(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 ID: 165342
• Molecular Formular: C31H33N7O9
• Molecular Mass: 647.63522
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: (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
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.1808147
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -1.8820078
• LogD (pH = 7.4): -1.8710713
• Log P: -1.8709922
• Molar Refractivity: 175.5597 cm^3
• Polarizability: 64.19599 Å^3
• Polar Surface Area: 246.44 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

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).

REFERENCES

• 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)