Glycolithocholic acid

Names

[ CAS No. ]:
474-74-8

[ Name ]:
Glycolithocholic acid

[Synonym ]:
Glycolithocholic acid
2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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]amino]acetic acid
Lithocholic acid glycine conjugate
Lithocholylglycine
Glycolithocholate

Biological Activity

[Description]:

Glycolithocholic acid, an endogenous metabolite, is a glycine-conjugated secondary bile acid. Glycolithocholic acid can be used to diagnose ulcerative colitis (UC), non-alcoholic steatohepatitis (NASH) and primary sclerosing cholangitis (PSC)[1][2][3][4].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[In Vivo]

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

[References]

[1]. Tanno N, et, al. Biliary lipid composition in heterozygous familial hypercholesterolemia and influence of treatment with probucol. Dig Dis Sci. 1994 Jul;39(7):1586-91.

[2]. Ang ZH, et, al. Altered profiles of fecal bile acids correlate with gut microbiota and inflammatory responses in patients with ulcerative colitis. World J Gastroenterol. 2021 Jun 28;27(24):3609-3629.

[3]. Bansal S, et, al. Inhibition of Human Sulfotransferase 2A1-Catalyzed Sulfonation of Lithocholic Acid, Glycolithocholic Acid, and Taurolithocholic Acid by Selective Estrogen Receptor Modulators and Various Analogs and Metabolites. J Pharmacol Exp Ther. 2019 Jun;369(3):389-405.

[4]. Sanyal AJ, et, al. Potent suppression of hydrophobic bile acids by aldafermin, an FGF19 analogue, across metabolic and cholestatic liver diseases. JHEP Rep. 2021 Feb 19;3(3):100255.

Chemical & Physical Properties

[ Density]:
1.112g/cm3

[ Boiling Point ]:
619.7ºC at 760mmHg

[ Melting Point ]:
212-214°C (lit.)

[ Molecular Formula ]:
C₂₆H₄₃NO₄

[ Molecular Weight ]:
433.62400

[ Flash Point ]:
328.6ºC

[ Exact Mass ]:
433.31900

[ PSA ]:
86.63000

[ LogP ]:
5.01420

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MC0594200

CHEMICAL NAME :: Glycine, N-((3-alpha,5-beta)-3-hydroxy-24-oxocholan-24-yl)-

CAS REGISTRY NUMBER :: 474-74-8

LAST UPDATED :: 199509

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C26-H43-N-O4

MOLECULAR WEIGHT :: 433.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 10 mg/L

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 15,1911,1994

Safety Information

[ Hazard Codes ]:
T