7.4

Cells/Cell Lines

red blood cell plasma membrane

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Substance RN

908277View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; Basil Don Roufogalis; Colin Charles Duke; Qian Li; US5859067; (A); (1999), View in Reaxys 61 of 64

Target Name

Calcium ATPase [human]

Target Synonyms

calcium atpase

Target, Subunit, Species Calcium ATPase [human] Target Mutant/Chimera Details

Calcium ATPase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of compound (dissolved in DMSO) against human Ca2+-ATPase in erythrocyte membranes upon incubation in 50 mM Hepes, pH 7.4 at 37 degree C for 1 h using Microplate method

Cells/Cell Lines

red blood cell membranes

Substance RN

908277View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; The University of Sydney; US5741821; (1998); (A1) English, View in Reaxys 62 of 64

Target Name

hydrogen:potassium-exchanging ATPase

Target Synonyms

(k+ + h+)-atpase; atp phosphohydrolase (h+/k+-exchanging); h(+)/k(+)-atpase; h(+)/k(+)exchanging atpase; h+-k+-atpase; h+/k+-atpase; h+/k+-exchanging atpase; h,k-atpase; hydrogen/potassium-exchanging atpase; hydrogen:potassium exchanging atpase; hydrogen:potassium-exchanging atpase

Target, Subunit, Species hydrogen:potassium-exchanging ATPase Target Mutant/Chimera Details

hydrogen:potassium-exchanging ATPase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of compound against H+,K+-ATPase was measured

Substance RN

908277View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; The University of Sydney; US5741821; (1998); (A1) English, View in Reaxys 63 of 64

Target Name

sodium:potassium-exchanging ATPase

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Target Synonyms

(na+ + k+)-activated atpase; (na+ + k+)-atpase; atp phosphohydrolase (na+/k+-exchanging); na(+)/k(+)-atpase; na(+)/k(+)-exchanging atpase; na+,k+-atpase; na+/k+-atpase; na +/k+-exchanging atpase; na,k-activated atpase; sodium/potassium-exchanging atpase; sodium/potassium-transporting atpase; sodium:potassium exchanging atpase; sodium:potassium-exchanging atpase

Target, Subunit, Species sodium:potassium-exchanging ATPase Target Mutant/Chimera Details

sodium:potassium-exchanging ATPase:Wild

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity of compound against Na+/K+ ATPase was measured

Substance RN

908277View in Reaxys

Qualitative Results

Not Published

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; The University of Sydney; US5741821; (1998); (A1) English, View in Reaxys 64 of 64

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal concentration of compound (dissolved in DMSO) against Brine shrimp (n=10) was determined after 24 h by measuring number of survival

Biological Species/NCBI Artemia salina ID Substance RN

908277View in Reaxys

Measurement Parameter

LC50

Unit

µM

Measurement Object

Number of survival

Qualitative value

Quantitative value

100

Measurement pX

Patent; The University of Sydney; US5741821; (1998); (A1) English, View in Reaxys

Reaxys ID 1970018 View in Reaxys

2/5 CAS Registry Number: 58545-61-2 Chemical Name: 1,3-dihydroxy-5-[5'-(2H3)-pentyl]benzene; 5'-2H3-olivetol; Olivetol-5'-D3 Linear Structure Formula: C11H13 (2)H3O2 Molecular Formula: C11H16O2 Molecular Weight: 183.223 Type of Substance: isocyclic InChI Key: IRMPFYJSHJGOPE-FIBGUPNXSA-N Note:

Substance Label (3) Label References 14c

Nikas, Spyros P.; Thakur, Ganesh A.; Parrish, Damon; Alapafuja, Shakiru O.; Huestis, Marilyn A.; Makriyannis, Alexandros; Tetrahedron; vol. 63; nb. 34; (2007); p. 8112 - 8123, View in Reaxys

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Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys

Girard, Michel; Moir, David B.; Apsimon, John W.; Canadian Journal of Chemistry; vol. 65; (1987); p. 189 - 190, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.818

