(2S)-2-[({[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]methyl}(hydroxy)phosphoryl)oxy]-3-phenylpropanoic acid

• ChemBase ID: 5002
• Molecular Formular: C21H25N2O8P
• Molecular Mass: 464.405561
• Monoisotopic Mass: 464.1348524
• SMILES: C(=O)(OCc1ccccc1)N[C@H](C(=O)NC[P@@](=O)(O)O[C@H](C(=O)O)Cc1ccccc1)C
• Canonical SMILES: O=C(N[C@H](C(=O)NC[P@](=O)(O[C@H](C(=O)O)Cc1ccccc1)O)C)OCc1ccccc1
• InChI: InChI=1S/C21H25N2O8P/c1-15(23-21(27)30-13-17-10-6-3-7-11-17)19(24)22-14-32(28,29)31-18(20(25)26)12-16-8-4-2-5-9-16/h2-11,15,18H,12-14H2,1H3,(H,22,24)(H,23,27)(H,25,26)(H,28,29)/t15-,18-/m0/s1
• InChIKey: ICACWKLCNCPHAM-YJBOKZPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[({[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]methyl}(hydroxy)phosphoryl)oxy]-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-({[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]methyl(hydroxy)phosphoryl}oxy)-3-phenylpropanoic acid
• Synonyms: O-(((1R)-((N-(PHENYL-METHOXY-CARBONYL)-ALANYL)-AMINO)METHYL)HYDROXYPHOSPHINYL)3-L-PHENYLLACTATE

Database IDs

• PubChem SID: 160968434; 99443822
• PubChem CID: 16741275

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.89551497
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.6170411
• LogD (pH = 7.4): -3.282744
• Log P: 2.2248669
• Molar Refractivity: 113.1527 cm^3
• Polarizability: 44.690918 Å^3
• Polar Surface Area: 151.26 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.21
• LOG S: -4.34
• Solubility (Water): 2.13e-02 g/l

DETAILS

DrugBank - DB07351

Drug information: experimental