4-({2-butyl-5-[(1E)-2-carboxyeth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid

• ChemBase ID: 166683
• Molecular Formular: C18H20N2O4
• Molecular Mass: 328.3624
• Monoisotopic Mass: 328.14230713
• SMILES: c1c(ccc(c1)Cn1c(cnc1CCCC)/C=C/C(=O)O)C(=O)O
• Canonical SMILES: CCCCc1ncc(n1Cc1ccc(cc1)C(=O)O)/C=C/C(=O)O
• InChI: InChI=1S/C18H20N2O4/c1-2-3-4-16-19-11-15(9-10-17(21)22)20(16)12-13-5-7-14(8-6-13)18(23)24/h5-11H,2-4,12H2,1H3,(H,21,22)(H,23,24)/b10-9+
• InChIKey: YOKNWHLCGXMWJI-MDZDMXLPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({2-butyl-5-[(1E)-2-carboxyeth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid
• IUPAC Traditional name: 4-({2-butyl-5-[(1E)-2-carboxyeth-1-en-1-yl]imidazol-1-yl}methyl)benzoic acid
• Synonyms: (E)-4-[[2-Butyl-5-(2-carboxyethenyl)-1H-imidazol-1-yl]methyl]benzoic Acid; SB 201972; Des[2-(2-thienylmethyl)] Eprosartan

Database IDs

• CAS Number: 148674-34-4
• PubChem SID: 162260816
• PubChem CID: 14952956

CALCULATED PROPERTIES

• Acid pKa: 3.6863923
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.979429
• LogD (pH = 7.4): -1.3552902
• Log P: 1.972499
• Molar Refractivity: 90.9273 cm^3
• Polarizability: 33.999687 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D297465

Des[2-(2-thienylmethyl)] Eprosartan is an impurity of Eprosartan (E590100), as an angiotensin II receptor antagonist.

REFERENCES

• Keenan, R.M., et al.: J. Med. Chem., 36, 1880 (1993)
• Schambye, H.T., et al.: Molec. Pharmacol., 47, 425 (1993)