(2S,3S,4S,5R,6S)-6-({2-[(3S)-3-{[(1R)-1-carboxy-3-phenylpropyl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 161127
• Molecular Formular: C28H32N2O11
• Molecular Mass: 572.56048
• Monoisotopic Mass: 572.20060985
• SMILES: C1[C@@H](C(=O)N(c2c(C1)cccc2)CC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)N[C@H](CCc1ccccc1)C(=O)O
• Canonical SMILES: O=C(CN1C(=O)[C@H](CCc2c1cccc2)N[C@@H](C(=O)O)CCc1ccccc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C28H32N2O11/c31-20(40-28-23(34)21(32)22(33)24(41-28)27(38)39)14-30-19-9-5-4-8-16(19)11-13-17(25(30)35)29-18(26(36)37)12-10-15-6-2-1-3-7-15/h1-9,17-18,21-24,28-29,32-34H,10-14H2,(H,36,37)(H,38,39)/t17-,18+,21-,22-,23+,24-,28+/m0/s1
• InChIKey: OJAPCMFSNNRWFW-IPFSVVGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[(3S)-3-{[(1R)-1-carboxy-3-phenylpropyl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[(3S)-3-{[(1R)-1-carboxy-3-phenylpropyl]amino}-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1'-epi-Benazeprilat Acyl-β-D-glucuronide; Benazeprilat Acyl-β-D-glucuronide

Database IDs

• CAS Number: 1240792-52-2
• PubChem SID: 162255262
• PubChem CID: 71313626

CALCULATED PROPERTIES

• Acid pKa: 2.7422109
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.645409
• LogD (pH = 7.4): -5.016204
• Log P: -1.7703961
• Molar Refractivity: 138.0088 cm^3
• Polarizability: 55.208046 Å^3
• Polar Surface Area: 203.16 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; DMSO; Methanol
• Apperance: Crystalline Solid
• Melting Point: 270-272°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - B119770

A metabolite of Benazepril, which is used as an antihypertensive.

Toronto Research Chemicals - B119775

A byproduct produced during the synthesis of Benazepril metabolites