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

• ChemBase ID: 165343
• Molecular Formular: C25H25N7O3
• Molecular Mass: 471.5111
• Monoisotopic Mass: 471.2018877
• SMILES: c1cnc(cc1)N(CCC(=O)O)C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)N
• Canonical SMILES: OC(=O)CCN(C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)N)c1ccccn1
• InChI: InChI=1S/C25H25N7O3/c1-31-20-10-7-17(25(35)32(13-11-23(33)34)21-4-2-3-12-28-21)14-19(20)30-22(31)15-29-18-8-5-16(6-9-18)24(26)27/h2-10,12,14,29H,11,13,15H2,1H3,(H3,26,27)(H,33,34)
• InChIKey: YBSJFWOBGCMAKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-(^2H₃)methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoic acid
• IUPAC Traditional name: 3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-(^2H₃)methyl-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoic acid
• Synonyms: N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-(methyl-d3)-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine; BIBR 953-d3; BIBR 953ZW-d3; Dabigatran-d3

Database IDs

• CAS Number: 1246817-44-6
• PubChem SID: 162259476
• PubChem CID: 71315160

CALCULATED PROPERTIES

• Acid pKa: 3.4953113
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.06167832
• LogD (pH = 7.4): 0.07667542
• Log P: 0.076810434
• Molar Refractivity: 143.2611 cm^3
• Polarizability: 50.504154 Å^3
• Polar Surface Area: 150.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 262-264°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D100092

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

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)