ethyl 3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-(2H3)methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoate

• ChemBase ID: 165344
• Molecular Formular: C27H29N7O3
• Molecular Mass: 499.56426
• Monoisotopic Mass: 499.23318782
• SMILES: c1cnc(cc1)N(CCC(=O)OCC)C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)N
• Canonical SMILES: CCOC(=O)CCN(C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)N)c1ccccn1
• InChI: InChI=1S/C27H29N7O3/c1-3-37-25(35)13-15-34(23-6-4-5-14-30-23)27(36)19-9-12-22-21(16-19)32-24(33(22)2)17-31-20-10-7-18(8-11-20)26(28)29/h4-12,14,16,31H,3,13,15,17H2,1-2H3,(H3,28,29)
• InChIKey: BGLLICFSSKPUMR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-(^2H₃)methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoate
• IUPAC Traditional name: ethyl 3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-(^2H₃)methyl-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoate
• Synonyms: N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-(methyl-d3)-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine Ethyl Ester; Dabigatran-d3 Ethyl Ester

Database IDs

• PubChem SID: 162259477
• PubChem CID: 71315161

CALCULATED PROPERTIES

• Acid pKa: 18.158268
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.20021173
• LogD (pH = 7.4): -0.19022527
• Log P: 2.2245002
• Molar Refractivity: 152.7788 cm^3
• Polarizability: 54.439396 Å^3
• Polar Surface Area: 139.22 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D100097

Labelled Dabigatran (D100090) derivative. Nonpeptide, direct thrombin inhibitor.

REFERENCES

• Hauel, N., et al.: J. Med. Chem., 45, 1757 (2002)
• Mungall, D., et al.: Curr. Opin. Invest. Drugs, 3, 095 (2002)
• Stangier, J., et al.: J. Clin. Pharmacol., 45, 555 (2002)