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

• ChemBase ID: 178703
• Molecular Formular: C20H20ClNO8
• Molecular Mass: 437.8277
• Monoisotopic Mass: 437.08774429
• SMILES: c1cccc(c1C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Nc1cccc(c1C)Cl
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2ccccc2Nc2cccc(c2C)Cl)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H20ClNO8/c1-9-11(21)6-4-8-12(9)22-13-7-3-2-5-10(13)19(28)30-20-16(25)14(23)15(24)17(29-20)18(26)27/h2-8,14-17,20,22-25H,1H3,(H,26,27)/t14-,15-,16+,17-,20-/m0/s1
• InChIKey: UOKJMFLLHHYVOM-GHHWKCCRSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 77605-75-5
• PubChem SID: 164234613
• PubChem CID: 71752608

CALCULATED PROPERTIES

• Acid pKa: 3.105437
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 1.3748306
• LogD (pH = 7.4): 0.27976575
• Log P: 3.740427
• Molar Refractivity: 103.945 cm^3
• Polarizability: 40.86799 Å^3
• Polar Surface Area: 145.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T535310

Tolfenamic Acid Acyl-β-D-Glucuronide is a metabolite of the non-steroidal anti-inflammatory drug Tolfenamic acid (T535300).

REFERENCES

• Hansen, S.H., et al.: J. Pharmaceut. Biomed. Anal., 4, 69 (1986)
• Sidelmann, U.G., et al.: Drug Metab. Dispos., 25, 725 (1986)