U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H43NO5
Molecular Weight 449.6233
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCOCHENODEOXYCHOLIC ACID

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O

InChI

InChIKey=GHCZAUBVMUEKKP-GYPHWSFCSA-N
InChI=1S/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-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H43NO5
Molecular Weight 449.6233
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Binding of bile acids by glutathione S-transferases from rat liver.
1986 Sep
Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter.
1998 Jan
Solubilization of drugs by physiological mixtures of bile salts.
2002 Aug
The human bile salt export pump: characterization of substrate specificity and identification of inhibitors.
2002 Nov
Unique inhibition of bile salt-induced apoptosis by lecithins and cytoprotective bile salts in immortalized mouse cholangiocytes.
2003 Dec
Bile salt-induced hepatocyte apoptosis involves epidermal growth factor receptor-dependent CD95 tyrosine phosphorylation.
2003 Sep
Expression of macrophage migration inhibitory factor in esophageal squamous cell carcinoma and effects of bile acids and NSAIDs.
2005 Jan
A nuclear receptor ligand down-regulates cytosolic phospholipase A2 expression to reduce bile acid-induced cyclooxygenase 2 activity in cholangiocytes: implications of anticarcinogenic action of farnesoid X receptor agonists.
2005 Mar
Bile salts inhibit growth and induce apoptosis of human esophageal cancer cell line.
2005 Sep 7
Sulfasalazine reduces bile acid induced apoptosis in human hepatoma cells and perfused rat livers.
2006 May
[Bile salts induce differentiation in cultured human normal esophageal mucosal epithelial cells].
2006 Sep 12
Hydrophobic bile salts induce hepatocyte shrinkage via NADPH oxidase activation.
2007
Bile salts regulate proliferation and apoptosis of liver cells by modulating the IGF1 system.
2007 Jul
Structural basis for bile salt inhibition of pancreatic phospholipase A2.
2007 Jun 1
Taurodeoxycholate modulates apical Cl-/OH- exchange activity in Caco2 cells.
2007 May
Activation of focal adhesion kinase and JNK contributes to the extracellular matrix and cAMP-GEF mediated survival from bile acid induced apoptosis in rat hepatocytes.
2008 Aug
Effects of bile acids on pancreatic ductal bicarbonate secretion in guinea pig.
2008 Aug
Cytoprotective effect of tauroursodeoxycholate on hepatocyte apoptosis induced by peroxisome proliferator-activated receptor gamma ligand.
2008 Jul
Bile acid-induced epidermal growth factor receptor activation in quiescent rat hepatic stellate cells can trigger both proliferation and apoptosis.
2009 Aug 14
Thermodynamics and structure of inclusion compounds of tauro- and glyco-conjugated bile salts and beta-cyclodextrin.
2009 Jul 7
Effect of membrane cholesterol on BSEP/Bsep activity: species specificity studies for substrates and inhibitors.
2009 Sep
Calcium-dependent nitric oxide production is involved in the cytoprotective properties of n-acetylcysteine in glycochenodeoxycholic acid-induced cell death in hepatocytes.
2010 Jan 15
HepatoNet1: a comprehensive metabolic reconstruction of the human hepatocyte for the analysis of liver physiology.
2010 Sep 7
Role of bile salt in regulating Mcl-1 phosphorylation and chemoresistance in hepatocellular carcinoma cells.
2011 Apr 20
Angiotensin II protects primary rat hepatocytes against bile salt-induced apoptosis.
2012
Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs.
2012 May
Ursodeoxycholyl lysophosphatidylethanolamide inhibits cholestasis- and hypoxia-induced apoptosis by upregulating antiapoptosis proteins.
2015 Feb
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:03:04 GMT 2023
Edited
by admin
on Sat Dec 16 01:03:04 GMT 2023
Record UNII
451ZNJ667Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLYCOCHENODEOXYCHOLIC ACID
Common Name English
12-DEOXYCHOLYLGLYCINE
Common Name English
CHENODEOXYGLYCOCHOLIC ACID
Common Name English
12-DESOXYCHOLYLGLYCINE
Common Name English
GLYCYLCHENODEOXYCHOLIC ACID
Common Name English
GLYCINE, N-(3.ALPHA.,7.ALPHA.-DIHYDROXY-5.BETA.-CHOLAN-24-OYL)-
Systematic Name English
GLYCINE, N-((3.ALPHA.,5.BETA.,7.ALPHA.)-3,7-DIHYDROXY-24-OXOCHOLAN-24-YL)-
Systematic Name English
CHENODEOXYCHOLYLGLYCINE
Common Name English
GLYCINE CHENODEOXYCHOLATE
Common Name English
Classification Tree Code System Code
LOINC 2066-9
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
Code System Code Type Description
WIKIPEDIA
Glycochenodeoxycholic acid
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID301020165
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
PRIMARY
CHEBI
36274
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
PRIMARY
PUBCHEM
12544
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
PRIMARY
DRUG BANK
DB02123
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
PRIMARY
CAS
640-79-9
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
PRIMARY
FDA UNII
451ZNJ667Y
Created by admin on Sat Dec 16 01:03:04 GMT 2023 , Edited by admin on Sat Dec 16 01:03:04 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE