4-{[(1S)-1-[hydroxy({[(2-phenylethyl)carbamoyl]methoxy})phosphoryl]-2-phenylethyl]carbamoyl}butanoic acid

• ChemBase ID: 5514
• Molecular Formular: C23H29N2O7P
• Molecular Mass: 476.459321
• Monoisotopic Mass: 476.17123791
• SMILES: c1(ccccc1)CCNC(=O)CO[P@](=O)(O)[C@@H](Cc1ccccc1)NC(=O)CCCC(=O)O
• Canonical SMILES: O=C(CO[P@@](=O)([C@@H](Cc1ccccc1)NC(=O)CCCC(=O)O)O)NCCc1ccccc1
• InChI: InChI=1S/C23H29N2O7P/c26-20(12-7-13-23(28)29)25-22(16-19-10-5-2-6-11-19)33(30,31)32-17-21(27)24-15-14-18-8-3-1-4-9-18/h1-6,8-11,22H,7,12-17H2,(H,24,27)(H,25,26)(H,28,29)(H,30,31)/t22-/m0/s1
• InChIKey: DKQZZKSBRCTCQU-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S)-1-[hydroxy({[(2-phenylethyl)carbamoyl]methoxy})phosphoryl]-2-phenylethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: 4-{[(1S)-1-{hydroxy[(2-phenylethyl)carbamoyl]methoxyphosphoryl}-2-phenylethyl]carbamoyl}butanoic acid
• Synonyms: N-{[2-({[1-(4-CARBOXYBUTANOYL)AMINO]-2-PHENYLETHYL}-HYDROXYPHOSPHINYL)OXY]ACETYL}-2-PHENYLETHYLAMINE

Database IDs

• PubChem SID: 99444352; 160968942
• PubChem CID: 447154

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2426745
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.9109547
• LogD (pH = 7.4): -3.6366663
• Log P: 1.7550628
• Molar Refractivity: 121.3997 cm^3
• Polarizability: 47.61285 Å^3
• Polar Surface Area: 142.03 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.88
• LOG S: -5.28
• Solubility (Water): 2.50e-03 g/l

DETAILS

DrugBank - DB07881

Drug information: experimental