3-[3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indol-1-yl]propanoic acid

• ChemBase ID: 179835
• Molecular Formular: C16H17N3O2
• Molecular Mass: 283.32508
• Monoisotopic Mass: 283.1320768
• SMILES: c1(c(n(c2c1cccc2)CCC(=O)O)C)Cn1cncc1
• Canonical SMILES: OC(=O)CCn1c2ccccc2c(c1C)Cn1cncc1
• InChI: InChI=1S/C16H17N3O2/c1-12-14(10-18-9-7-17-11-18)13-4-2-3-5-15(13)19(12)8-6-16(20)21/h2-5,7,9,11H,6,8,10H2,1H3,(H,20,21)
• InChIKey: DEQLGSOHGTZKFB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indol-1-yl]propanoic acid
• IUPAC Traditional name: 3-[3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indol-1-yl]propanoic acid
• Synonyms: Dazmegrel

Database IDs

• CAS Number: 76894-77-4
• PubChem SID: 164235745
• PubChem CID: 53555

CALCULATED PROPERTIES

• Acid pKa: 4.4657216
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.2341934
• LogD (pH = 7.4): 0.50137085
• Log P: 1.1718634
• Molar Refractivity: 80.439 cm^3
• Polarizability: 31.493021 Å^3
• Polar Surface Area: 60.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Prostaglandin antagonist; Thromboxane antagonist

Product Information

• Application(s): Antiaggregant

REFERENCES

• U.K. Pat., 1980, Pfizer, 2 045 244; CA, 94, 156925g, (synth, pharmacol)
• Fischer, S. et al., Circulation, 1983, 68, 821, (pharmacol)
• Rebec, M.V. et al., Prostaglandins, Leukotrienes, Essent. Fatty Acids, 1989, 38, 207, (pharmacol)
• Gladue, R.P. et al., Transplantation, 1991, 52, 837, (use)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1360