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
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
| 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
| Title | Date | PubMed |
|---|---|---|
| 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
Edited
Sat Jun 26 12:47:31 UTC 2021
by
admin
on
Sat Jun 26 12:47:31 UTC 2021
|
| Record UNII |
451ZNJ667Y
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
