4-(2-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}propan-2-yl)-2-propyl-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylic acid

• ChemBase ID: 175869
• Molecular Formular: C30H34N6O9
• Molecular Mass: 622.62576
• Monoisotopic Mass: 622.2387267
• SMILES: c1(c(cccc1)c1ccc(cc1)Cn1c(c(nc1CCC)C(O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)(C)C)C(=O)O)c1nn[nH]n1
• Canonical SMILES: CCCc1nc(c(n1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)C(=O)O)C(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)(C)C
• InChI: InChI=1S/C30H34N6O9/c1-4-7-19-31-25(30(2,3)45-29-23(39)21(37)22(38)24(44-29)28(42)43)20(27(40)41)36(19)14-15-10-12-16(13-11-15)17-8-5-6-9-18(17)26-32-34-35-33-26/h5-6,8-13,21-24,29,37-39H,4,7,14H2,1-3H3,(H,40,41)(H,42,43)(H,32,33,34,35)/t21-,22-,23+,24-,29-/m0/s1
• InChIKey: WEKAQESFGDVLAF-UMWNSNATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}propan-2-yl)-2-propyl-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylic acid
• IUPAC Traditional name: 5-(2-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}propan-2-yl)-2-propyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)imidazole-4-carboxylic acid
• Synonyms: 1-[5-Carboxy-2-propyl-1-[[2’-(1H-tetrazol-5-yl)[1,1’-biphenyl]-4-yl]methyl]-1H-imidazol-4-yl]-1-methylethyl β-D-Glucopyranosiduronic Acid; Olmesartan Acid O-β-D-Glucuronide

Database IDs

• CAS Number: 369395-57-3
• PubChem SID: 164231779
• PubChem CID: 71751319

CALCULATED PROPERTIES

• Acid pKa: 0.90181184
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -1.7982998
• LogD (pH = 7.4): -4.0763607
• Log P: 0.75459516
• Molar Refractivity: 169.6044 cm^3
• Polarizability: 62.264984 Å^3
• Polar Surface Area: 226.03 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O550005

A metabolite of Olmesartan Medoxomil (O550000).

REFERENCES

• Gabriel, M., et al.: Biochem. J., 124, 793 (1971)
• Awata, N., et al.: Jpn. J. Antibiot., 38, 1785 (1971)
• Otsuka, M., et al.: J. Biochem., 119, 246 (1971)