(2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]prop-2-enoic acid

• ChemBase ID: 73046
• Molecular Formular: C13H12N2O2
• Molecular Mass: 228.24658
• Monoisotopic Mass: 228.08987763
• SMILES: c1c(ccc(c1)/C=C/C(=O)O)Cn1cncc1
• Canonical SMILES: OC(=O)/C=C/c1ccc(cc1)Cn1ccnc1
• InChI: InChI=1S/C13H12N2O2/c16-13(17)6-5-11-1-3-12(4-2-11)9-15-8-7-14-10-15/h1-8,10H,9H2,(H,16,17)/b6-5+
• InChIKey: SHZKQBHERIJWAO-AATRIKPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]prop-2-enoic acid
• IUPAC Traditional name: (2E)-3-[4-(imidazol-1-ylmethyl)phenyl]prop-2-enoic acid
• Synonyms: Ozagrel

Database IDs

• CAS Number: 82571-53-7
• PubChem SID: 162037966
• PubChem CID: 5282440

CALCULATED PROPERTIES

• Acid pKa: 4.2126107
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1445775
• LogD (pH = 7.4): 0.42113405
• Log P: 1.1854364
• Molar Refractivity: 65.524 cm^3
• Polarizability: 24.360437 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2496

Research Area: Cardiovascular Disease
Biological Activity:
Ozagrel is a potent and selective thromboxane A2 synthetase inhibitor with an IC50 of 4 nM. It does not inhibit prostacyclin (PGI2) synthetase, cyclooxygenase or PGE2 isomerase (IC50 > 1 mM). Inhibits platelet aggregation in vitro and arachidonate-induced arterial contraction in vivo. The beneficial effects of TXAS inhibition by ozagrel include improved motor coordination after experimental stroke and antihypertensive effects in spontaneously hypertensive rats. [1][2][3]References on Ozagrel[1] http://en.wikipedia.org/wiki/Ozagrel, , [2] Jpn J Pharmacol., 1986 Jul, 41(3):393-401.[3] J Urol., 1987 Mar, 137(3):571-6.

REFERENCES

• Loo MH et al. J Urol. 1987 Mar;137(3):571-6