Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C26H42NO6.Na |
| Molecular Weight | 487.6045 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].C[C@H](CCC(=O)NCC([O-])=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
InChI
InChIKey=OABYVIYXWMZFFJ-ZUHYDKSRSA-M
InChI=1S/C26H43NO6.Na/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29;/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33);/q;+1/p-1/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-;/m1./s1
| Molecular Formula | C26H42NO6 |
| Molecular Weight | 464.6148 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Glycocholic acid (GCA) is an important metabolite of bile acids, a conjugate of cholic acid with glycine. GCA urine levels are expected to be a specific diagnostic biomarker for hepatocellular carcinoma (HCC). The average GCA concentrations of HCC patients in plasma and urine were about 25 and 2.8 times than that of healthy volunteers.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ileal bile acid-binding protein, functionally associated with the farnesoid X receptor or the ileal bile acid transporter, regulates bile acid activity in the small intestine. | 2005-12-23 |
|
| Diastereomeric molecular recognition and binding behavior of bile acids by L/D-tryptophan-modified beta-cyclodextrins. | 2005-10-28 |
|
| Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles. | 2005-10-03 |
|
| mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man. | 2005-10 |
|
| Proapoptotic effect on normal and tumor intestinal cells of cytostatic drugs with enterohepatic organotropism. | 2005-10 |
|
| Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats. | 2005-09-08 |
|
| Bile salts inhibit growth and induce apoptosis of human esophageal cancer cell line. | 2005-09-07 |
|
| Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts. | 2005-08-17 |
|
| [Cholyl glycine (CG)]. | 2005-08 |
|
| Octreotide induced prolongation of colonic transit increases faecal anaerobic bacteria, bile acid metabolising enzymes, and serum deoxycholic acid in patients with acromegaly. | 2005-05 |
|
| Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules. | 2005-04-11 |
|
| The influence of the ionic medium on the behaviour of sodium glycocholate and cholate aqueous solutions. | 2005-04-02 |
|
| High-speed digital imaging method for ciliary beat frequency measurement. | 2005-04 |
|
| Two common PFIC2 mutations are associated with the impaired membrane trafficking of BSEP/ABCB11. | 2005-04 |
|
| Stable ciliary activity in human nasal epithelial cells grown in a perfusion system. | 2005-03-23 |
|
| Quantitative estimation of the effects of bile salt surfactant systems on insulin stability and permeability in the rat intestine using a mass balance model. | 2005-02 |
|
| Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts. | 2005-02 |
|
| Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11). | 2005-02 |
|
| Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. | 2005-01 |
|
| Noninvasive methods to determine the critical micelle concentration of some bile acid salts. | 2004-11-01 |
|
| Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s. | 2004-10-01 |
|
| Adsorption of bile acid by chitosan-orotic acid salt and its application as an oral preparation. | 2004-10 |
|
| Evaluation of different toxicity assays applied to proliferating cells and to stratified epithelium in relation to permeability enhancement with glycocholate. | 2004-10 |
|
| Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids. | 2004-08-06 |
|
| Functional assessment of bacterial colonization in patients with ileal pouch-anal anastomosis and Brooke ileostomy. | 2004-08 |
|
| Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging. | 2004-07-01 |
|
| [Study on relationship between serum cholylglycine and placental apoptosis in patients with intrahepatic cholestasis of pregnancy]. | 2004-07 |
|
| Acid and bile salts induce DNA damage in human oesophageal cell lines. | 2004-07 |
|
| Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers. | 2004-05 |
|
| Metabolism and absorption enhancement of methionine enkephalin in human nasal epithelium. | 2004-04 |
|
| [Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy]. | 2004-04 |
|
| Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin. | 2004-04 |
|
| Quantification of bile acids directly from plasma by MALDI-TOF-MS. | 2004-03 |
|
| Transcriptional regulation of human mucin MUC4 by bile acids in oesophageal cancer cells is promoter-dependent and involves activation of the phosphatidylinositol 3-kinase signalling pathway. | 2004-02-01 |
|
| [Effects of protease inhibitors on intestinal absorption of insulin]. | 2004-02 |
|
| Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction. | 2004-01-13 |
|
| Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats. | 2004-01 |
|
| Potential utility of various protease inhibitors for improving the intestinal absorption of insulin in rats. | 2003-11 |
|
| Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. | 2003-11 |
|
| Steroid ring hydroxylation patterns govern cooperativity in human bile acid binding protein. | 2003-10-14 |
|
| Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor. | 2003-10 |
|
| Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection. | 2003-08-08 |
|
| Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. | 2003-08 |
|
| Influence of emulsifiers on the crystallization of solid lipid nanoparticles. | 2003-07 |
|
| Variation in plasma amino acid concentrations during a cycling competition. | 2003-06 |
|
| Protease inhibitors: synthesis of bacterial collagenase and matrix metalloproteinase inhibitors incorporating arylsulfonylureido and 5-dibenzo-suberenyl/suberyl moieties. | 2003-05-15 |
|
| Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH. | 2003-04-01 |
|
| Effect of sodium glycocholate on development of tolerance to Parthenium hysterophorus extracts. | 2003-04 |
|
| Quantification of bile acids directly from urine by MALDI-TOF-MS. | 2003-03 |
|
| [Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis]. | 2003 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:48:53 GMT 2025
by
admin
on
Mon Mar 31 17:48:53 GMT 2025
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| Record UNII |
V06CXA1W3K
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
