(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-(2H5)phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase ID: 177272
• Molecular Formular: C23H26N2O5
• Molecular Mass: 410.46294
• Monoisotopic Mass: 410.18417194
• SMILES: c1ccccc1CC[C@H](N[C@H](C(=O)N1Cc2c(C[C@H]1C(=O)O)cccc2)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-YSSFQJQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-(^2H₅)phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC Traditional name: (3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-(^2H₅)phenylpropyl]amino}propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
• Synonyms: (3S)-2-[(2S)-2-[[(1S)-1-Carboxy-(3-phenyl-d5)propyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acid; Accuprin-d5; CI-928-d5; Quinaprilat-d5

Database IDs

• CAS Number: 1279034-23-9
• PubChem SID: 164233182
• PubChem CID: 45040315

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: 43.240852 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Crystalline Solid
• Melting Point: 166-168°C

DETAILS

Toronto Research Chemicals - Q670012

A labelled 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)