2-{[(2R)-2-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-1,3-benzodiazol-5-yl)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl]amino}acetic acid; methane

• ChemBase ID: 178072
• Molecular Formular: C26H35N7O3
• Molecular Mass: 493.6012
• Monoisotopic Mass: 493.28013802
• SMILES: N1(C(=O)C(c2ccc3c(c2)nc(n3C)CNc2ccc(cc2)C(=N)N)(NCC(=O)O)C)CCCC1.C
• Canonical SMILES: OC(=O)CNC(C(=O)N1CCCC1)(c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)N)C.C
• InChI: InChI=1S/C25H31N7O3.CH4/c1-25(29-15-22(33)34,24(35)32-11-3-4-12-32)17-7-10-20-19(13-17)30-21(31(20)2)14-28-18-8-5-16(6-9-18)23(26)27;/h5-10,13,28-29H,3-4,11-12,14-15H2,1-2H3,(H3,26,27)(H,33,34);1H4/t25-;/m1./s1
• InChIKey: FVEWNVFJAAPECK-VQIWEWKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2R)-2-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-1,3-benzodiazol-5-yl)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl]amino}acetic acid; methane
• IUPAC Traditional name: methane; tanogitran
• Synonyms: N-[(1R)-1-[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]-1-methyl-2-oxo-2-(1-pyrrolidinyl)ethyl]glycine Dihydrochloride; BIBT 986 Dihydrochloride; Tanogitran Dihydrochloride

Database IDs

• CAS Number: 253796-69-9
• PubChem SID: 164233982
• PubChem CID: 71752322

CALCULATED PROPERTIES

• Acid pKa: 3.0069404
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.2996645
• LogD (pH = 7.4): -0.9014012
• Log P: -0.7673038
• Molar Refractivity: 144.7035 cm^3
• Polarizability: 51.75655 Å^3
• Polar Surface Area: 149.36 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T006750

A novel synthetic, specific, direct, competitive and reversible inhibitor of both, FXa (Ki 26 nM) and thrombin (K i=2.7 nM). It showed a high anticoagulant potency in preclinical models of venous thrombosis in rats and rabbits.

REFERENCES

• Gomerz-Outes, A. et al.: Ther. Adv. Cardiovasc. Dis., 5, 33 (2011)