(2R,3R,4R,5S,6R)-6-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171627
• Molecular Formular: C25H24ClNO10
• Molecular Mass: 533.91176
• Monoisotopic Mass: 533.10887365
• SMILES: C(C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)c1c2cc(ccc2n(c1C)C(=O)c1ccc(cc1)Cl)OC
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)c(n2C(=O)c1ccc(cc1)Cl)C
• InChI: InChI=1S/C25H24ClNO10/c1-11-15(10-18(28)36-25-21(31)19(29)20(30)22(37-25)24(33)34)16-9-14(35-2)7-8-17(16)27(11)23(32)12-3-5-13(26)6-4-12/h3-9,19-22,25,29-31H,10H2,1-2H3,(H,33,34)/t19-,20-,21+,22-,25+/m1/s1
• InChIKey: QCBWEVBGELGABM-ILJOYBHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate] β-D-Glucopyranuronic Acid; Indomethacin Glucuronide; Indomethacin Acyl-β-D-glucuronide

Database IDs

• CAS Number: 75523-11-4
• PubChem SID: 164227537
• PubChem CID: 71749490

CALCULATED PROPERTIES

• Acid pKa: 3.1912348
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -0.703643
• LogD (pH = 7.4): -1.8650981
• Log P: 1.5818808
• Molar Refractivity: 127.1092 cm^3
• Polarizability: 51.152077 Å^3
• Polar Surface Area: 164.75 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light-Green Solid
• Melting Point: 82-84°C

Safety Information

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

DETAILS

Toronto Research Chemicals - I641010

Indomethacin Acyl-β-D-glucuronide is a metabolite of Indomethacin (I641000). Acyl glucuronides have been implicated in the toxicity of many xenobiotics and marketed drugs.

REFERENCES

• Abid, A., et al.: Biochem. Pharmacol., 50, 557 (1995)
• Gamage, N., et al.: Toxicol. Sci., 90, 5 (1995)
• Cerveny, L., et al.: Drug Metab. Dispos., 35, 1032 (1995)
• Hayeshi, R., et al.: Eur. J. Pharm. Sci., 35, 383 (1995)