2-[(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-(2H5)phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetic acid

• ChemBase ID: 161118
• Molecular Formular: C24H28N2O5
• Molecular Mass: 424.48952
• Monoisotopic Mass: 424.19982201
• SMILES: c1cccc(c1)CC[C@H](N[C@@H]1C(=O)N(c2c(CC1)cccc2)CC(=O)O)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H]1CCc2c(N(C1=O)CC(=O)O)cccc2)CCc1ccccc1
• InChI: InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)/t19-,20-/m0/s1
• InChIKey: XPCFTKFZXHTYIP-PMACEKPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetic acid
• IUPAC Traditional name: [(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid
• Synonyms: (3S)-3-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid; Lotensin; Benazepril-d5

Database IDs

• PubChem SID: 162255253
• PubChem CID: 71313620

CALCULATED PROPERTIES

• Acid pKa: 3.52708
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.3033304
• LogD (pH = 7.4): 0.0697504
• Log P: 1.5374391
• Molar Refractivity: 115.2279 cm^3
• Polarizability: 45.31915 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Low Melting Off-White Solid
• Melting Point: 49-51°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B119752

Labelled Benazepril, which is used as an antihypertensive.

REFERENCES

• Schaller, M.D., et al.: Eur. J. Clin. Pharmacol., 28, 267 (985)
• Colfer, H.T., et al.: Am. J. Cardiol., 70, 354 (1992)