benzyl N-[(1R)-1-{[(2S,3E)-5,6-dioxohex-3-en-2-yl]carbamoyl}-2-phenylethyl]carbamate

• ChemBase ID: 1580
• Molecular Formular: C23H24N2O5
• Molecular Mass: 408.44706
• Monoisotopic Mass: 408.16852188
• SMILES: O=C(OCc1ccccc1)N[C@H](Cc1ccccc1)C(=O)N[C@@H](C)/C=C/C(=O)C=O
• Canonical SMILES: O=CC(=O)/C=C/[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C23H24N2O5/c1-17(12-13-20(27)15-26)24-22(28)21(14-18-8-4-2-5-9-18)25-23(29)30-16-19-10-6-3-7-11-19/h2-13,15,17,21H,14,16H2,1H3,(H,24,28)(H,25,29)/b13-12+/t17-,21+/m0/s1
• InChIKey: NOXVWFAAXREWMI-GURWAVDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1R)-1-{[(2S,3E)-5,6-dioxohex-3-en-2-yl]carbamoyl}-2-phenylethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1R)-1-{[(2S,3E)-5,6-dioxohex-3-en-2-yl]carbamoyl}-2-phenylethyl]carbamate
• Synonyms: [1-(1-Methyl-4,5-Dioxo-Pent-2-Enylcarbamoyl)-2-Phenyl-Ethyl]-Carbamic Acid Benzyl Ester

Database IDs

• PubChem SID: 160965037; 46507094
• PubChem CID: 5287438

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.429878
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6502187
• LogD (pH = 7.4): 3.6502185
• Log P: 3.6502187
• Molar Refractivity: 112.8197 cm^3
• Polarizability: 43.199146 Å^3
• Polar Surface Area: 101.57 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.49
• LOG S: -5.38
• Solubility (Water): 1.70e-03 g/l

DETAILS

DrugBank - DB01810

Drug information: experimental