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

• ChemBase ID: 177273
• Molecular Formular: C27H34N2O5
• Molecular Mass: 466.56926
• Monoisotopic Mass: 466.2467722
• SMILES: c1ccc2c(c1)C[C@H](N(C2)C(=O)[C@@H](N[C@H](C(=O)OCC)CCc1ccccc1)C)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H](C(=O)N1Cc2ccccc2C[C@H]1C(=O)OCC)C)CCc1ccccc1
• InChI: InChI=1S/C27H34N2O5/c1-4-33-26(31)23(16-15-20-11-7-6-8-12-20)28-19(3)25(30)29-18-22-14-10-9-13-21(22)17-24(29)27(32)34-5-2/h6-14,19,23-24,28H,4-5,15-18H2,1-3H3/t19-,23-,24-/m0/s1
• InChIKey: DRKDCOUMTGAAKG-IGKWTDBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• IUPAC Traditional name: ethyl (3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylate
• Synonyms: [3S-[2[R*(R*)],3R*]]-2-[2-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acid Ethyl Ester (2Z)-2-Butenedioate; Quinapril Ethyl Ester Maleic Acid Salt

Database IDs

• CAS Number: 103733-36-4
• PubChem SID: 164233183
• PubChem CID: 71751931

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.929924
• LogD (pH = 7.4): 4.0989823
• Log P: 4.1016264
• Molar Refractivity: 129.4735 cm^3
• Polarizability: 51.077904 Å^3
• Polar Surface Area: 84.94 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 117-119°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - Q670015

An impurity of Quinapril (Q670000), an angiotensin converting enzyme (ACE) inhibitor.

REFERENCES

• Klutchko, S. et al.: J. Med. Chem., 29, 1953 (1986)