2-(hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)pyridine-3-carboxylic acid

• ChemBase ID: 170428
• Molecular Formular: C16H14N2O7
• Molecular Mass: 346.29156
• Monoisotopic Mass: 346.0801008
• SMILES: n1c(c(c(c(c1C)C(=O)OC)c1ccccc1[N+](=O)[O-])C(=O)O)CO
• Canonical SMILES: COC(=O)c1c(C)nc(c(c1c1ccccc1[N+](=O)[O-])C(=O)O)CO
• InChI: InChI=1S/C16H14N2O7/c1-8-12(16(22)25-2)13(14(15(20)21)10(7-19)17-8)9-5-3-4-6-11(9)18(23)24/h3-6,19H,7H2,1-2H3,(H,20,21)
• InChIKey: ARDQNVJJIRIJPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)pyridine-3-carboxylic acid
• IUPAC Traditional name: 2-(hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)pyridine-3-carboxylic acid
• Synonyms: 2-(Hydroxymethyl)-6-methyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic Acid 5-Methyl Ester; 4-(2-Nitrophenyl)-2-hydroxymethyl-5-methoxycarbonyl-6-methylpyridine-3-carboxylic Acid; Hydroxydehydro Nifedipine Carboxylate

Database IDs

• CAS Number: 34783-31-8
• PubChem SID: 164226338
• PubChem CID: 13599653

CALCULATED PROPERTIES

• Acid pKa: 3.734525
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.4133672
• LogD (pH = 7.4): -1.8810432
• Log P: 1.2246168
• Molar Refractivity: 86.5287 cm^3
• Polarizability: 33.326557 Å^3
• Polar Surface Area: 142.54 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 134-136°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under inert atmosphere
• Storage Warning: Temperature Sensitive

DETAILS

Toronto Research Chemicals - H934500

A main metabolite of Nifedipine.

REFERENCES

• Moldeus, P., et al.: Methods Enzymol., 52, 60 (1978)
• Stopher, D., et al.: J. Cardiovasc. Pharmacol., 12, S55 (1978)
• Mahmoudian, M., et al.: J. Pharm. Pharmacol., 49, 1229 (1978)
• Mohri, K., et al.: Drug Metab. Dispos., 28, 482 (1978)