Home Other Building Blocks Glycochenodeoxycholic Acid

Glycochenodeoxycholic Acid

CAS No.:
640-79-9
Catalog Number:
AG00EBG1
Molecular Formula:
C26H43NO5
Molecular Weight:
449.6233
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
98%
1 week
United States
$140
- +
Product Description
Catalog Number:
AG00EBG1
Chemical Name:
Glycochenodeoxycholic Acid
CAS Number:
640-79-9
Molecular Formula:
C26H43NO5
Molecular Weight:
449.6233
MDL Number:
MFCD00271498
IUPAC Name:
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
InChI:
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
InChI Key:
GHCZAUBVMUEKKP-GYPHWSFCSA-N
SMILES:
O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCC(=O)O)C)C)O)C
UNII:
451ZNJ667Y
Properties
Complexity:
727  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
0
Exact Mass:
449.314g/mol
Formal Charge:
0
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
449.632g/mol
Monoisotopic Mass:
449.314g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
107A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.3  
Literature
Title Journal
Kinetic characterization of bile salt transport by human NTCP (SLC10A1). Toxicology in vitro : an international journal published in association with BIBRA 20180201
Bile Acid-Induced Toxicity in HepaRG Cells Recapitulates the Response in Primary Human Hepatocytes. Basic & clinical pharmacology & toxicology 20160201
Ursodeoxycholyl lysophosphatidylethanolamide inhibits cholestasis- and hypoxia-induced apoptosis by upregulating antiapoptosis proteins. Experimental biology and medicine (Maywood, N.J.) 20150201
11β-Hydroxysteroid dehydrogenase-1 is involved in bile acid homeostasis by modulating fatty acid transport protein-5 in the liver of mice. Molecular metabolism 20140801
Tauro-β-muricholic acid restricts bile acid-induced hepatocellular apoptosis by preserving the mitochondrial membrane potential. Biochemical and biophysical research communications 20120810
Glycochenodeoxycholate induces rat alveolar epithelial type II cell death and inhibits surfactant secretion in vitro. Free radical biology & medicine 20120701
Glycochenodeoxycholic acid promotes proliferation of intestinal epithelia via reduction of cyclic AMP and increase in H2AX phosphorylation after exposure to γ-rays. Biomedical research (Tokyo, Japan) 20120601
Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. Journal of medicinal chemistry 20120524
Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs. Toxicological sciences : an official journal of the Society of Toxicology 20120501
Plasma metabonomics study of rheumatoid arthritis and its Chinese medicine subtypes by using liquid chromatography and gas chromatography coupled with mass spectrometry. Molecular bioSystems 20120401
Internal motions and exchange processes in human ileal bile acid binding protein as studied by backbone (15)N nuclear magnetic resonance spectroscopy. Biochemistry 20120306
In vitro and in silico strategies to identify OATP1B1 inhibitors and predict clinical drug-drug interactions. Pharmaceutical research 20120201
The evolving landscape of neurotoxicity by unconjugated bilirubin: role of glial cells and inflammation. Frontiers in pharmacology 20120101
Pertussis toxin, an inhibitor of G(αi) PCR, inhibits bile acid- and cytokine-induced apoptosis in primary rat hepatocytes. PloS one 20120101
Angiotensin II protects primary rat hepatocytes against bile salt-induced apoptosis. PloS one 20120101
Structural requirements for cooperativity in ileal bile acid-binding proteins. The Journal of biological chemistry 20111111
Complexation of tauro- and glyco-conjugated bile salts with α-cyclodextrin and hydroxypropyl-α-cyclodextrin studied by affinity capillary electrophoresis and molecular modelling. Journal of separation science 20111101
iNOS/NO signaling regulates apoptosis induced by glycochenodeoxycholate in hepatocytes. Cellular signalling 20111001
Cytoprotective properties of rifampicin are related to the regulation of detoxification system and bile acid transporter expression during hepatocellular injury induced by hydrophobic bile acids. Journal of hepato-biliary-pancreatic sciences 20110901
C/EBPα and C/EBPβ binding proteins modulate hepatocyte apoptosis through iNOS signaling pathway. Biochimica et biophysica acta 20110801
