5-hydroxy-4-(4-methanesulfonylphenyl)-3-phenyl-2,5-dihydrofuran-2-one

• ChemBase ID: 171182
• Molecular Formular: C17H14O5S
• Molecular Mass: 330.35506
• Monoisotopic Mass: 330.05619455
• SMILES: c1ccc(cc1)C1=C(C(OC1=O)O)c1ccc(cc1)S(=O)(=O)C
• Canonical SMILES: OC1OC(=O)C(=C1c1ccc(cc1)S(=O)(=O)C)c1ccccc1
• InChI: InChI=1S/C17H14O5S/c1-23(20,21)13-9-7-12(8-10-13)15-14(16(18)22-17(15)19)11-5-3-2-4-6-11/h2-10,17,19H,1H3
• InChIKey: NCBVUSNBLYMFPP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-4-(4-methanesulfonylphenyl)-3-phenyl-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 5-hydroxy-4-(4-methanesulfonylphenyl)-3-phenyl-5H-furan-2-one
• Synonyms: 5-Hydroxy-4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone; 5-Hydroxyrofecoxib; 5-Hydroxy Vioxx

Database IDs

• CAS Number: 185147-17-5
• PubChem SID: 164227092
• PubChem CID: 9973893

CALCULATED PROPERTIES

• Acid pKa: 11.471848
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.196686
• LogD (pH = 7.4): 2.1966498
• Log P: 2.1966865
• Molar Refractivity: 85.11 cm^3
• Polarizability: 33.828907 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H995750

A metabolite of Vioxx. The biotransformation of Rofecoxib (Vioxx) was highly dependent on the subcellular fraction and the redox system used.

REFERENCES

• Funaki, T., et al.: Biochem. Pharmacol., 38, 4213 (1989)
• John, B., et al.: Xenobiotica, 22, 1339 (1989)
• Jouzeau, J., et al.: Drugs, 53, 563 (1989)
• Baillie, T., et al.: Drug Metab. Dispos., 29, 1614 (1989)