1-{[4-(2-{1-[(2S,3S,4R,5R,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-1H-1,2,3,4-tetrazol-5-yl}phenyl)phenyl]methyl}-2-ethoxy-1H-1,3-benzodiazole-7-carboxylic acid

• ChemBase ID: 163594
• Molecular Formular: C30H28N6O9
• Molecular Mass: 616.57812
• Monoisotopic Mass: 616.19177651
• SMILES: c1ccc(c2c1nc(n2Cc1ccc(cc1)c1ccccc1c1n(nnn1)[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)OCC)C(=O)O
• Canonical SMILES: CCOc1nc2c(n1Cc1ccc(cc1)c1ccccc1c1nnnn1[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)c(ccc2)C(=O)O
• InChI: InChI=1S/C30H28N6O9/c1-2-44-30-31-20-9-5-8-19(28(40)41)21(20)35(30)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)26-32-33-34-36(26)27-24(39)22(37)23(38)25(45-27)29(42)43/h3-13,22-25,27,37-39H,2,14H2,1H3,(H,40,41)(H,42,43)/t22-,23-,24+,25-,27+/m1/s1
• InChIKey: RGWIRVSYWBHDIC-NUPXYHBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[4-(2-{1-[(2S,3S,4R,5R,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-1H-1,2,3,4-tetrazol-5-yl}phenyl)phenyl]methyl}-2-ethoxy-1H-1,3-benzodiazole-7-carboxylic acid
• IUPAC Traditional name: 3-{[4-(2-{1-[(2S,3S,4R,5R,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-1,2,3,4-tetrazol-5-yl}phenyl)phenyl]methyl}-2-ethoxy-1,3-benzodiazole-4-carboxylic acid
• Synonyms: 1-[5-[4'-[(7-Carboxy-2-ethoxy-1H-benzimidazol-1-yl)methyl][1,1'-biphenyl]-2-yl]-2H-tetrazol-2-yl]-1-deoxy-α-D-glucopyranuronic Acid; Candesartan N2-Glucuronide

Database IDs

• CAS Number: 180603-76-3
• PubChem SID: 162257729
• PubChem CID: 71314494

CALCULATED PROPERTIES

• Acid pKa: 2.8611953
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -1.8554933
• LogD (pH = 7.4): -4.1609235
• Log P: 2.428546
• Molar Refractivity: 177.663 cm^3
• Polarizability: 62.424347 Å^3
• Polar Surface Area: 215.17 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C175590

A metabolite of Candesartan (C175575).

REFERENCES

• Huskey, S., et al.: Drug Metab. Dispos., 21, 792 (1993)
• Hilditch, A., et al.: Br. J. Pharmacol., 111, 137 (1993)
• Reiss, P., et al.: Bioorg. Med. Chem., 7, 2199 (1993)
• Soars, M., et al.: J. Pharmacol. Toxicol. Methods, 47, 161 (1993)
• Soars, M., et al.: