2-(2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

• ChemBase ID: 124978
• Molecular Formular: C25H31ClN2O5
• Molecular Mass: 474.97704
• Monoisotopic Mass: 474.19214978
• SMILES: N1(C(=O)C(N[C@H](C(=O)OCC)CCc2ccccc2)C)C(Cc2c(C1)cccc2)C(=O)O.Cl
• Canonical SMILES: CCOC(=O)[C@@H](NC(C(=O)N1Cc2ccccc2CC1C(=O)O)C)CCc1ccccc1.Cl
• InChI: InChI=1S/C25H30N2O5.ClH/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30;/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30);1H/t17?,21-,22?;/m0./s1
• InChIKey: IBBLRJGOOANPTQ-RZIUUCJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: 2-(2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride; 2-(2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl)-3,4-dihydro-1H-isoquinoline-3-carboxylic acid hydrochloride
• Synonyms: Accupril; Accuprin; Accupro; Accuretic; Acequin; Acupril; Quinazil; Quinapril Hydrochloride; 2-(2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Database IDs

• CAS Number: 82586-55-8
• PubChem SID: 162219331
• PubChem CID: 51052076

CALCULATED PROPERTIES

• Acid pKa: 3.7003553
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6842206
• LogD (pH = 7.4): 0.31489024
• Log P: 1.9639356
• Molar Refractivity: 119.9558 cm^3
• Polarizability: 47.146 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Angiotensin converting enzyme inhibitor

Product Information

• Salt Data: HCl
• Application(s): Antihypertensive agent

REFERENCES

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• Kaplan, H.R. et al., Angiology, 1989, 40, 335, (tox, exp)
• Frank, G.J. et al., J. Cardiovasc. Pharmacol., 1990, 15, S14, (Quinapril)
• Wadworth, A.N. et al., Drugs, 1991, 41, 378, (rev)
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• Materson, B.J., Am. J. Cardiol., 1992, 69, 46C, (tox)
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