cAMP-guanine exchange factor protection from bile acid-induced hepatocyte apoptosis involves glycogen synthase kinase regulation of c-Jun NH2-terminal kinase. American journal of physiology. Gastrointestinal and liver physiology 20110801
Nitric oxide mimics transcriptional and post-translational regulation during α-tocopherol cytoprotection against glycochenodeoxycholate-induced cell death in hepatocytes. Journal of hepatology 20110701
Mitochondrial genome depletion dysregulates bile acid- and paracetamol-induced expression of the transporters Mdr1, Mrp1 and Mrp4 in liver cells. British journal of pharmacology 20110401
Plasma metabolomic profile in nonalcoholic fatty liver disease. Metabolism: clinical and experimental 20110301
Anti-oxidants do not prevent bile acid-induced cell death in rat hepatocytes. Liver international : official journal of the International Association for the Study of the Liver 20110201
Non-conjugated chenodeoxycholate induces severe mitochondrial damage and inhibits bicarbonate transport in pancreatic duct cells. Gut 20110101
The relationship between postprandial bile acid concentration, GLP-1, PYY and ghrelin. Clinical endocrinology 20110101
Role of bile salt in regulating Mcl-1 phosphorylation and chemoresistance in hepatocellular carcinoma cells. Molecular cancer 20110101
Hepatocyte IKK2 protects Mdr2-/- mice from chronic liver failure. PloS one 20110101
Survivin signaling is regulated through nuclear factor-kappa B pathway during glycochenodeoxycholate-induced hepatocyte apoptosis. Biochimica et biophysica acta 20101201
Phosphatidylinositol-3-kinase p110γ contributes to bile salt-induced apoptosis in primary rat hepatocytes and human hepatoma cells. Journal of hepatology 20101101
Anti-oxidants do not prevent bile acid-induced cell death in rat hepatocytes. Liver international : official journal of the International Association for the Study of the Liver 20101101
Inhibition of interferon-α-induced signaling by hyperosmolarity and hydrophobic bile acids. Biological chemistry 20101001
Protective effects of glycoursodeoxycholic acid in Barrett's esophagus cells. Diseases of the esophagus : official journal of the International Society for Diseases of the Esophagus 20100201
Pregnane X receptor activation protects rat hepatocytes against deoxycholic acid-induced apoptosis. Liver international : official journal of the International Association for the Study of the Liver 20100201
Interpreting metabolomic profiles using unbiased pathway models. PLoS computational biology 20100201
Learning from the pregnane X receptor: how to fight one aggressor with two strategies. Liver international : official journal of the International Association for the Study of the Liver 20100201
Calcium-dependent nitric oxide production is involved in the cytoprotective properties of n-acetylcysteine in glycochenodeoxycholic acid-induced cell death in hepatocytes. Toxicology and applied pharmacology 20100115
Glycochenodeoxycholate-induced apoptosis is not reduced by augmenter of liver regeneration in the human hepatoma cell line HuH-7. Digestion 20100101
HepatoNet1: a comprehensive metabolic reconstruction of the human hepatocyte for the analysis of liver physiology. Molecular systems biology 20100101
Bile acid-induced virulence gene expression of Vibrio parahaemolyticus reveals a novel therapeutic potential for bile acid sequestrants. PloS one 20100101
Mitochondrial-driven ubiquinone enhances extracellular calcium-dependent nitric oxide production and reduces glycochenodeoxycholic acid-induced cell death in hepatocytes. Chemical research in toxicology 20091201
Effect of membrane cholesterol on BSEP/Bsep activity: species specificity studies for substrates and inhibitors. Drug metabolism and disposition: the biological fate of chemicals 20090901
Bile acid-induced epidermal growth factor receptor activation in quiescent rat hepatic stellate cells can trigger both proliferation and apoptosis. The Journal of biological chemistry 20090814
Current concepts of mechanisms in drug-induced hepatotoxicity. Current medicinal chemistry 20090801
Thermodynamics and structure of inclusion compounds of tauro- and glyco-conjugated bile salts and beta-cyclodextrin. Physical chemistry chemical physics : PCCP 20090707
