2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid

• ChemBase编号: 178011
• 分子式: C20H17FO3S
• 平均质量: 356.4105832
• 单一同位素质量: 356.08824362
• SMILES: c1(ccc2c(c1)C(=C(/C/2=C/c1ccc(cc1)[S@@](=O)C)C)CC(=O)O)F
• Canonical SMILES: OC(=O)CC1=C(C)/C(=C/c2ccc(cc2)[S@@](=O)C)/c2c1cc(F)cc2
• InChI: InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-/t25-/m0/s1
• InChIKey: MLKXDPUZXIRXEP-WXKFDZDZSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
• IUPAC传统名: [(3Z)-6-fluoro-3-({4-[(S)-methanesulfinyl]phenyl}methylidene)-2-methylinden-1-yl]acetic acid
• 别名: (1Z)-5-Fluoro-2-methyl-1-[[4-[(S)-methylsulfinyl]phenyl]methylene]-1H-indene-3-acetic Acid; S-Sulindac Sulfoxide; (S)-Sulindac

登记号

• CAS号: 149116-77-8
• PubChem SID: 164233921
• PubChem CID: 11245227

理论计算性质

• Acid pKa: 4.090206
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.5030619
• LogD (pH = 7.4): -0.17891507
• Log P: 2.9261546
• 摩尔折射率: 99.5588 cm^3
• 极化性: 37.41637 Å^3
• 极化表面积: 54.37 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - S699210

(S)-Sulindac is the S-epimer metabolite of Sulinac (S699215). (S)-Sulindac increases the activity of the P 450 system better than (R)-Sulindac, but both epimers increase primarily the enzymes that oxidize (R)-Sulindac.

参考文献

• Duggan, D., et al.: J. Pharmacol. Exp. Ther., 1977, 201, 8 (1977)
• Hamman, M., et al.: Biochem. Pharmacol., 60, 7 (1977)
• Grimaud, R., et al.: J. Biol. Chem., 276, 48915 (1977)