4-(2,3-dichlorophenyl)-5-(ethoxycarbonyl)-2-(hydroxymethyl)-6-methylpyridine-3-carboxylic acid

• ChemBase ID: 163757
• Molecular Formular: C17H15Cl2NO5
• Molecular Mass: 384.2107
• Monoisotopic Mass: 383.03272795
• SMILES: n1c(c(c(c(c1C)C(=O)OCC)c1c(c(ccc1)Cl)Cl)C(=O)O)CO
• Canonical SMILES: CCOC(=O)c1c(C)nc(c(c1c1cccc(c1Cl)Cl)C(=O)O)CO
• InChI: InChI=1S/C17H15Cl2NO5/c1-3-25-17(24)12-8(2)20-11(7-21)14(16(22)23)13(12)9-5-4-6-10(18)15(9)19/h4-6,21H,3,7H2,1-2H3,(H,22,23)
• InChIKey: YUUOWPFADBOBKZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2,3-dichlorophenyl)-5-(ethoxycarbonyl)-2-(hydroxymethyl)-6-methylpyridine-3-carboxylic acid
• IUPAC Traditional name: 4-(2,3-dichlorophenyl)-5-(ethoxycarbonyl)-2-(hydroxymethyl)-6-methylpyridine-3-carboxylic acid
• Synonyms: 4-(2,3-Dichlorophenyl)-2-(hydroxymethyl)-6-methyl-3,5-pyridinedicarboxylic Acid 5-Ethyl Ester; H 151/73; 5-Carboxy-6-hydroxymethyl Dehydro Felodipine

Database IDs

• CAS Number: 96558-29-1
• PubChem SID: 162257892
• PubChem CID: 10045532

CALCULATED PROPERTIES

• Acid pKa: 3.8524983
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2163686
• LogD (pH = 7.4): -0.25347584
• Log P: 2.7104297
• Molar Refractivity: 93.5622 cm^3
• Polarizability: 37.060917 Å^3
• Polar Surface Area: 96.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C178480

A metabolite of Felodipine (F232375).

REFERENCES

• Wang, S.X. et al.: J. Pharmacol. Exp. Therap., 250, 632 (1989)
• Baeaernhielm, C. et al.: Drug Metab. Disp., 14, 613 (1989)