(2R,3R,4R,5S,6S)-6-(5-{2-[4-({2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl}methyl)phenyl]phenyl}-2H-1,2,3,4-tetrazol-2-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171740
• Molecular Formular: C31H36N6O7
• Molecular Mass: 604.65354
• Monoisotopic Mass: 604.26454752
• SMILES: c1c(ccc(c1)c1ccccc1c1nn(nn1)[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)CN1C(=O)C2(N=C1CCCC)CCCC2
• Canonical SMILES: CCCCC1=NC2(C(=O)N1Cc1ccc(cc1)c1ccccc1c1nnn(n1)[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)CCCC2
• InChI: InChI=1S/C31H36N6O7/c1-2-3-10-22-32-31(15-6-7-16-31)30(43)36(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)27-33-35-37(34-27)28-25(40)23(38)24(39)26(44-28)29(41)42/h4-5,8-9,11-14,23-26,28,38-40H,2-3,6-7,10,15-17H2,1H3,(H,41,42)/t23-,24-,25+,26-,28+/m1/s1
• InChIKey: FVBDVTHTYLLSQE-CBNWRBMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-6-(5-{2-[4-({2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl}methyl)phenyl]phenyl}-2H-1,2,3,4-tetrazol-2-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-6-(5-{2-[4-({2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl}methyl)phenyl]phenyl}-1,2,3,4-tetrazol-2-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[5-[4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl][1,1'-biphenyl]-2-yl]-2H-tetrazol-2-yl]-1-deoxy-β-D-glucopyranuronic Acid; Irbesartan N-β-D-Glucuronide

Database IDs

• CAS Number: 160205-58-3
• PubChem SID: 164227650
• PubChem CID: 71749529

CALCULATED PROPERTIES

• Acid pKa: 3.0750597
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 1.2312472
• LogD (pH = 7.4): 0.04570398
• Log P: 2.3142474
• Molar Refractivity: 179.4616 cm^3
• Polarizability: 62.60994 Å^3
• Polar Surface Area: 183.49 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 155-158°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I751010

A metabolite of Irbesartan (M8).

REFERENCES

• Cazaubon, C., et al.: J. Pharmacol. Exp. Ther., 265, 826 (1993)
• Eberhardt, R., et al.: J. Clin. Pharmacol., 33, 1023 (1993)
• Huskey, S., et al.: Drug Metab. Dispos., 21, 792 (1993)
• van Den Meiracker, A., et al.: Hypertension, 25, 22 (1993)