benzyl N-[(1S)-1-{[(2R)-5-hydroxy-3-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamate

• ChemBase ID: 6335
• Molecular Formular: C22H26N2O5
• Molecular Mass: 398.45224
• Monoisotopic Mass: 398.18417194
• SMILES: O=C(OCc1ccccc1)N[C@@H](Cc1ccccc1)C(=O)N[C@H](C)C(=O)CCO
• Canonical SMILES: OCCC(=O)[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C22H26N2O5/c1-16(20(26)12-13-25)23-21(27)19(14-17-8-4-2-5-9-17)24-22(28)29-15-18-10-6-3-7-11-18/h2-11,16,19,25H,12-15H2,1H3,(H,23,27)(H,24,28)/t16-,19+/m1/s1
• InChIKey: UUOOAGBWJUGBMV-APWZRJJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(2R)-5-hydroxy-3-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(2R)-5-hydroxy-3-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• Synonyms: NALPHA-[(BENZYLOXY)CARBONYL]-N-[(1R)-4-HYDROXY-1-METHYL-2-OXOBUTYL]-L-PHENYLALANINAMIDE

Database IDs

• PubChem SID: 162103382
• PubChem CID: 16220131

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.700426
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.453097
• LogD (pH = 7.4): 2.4530952
• Log P: 2.453097
• Molar Refractivity: 108.0464 cm^3
• Polarizability: 42.14984 Å^3
• Polar Surface Area: 104.73 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.55
• LOG S: -4.44
• Solubility (Water): 1.46e-02 g/l

DETAILS

DrugBank - DB08732

Drug information: experimental