3-{1-[2-({[4-({[(hexyloxy)carbonyl]amino}methanimidoyl)phenyl]amino}methyl)-1-methyl-1H-1,3-benzodiazol-5-yl]-N-(pyridin-2-yl)formamido}propanoic acid

• ChemBase ID: 166209
• Molecular Formular: C32H37N7O5
• Molecular Mass: 599.68008
• Monoisotopic Mass: 599.28561732
• SMILES: c1cnc(cc1)N(CCC(=O)O)C(=O)c1ccc2c(c1)nc(n2C)CNc1ccc(cc1)C(=N)NC(=O)OCCCCCC
• Canonical SMILES: CCCCCCOC(=O)NC(=N)c1ccc(cc1)NCc1nc2c(n1C)ccc(c2)C(=O)N(c1ccccn1)CCC(=O)O
• InChI: InChI=1S/C32H37N7O5/c1-3-4-5-8-19-44-32(43)37-30(33)22-10-13-24(14-11-22)35-21-28-36-25-20-23(12-15-26(25)38(28)2)31(42)39(18-16-29(40)41)27-9-6-7-17-34-27/h6-7,9-15,17,20,35H,3-5,8,16,18-19,21H2,1-2H3,(H,40,41)(H2,33,37,43)
• InChIKey: UGEWTLXHMYKLCO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-[2-({[4-({[(hexyloxy)carbonyl]amino}methanimidoyl)phenyl]amino}methyl)-1-methyl-1H-1,3-benzodiazol-5-yl]-N-(pyridin-2-yl)formamido}propanoic acid
• IUPAC Traditional name: 3-{1-[2-({[4-({[(hexyloxy)carbonyl]amino}methanimidoyl)phenyl]amino}methyl)-1-methyl-1,3-benzodiazol-5-yl]-N-(pyridin-2-yl)formamido}propanoic acid
• Synonyms: N-[[2-[[[4-[[[(Hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine; Desethyl Pradaxa; Desethyl Dabigatran Etexilate

Database IDs

• CAS Number: 212321-78-3
• PubChem SID: 162260342
• PubChem CID: 10290289

CALCULATED PROPERTIES

• Acid pKa: 3.6535144
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 2.6702173
• LogD (pH = 7.4): 1.1777488
• Log P: 3.6851516
• Molar Refractivity: 177.4041 cm^3
• Polarizability: 64.08649 Å^3
• Polar Surface Area: 162.53 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D289070

A metabolite of Dabigatran Etexilate (D100150).

REFERENCES

• Clarke, S., et al.: Chem. Res. Toxicol., 7, 836 (1994)
• Amet, Y., et al.: Biochem. Pharmacol., 50, 1775 (1994)
• Clement, B., et al.: Drug Metab. Dispos., 31, 645 (1994)