1-[4-chloro-5-(hydroxymethyl)-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-2-yl]butan-1-ol

• ChemBase ID: 170786
• Molecular Formular: C22H23ClN6O2
• Molecular Mass: 438.91002
• Monoisotopic Mass: 438.15710169
• SMILES: c1(c(cccc1)c1ccc(cc1)Cn1c(nc(c1CO)Cl)C(CCC)O)c1nn[nH]n1
• Canonical SMILES: CCCC(c1nc(c(n1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)CO)Cl)O
• InChI: InChI=1S/C22H23ClN6O2/c1-2-5-19(31)22-24-20(23)18(13-30)29(22)12-14-8-10-15(11-9-14)16-6-3-4-7-17(16)21-25-27-28-26-21/h3-4,6-11,19,30-31H,2,5,12-13H2,1H3,(H,25,26,27,28)
• InChIKey: MGRMJQDIUBITKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-chloro-5-(hydroxymethyl)-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-2-yl]butan-1-ol
• IUPAC Traditional name: 1-[4-chloro-5-(hydroxymethyl)-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)imidazol-2-yl]butan-1-ol
• Synonyms: ω-3-Hydroxy Losartan; 4-Chloro-α2-propyl-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-2,5-dimethanol

Database IDs

• CAS Number: 141675-59-4
• PubChem SID: 164226696
• PubChem CID: 9911047

CALCULATED PROPERTIES

• Acid pKa: 7.3997307
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 4.2251616
• LogD (pH = 7.4): 3.9418359
• Log P: 4.230954
• Molar Refractivity: 133.3418 cm^3
• Polarizability: 47.158077 Å^3
• Polar Surface Area: 112.74 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H946605

A metabolite of Losartan (L470500).

REFERENCES

• Honig, P., et al.: Clin. Pharmacol. Ther., 1992, 52, 231(1992)
• Okuda, H., et al.: Xenobiotic Metab. Dispos., 1995, 10, S166 (1992)
• Ueng, Y., et al.: Biochemistry, 36, 370 (1992)