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.46

Lipinski Number

Veber Number

Melting Point (3) 1 of 3

Melting Point [°C]

50 - 51

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 2 of 3

Melting Point [°C]

38 - 39

Girard, Michel; Moir, David B.; Apsimon, John W.; Canadian Journal of Chemistry; vol. 65; (1987); p. 189 - 190, View in Reaxys 3 of 3

Melting Point [°C]

39 - 40

Pitt; Hobbs; Schran; et al.; Journal of Labelled Compounds; vol. 11; nb. 4; (1975); p. 551 - 575, View in Reaxys NMR Spectroscopy (5) 1 of 5

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

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

500.13

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 2 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

500.13

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 3 of 5

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

13C

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

125.77

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Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 4 of 5

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

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

125.77

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 5 of 5

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

Solvents (NMR Spectro- CDCl3 scopy) Girard, Michel; Moir, David B.; Apsimon, John W.; Canadian Journal of Chemistry; vol. 65; (1987); p. 189 - 190, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CDCl3

Comment (IR Spectroscopy)

3400 cm**(-1)

Girard, Michel; Moir, David B.; Apsimon, John W.; Canadian Journal of Chemistry; vol. 65; (1987); p. 189 - 190, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys

Reaxys ID 1970044 View in Reaxys

3/5

H C

CAS Registry Number: 34818-58-1 Chemical Name: 5-n-Amylresorcin-<4,6-14C>; 5-n-Amylresorcin-[4,6-14C] Linear Structure Formula: C9 (14)C2H16O2 Molecular Formula: C11H16O2 Molecular Weight: 184.225 Type of Substance: isocyclic InChI Key: IRMPFYJSHJGOPE-DEKVXHJQSA-N Note:

H 14C OH

Substance Label (1) Label References III

Liebman et al.; Journal of Labelled Compounds; vol. 7; (1971); p. 241,243, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.818

H Bond Donors

H Bond Acceptors

38/40

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Rotatable Bonds

TPSA

40.46

Lipinski Number

Veber Number

Reaxys ID 2453685 View in Reaxys

4/5 CAS Registry Number: 38228-31-8 Chemical Name: 3H-Olivetol Linear Structure Formula: C11H14T2O2 Molecular Formula: C11H16O2 Molecular Weight: 184.231 Type of Substance: isocyclic InChI Key: IRMPFYJSHJGOPE-WNNBQYHSSA-N Note:

OH 3H

H OH

Substance Label (1) Label References 5

Gill; Jones; Journal of Labelled Compounds; vol. 8; (1972); p. 237,241, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.818

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.46

Lipinski Number

Veber Number

Reaxys ID 9333775 View in Reaxys

5/5 CAS Registry Number: 504396-87-6 Chemical Name: 1,3-dihydroxy-5-[4'-(2H2)-5'-(2H3)-pentyl]benzene Linear Structure Formula: C11H11 (2)H5O2 Molecular Formula: C11H16O2 Molecular Weight: 185.207 Type of Substance: isocyclic InChI Key: IRMPFYJSHJGOPE-ZBJDZAJPSA-N Note:

H OH

H 2

Substance Label (2) Label References 14b

Nikas, Spyros P.; Thakur, Ganesh A.; Parrish, Damon; Alapafuja, Shakiru O.; Huestis, Marilyn A.; Makriyannis, Alexandros; Tetrahedron; vol. 63; nb. 34; (2007); p. 8112 - 8123, View in Reaxys

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.818

H Bond Donors

H Bond Acceptors

Rotatable Bonds

39/40

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TPSA

40.46

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

50 - 51

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys NMR Spectroscopy (4) 1 of 4

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

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

500.13

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 2 of 4

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

500.13

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 3 of 4

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

13C

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

125.77

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys 4 of 4

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

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

125.77

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 45; nb. 12; (2002); p. 1065 - 1076, View in Reaxys

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