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

• ChemBase ID: 172609
• Molecular Formular: C21H23NO8
• Molecular Mass: 417.40922
• Monoisotopic Mass: 417.1423667
• SMILES: c1ccc(c(c1C)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: OC(=O)[C@@H]1O[C@@H](OC(=O)c2ccccc2Nc2cccc(c2C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H23NO8/c1-10-6-5-9-13(11(10)2)22-14-8-4-3-7-12(14)20(28)30-21-17(25)15(23)16(24)18(29-21)19(26)27/h3-9,15-18,21-25H,1-2H3,(H,26,27)/t15-,16-,17+,18-,21-/m0/s1
• InChIKey: DAHIGOGKMFBIOR-CURYNPBISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 102623-18-7
• PubChem SID: 164228519
• PubChem CID: 128135

CALCULATED PROPERTIES

• Acid pKa: 3.115927
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 1.2939314
• LogD (pH = 7.4): 0.19069305
• Log P: 3.6498036
• Molar Refractivity: 104.1814 cm^3
• Polarizability: 40.681393 Å^3
• Polar Surface Area: 145.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Solid
• Melting Point: 110-112°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - M205060

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)