(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-({2-[(4-methoxyphenoxycarbonyl)({4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}methyl)amino]acetyl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 174861
• Molecular Formular: C35H36N2O13
• Molecular Mass: 692.66594
• Monoisotopic Mass: 692.22173922
• SMILES: O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)OC(=O)CN(Cc1ccc(cc1)OCCc1nc(oc1C)c1ccccc1)C(=O)Oc1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)OC(=O)N(Cc1ccc(cc1)OCCc1nc(oc1C)c1ccccc1)CC(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C35H36N2O13/c1-20-26(36-32(47-20)22-6-4-3-5-7-22)16-17-46-24-10-8-21(9-11-24)18-37(35(44)48-25-14-12-23(45-2)13-15-25)19-27(38)49-34-30(41)28(39)29(40)31(50-34)33(42)43/h3-15,28-31,34,39-41H,16-19H2,1-2H3,(H,42,43)/t28-,29-,30+,31-,34+/m1/s1
• InChIKey: VLMNHAOSAKQBJM-WVXFORMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-({2-[(4-methoxyphenoxycarbonyl)({4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}methyl)amino]acetyl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-({2-[(4-methoxyphenoxycarbonyl)({4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}methyl)amino]acetyl}oxy)oxane-2-carboxylic acid
• Synonyms: N-[(4-Methoxyphenoxy)carbonyl]-N-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]glycine β-D-Glucopyranuronic Acid 1-Ester; Muraglitazar Acyl-β-D-glucuronide

Database IDs

• CAS Number: 875430-26-5
• PubChem SID: 164230771
• PubChem CID: 71750863

CALCULATED PROPERTIES

• Acid pKa: 3.1129515
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 0.48156023
• LogD (pH = 7.4): -0.61715645
• Log P: 2.8428144
• Molar Refractivity: 181.3332 cm^3
• Polarizability: 67.910576 Å^3
• Polar Surface Area: 207.55 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M796510

A major metabolite of Muraglitazar.

REFERENCES

• Parker, R., et al.: Xenobiotica, 10, 689 (1980)
• Gillies, P., et al.: Drugs, 60, 333 (1980)
• Yajima, H., et al.: J. Biol. Chem., 279, 33456 (1980)
• Devasthale, P., et al.: J. Med. Chem., 48, 2248 (1980)
• Zhang, D., et al.: Drug Metab. Dispos., 34, 267 (20