4-({2-[(4,4,4-2H3)butyl]-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid

• ChemBase ID: 168135
• Molecular Formular: C23H24N2O4S
• Molecular Mass: 424.51266
• Monoisotopic Mass: 424.14567826
• SMILES: c1c(ccc(c1)Cn1c(cnc1CCCC)/C=C(\Cc1sccc1)/C(=O)O)C(=O)O
• Canonical SMILES: CCCCc1ncc(n1Cc1ccc(cc1)C(=O)O)/C=C(/C(=O)O)\Cc1cccs1
• InChI: InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+
• InChIKey: OROAFUQRIXKEMV-LDADJPATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({2-[(4,4,4-^2H₃)butyl]-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid
• IUPAC Traditional name: 4-({2-[(4,4,4-^2H₃)butyl]-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]imidazol-1-yl}methyl)benzoic acid
• Synonyms: (αE)-α-[[2-(Butyl-d3)-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophenepropanoic Acid; (E)-2-(Butyl-d3)-1-(p-carboxybenzyl)-α-2-thenylimidazole-5-acrylic Acid; Navixen-d3; SKB 108566-d3; SKF 108566-d3; Teveten-d3; Eprosartan-d3

Database IDs

• PubChem SID: 162262267
• PubChem CID: 46781481

CALCULATED PROPERTIES

• Acid pKa: 3.6324818
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.6257877
• LogD (pH = 7.4): 0.3021144
• Log P: 3.7972305
• Molar Refractivity: 117.0243 cm^3
• Polarizability: 44.08464 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform: Methanol; 1: 1; DMSO
• Apperance: Off-White Solid
• Melting Point: >235°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E590102

Labelled Eprosartan, a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists. Eprosartan is an antihypertensive.

REFERENCES

• Edwards, R.M., et al.: J. Pharmacol. Exp. Ther., 260, 175 (1992)
• Schambye, H.T., et al.: Mol. Pharmacol., 47, 425 (1992)
• Tenero, D., et al.: Biopharma Drug Dispos., 19, 351 (1992)
• Elliott, W.J., et al.: J. Hum. Hypertens., 13, 413 (1999)