3-(4-methanesulfonylphenyl)-4-phenyl-2,5-dihydrofuran-2,5-dione

• ChemBase ID: 172131
• Molecular Formular: C17H12O5S
• Molecular Mass: 328.33918
• Monoisotopic Mass: 328.04054448
• SMILES: c1ccc(cc1)C1=C(C(=O)OC1=O)c1ccc(cc1)S(=O)(=O)C
• Canonical SMILES: O=C1OC(=O)C(=C1c1ccc(cc1)S(=O)(=O)C)c1ccccc1
• InChI: InChI=1S/C17H12O5S/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/h2-10H,1H3
• InChIKey: LJZJWBAPABMSII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-methanesulfonylphenyl)-4-phenyl-2,5-dihydrofuran-2,5-dione
• IUPAC Traditional name: 3-(4-methanesulfonylphenyl)-4-phenylfuran-2,5-dione
• Synonyms: 3-[4-(Methylsulfonyl)phenyl]-4-phenyl-2,5-furandione; 5-Keto Vioxx

Database IDs

• CAS Number: 179175-15-6
• PubChem SID: 164228041
• PubChem CID: 12185669

CALCULATED PROPERTIES

• Acid pKa: 19.681164
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.7364085
• LogD (pH = 7.4): 2.7364085
• Log P: 2.7364085
• Molar Refractivity: 84.3094 cm^3
• Polarizability: 33.28069 Å^3
• Polar Surface Area: 77.51 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K315900

An impurity in Vioxx bulk drug, a possible contributor to chronic human toxicity.

REFERENCES

• Sorbera, L., et al.: Drugs Future, 23, 1287 (1998)
• Halpin, R., et al.: Drug Metab. Dispos., 28, 1244 (1998)
• Nicoll-Griffith, D., et al.: Bioorg. Med. Chem. Lett., 10, 2683 (1998)
• Radhakrishna, T., et al.: J. Pharm. Boimed. Anal., 26, 617 (1998)