(2R,3R,4R,5S)-6-({2-carbamoyl-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-9-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase编号: 176070
• 分子式: C21H20N2O8
• 平均质量: 428.3921
• 单一同位素质量: 428.12196561
• SMILES: c12c(cccc1)N(c1c(cccc1)C=C2OC1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)C(=O)N
• Canonical SMILES: O[C@H]1[C@@H](O)C(O[C@@H]([C@@H]1O)C(=O)O)OC1=Cc2ccccc2N(c2c1cccc2)C(=O)N
• InChI: InChI=1S/C21H20N2O8/c22-21(29)23-12-7-3-1-5-10(12)9-14(11-6-2-4-8-13(11)23)30-20-17(26)15(24)16(25)18(31-20)19(27)28/h1-9,15-18,20,24-26H,(H2,22,29)(H,27,28)/t15-,16-,17+,18-,20?/m1/s1
• InChIKey: YPDZOCJZGXGBAP-HPUPVJTASA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R,4R,5S)-6-({2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-9-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: (2R,3R,4R,5S)-6-({2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-9-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: 5-(Aminocarbonyl)-5H-dibenz[b,f]azepin-10-yl D-Glucopyranosiduronic Acid; Oxcarbazepine D-Glucuronide

登记号

• PubChem SID: 164231980
• PubChem CID: 71751391

理论计算性质

• Acid pKa: 3.1765954
• 质子受体: 8
• 质子供体: 5
• LogD (pH = 5.5): -2.2676241
• LogD (pH = 7.4): -3.4178529
• Log P: 0.031623267
• 摩尔折射率: 106.061 cm^3
• 极化性: 41.149185 Å^3
• 极化表面积: 162.78 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Dimethyl Sulfoxide; Methanol
• 外观: Off-White Solid
• 熔点: 158-164°C (dec.)

详细说明

Toronto Research Chemicals - O869260

A metabolite of Oxcarbazepine (O869250).

参考文献

• Schuetz, H., et al.: Xenobiotica, 16, 769 (1986)
• Rouan, M.C., et al.: Eur. J. Clin. Pharmcol., 47, 61 (1986)