(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

• ChemBase编号: 170386
• 分子式: C16H20N2O8
• 平均质量: 368.3386
• 单一同位素质量: 368.12196561
• SMILES: [C@H]1(C[C@H](N(C1=O)C)c1cnccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](O[C@@H]2C[C@H](N(C2=O)C)c2cccnc2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8-,9+,10-,11-,12+,13-,16+/m0/s1
• InChIKey: WALNNKZUGHYSCT-MGKNELHOSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid
• 别名: (3R,5S)-1-Methyl-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl β-D-Glucopyranosiduronic Acid; trans-3'-Hydroxycotinine-O-glucuronide; trans-3'-Hydroxy Cotinine O-β-D-Glucuronide

登记号

• CAS号: 132929-88-5
• PubChem SID: 164226296
• PubChem CID: 183115

理论计算性质

• Acid pKa: 3.2272434
• 质子受体: 9
• 质子供体: 4
• LogD (pH = 5.5): -4.0141277
• LogD (pH = 7.4): -5.47405
• Log P: -3.2885127
• 摩尔折射率: 83.0098 cm^3
• 极化性: 33.483658 Å^3
• 极化表面积: 149.65 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: White to Pale Yellow Solid
• 熔点: 180-182°C

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - H924540

A Nicotine (N412420) metabolite. Carcinogen.

参考文献

• Le Marchand, L., et al.: Cancer Res., 58, 4858 (1998)
• Minna, J., et al.: J. Clin. Invest., 111, 31 (1998)
• Bierut, L., et al.: Hum. Mol. Genet., 16, 24 (1998)
• Thorgeirsson, T., et al.: Nature, 452, 638 (1998)