1-(1H-1,3-benzodiazol-2-yl)-3-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

• ChemBase ID: 161262
• Molecular Formular: C14H11N3O3
• Molecular Mass: 269.25544
• Monoisotopic Mass: 269.08004123
• SMILES: c1ccc2c(c1)nc([nH]2)n1c(c(c(=O)cc1)C)C(=O)O
• Canonical SMILES: OC(=O)c1c(C)c(=O)ccn1c1nc2c([nH]1)cccc2
• InChI: InChI=1S/C14H11N3O3/c1-8-11(18)6-7-17(12(8)13(19)20)14-15-9-4-2-3-5-10(9)16-14/h2-7H,1H3,(H,15,16)(H,19,20)
• InChIKey: CBHQVBYUZFZICT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(1H-1,3-benzodiazol-2-yl)-3-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid
• IUPAC Traditional name: 1-(1H-1,3-benzodiazol-2-yl)-3-methyl-4-oxopyridine-2-carboxylic acid
• Synonyms: 1-(1H-Benzimidazol-2-yl)-1,4-dihydro-3-methyl-4-oxo-2-pyridinecarboxylic Acid; 1-(1H-Benzo[d]imidazol-2-yl)-3-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

Database IDs

• CAS Number: 1163685-30-0
• PubChem SID: 162255397
• PubChem CID: 66603894

CALCULATED PROPERTIES

• Acid pKa: 3.6841116
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.3567096
• LogD (pH = 7.4): -0.9955419
• Log P: 1.8765043
• Molar Refractivity: 73.4558 cm^3
• Polarizability: 28.044067 Å^3
• Polar Surface Area: 86.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B203960

Rabeprazole (R070500) impurity. A degradation product formed in stressed tablets of Rabeprazole sodium.

REFERENCES

• Kommanaboyina, B., et al.: Drug Dev. Ind. Pharm., 25, 857 (1999)
• Carswel, C., et al.: Drugs, 61, 2327 (1999)
• Garcia, C., et al.: J. Pharm. Biomed. Anal., 46, 88 (1999)