Absence of glycochenodeoxycholic acid (GCDCA) in human bile is an indication of cholestasis: a 1H MRS study. NMR in biomedicine 20090601
The effect of capillarisin on glycochenodeoxycholic acid-induced apoptosis and heme oxygenase-1 in rat primary hepatocytes. Molecular and cellular biochemistry 20090501
cAMP-GEF cytoprotection by Src tyrosine kinase activation of phosphoinositide-3-kinase p110 beta/alpha in rat hepatocytes. American journal of physiology. Gastrointestinal and liver physiology 20090401
Bile acid-induced apoptosis in hepatocytes is caspase-6-dependent. The Journal of biological chemistry 20090130
Determination of intralumenal individual bile acids by HPLC with charged aerosol detection. Journal of lipid research 20081201
Resistance of young rat hepatic mitochondria to bile acid-induced permeability transition: potential role of alpha-tocopherol. Pediatric research 20081101
The active metabolite of leflunomide, A77 1726, protects rat hepatocytes against bile acid-induced apoptosis. Journal of hepatology 20081101
Insulin-like growth factor-1 isoforms in rat hepatocytes and cholangiocytes and their involvement in protection against cholestatic injury. Laboratory investigation; a journal of technical methods and pathology 20080901
Effects of bile acids on pancreatic ductal bicarbonate secretion in guinea pig. Gut 20080801
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. Journal of hepatology 20080801
Free fatty acids sensitize hepatocytes to bile acid-induced apoptosis. Biochemical and biophysical research communications 20080704
Cytoprotective effect of tauroursodeoxycholate on hepatocyte apoptosis induced by peroxisome proliferator-activated receptor gamma ligand. Journal of gastroenterology and hepatology 20080701
Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies. Journal of medicinal chemistry 20080327
CHOP deficiency attenuates cholestasis-induced liver fibrosis by reduction of hepatocyte injury. American journal of physiology. Gastrointestinal and liver physiology 20080201
Hydrophobic bile acids, genomic instability, Darwinian selection, and colon carcinogenesis. Clinical and experimental gastroenterology 20080101
Interaction between caspase-8 activation and endoplasmic reticulum stress in glycochenodeoxycholic acid-induced apoptotic HepG2 cells. Toxicology 20071130
PF2401-SF, standardized fraction of Salvia miltiorrhiza and its constituents, tanshinone I, tanshinone IIA, and cryptotanshinone, protect primary cultured rat hepatocytes from bile acid-induced apoptosis by inhibiting JNK phosphorylation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20071001
Complexation of tauro- and glyco-conjugated bile salts with three neutral beta-CDs studied by ACE. Electrophoresis 20071001
Subcutaneous vitamin E ameliorates liver injury in an in vivo model of steatocholestasis. Hepatology (Baltimore, Md.) 20070801
Is vitamin E beneficial in chronic liver disease? Hepatology (Baltimore, Md.) 20070801
Bile salts regulate proliferation and apoptosis of liver cells by modulating the IGF1 system. Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver 20070701
Structural basis for bile salt inhibition of pancreatic phospholipase A2. Journal of molecular biology 20070601
Kinetic mechanism of ligand binding in human ileal bile acid binding protein as determined by stopped-flow fluorescence analysis. Biochemistry 20070508
Taurodeoxycholate modulates apical Cl-/OH- exchange activity in Caco2 cells. Digestive diseases and sciences 20070501
Glycochenodeoxycholate (GCDC) inhibits cytokine induced iNOS expression in rat hepatocytes. The Journal of surgical research 20070301
Hydrophobic bile salts induce hepatocyte shrinkage via NADPH oxidase activation. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20070101
Bile acid salt binding with colesevelam HCl is not affected by suspension in common beverages. Journal of pharmaceutical sciences 20061201
Bile acids inhibit interleukin-6 signaling via gp130 receptor-dependent and -independent pathways in rat liver. Hepatology (Baltimore, Md.) 20061101
Involvement of endoplasmic reticulum in glycochenodeoxycholic acid-induced apoptosis in rat hepatocytes. Toxicology letters 20061010
[Bile salts induce differentiation in cultured human normal esophageal mucosal epithelial cells]. Zhonghua yi xue za zhi 20060912
