(2R,3R,4R,5S,6R)-6-{2-[(3-carboxy-2-methylphenyl)amino]benzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 163764
• Molecular Formular: C21H21NO10
• Molecular Mass: 447.39214
• Monoisotopic Mass: 447.11654588
• SMILES: c1ccc(c(c1C(=O)O)C)Nc1c(cccc1)C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O
• Canonical SMILES: O[C@H]1[C@@H](O)[C@H](O[C@@H]([C@@H]1O)C(=O)O)OC(=O)c1ccccc1Nc1cccc(c1C)C(=O)O
• InChI: InChI=1S/C21H21NO10/c1-9-10(18(26)27)6-4-8-12(9)22-13-7-3-2-5-11(13)20(30)32-21-16(25)14(23)15(24)17(31-21)19(28)29/h2-8,14-17,21-25H,1H3,(H,26,27)(H,28,29)/t14-,15-,16+,17-,21-/m1/s1
• InChIKey: QTCMFDMVQUHRND-OVNJDOEUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{2-[(3-carboxy-2-methylphenyl)amino]benzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{2-[(3-carboxy-2-methylphenyl)amino]benzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[2-[(3-Carboxy-2-methylphenyl)amino]benzoate] β-D-Glucopyranuronic Acid; 3-Carboxy Mefenamic Acid Acyl-β-D-glucuronide

Database IDs

• CAS Number: 152832-30-9
• PubChem SID: 162257899
• PubChem CID: 71314546

CALCULATED PROPERTIES

• Acid pKa: 3.08576
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -0.49414352
• LogD (pH = 7.4): -3.3607628
• Log P: 2.7939653
• Molar Refractivity: 106.3964 cm^3
• Polarizability: 41.37962 Å^3
• Polar Surface Area: 182.85 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C178650

Mefenamic acid metabolite.

REFERENCES

• Besunder, J., et al.: Clin. Pharmacokinet., 14, 261 (1988)
• Smith, P., et al.: Drug Metab. Dipos., 18, 639 (1988)
• Kraus, D., et al.: Clin. Pharmacol. Ther., 54, 351 (1988)
• Sato, J., et al.: Biol. Pharm. Bull., 16, 811 (1988)