ethyl (2S)-2-[(3S,11aS)-3-methyl-1,4-dioxo-1H,2H,3H,4H,6H,11H,11aH-piperazino[1,2-b]isoquinolin-2-yl]-4-phenylbutanoate

• ChemBase ID: 177270
• Molecular Formular: C25H28N2O4
• Molecular Mass: 420.50082
• Monoisotopic Mass: 420.20490739
• SMILES: c1ccc2c(c1)C[C@@H]1N(C2)C(=O)[C@@H](N(C1=O)[C@@H](CCc1ccccc1)C(=O)OCC)C
• Canonical SMILES: CCOC(=O)[C@@H](N1[C@@H](C)C(=O)N2[C@H](C1=O)Cc1c(C2)cccc1)CCc1ccccc1
• InChI: InChI=1S/C25H28N2O4/c1-3-31-25(30)21(14-13-18-9-5-4-6-10-18)27-17(2)23(28)26-16-20-12-8-7-11-19(20)15-22(26)24(27)29/h4-12,17,21-22H,3,13-16H2,1-2H3/t17-,21-,22-/m0/s1
• InChIKey: NDDYKENLGBOEPD-HSQYWUDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-[(3S,11aS)-3-methyl-1,4-dioxo-1H,2H,3H,4H,6H,11H,11aH-piperazino[1,2-b]isoquinolin-2-yl]-4-phenylbutanoate
• IUPAC Traditional name: ethyl (2S)-2-[(3S,11aS)-3-methyl-1,4-dioxo-3H,6H,11H,11aH-piperazino[1,2-b]isoquinolin-2-yl]-4-phenylbutanoate
• Synonyms: (αS,3S,11aS)-1,3,4,6,11,11a-Hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino[1,2-b]isoquinoline-2-acetic Acid; PD 109488; Quinapril Diketopiperazine

Database IDs

• CAS Number: 103733-49-9
• PubChem SID: 164233180
• PubChem CID: 29986779

CALCULATED PROPERTIES

• Acid pKa: 18.700289
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.4322124
• LogD (pH = 7.4): 3.4322124
• Log P: 3.4322124
• Molar Refractivity: 116.878 cm^3
• Polarizability: 45.583576 Å^3
• Polar Surface Area: 66.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Q670005

Quinapril derivative. ACE inhibitor.

REFERENCES

• Guo, Y., et al.: Pharm. Res., 17, 930 (2000)
• Li, J., et al.: J. Pharm. Sci., 91, 229 (2000)