(2S,3S,4S,5R,6S)-6-({3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase编号: 165342
• 分子式: C31H33N7O9
• 平均质量: 647.63522
• 单一同位素质量: 647.23397567
• SMILES: c1cnc(cc1)N(CCC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)N
• Canonical SMILES: O=C(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CCN(C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)N)c1ccccn1
• InChI: InChI=1S/C31H33N7O9/c1-37-20-10-7-17(14-19(20)36-22(37)15-35-18-8-5-16(6-9-18)28(32)33)29(43)38(21-4-2-3-12-34-21)13-11-23(39)46-31-26(42)24(40)25(41)27(47-31)30(44)45/h2-10,12,14,24-27,31,35,40-42H,11,13,15H2,1H3,(H3,32,33)(H,44,45)/t24-,25-,26+,27-,31+/m0/s1
• InChIKey: CSZFDMHIDSUHPI-KWONYSJQSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-6-({3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6S)-6-({3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• 别名: N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine β-D-Glucopyranuronosyl Ester; Dabigatran Acyl-β-D-Glucuronide

登记号

• CAS号: 1015167-40-4
• PubChem SID: 162259475
• PubChem CID: 71315159

理论计算性质

• Acid pKa: 3.1808147
• 质子受体: 13
• 质子供体: 7
• LogD (pH = 5.5): -1.8820078
• LogD (pH = 7.4): -1.8710713
• Log P: -1.8709922
• 摩尔折射率: 175.5597 cm^3
• 极化性: 64.19599 Å^3
• 极化表面积: 246.44 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

详细说明

Toronto Research Chemicals - D100085

The major metabolite of Dabigatran (D100090) in humans. Four isomeric acylglucuronides of Dabigatran were isolated and purified from urine of dosed rhesus monkeys. NMR analysis confirmed the structures of the four metabolites as the 1-O-acylglucuronide (β anomer) and the 2-O-, 3-O-, and 4-O-acylglucuronides (α and β anomers).

参考文献

• Becker, B., et al.: Biochem. J., 314, 249 (1996)
• Bailey, M., et al.: Chem. Biol. Interact., 145, 117 (1996)
• Blech, S., et al.: Drug Metab. Dispos., 2008, 36, 386 (1996)