Maternal ethanol consumption during pregnancy enhances bile acid-induced oxidative stress and apoptosis in fetal rat liver. Toxicology 20060815
Characterization of fasted-state human intestinal fluids collected from duodenum and jejunum. The Journal of pharmacy and pharmacology 20060801
Honokiol reduces oxidative stress, c-jun-NH2-terminal kinase phosphorylation and protects against glycochenodeoxycholic acid-induced apoptosis in primary cultured rat hepatocytes. Planta medica 20060601
Single-step analysis of individual conjugated bile acids in human bile using 1H NMR spectroscopy. Lipids 20060601
Sulfasalazine reduces bile acid induced apoptosis in human hepatoma cells and perfused rat livers. Gut 20060501
Substrate specificity of human ABCC4 (MRP4)-mediated cotransport of bile acids and reduced glutathione. American journal of physiology. Gastrointestinal and liver physiology 20060401
High performance liquid chromatography-mass spectrometry for metabonomics: potential biomarkers for acute deterioration of liver function in chronic hepatitis B. Journal of proteome research 20060301
The human transcription factor AP-1 is a mediator of bile acid-induced liver cell apoptosis. Biochemical and biophysical research communications 20060217
Determinants of cooperativity and site selectivity in human ileal bile acid binding protein. Biochemistry 20060124
Effect of tamoxifen and raloxifene on the conjugation of bile acids with taurine and glycine in ovariectomized rats. Pharmacological reports : PR 20060101
Glycochenodeoxycholate plays a carcinogenic role in immortalized mouse cholangiocytes via oxidative DNA damage. Free radical biology & medicine 20051201
Conjugated bile acids promote ERK1/2 and AKT activation via a pertussis toxin-sensitive mechanism in murine and human hepatocytes. Hepatology (Baltimore, Md.) 20051201
Bile salts inhibit growth and induce apoptosis of culture human normal esophageal mucosal epithelial cells. World journal of gastroenterology 20051107
The effect of ursodeoxycholic acid on glycochenodeoxycholic acid-induced apoptosis in rat hepatocytes. Toxicology 20051015
Bile salts inhibit growth and induce apoptosis of human esophageal cancer cell line. World journal of gastroenterology 20050907
Human hepatic mitochondria generate reactive oxygen species and undergo the permeability transition in response to hydrophobic bile acids. Journal of pediatric gastroenterology and nutrition 20050801
Phosphatidylinositol 3-kinase-dependent signaling modulates taurochenodeoxycholic acid-induced liver injury and cholestasis in perfused rat livers. American journal of physiology. Gastrointestinal and liver physiology 20050701
Reversibility of caspase activation and its role during glycochenodeoxycholate-induced hepatocyte apoptosis. The Journal of biological chemistry 20050624
Increased susceptibility of fat-laden Zucker-rat hepatocytes to bile acid-induced oncotic necrosis: an in vitro model of steatocholestasis. The Journal of laboratory and clinical medicine 20050501
Inhibition of hepatocyte growth factor production in human fibroblasts by ursodeoxycholic acid. Biological & pharmaceutical bulletin 20050401
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. Digestive diseases and sciences 20050301
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. American journal of physiology. Gastrointestinal and liver physiology 20050101
Expression of macrophage migration inhibitory factor in esophageal squamous cell carcinoma and effects of bile acids and NSAIDs. Carcinogenesis 20050101
Roles of protein kinase C and fructose in hepatic injury caused by obstructive jaundice. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20050101
Bifidobacterium animalis strain DN-173 010 hydrolyses bile salts in the gastrointestinal tract of pigs. Scandinavian journal of gastroenterology 20041201
Bile salt exposure causes phosphatidyl-inositol-3-kinase-mediated proliferation in a Barrett's adenocarcinoma cell line. Surgery 20040801
Tauroursodeoxycholic acid protects rat hepatocytes from bile acid-induced apoptosis via activation of survival pathways. Hepatology (Baltimore, Md.) 20040601
Beta-carotene prevents bile acid-induced cytotoxicity in the rat hepatocyte: Evidence for an antioxidant and anti-apoptotic role of beta-carotene in vitro. Pediatric research 20040501
