Cholic Acid Acyl Glucuronide

• CAT Number: C000881
• CAS Number: 208038-30-6
• Molecular Formula: C₃₀H₄₈O₁₁
• Molecular Weight: 584.7
• Purity: ≥95%
• Synonyms: (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)oxy)tetrahydro-2H-pyran-2-carboxylic Acid; ?-D-Glucopyranuronic Acid, 1-[(3?,5?,7?,12?)-3,7,12-Trihydroxycholan-24-oate
• Solubility: Methanol (Slightly), Water (Slightly)
• Appearance: White to Off-White Solid
• Storage: -20°C, Hygroscopic
• IUPAC Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxyoxane-2-carboxylic acid
• InChI: InChI=1S/C30H48O11/c1-13(4-7-21(34)40-28-25(37)23(35)24(36)26(41-28)27(38)39)16-5-6-17-22-18(12-20(33)30(16,17)3)29(2)9-8-15(31)10-14(29)11-19(22)32/h13-20,22-26,28,31-33,35-37H,4-12H2,1-3H3,(H,38,39)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24+,25-,26+,28-,29+,30-/m1/s1
• InChIKey: AIUGVBWFKAVAIZ-SXYQVCRBSA-N
• SMILES: CC(CCC(=O)OC1C(C(C(C(O1)C(=O)O)O)O)O)C2CCC3C2(C(CC4C3C(CC5C4(CCC(C5)O)C)O)O)C

Cholic Acid Acyl Glucuronide (Cat No.:C000881) is a metabolite formed in the liver by the glucuronidation of cholic acid, a primary bile acid. Glucuronidation involves attaching a glucuronide moiety to the cholic acid molecule, enhancing its water solubility and facilitating excretion from the body. Cholic Acid Acyl Glucuronide is inactive and serves as a means of eliminating cholic acid from the body. This metabolic pathway is crucial for the regulation of bile acid levels and overall bile acid homeostasis.

Reference

Maekawa, M., et al.: Steroids, 80, 80 (2014); Goto, J., et al.: Steroids, 63, 180 (1998); Murao, N., et al.: Chromatography, 19, 276 (1998)