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Date
1 substances in Reaxys
2018-03-20 14h:30m:50s (EST)
O
1. Query HO H 2N
Search as: As drawn AND (IDE.XRN=2803960)
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Reaxys ID 2803960 View in Reaxys
1/1 CAS Registry Number: 1132-26-9 Chemical Name: 2-methyl-3-phenylalanine; alpha-methylphenylalanine; 2-amino-3-phenyl-2-methylpropanoic acid; α-methylphenylalaninne; α-Methylphenylalanine; 2-amino-2-methyl-3phenyl-propionic acid; 2-Amino-2-methyl-3-phenyl-propionsaeure Linear Structure Formula: C10H13NO2 Molecular Formula: C10H13NO2 Molecular Weight: 179.219 Type of Substance: isocyclic InChI Key: HYOWVAAEQCNGLE-UHFFFAOYSA-N Note:
O HO
H 2N
Substance Label (6) Label References 14
Lacivita, Enza; Kwizera, Chantal; Perrone, Roberto; Lucente, Ermelinda; Antunes, Ines F.; Colabufo, Nicola A.; Niso, Mauro; Elsinga, Philip H.; Leopoldo, Marcello; De Giorgio, Paola; Bioorganic and Medicinal Chemistry; vol. 25; nb. 1; (2017); p. 277 - 292, View in Reaxys
α-methyl-Phe
Remelli, Maurizio; Faccini, Stefania; Conato, Chiara; Chirality; vol. 26; nb. 6; (2014); p. 313 - 318, View in Reaxys
3c
Wang, Boyuan; Zhang, Wei; Zhang, Leilei; Du, Da-Ming; Liu, Gang; Xu, Jiaxi; European Journal of Organic Chemistry; nb. 2; (2008); p. 350 - 355, View in Reaxys
7+BnBr
Belokon', Yuri N.; Bhave, Devayani; D'Addario, Daniela; Groaz, Elizabetta; Maleev, Viktor; North, Michael; Pertrosyan, Armine; Tetrahedron Letters; vol. 44; nb. 10; (2003); p. 2045 - 2048, View in Reaxys
α-Me-Phe
Belokon, Yuri N.; Kochetkov, Konstantin A.; Churkina, Tatiana D.; Ikonnikov, Nikolai S.; Chesnokov, Alexey A.; Larionov, Oleg V.; Singh, Ishwar; Parmar, Virinder S.; Vyskocil, Stepan; Kagan, Henri B.; Journal of Organic Chemistry; vol. 65; nb. 21; (2000); p. 7041 - 7048, View in Reaxys
DL-43
Chenault, H. Keith; Dahmer, Juergen; Whitesides, George M.; Journal of the American Chemical Society; vol. 111; nb. 16; (1989); p. 6354 - 6364, View in Reaxys
Patent-Specific Data (2) Prophetic ComLocation in Patent References pound prophetic product
Patent; VERENIUM CORPORATION; US2011/27346; (2011); (A1) English, View in Reaxys; Patent; Weiner, David P.; Varvak, Alexander; Richardson, Toby; Podar, Mircea; Burke, Ellen; Healey, Shaun; US2012/177722; (2012); (A1) English, View in Reaxys Claim
Patent; Imperial Chemical Industries PLC; US4474767; (1984); (A1) English, View in Reaxys; Patent; The Rockefeller University; US5817628; (1998); (A1) English, View in Reaxys
Druglikeness (1) 1 of 1
LogP
-1.269
H Bond Donors
2
H Bond Acceptors
3
Rotatable Bonds
3
TPSA
63.32
Lipinski Number
4
Veber Number
2
Related Structure (1) References Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys Derivative (5) Comment (Derivative)
References
Hydrochlorid. F: Patent; Merck and Co.; Inc.; US3758559; (1973); Chem.Abstr.; vol. 79; nb. 146849, View in Reaxys 241-244 grad; UV
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HCl: Bollinger; Journal of medicinal chemistry; vol. 14; nb. 4; (1971); p. 373 - 375, View in Reaxys C10H13NO2*HCl: aus gleichen Teilen der enantiomeren Basen u. wss. Salzsaeure; F: 241-244grad, UV-Max. (Me.): 252.5 nm, 258 nm u. 264 nm Hydrochlorid: F: 214grad; <α>(589)20: -8.6grad (c=1, H2O)
Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys
Hydrochlorid: F: 240-245grad <Zers.>
Cohen; Lo; Journal of Biological Chemistry; vol. 245; (1970); p. 5718,5724, View in Reaxys
Hydrochlorid Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143, View in Reaxys C10H13NO2*HCl: Zers.-Pkt.: 234.5-241grad (aus 95percentig. wss. A.+Ae.); sintert bei ca. 220grad; IR-Banden; NMR-Sp. Melting Point (6) 1 of 6
Melting Point [°C]
230
Comment (Melting Point)
with Sublimation
Kuebel,B. et al.; Chemische Berichte; vol. 112; (1979); p. 128 - 137, View in Reaxys 2 of 6
Melting Point [°C]
275 - 276
Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955, View in Reaxys 3 of 6
Melting Point [°C]
318
Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys 4 of 6
Melting Point [°C]
275 - 276
Solvent (Melting Point)
aq. ethanol
Jean; Anatol; Bulletin de la Societe chimique de France; vol. 10; (1970); p. 3698 - 3703, View in Reaxys 5 of 6
Melting Point [°C]
294.5 - 295
Comment (Melting Point)
Decomposition.
Stein et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 700,702, View in Reaxys 6 of 6
Melting Point [°C]
293 - 294
Solvent (Melting Point)
H2O
Comment (Melting Point)
Decomposition.
