ChemicalBook CAS DataBase List 640-79-9

640-79-9

Name	Glycochenodeoxycholic Acid
CAS	640-79-9
Molecular Formula	C26H43NO5
MDL Number	MFCD00271498
Molecular Weight	449.62
MOL File	640-79-9.mol

Synonyms

GCDC GCDCA Glycochenodeoxycholate Chenodeoxycholylglycine Glycine chenodeoxycholate glycochenodeoxycholic aci GLYCOCHENODEOXYCHOLIC ACID Glycoanthropodeoxycholic acid Glycochenodeoxycholic-d4 Acid Glycochenodeoxycholic acid, >98% glycochenodeoxycholic acid (GCDCA) N-[(3a,5b,7a)-3,7-dihydroxy-24-oxocholan-24-yl]-Glycine Glycine, N-[(3a,5b,7a)-3,7-dihydroxy-24-oxocholan-24-yl] Glycine, N-[(3α,5β,7α)-3,7-dihydroxy-24-oxocholan-24-yl]- 3alpha,7alpha-Dihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide 2-((R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)acetic acid 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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]ethanoic acid

Chemical Properties

Boiling point	655.6±40.0 °C(Predicted)
density	1.162±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMSO : ≥ 29 mg/mL (64.50 mM)
form	Solid
pka	3.58±0.10(Predicted)
color	White to off-white
InChIKey	GHCZAUBVMUEKKP-VHGKAQQHNA-N
SMILES	C(O)(=O)CNC(=O)CC[C@@H](C)[C@@H]1[C@]2(CCC3[C@]4(C)[C@]([H])(C[C@@H](O)C3C2CC1)C[C@H](O)CC4)C \|&1:9,11,12,16,18,21,28,r\|

Safety Data

Symbol(GHS)	GHS02,GHS06,GHS08
Signal word	Danger
Hazard statements	H225-H301+H311+H331-H370
Precautionary statements	P210-P240-P241-P242-P243-P260-P264-P270-P271-P280-P301+P310-P321-P330-P303+P361+P353-P304+P340-P307+P311-P312-P361+P364-P370+P378-P403+P233-P403+P235-P405-P501
WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Hazard Information

Uses

Glycochenodeoxycholic acid (Chenodeoxycholylglycine) is a relatively toxic bile salt generated in the liver from chenodeoxycholic acid and glycine. Glycochenodeoxycholic acid inhibits Autophagosome formation and impairs lysosomal function by inhibiting lysosomal proteolysis and increasing lysosomal pH in human normal liver cells, leading to the Apoptosis of human hepatocyte cells. Glycochenodeoxycholic acid induces stemness and chemoresistance via activating STAT3 signaling pathway in hepatocellular carcinoma cells (HCC). Glycochenodeoxycholic acid is promising for research in the field of cholestasis desease, hepatocellular carcinoma and primary sclerosing cholangitis (PSC)[1][2][3][4].

Definition

ChEBI: A bile acid glycine conjugate having 3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl as the bile acid component.

IC 50

Microbial Metabolite; Human Endogenous Metabolite

storage

Store at -20°C

References

[1] Lan W, et al. Glycochenodeoxycholic acid impairs transcription factor E3 -dependent autophagy-lysosome machinery by disrupting reactive oxygen species homeostasis in L02 cells[J]. Toxicol Lett. 2020 Oct 1;331:11-21. DOI:10.1016/j.toxlet.2020.05.017
[2] Wang A, et al. Glycochenodeoxycholic Acid Does Not Increase Transforming Growth Factor-Beta Expression in Bile Duct Epithelial Cells or Collagen Synthesis in Myofibroblasts[J]. J Clin Exp Hepatol. 2017 Dec;7(4):316-320. DOI:10.1016/j.jceh.2017.04.002
[3] Gonzalez B, et al. Glycochenodeoxycholic acid (GCDC) induced hepatocyte apoptosis is associated with early modulation of intracellular PKC activity. Mol Cell Biochem. 2000 Apr;207(1-2):19-27. DOI:10.1023/a:1007021710825
[4] Shi C, et al. Glycochenodeoxycholic acid induces stemness and chemoresistance via the STAT3 signaling pathway in hepatocellular carcinoma cells[J]. Aging (Albany NY). 2020 Aug 3;12(15):15546-15555. DOI:10.18632/aging.103751

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