(2S)-2-[3-(aminomethyl)phenyl]-3-{[(1R)-1-{[(benzyloxy)carbonyl]amino}-2-methylpropyl](hydroxy)phosphoryl}propanoic acid

• ChemBase ID: 4920
• Molecular Formular: C22H29N2O6P
• Molecular Mass: 448.449221
• Monoisotopic Mass: 448.17632329
• SMILES: [C@@H](C(=O)O)(c1cccc(c1)CN)C[P@](=O)([C@H](C(C)C)NC(=O)OCc1ccccc1)O
• Canonical SMILES: NCc1cccc(c1)[C@@H](C(=O)O)C[P@](=O)([C@H](C(C)C)NC(=O)OCc1ccccc1)O
• InChI: InChI=1S/C22H29N2O6P/c1-15(2)20(24-22(27)30-13-16-7-4-3-5-8-16)31(28,29)14-19(21(25)26)18-10-6-9-17(11-18)12-23/h3-11,15,19-20H,12-14,23H2,1-2H3,(H,24,27)(H,25,26)(H,28,29)/t19-,20+/m0/s1
• InChIKey: SFUOOKBZBVUDBC-VQTJNVASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[3-(aminomethyl)phenyl]-3-{[(1R)-1-{[(benzyloxy)carbonyl]amino}-2-methylpropyl](hydroxy)phosphoryl}propanoic acid
• IUPAC Traditional name: (2S)-2-[3-(aminomethyl)phenyl]-3-[(1R)-1-{[(benzyloxy)carbonyl]amino}-2-methylpropyl(hydroxy)phosphoryl]propanoic acid
• Synonyms: (2S)-2-[3-(AMINOMETHYL)PHENYL]-3-[(R)-[(1R)-1-{[(BENZYLOXY)CARBONYL]AMINO}-2-METHYLPROPYL](HYDROXY)PHOSPHORYL]PROPANOIC ACID

Database IDs

• PubChem SID: 99443740; 160968352
• PubChem CID: 23653503

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.5329543
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.09898633
• LogD (pH = 7.4): -1.857189
• Log P: 1.2928472
• Molar Refractivity: 116.954 cm^3
• Polarizability: 46.03099 Å^3
• Polar Surface Area: 138.95 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.01
• LOG S: -4.3
• Solubility (Water): 2.27e-02 g/l

DETAILS

DrugBank - DB07269

Drug information: experimental