Herbst; Johnson; Journal of the American Chemical Society; vol. 54; (1932); p. 2463,2467, View in Reaxys Sublimation (1) Comment (Sublimation)
References
>230grad
Patent; BASF AG; FR2237892; (1975); DE2336718; Chem.Abstr.; vol. 82; nb. 156263, View in Reaxys
Further Information (4) Description (Fur- References ther Information)
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Further information
Patent; Merck and Co.; Inc.; US3758559; (1973); Chem.Abstr.; vol. 79; nb. 146849, View in Reaxys
Further information
Bollinger; Journal of medicinal chemistry; vol. 14; nb. 4; (1971); p. 373 - 375, View in Reaxys
Further information
Lee et al.; Chemical and Pharmaceutical Bulletin; vol. 17; (1969); p. 2540,2544, View in Reaxys
Further information
Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143, View in Reaxys
Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
aq. HCl
Optical Rotatory Power [deg]
-4.5
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
20
Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606, View in Reaxys NMR Spectroscopy (7) 1 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- D2O scopy) Liu, Weiguo; Ray, Paul; Benezra, Steven A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1995); p. 553 - 560, View in Reaxys 2 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476, View in Reaxys 3 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476, View in Reaxys 4 of 7
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- D2O scopy) Comment (NMR Spectroscopy)
1H-1H
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Liu, Weiguo; Ray, Paul; Benezra, Steven A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1995); p. 553 - 560, View in Reaxys 5 of 7
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- tetradeuteriomethanol scopy) Comment (NMR Spectroscopy)
1H-1H.
Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476, View in Reaxys 6 of 7
Description (NMR Spec- NMR with shift reagents troscopy) Hulst; De Vries; Feringa; Journal of Organic Chemistry; vol. 59; nb. 24; (1994); p. 7453 - 7458, View in Reaxys
7 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Kuebel,B. et al.; Chemische Berichte; vol. 112; (1979); p. 128 - 137, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Jean; Anatol; Bulletin de la Societe chimique de France; vol. 10; (1970); p. 3698 - 3703, View in Reaxys Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence
Delvalle et al.; Biochemical Journal; vol. 170; (1978); p. 449,451, View in Reaxys
Medchem (4) 1 of 4
Target Name
Phenylalanine-4-hydroxylase [Rattus norvegicus]
Target Synonyms
pah; phe-4-monooxygenase; phenylalanine-4-hydroxylase
Target Uniprot ID
p04176
Target PDB ID
1phz; 2phm
Target, Subunit, Species Phenylalanine-4-hydroxylase [Rattus norvegicus] Target Mutant/Chimera Details
Phenylalanine-4-hydroxylase [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Substance Action on Target
Inhibitor
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Ratio of substrate to that of compound to give less than 50 inhibition of rat liver phenylalanine hydroxylase; 1/1 upon incubation in 10 umoles of sodium phosphate, pH 7.4 for 20 minutes at 37 degree C
Biological Species/NCBI Rattus norvegicus ID
2 of 4
Substance RN
2803960View in Reaxys
Measurement Parameter
Ratio
Qualitative value
ND
Target Name
Tyrosine 3-monooxygenase [taurine cattle]
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Target Synonyms
th; tyrosine 3-hydroxylase; tyrosine 3-monooxygenase
Target Uniprot ID
p17289
Target, Subunit, Species Tyrosine 3-monooxygenase [taurine cattle] Target Mutant/Chimera Details
Tyrosine 3-monooxygenase [taurine cattle]:Wild
Target Species (Bioactivity)
taurine cattle
Substance Action on Target
Inhibitor
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Percent inhibition of Tyrosine hydroxylase at a concentration of 1E-4 M using unfortified (without addition of reduced pteridine cofactor) beef adrenal medulla tissue
Biological Species/NCBI taurine cattle ID
3 of 4
Substance RN
2803960View in Reaxys
Substance Dose
= 0.0001 M
Measurement Parameter
% Inhibition
Unit
%
Qualitative value
=
Quantitative value
86
Measurement pX
4.79
Target Name
General Amino-Acid Permease Gap1 [Saccharomyces cerevisiae]
Target Synonyms
general amino-acid permease gap1
Target, Subunit, Species General Amino-Acid Permease Gap1 [Saccharomyces cerevisiae] Target Mutant/Chimera Details
General Amino-Acid Permease Gap1 [Saccharomyces cerevisiae]:Wild
Target Species (Bioactivity)
Saccharomyces cerevisiae
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Percent inhibition of [14C] L-citrulline (1 mM ) transport in nitrogen-starved Saccharomyces cerevisiae by General amino acid permease (Gap1) upon incubation with compound using short term assay
Biological Species/NCBI Saccharomyces cerevisiae ID
4 of 4
Substance RN
2803960View in Reaxys
Qualitative Results
No inhibition
Measurement Parameter
Activity
Unit
%
Measurement Object
Inhibition
Qualitative value
<
Quantitative value
15
Target Name
Pyridoxal Phosphate [Rattus norvegicus]
Target Synonyms
pyridoxal phosphate
Target, Subunit, Species Pyridoxal Phosphate [Rattus norvegicus] Target Mutant/Chimera Details
Pyridoxal Phosphate [Rattus norvegicus]:Wild
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Target Species (Bioactivity)
Rattus norvegicus
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Affinity constant was evaluated for rat Pyridoxal phosphate (0.1 mM) by ''deltaA method''
Biological Species/NCBI Rattus norvegicus ID Substance RN
2803960View in Reaxys
Qualitative Results
1/Kd not calculated
Measurement Parameter
Qualitative
Measurement Object
1/Kd
Concomitants: Compound name
Pyridoxal phosphate
Concomitants: Compound role
SUB
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