(4S)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

• ChemBase ID: 167622
• Molecular Formular: C16H16N2O6
• Molecular Mass: 332.30804
• Monoisotopic Mass: 332.10083624
• SMILES: C1(=C([C@@H](C(=C(N1)C)C(=O)OC)c1cc(ccc1)[N+](=O)[O-])C(=O)O)C
• Canonical SMILES: COC(=O)C1=C(C)NC(=C([C@@H]1c1cccc(c1)[N+](=O)[O-])C(=O)O)C
• InChI: InChI=1S/C16H16N2O6/c1-8-12(15(19)20)14(13(9(2)17-8)16(21)24-3)10-5-4-6-11(7-10)18(22)23/h4-7,14,17H,1-3H3,(H,19,20)/t14-/m0/s1
• InChIKey: JPXPPUOCSLMCHK-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
• IUPAC Traditional name: (4S)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
• Synonyms: (+)-1,4-Dihydro-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic Acid; (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester

Database IDs

• CAS Number: 76093-34-0
• PubChem SID: 162261755
• PubChem CID: 748474

CALCULATED PROPERTIES

• Acid pKa: 3.764913
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.4206924
• LogD (pH = 7.4): -1.8917458
• Log P: 1.1020321
• Molar Refractivity: 87.3956 cm^3
• Polarizability: 31.914448 Å^3
• Polar Surface Area: 121.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: Light-Yellow Solid

DETAILS

Toronto Research Chemicals - D449121

1,4-Dihydropyridine derivative used in the prevention and therapy of atherosclerotic degradation of arterial walls.

REFERENCES

• Henry, P.D., et al.: Clin. Invest. Med., 10, 601 (1987)
• Weinstein, D.B., et al.: Am. J. Med., 86, 27 (1987)
• Gaviraghi, G., et al.: Pharmacol. Res., 31, 251 (1987)