(3R)-2-[(2S)-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase ID: 177271
• Molecular Formular: C23H26N2O5
• Molecular Mass: 410.46294
• Monoisotopic Mass: 410.18417194
• SMILES: c1ccc2c(c1)C[C@@H](N(C2)C(=O)[C@@H](N[C@H](CCc1ccccc1)C(=O)O)C)C(=O)O
• Canonical SMILES: OC(=O)[C@H](N[C@H](C(=O)N1Cc2ccccc2C[C@@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C23H26N2O5/c1-15(24-19(22(27)28)12-11-16-7-3-2-4-8-16)21(26)25-14-18-10-6-5-9-17(18)13-20(25)23(29)30/h2-10,15,19-20,24H,11-14H2,1H3,(H,27,28)(H,29,30)/t15-,19+,20+/m0/s1
• InChIKey: FLSLEGPOVLMJMN-CWFSZBLJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-2-[(2S)-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC Traditional name: (3R)-2-[(2S)-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
• Synonyms: (3S)-2-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acid; Accuprin; CI-928; Quinaprilat

Database IDs

• CAS Number: 82768-85-2
• PubChem SID: 164233181
• PubChem CID: 71751930

CALCULATED PROPERTIES

• Acid pKa: 3.066926
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.9201111
• LogD (pH = 7.4): -2.675691
• Log P: 0.29924572
• Molar Refractivity: 110.4381 cm^3
• Polarizability: 43.2194 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 144-146°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Q670010

A metabolite of Quinapril, an angiotensin converting enzyme (ACE) inhibitor.

REFERENCES

• Maurer, H., et al.: Ther. Drug. Monit., 20, 706 (1998)
• Yamada, S., et al.: Biol. Pharm. Bull., 26, 872 (1998)