(3S)-1-[3,4-dihydroxy-4,4-bis(3-methylthiophen-2-yl)butyl]piperidine-3-carboxylic acid

• ChemBase编号: 167884
• 分子式: C20H27NO4S2
• 平均质量: 409.56268
• 单一同位素质量: 409.13815035
• SMILES: C(C(CCN1C[C@H](CCC1)C(=O)O)O)(c1c(ccs1)C)(c1c(ccs1)C)O
• Canonical SMILES: OC(=O)[C@H]1CCCN(C1)CCC(C(c1sccc1C)(c1sccc1C)O)O
• InChI: InChI=1S/C20H27NO4S2/c1-13-6-10-26-17(13)20(25,18-14(2)7-11-27-18)16(22)5-9-21-8-3-4-15(12-21)19(23)24/h6-7,10-11,15-16,22,25H,3-5,8-9,12H2,1-2H3,(H,23,24)/t15-,16?/m0/s1
• InChIKey: LRLPWDNQYQPWNA-VYRBHSGPSA-N

名称和登记号

名称

• IUPAC标准名: (3S)-1-[3,4-dihydroxy-4,4-bis(3-methylthiophen-2-yl)butyl]piperidine-3-carboxylic acid
• IUPAC传统名: (3S)-1-[3,4-dihydroxy-4,4-bis(3-methylthiophen-2-yl)butyl]piperidine-3-carboxylic acid
• 别名: (R)-1-[4,4-Bis(3-methyl-2-thienyl)-3,4-dihydroxybutyl]-3-piperidinecarboxylic Acid; Dihydroxytiagabine; Tiagabine Impurity 1; Dihydroxy Tiagabine (Mixture of Diastereomers)

登记号

• PubChem SID: 162262017
• PubChem CID: 71316276

理论计算性质

• Acid pKa: 3.8981323
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.57960534
• LogD (pH = 7.4): 0.56929654
• Log P: 0.5851541
• 摩尔折射率: 108.1844 cm^3
• 极化性: 41.757927 Å^3
• 极化表面积: 81.0 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - D455030

Dihydroxy Tiagabine is an impurity of the GABA uptake inhibitor Tiagabine (T436400).

参考文献

• Hubert-Roux, M. et al.: Rap. Comm. Mass Spec., 26, 287 (2012)