(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(4-sulfamoylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoyloxy}oxane-2-carboxylic acid

• ChemBase ID: 163955
• Molecular Formular: C23H20F3N3O10S
• Molecular Mass: 587.4792096
• Monoisotopic Mass: 587.08214952
• SMILES: c1c(nn(c1c1ccc(cc1)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)c1ccc(cc1)S(=O)(=O)N)C(F)(F)F
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2ccc(cc2)c2cc(nn2c2ccc(cc2)S(=O)(=O)N)C(F)(F)F)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H20F3N3O10S/c24-23(25,26)15-9-14(29(28-15)12-5-7-13(8-6-12)40(27,36)37)10-1-3-11(4-2-10)21(35)39-22-18(32)16(30)17(31)19(38-22)20(33)34/h1-9,16-19,22,30-32H,(H,33,34)(H2,27,36,37)/t16-,17-,18+,19-,22-/m0/s1
• InChIKey: ZSTBSABHKHAHNU-QUXXCFOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(4-sulfamoylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoyloxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]benzoyloxy}oxane-2-carboxylic acid
• Synonyms: 1-[4-[1-[4-(Aminosulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoate] β-D-Glucopyranuronic Αcid; Celecoxib Carboxylic Acid Acyl-β-D-glucuronide

Database IDs

• CAS Number: 264236-79-5
• PubChem SID: 162258090
• PubChem CID: 10415951

CALCULATED PROPERTIES

• Acid pKa: 3.1732156
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.8966949
• LogD (pH = 7.4): -2.0444417
• Log P: 1.4058098
• Molar Refractivity: 126.7478 cm^3
• Polarizability: 51.038692 Å^3
• Polar Surface Area: 211.5 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C251015

Celecoxib Carboxylic Acid Acyl-β-D-glucuronide is a glucuronide metabolite of Celecoxib (C251000), a Cox-2 inhibitor.

REFERENCES

• Penning, T., et al.: J. Med. Chem., 40, 1347 (1997)
• Barta, T., et al.: Bioorg. Med. Chem. Lett., 8, 3443 (1997)
• Paulson, S., et al.: Drug Metab. Dispos., 28, 514 (1997)