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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H43NO5
Molecular Weight 449.6243
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCOCHENODEOXYCHOLIC ACID

SMILES

C[C@]([H])(CCC(=NCC(=O)O)O)[C@@]1([H])CC[C@@]2([H])[C@@]3([H])[C@]([H])(CC[C@]12C)[C@@]4(C)CC[C@]([H])(C[C@@]4([H])C[C@@]3([H])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 449.6243
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 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
The bcl-2 mRNA expression in GCDC-induced obstructive jaundice in rats and its implication in hepatocellular apoptosis.
2002
[Release of cytochrome C with the interaction of bilirubin, amyloid beta-peptide and glycochenodeoxycholate from isolated mitochondria].
2002 Jul-Aug
The human bile salt export pump: characterization of substrate specificity and identification of inhibitors.
2002 Nov
Membrane structural changes support the involvement of mitochondria in the bile salt-induced apoptosis of rat hepatocytes.
2002 Nov
Resistance of rat hepatocytes against bile acid-induced apoptosis in cholestatic liver injury is due to nuclear factor-kappa B activation.
2003 Aug
Unique inhibition of bile salt-induced apoptosis by lecithins and cytoprotective bile salts in immortalized mouse cholangiocytes.
2003 Dec
Gallium-67 activated charcoal: a new method for preparation of radioactive capsules for colonic transit study.
2003 Jun
Bile salt-induced hepatocyte apoptosis involves epidermal growth factor receptor-dependent CD95 tyrosine phosphorylation.
2003 Sep
Inhibition of hepatocyte growth factor production in human fibroblasts by ursodeoxycholic acid.
2005 Apr
Glycochenodeoxycholate plays a carcinogenic role in immortalized mouse cholangiocytes via oxidative DNA damage.
2005 Dec 1
Expression of macrophage migration inhibitory factor in esophageal squamous cell carcinoma and effects of bile acids and NSAIDs.
2005 Jan
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
2005 Jan
Reversibility of caspase activation and its role during glycochenodeoxycholate-induced hepatocyte apoptosis.
2005 Jun 24
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 culture human normal esophageal mucosal epithelial cells.
2005 Nov 7
Bile salts inhibit growth and induce apoptosis of human esophageal cancer cell line.
2005 Sep 7
Substrate specificity of human ABCC4 (MRP4)-mediated cotransport of bile acids and reduced glutathione.
2006 Apr
Characterization of fasted-state human intestinal fluids collected from duodenum and jejunum.
2006 Aug
Determinants of cooperativity and site selectivity in human ileal bile acid binding protein.
2006 Jan 24
Sulfasalazine reduces bile acid induced apoptosis in human hepatoma cells and perfused rat livers.
2006 May
Bile acids inhibit interleukin-6 signaling via gp130 receptor-dependent and -independent pathways in rat liver.
2006 Nov
[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
Glycochenodeoxycholate (GCDC) inhibits cytokine induced iNOS expression in rat hepatocytes.
2007 Mar
Taurodeoxycholate modulates apical Cl-/OH- exchange activity in Caco2 cells.
2007 May
Complexation of tauro- and glyco-conjugated bile salts with three neutral beta-CDs studied by ACE.
2007 Oct
Hydrophobic bile acids, genomic instability, Darwinian selection, and colon carcinogenesis.
2008
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
Determination of intralumenal individual bile acids by HPLC with charged aerosol detection.
2008 Dec
Cytoprotective effect of tauroursodeoxycholate on hepatocyte apoptosis induced by peroxisome proliferator-activated receptor gamma ligand.
2008 Jul
Insulin-like growth factor-1 isoforms in rat hepatocytes and cholangiocytes and their involvement in protection against cholestatic injury.
2008 Sep
Current concepts of mechanisms in drug-induced hepatotoxicity.
2009
Bile acid-induced epidermal growth factor receptor activation in quiescent rat hepatic stellate cells can trigger both proliferation and apoptosis.
2009 Aug 14
Mitochondrial-driven ubiquinone enhances extracellular calcium-dependent nitric oxide production and reduces glycochenodeoxycholic acid-induced cell death in hepatocytes.
2009 Dec
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
Survivin signaling is regulated through nuclear factor-kappa B pathway during glycochenodeoxycholate-induced hepatocyte apoptosis.
2010 Dec
Interpreting metabolomic profiles using unbiased pathway models.
2010 Feb 26
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
Bile acid-induced virulence gene expression of Vibrio parahaemolyticus reveals a novel therapeutic potential for bile acid sequestrants.
2010 Oct 13
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 Jun 26 12:47:31 UTC 2021
Edited
by admin
on Sat Jun 26 12:47:31 UTC 2021
Record UNII
451ZNJ667Y
Record Status Validated (UNII)
Record Version
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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 Jun 26 12:47:31 UTC 2021 , Edited by admin on Sat Jun 26 12:47:31 UTC 2021
Code System Code Type Description
WIKIPEDIA
Glycochenodeoxycholic acid
Created by admin on Sat Jun 26 12:47:31 UTC 2021 , Edited by admin on Sat Jun 26 12:47:31 UTC 2021
PRIMARY
PUBCHEM
12544
Created by admin on Sat Jun 26 12:47:31 UTC 2021 , Edited by admin on Sat Jun 26 12:47:31 UTC 2021
PRIMARY
DRUG BANK
DB02123
Created by admin on Sat Jun 26 12:47:31 UTC 2021 , Edited by admin on Sat Jun 26 12:47:31 UTC 2021
PRIMARY
CAS
640-79-9
Created by admin on Sat Jun 26 12:47:31 UTC 2021 , Edited by admin on Sat Jun 26 12:47:31 UTC 2021
PRIMARY
FDA UNII
451ZNJ667Y
Created by admin on Sat Jun 26 12:47:31 UTC 2021 , Edited by admin on Sat Jun 26 12:47:31 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE