(3R)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(2H5)phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase ID: 174689
• Molecular Formular: C27H34N2O7
• Molecular Mass: 498.56806
• Monoisotopic Mass: 498.23660144
• SMILES: c1(c(cc2c(c1)C[C@@H](N(C2)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)OCC)C)C(=O)O)OC)OC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H](C(=O)N1Cc2cc(OC)c(cc2C[C@@H]1C(=O)O)OC)C)CCc1ccccc1
• InChI: InChI=1S/C27H34N2O7/c1-5-36-27(33)21(12-11-18-9-7-6-8-10-18)28-17(2)25(30)29-16-20-15-24(35-4)23(34-3)14-19(20)13-22(29)26(31)32/h6-10,14-15,17,21-22,28H,5,11-13,16H2,1-4H3,(H,31,32)/t17-,21-,22+/m0/s1
• InChIKey: UWWDHYUMIORJTA-BULFRSBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC Traditional name: (3R)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
• Synonyms: (3S)-2-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-(phenyl-d5)propyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic Acid; RS-10085-d5; Moexipril-d5

Database IDs

• PubChem SID: 164230599
• PubChem CID: 71750765

CALCULATED PROPERTIES

• Acid pKa: 3.462318
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.1609751
• LogD (pH = 7.4): -0.08144003
• Log P: 1.5021217
• Molar Refractivity: 132.8822 cm^3
• Polarizability: 52.23141 Å^3
• Polar Surface Area: 114.4 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 141-161°C

DETAILS

Toronto Research Chemicals - M485352

Angiotensin converting enzyme (ACE) inhibitor; dimethoxy analog of quinapril.

REFERENCES

• Edling, O., et al.: J. Pharmacol. Exp. Ther., 275, 854 (1995)
• White, W.B., et al.: J. Hum. Hypertens., 8, 917 (1995)
• Stimpel, M., et al.: Cardiology 87, 313 (1996)