(2S,3S,4S,5R,6S)-6-{3-[(2R,3R)-1-(dimethylamino)-2-methyl(4,4,5,5,5-2H5)pentan-3-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase编号: 178077
• 分子式: C20H31NO7
• 平均质量: 397.46264
• 单一同位素质量: 397.21005234
• SMILES: c1(cccc(c1)[C@@H]([C@H](CN(C)C)C)CC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC[C@@H](c1cccc(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)[C@H](CN(C)C)C
• InChI: InChI=1S/C20H31NO7/c1-5-14(11(2)10-21(3)4)12-7-6-8-13(9-12)27-20-17(24)15(22)16(23)18(28-20)19(25)26/h6-9,11,14-18,20,22-24H,5,10H2,1-4H3,(H,25,26)/t11-,14+,15-,16-,17+,18-,20+/m0/s1
• InChIKey: CTYJDHSTNLOUMT-PJOQTPGLSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-6-{3-[(2R,3R)-1-(dimethylamino)-2-methyl(4,4,5,5,5-^2H₅)pentan-3-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6S)-6-{3-[(2R,3R)-1-(dimethylamino)-2-methyl(4,4,5,5,5-^2H₅)pentan-3-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: 3-[(1R,2R)-3-(Dimethylamino)-1-(ethyl-d5)-2-methylpropyl]phenyl β-D-Glucopyranosiduronic Acid; Tapentadol-d5 O-β-D-Glucuronide

登记号

• PubChem SID: 164233987
• PubChem CID: 71752324

理论计算性质

• Acid pKa: 2.9902072
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -1.2388824
• LogD (pH = 7.4): -1.2391925
• Log P: -1.2381607
• 摩尔折射率: 101.5706 cm^3
• 极化性: 40.64097 Å^3
• 极化表面积: 119.69 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - T007212

A labelled metabolite of Tapentadol (T007200).

参考文献

• Terlinden, R., et al.: Eur. J. Drug Metab. Pharmacokinet., 32, 163 (2007)
• Tzschentke, T., et al.: J. Pharmacol. Exp. Ther., 323, 256 (2007)
• Wade, W., et al.: Clin. Ther., 31, 2804 (2007)