3-[(2-carboxyphenyl)amino]-2-methylbenzoic acid

• ChemBase ID: 163763
• Molecular Formular: C15H13NO4
• Molecular Mass: 271.26802
• Monoisotopic Mass: 271.0844579
• SMILES: c1ccc(c(c1C(=O)O)C)Nc1c(cccc1)C(=O)O
• Canonical SMILES: OC(=O)c1ccccc1Nc1cccc(c1C)C(=O)O
• InChI: InChI=1S/C15H13NO4/c1-9-10(14(17)18)6-4-8-12(9)16-13-7-3-2-5-11(13)15(19)20/h2-8,16H,1H3,(H,17,18)(H,19,20)
• InChIKey: OOQQWHSTKBWQPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2-carboxyphenyl)amino]-2-methylbenzoic acid
• IUPAC Traditional name: 3-[(2-carboxyphenyl)amino]-2-methylbenzoic acid
• Synonyms: 3-[(2-Carboxyphenyl)amino]-2-methylbenzoic Acid; 3-Carboxy Mefenamic Acid

Database IDs

• CAS Number: 190379-82-9
• PubChem SID: 162257898
• PubChem CID: 542022

CALCULATED PROPERTIES

• Acid pKa: 3.8081403
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.9987638
• LogD (pH = 7.4): -1.3761494
• Log P: 4.541759
• Molar Refractivity: 74.0978 cm^3
• Polarizability: 27.500029 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C178645

A metabolite of Mefenamic acid.

REFERENCES

• Besunder, J., et al.: Clin. Pharmacokinet., 14, 261 (1988)
• Kraus, D., et al.: Clin. Pharmacol. Ther., 54, 351 (1988)
• Sato, J., et al.: Biol. Pharm. Bull., 20, 443 (1988)