(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{2-[4-({4-methyl-6-[1-(2H3)methyl-1H-1,3-benzodiazol-2-yl]-2-propyl-1H-1,3-benzodiazol-1-yl}methyl)phenyl]benzoyloxy}oxane-2-carboxylic acid

• ChemBase ID: 178122
• Molecular Formular: C39H38N4O8
• Molecular Mass: 690.74102
• Monoisotopic Mass: 690.2689642
• SMILES: c1cccc2c1nc(n2C)c1cc2c(c(c1)C)nc(n2Cc1ccc(cc1)c1ccccc1C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)CCC
• Canonical SMILES: CCCc1nc2c(n1Cc1ccc(cc1)c1ccccc1C(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)cc(cc2C)c1nc2c(n1C)cccc2
• InChI: InChI=1S/C39H38N4O8/c1-4-9-30-41-31-21(2)18-24(36-40-27-12-7-8-13-28(27)42(36)3)19-29(31)43(30)20-22-14-16-23(17-15-22)25-10-5-6-11-26(25)38(49)51-39-34(46)32(44)33(45)35(50-39)37(47)48/h5-8,10-19,32-35,39,44-46H,4,9,20H2,1-3H3,(H,47,48)/t32-,33-,34+,35-,39-/m1/s1
• InChIKey: RCOBUBSULFIXAR-CPUXHBFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{2-[4-({4-methyl-6-[1-(^2H₃)methyl-1H-1,3-benzodiazol-2-yl]-2-propyl-1H-1,3-benzodiazol-1-yl}methyl)phenyl]benzoyloxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{2-[4-({4-methyl-6-[1-(^2H₃)methyl-1,3-benzodiazol-2-yl]-2-propyl-1,3-benzodiazol-1-yl}methyl)phenyl]benzoyloxy}oxane-2-carboxylic acid
• Synonyms: 1-[4'-[(1',4-Dimethyl-2-propyl[2',6-bi-1H-benzimidazol]-1-yl)methyl][1,1'-biphenyl]-2-carboxylate]-d3 β-D-Glucopyranuronic Acid; Telmisartan-d3 Glucuronide; Telmisartan-d3 Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 164234032
• PubChem CID: 71752346

CALCULATED PROPERTIES

• Acid pKa: 3.2640872
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 4.3042946
• LogD (pH = 7.4): 3.2448952
• Log P: 4.2507124
• Molar Refractivity: 196.7874 cm^3
• Polarizability: 76.539894 Å^3
• Polar Surface Area: 169.16 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T017012

Labelled Telmisartan Acyl-β-D-glucuronide (T017010). Telmisartan Acyl-β-D-glucuronide is a metabolite of Telmisartan (T017000).

REFERENCES

• Abe, T., et al.: J. Biol. Chem., 274, 17159 (1999)
• Hirano, M., et al.: Drug Metab. Dispos., 34, 1229 (1999)