benzyl (3S,6S)-6-({2-[(3S)-3-{[(2R)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 161133
• Molecular Formular: C42H44N2O11
• Molecular Mass: 752.80556
• Monoisotopic Mass: 752.29451024
• SMILES: C1([C@@H](OC([C@H](C1O)O)C(=O)OCc1ccccc1)OC(=O)CN1C(=O)[C@H](CCc2c1cccc2)N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1)O
• Canonical SMILES: O=C(CN1C(=O)[C@H](CCc2c1cccc2)N[C@@H](C(=O)OCc1ccccc1)CCc1ccccc1)O[C@@H]1OC(C(=O)OCc2ccccc2)[C@H](C(C1O)O)O
• InChI: InChI=1S/C42H44N2O11/c45-34(54-42-37(48)35(46)36(47)38(55-42)41(51)53-26-29-16-8-3-9-17-29)24-44-33-19-11-10-18-30(33)21-23-31(39(44)49)43-32(22-20-27-12-4-1-5-13-27)40(50)52-25-28-14-6-2-7-15-28/h1-19,31-32,35-38,42-43,46-48H,20-26H2/t31-,32+,35?,36-,37?,38?,42+/m0/s1
• InChIKey: KFDKDEAVRBTETI-JWAAWQDOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (3S,6S)-6-({2-[(3S)-3-{[(2R)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: benzyl (3S,6S)-6-({2-[(3S)-3-{[(2R)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 1'-epi-Benazeprilat Acyl-β-D-glucuronide Dibenzyl Ester

Database IDs

• PubChem SID: 162255268
• PubChem CID: 71313631

CALCULATED PROPERTIES

• Acid pKa: 12.161957
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 4.466618
• LogD (pH = 7.4): 4.694604
• Log P: 4.698453
• Molar Refractivity: 196.7722 cm^3
• Polarizability: 78.40719 Å^3
• Polar Surface Area: 181.16 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate

DETAILS

Toronto Research Chemicals - B119795

A protected byproduct produced during the synthesis of Benazepril metabolites