benzyl N-[(2S)-1-[(2S)-2-{[(2S,3R)-3-hydroxy-1-phenylbutan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate

• ChemBase ID: 4541
• Molecular Formular: C26H33N3O5
• Molecular Mass: 467.55732
• Monoisotopic Mass: 467.24202117
• SMILES: C(c1ccccc1)OC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H]([C@H](O)C)Cc1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H]([C@H](O)C)Cc1ccccc1)C)OCc1ccccc1
• InChI: InChI=1S/C26H33N3O5/c1-18(27-26(33)34-17-21-12-7-4-8-13-21)25(32)29-15-9-14-23(29)24(31)28-22(19(2)30)16-20-10-5-3-6-11-20/h3-8,10-13,18-19,22-23,30H,9,14-17H2,1-2H3,(H,27,33)(H,28,31)/t18-,19+,22-,23-/m0/s1
• InChIKey: MACLRJNEKXUAJK-YDLSIGKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(2S)-1-[(2S)-2-{[(2S,3R)-3-hydroxy-1-phenylbutan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate
• IUPAC Traditional name: benzyl N-[(2S)-1-[(2S)-2-{[(2S,3R)-3-hydroxy-1-phenylbutan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate
• Synonyms: N-BENZYLOXYCARBONYL-ALA-PRO-3-AMINO-4-PHENYL-BUTAN-2-OL

Database IDs

• PubChem SID: 160967973; 99443357
• PubChem CID: 6323185

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.287801
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.536154
• LogD (pH = 7.4): 2.5361536
• Log P: 2.536154
• Molar Refractivity: 127.6316 cm^3
• Polarizability: 49.922974 Å^3
• Polar Surface Area: 107.97 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.87
• LOG S: -4.5
• Solubility (Water): 1.49e-02 g/l

DETAILS

DrugBank - DB06886

Drug information: experimental