(2R)-2-{[(3S)-1-(carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid

• ChemBase ID: 161123
• Molecular Formular: C22H24N2O5
• Molecular Mass: 396.43636
• Monoisotopic Mass: 396.16852188
• SMILES: C1[C@@H](C(=O)N(c2c(C1)cccc2)CC(=O)O)N[C@H](CCc1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)CN1C(=O)[C@H](CCc2c1cccc2)N[C@@H](C(=O)O)CCc1ccccc1
• InChI: InChI=1S/C22H24N2O5/c25-20(26)14-24-19-9-5-4-8-16(19)11-13-17(21(24)27)23-18(22(28)29)12-10-15-6-2-1-3-7-15/h1-9,17-18,23H,10-14H2,(H,25,26)(H,28,29)/t17-,18+/m0/s1
• InChIKey: MADRIHWFJGRSBP-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(3S)-1-(carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid
• IUPAC Traditional name: (2R)-2-{[(3S)-1-(carboxymethyl)-2-oxo-4,5-dihydro-3H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid
• Synonyms: (3S)-3-[[(1S)-1-Carboxy-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid; Benazeprilat

Database IDs

• CAS Number: 86541-78-8
• PubChem SID: 162255258
• PubChem CID: 63001

CALCULATED PROPERTIES

• Acid pKa: 3.0840318
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.0197214
• LogD (pH = 7.4): -2.7792194
• Log P: 0.15017611
• Molar Refractivity: 105.7102 cm^3
• Polarizability: 41.37309 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: White Solid
• Melting Point: 254-256°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B119760

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

REFERENCES

• Kitagawa, H., et al.: J. Vet. Med. Sci., 65, 701 (2003)
• Toutain, P., et al.: J. Vet. Pharmacol. Ther., 27, 515 (2003)
• Wang, X., et al.: J. Pharm. Biomed. Anal., 44, 224 (2003)