2-{[3-(hydroxymethyl)-2-methylphenyl]amino}benzoic acid

• ChemBase ID: 170843
• Molecular Formular: C15H15NO3
• Molecular Mass: 257.2845
• Monoisotopic Mass: 257.10519335
• SMILES: c1ccc(c(c1CO)C)Nc1c(cccc1)C(=O)O
• Canonical SMILES: OCc1cccc(c1C)Nc1ccccc1C(=O)O
• InChI: InChI=1S/C15H15NO3/c1-10-11(9-17)5-4-8-13(10)16-14-7-3-2-6-12(14)15(18)19/h2-8,16-17H,9H2,1H3,(H,18,19)
• InChIKey: QBONJEHEDCBRMZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[3-(hydroxymethyl)-2-methylphenyl]amino}benzoic acid
• IUPAC Traditional name: 2-{[3-(hydroxymethyl)-2-methylphenyl]amino}benzoic acid
• Synonyms: 2-[[3-(Hydroxymethyl)-2-methylphenyl]amino]-benzoic Acid; N-(α3-Hydroxy-2,3-xylyl)-anthranilic Acid; 3-Hydroxymethyl Mefenamic Acid

Database IDs

• CAS Number: 5129-20-4
• PubChem SID: 164226753
• PubChem CID: 610738

CALCULATED PROPERTIES

• Acid pKa: 3.8836582
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.4952555
• LogD (pH = 7.4): 0.89480686
• Log P: 4.116826
• Molar Refractivity: 73.6575 cm^3
• Polarizability: 27.60385 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Tan Solid
• Melting Point: 219-222°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H947845

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)