N-[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]-(9CI) Glycine

Product NameN-[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]-(9CI) Glycine
CAS474-74-8
MFC26H43NO4
MW433.63
EINECS207-494-9
MOL File474-74-8.mol

Chemical Properties

Melting point	212-214 °C
Boiling point	546.95°C (rough estimate)
Density	1.0738 (rough estimate)
refractive index	1.6000 (estimate)
storage temp.	Refrigerator
solubility	Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
form	Solid
pka	3.58±0.10(Predicted)
color	White to Off-White
InChIKey	XBSQTYHEGZTYJE-LNYAHCOINA-N
SMILES	C[C@]12CC[C@]3([H])[C@]4(CC[C@@H](O)C[C@@]4([H])CC[C@@]3([H])[C@]1([H])CC[C@]2([H])[C@H](C)CCC(=O)NCC(=O)O)C \|&1:1,4,6,9,12,16,18,22,24,r\|

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Glycolithocholic acid is a glycine-conjugated form of the secondary bile acid lithocholic acid . It is increased in the liver of mice fed a diet supplemented with ursodeoxycholic acid . Glycolithocholic acid levels are decreased in the plasma following subcutaneous administration of PEG-obestatin(Cys¹⁰, Cys¹³), a modified peptide hormone, in lean or diet-induced obese mice. Serum glycolithocholic acid levels increase with age in children.

Uses

A metabolite in human hepatic bile. A lithocholic acid analog that inhibit sialyltransferase.

Definition

ChEBI: The glycine conjugate of lithocholic acid.

in vivo

The concentrations of Glycolithocholic acid in ulcerative colitis (UC) patients were significantly lower than those in healthy controls (HCs)^[2].

IC 50

Microbial Metabolite

References

[1] P. LEFEBVRE. Role of bile acids and bile acid receptors in metabolic regulation.[J]. Physiological reviews, 2009, 89 1 1: 147-191. DOI: 10.1152/physrev.00010.2008
[2] YOUCAI ZHANG Curtis D K. Effects of feeding bile acids and a bile acid sequestrant on hepatic bile acid composition in mice.[J]. Journal of Lipid Research, 2010, 51 11: 3230-3242. DOI: 10.1194/jlr.m007641
[3] ELAINE COWAN. Treatment of lean and diet-induced obesity (DIO) mice with a novel stable obestatin analogue alters plasma metabolite levels as detected by untargeted LC-MS metabolomics.[J]. Metabolomics, 2016, 12: 124. DOI: 10.1007/s11306-016-1063-0
[4] RICHARD D SEMBA. Environmental Enteric Dysfunction Is Associated With Altered Bile Acid Metabolism.[J]. Journal of Pediatric Gastroenterology and Nutrition, 2017, 64 4: 536-540. DOI: 10.1097/mpg.0000000000001313

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