Glycochenodeoxycholic 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

InChI

InChI=1/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19?,20?,21-,24?,25+,26-/s3

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|

Glycochenodeoxycholic Acid Usage And Synthesis

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

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

Glycochenodeoxycholic Acid(640-79-9)Related Product Information

• Glycochenodeoxycholic Acid 3-Sulfate DisodiuM Salt
• Glycochenodeoxycholic Acid-3-O-β-glucuronide Disodium Salt
• (3a,5b,7a)-24-[(carboxymethyl)amino]-7-hydroxy-24-oxocholan-3-yl b-D-glucopyranosiduronic acid
• Glycine methyl ester hydrochloride
• Glycochenodeoxycholic acid sodium salt
• TAUROCHENODEOXYCHOLIC ACID SODIUM SALT