(2S)-2-({[(1R)-1-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]ethyl](hydroxy)phosphoryl}oxy)-3-phenylpropanoic acid

• ChemBase ID: 6365
• Molecular Formular: C22H27N2O8P
• Molecular Mass: 478.432141
• Monoisotopic Mass: 478.15050246
• SMILES: C(=O)(O)[C@H](Cc1ccccc1)O[P@](=O)(O)[C@H](C)NC(=O)[C@H](C)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H]([P@](=O)(O[C@H](C(=O)O)Cc1ccccc1)O)C)C)OCc1ccccc1
• InChI: InChI=1S/C22H27N2O8P/c1-15(23-22(28)31-14-18-11-7-4-8-12-18)20(25)24-16(2)33(29,30)32-19(21(26)27)13-17-9-5-3-6-10-17/h3-12,15-16,19H,13-14H2,1-2H3,(H,23,28)(H,24,25)(H,26,27)(H,29,30)/t15-,16+,19-/m0/s1
• InChIKey: UPJNMOBJDSFRTI-FCEWJHQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-({[(1R)-1-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]ethyl](hydroxy)phosphoryl}oxy)-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-{[(1R)-1-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]ethyl(hydroxy)phosphoryl]oxy}-3-phenylpropanoic acid
• Synonyms: O-(((1R)-((N-PHENYLMETHOXYCARBONYL-L-ALANYL)AMINO)ETHYL)HYDROXYPHOSPHONO)-L-BENZYLACETIC ACID

Database IDs

• PubChem SID: 162103393
• PubChem CID: 5492457

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8442411
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.4515146
• LogD (pH = 7.4): -3.1338668
• Log P: 2.3451416
• Molar Refractivity: 117.9016 cm^3
• Polarizability: 46.516586 Å^3
• Polar Surface Area: 151.26 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.35
• LOG S: -4.41
• Solubility (Water): 1.87e-02 g/l

DETAILS

DrugBank - DB08762

Drug information: experimental