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

• ChemBase ID: 170844
• Molecular Formular: C21H23NO9
• Molecular Mass: 433.40862
• Monoisotopic Mass: 433.13728132
• SMILES: c1ccc(c(c1CO)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: OCc1cccc(c1C)Nc1ccccc1C(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C21H23NO9/c1-10-11(9-23)5-4-8-13(10)22-14-7-3-2-6-12(14)20(29)31-21-17(26)15(24)16(25)18(30-21)19(27)28/h2-8,15-18,21-26H,9H2,1H3,(H,27,28)/t15-,16-,17+,18-,21-/m1/s1
• InChIKey: GQQNPPRHZMQONU-ZIKOTGLESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 152832-29-6
• PubChem SID: 164226754
• PubChem CID: 71749155

CALCULATED PROPERTIES

• Acid pKa: 3.1111367
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 0.008720367
• LogD (pH = 7.4): -1.0907898
• Log P: 2.3690326
• Molar Refractivity: 105.9561 cm^3
• Polarizability: 41.42276 Å^3
• Polar Surface Area: 165.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H947848

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)