(3R)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

• ChemBase ID: 174691
• Molecular Formular: C25H30N2O7
• Molecular Mass: 470.5149
• Monoisotopic Mass: 470.20530131
• SMILES: c1(c(cc2c(c1)C[C@@H](N(C2)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)O)C)C(=O)O)OC)OC
• Canonical SMILES: COc1cc2C[C@H](C(=O)O)N(Cc2cc1OC)C(=O)[C@@H](N[C@H](C(=O)O)CCc1ccccc1)C
• InChI: InChI=1S/C25H30N2O7/c1-15(26-19(24(29)30)10-9-16-7-5-4-6-8-16)23(28)27-14-18-13-22(34-3)21(33-2)12-17(18)11-20(27)25(31)32/h4-8,12-13,15,19-20,26H,9-11,14H2,1-3H3,(H,29,30)(H,31,32)/t15-,19-,20+/m0/s1
• InChIKey: CMPAGYDKASJORH-RYGJVYDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• IUPAC Traditional name: (3R)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-6,7-dimethoxy-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-6,7-dimethoxy-3-isoquinolinecarboxylic Acid; [3S-[2[R*(R*)],3R*]]-2-[2-[(1-Carboxy-3-phenylpropyl)amino]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic Acid; RS 10029; Moexiprilat

Database IDs

• CAS Number: 103775-14-0
• PubChem SID: 164230601
• PubChem CID: 58227045

CALCULATED PROPERTIES

• Acid pKa: 2.9083858
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.470727
• LogD (pH = 7.4): -3.1098726
• Log P: 0.074270934
• Molar Refractivity: 123.3645 cm^3
• Polarizability: 48.293438 Å^3
• Polar Surface Area: 125.4 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Tetrahydrofuran
• Apperance: White to Off-White Solid
• Melting Point: 155-160°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M485360

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

REFERENCES

• Klutchko, et al.: J. Med. Chem., 29, 1953 (1986)
• Edling, O., et al.: J. Pharmacol. Exp. Ther., 275, 854 (1986)
• Stimpel, M., et al.: Cardiology, 87, 313 (1986)