(2S,3S,4S,5R,6S)-6-{2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase编号: 168873
• 分子式: C22H24N2O9S
• 平均质量: 492.49896
• 单一同位素质量: 492.12025136
• SMILES: c1(c(cc(cc1)c1sc(c(n1)C)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C#N)OCC(C)C
• Canonical SMILES: N#Cc1cc(ccc1OCC(C)C)c1nc(c(s1)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C22H24N2O9S/c1-9(2)8-31-13-5-4-11(6-12(13)7-23)19-24-10(3)18(34-19)21(30)33-22-16(27)14(25)15(26)17(32-22)20(28)29/h4-6,9,14-17,22,25-27H,8H2,1-3H3,(H,28,29)/t14-,15-,16+,17-,22-/m0/s1
• InChIKey: ZRXRMGPMLDOOKN-FVMGUFKOSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-6-{2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6S)-6-{2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylate β-D-Glucopyranuronic Acid; 2-(3-Cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylate β-D-Glucopyranuronic Acid; Febuxostat Acyl-β-D-glucuronide

登记号

• CAS号: 1351692-92-6
• PubChem SID: 162263005
• PubChem CID: 71316713

理论计算性质

• Acid pKa: 3.5654547
• 质子受体: 10
• 质子供体: 4
• LogD (pH = 5.5): -0.15601844
• LogD (pH = 7.4): -1.5818214
• Log P: 1.7731359
• 摩尔折射率: 126.2274 cm^3
• 极化性: 46.2474 Å^3
• 极化表面积: 179.43 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: White Solid
• 熔点: 172-175°C

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - F229030

A metabolite of Febuxostat (F229000), a novel nonpurine selective inhibitor of Xanthin Oxidase.

参考文献

• Grabowski, B., et al.: J. Clin. Pharmacol., 51, 189 (2011)
• Osada, Y., et al.: Eur. J. Pharmacol., 241, 183 (2011)
• Okamoto, K., et al.: J. Biol. Chem., 278, 1848 (2011)
• Mayer, M.D., et al.: Am. J. Therap., 12, 22 (2011)
• Tomlinson, B., et al.: Curr. Opi