4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonic acid

• ChemBase ID: 179415
• Molecular Formular: C16H13NO4S
• Molecular Mass: 315.34372
• Monoisotopic Mass: 315.0565289
• SMILES: c1cc(ccc1c1c(onc1c1ccccc1)C)S(=O)(=O)O
• Canonical SMILES: Cc1onc(c1c1ccc(cc1)S(=O)(=O)O)c1ccccc1
• InChI: InChI=1S/C16H13NO4S/c1-11-15(12-7-9-14(10-8-12)22(18,19)20)16(17-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H,18,19,20)
• InChIKey: LLWOSCPRJRUVST-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonic acid
• IUPAC Traditional name: 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonic acid
• Synonyms: 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonic Acid; Valdecoxib Impurity D; Valdecoxib Sulfonic Acid

Database IDs

• CAS Number: 181696-35-5
• PubChem SID: 164235325
• PubChem CID: 11565904

CALCULATED PROPERTIES

• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: -1.8944519
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0221686
• LogD (pH = 7.4): 1.0221616
• Log P: 1.4020989
• Molar Refractivity: 83.1726 cm^3
• Polarizability: 34.549706 Å^3
• Polar Surface Area: 80.4 Å^2

DETAILS

Toronto Research Chemicals - V090010

Valdecoxib Sulfonic Acid is a metabolite of the potent and specific inhibitor of cyclooxygenase-2, Valdecoxib (V090000).

REFERENCES

• Zhang, J.I. et al.: Drug Metab. Dispos., 31, 491 (2003)
• Yuan, J.J. et al.: Drug Metab. Dispos., 30, 1013 (2003)