Unique inhibition of bile salt-induced apoptosis by lecithins and cytoprotective bile salts in immortalized mouse cholangiocytes. Digestive diseases and sciences 20031201
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. American journal of physiology. Gastrointestinal and liver physiology 20031101
Roles of reactive oxygen species, NF-kappaB, and peroxiredoxins in glycochenodeoxycholic acid-induced rat hepatocytes death. Pharmacology 20030901
Bile salt-induced hepatocyte apoptosis involves epidermal growth factor receptor-dependent CD95 tyrosine phosphorylation. Gastroenterology 20030901
Resistance of rat hepatocytes against bile acid-induced apoptosis in cholestatic liver injury is due to nuclear factor-kappa B activation. Journal of hepatology 20030801
Binding mode of 6ECDCA, a potent bile acid agonist of the farnesoid X receptor (FXR). Bioorganic & medicinal chemistry letters 20030602
Gallium-67 activated charcoal: a new method for preparation of radioactive capsules for colonic transit study. European journal of nuclear medicine and molecular imaging 20030601
Bile acids stimulate cFLIP phosphorylation enhancing TRAIL-mediated apoptosis. The Journal of biological chemistry 20030103
Membrane structural changes support the involvement of mitochondria in the bile salt-induced apoptosis of rat hepatocytes. Clinical science (London, England : 1979) 20021101
The human bile salt export pump: characterization of substrate specificity and identification of inhibitors. Gastroenterology 20021101
Prevention of bile acid-induced apoptosis by betaine in rat liver. Hepatology (Baltimore, Md.) 20021001
Solubilization of drugs by physiological mixtures of bile salts. Pharmaceutical research 20020801
Nitric oxide ameliorates hydrophobic bile acid-induced apoptosis in isolated rat hepatocytes by non-mitochondrial pathways. The Journal of biological chemistry 20020712
High metabolic function of primary human and porcine hepatocytes in a polyurethane foam/spheroid culture system in plasma from patients with fulminant hepatic failure. Cell transplantation 20020101
[Release of cytochrome C with the interaction of bilirubin, amyloid beta-peptide and glycochenodeoxycholate from isolated mitochondria]. Acta medica portuguesa 20020101
The bcl-2 mRNA expression in GCDC-induced obstructive jaundice in rats and its implication in hepatocellular apoptosis. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20020101
Spontaneous nitric oxide in hepatocyte monolayers and inhibition of compound-induced apoptosis. Toxicology in vitro : an international journal published in association with BIBRA 20011201
Bid antisense attenuates bile acid-induced apoptosis and cholestatic liver injury. The Journal of pharmacology and experimental therapeutics 20011201
Duodenal reflux induces cyclooxygenase-2 in the esophageal mucosa of rats: evidence for involvement of bile acids. Gastroenterology 20011201
The bile acid glycochenodeoxycholate induces trail-receptor 2/DR5 expression and apoptosis. The Journal of biological chemistry 20011019
The bile acid-activated phosphatidylinositol 3-kinase pathway inhibits Fas apoptosis upstream of bid in rodent hepatocytes. Gastroenterology 20010601
Effect of bile acids on the proliferative activity and apoptosis of rat hepatocytes. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20010601
Phosphoinositide 3-kinase, but not mitogen-activated protein kinase, pathway is involved in hepatocyte growth factor-mediated protection against bile acid-induced apoptosis in cultured rat hepatocytes. Hepatology (Baltimore, Md.) 20010301
Bile acid-induced rat hepatocyte apoptosis is inhibited by antioxidants and blockers of the mitochondrial permeability transition. Hepatology (Baltimore, Md.) 20010301
[Effects of bile acid preparations on DNA biosynthesis, apoptosis, and necrosis in hepatocytes in vitro]. Voprosy meditsinskoi khimii 20010101
Cystatin A expression reduces bile salt-induced apoptosis in a rat hepatoma cell line. The American journal of physiology 19981001
Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. The American journal of physiology 19980101
Binding of bile acids by glutathione S-transferases from rat liver. Journal of lipid research 19860901
Properties