(2S,3S,4S,5R,6R)-6-({[(1-carboxy-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethyl)sulfanyl]carbonyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase编号: 176747
• 分子式: C25H30N2O10S
• 平均质量: 550.5781
• 单一同位素质量: 550.16211617
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC(SC(=O)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(=O)O)CC
• Canonical SMILES: CCc1ccc(nc1)CCOc1ccc(cc1)CC(C(=O)O)SC(=O)N[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H30N2O10S/c1-2-13-3-6-15(26-12-13)9-10-36-16-7-4-14(5-8-16)11-17(23(31)32)38-25(35)27-22-20(30)18(28)19(29)21(37-22)24(33)34/h3-8,12,17-22,28-30H,2,9-11H2,1H3,(H,27,35)(H,31,32)(H,33,34)/t17?,18-,19-,20+,21-,22+/m0/s1
• InChIKey: GQCWGHHINCKKGE-DVGPLREDSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6R)-6-({[(1-carboxy-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethyl)sulfanyl]carbonyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6R)-6-({[(1-carboxy-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethyl)sulfanyl]carbonyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: 1-[[[[1-Carboxy-2-[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]ethyl]thio]carbonyl]amino]-1-deoxy-β-D-glucopyranuronic Acid; Pioglitazone Thiazolidinedione Ring-opened N-β-D-Glucuronide

登记号

• CAS号: 1296832-76-2
• PubChem SID: 164232657
• PubChem CID: 71751677

理论计算性质

• Acid pKa: 2.9439218
• 质子受体: 11
• 质子供体: 6
• LogD (pH = 5.5): -2.1794283
• LogD (pH = 7.4): -4.993518
• Log P: -0.09546171
• 摩尔折射率: 132.8948 cm^3
• 极化性: 52.716232 Å^3
• 极化表面积: 195.74 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

详细说明

Toronto Research Chemicals - P471020

A ring-opened metabolite of Pioglitazone (P471015) formed via N-glucuronidation of thiazolidinedione ring.

参考文献

• Uchiyama, M. et al.: Drug Metab. Disp., 38, 946 (2010)