2-{5-fluoro-1-[(4-methanesulfonylphenyl)methylidene]-2-methyl-1H-inden-3-yl}acetic acid

• ChemBase ID: 155115
• Molecular Formular: C20H17FO4S
• Molecular Mass: 372.4099832
• Monoisotopic Mass: 372.08315824
• SMILES: CC1=C(c2cc(ccc2/C/1=C/c1ccc(cc1)S(=O)(=O)C)F)CC(=O)O
• Canonical SMILES: OC(=O)CC1=C(C)/C(=C\c2ccc(cc2)S(=O)(=O)C)/c2c1cc(F)cc2
• InChI: InChI=1S/C20H17FO4S/c1-12-17(9-13-3-6-15(7-4-13)26(2,24)25)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)
• InChIKey: MVGSNCBCUWPVDA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{5-fluoro-1-[(4-methanesulfonylphenyl)methylidene]-2-methyl-1H-inden-3-yl}acetic acid
• IUPAC Traditional name: {6-fluoro-3-[(4-methanesulfonylphenyl)methylidene]-2-methylinden-1-yl}acetic acid
• Synonyms: (Z)-5-Fluoro-2-methyl-1-[p-(methylsulfonyl)benzylidene]indene-3-acetic acid; Sulindac sulfone

Database IDs

• CAS Number: 59864-04-9
• MDL Number: MFCD01317811
• PubChem SID: 24278693; 162249253
• PubChem CID: 6158261

CALCULATED PROPERTIES

• Acid pKa: 3.9373763
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.4633576
• LogD (pH = 7.4): -0.16083205
• Log P: 3.0330486
• Molar Refractivity: 99.2008 cm^3
• Polarizability: 37.97721 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble5 mg (plus 0.1 ml); DMSO: >25 mg/mL; ethanol: soluble3 mg/mL (warm)
• Apperance: , Light Yellow to Dark Yellow (solid or powder)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97% (TLC)
• Empirical Formula (Hill Notation): C20H17FO4S

DETAILS

Sigma Aldrich - S1438

Biochem/physiol Actions
Metabolite of sulindac that inhibits cell growth by inducing apoptosis independently of cyclooxygenase inhibition. Inhibits the development and induces regression of premalignant adenomatous polyps.