Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H43NO6 |
Molecular Weight | 465.6237 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
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])(C[C@@]([H])([C@]12C)O)[C@@]4(C)CC[C@]([H])(C[C@@]4([H])C[C@@]3([H])O)O
InChI
InChIKey=RFDAIACWWDREDC-FRVQLJSFSA-N
InChI=1S/C26H43NO6/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)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1
Molecular Formula | C26H43NO6 |
Molecular Weight | 465.6237 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28942640
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28942640
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 |
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[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis]. | 2003 |
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Effect of sodium glycocholate on development of tolerance to Parthenium hysterophorus extracts. | 2003 Apr |
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Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH. | 2003 Apr 1 |
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Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. | 2003 Aug |
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Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection. | 2003 Aug 8 |
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Influence of emulsifiers on the crystallization of solid lipid nanoparticles. | 2003 Jul |
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Variation in plasma amino acid concentrations during a cycling competition. | 2003 Jun |
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Quantification of bile acids directly from urine by MALDI-TOF-MS. | 2003 Mar |
|
Protease inhibitors: synthesis of bacterial collagenase and matrix metalloproteinase inhibitors incorporating arylsulfonylureido and 5-dibenzo-suberenyl/suberyl moieties. | 2003 May 15 |
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Potential utility of various protease inhibitors for improving the intestinal absorption of insulin in rats. | 2003 Nov |
|
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. | 2003 Nov |
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Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor. | 2003 Oct |
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Steroid ring hydroxylation patterns govern cooperativity in human bile acid binding protein. | 2003 Oct 14 |
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Metabolism and absorption enhancement of methionine enkephalin in human nasal epithelium. | 2004 Apr |
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[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy]. | 2004 Apr |
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Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin. | 2004 Apr |
|
Functional assessment of bacterial colonization in patients with ileal pouch-anal anastomosis and Brooke ileostomy. | 2004 Aug |
|
Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids. | 2004 Aug 6 |
|
[Effects of protease inhibitors on intestinal absorption of insulin]. | 2004 Feb |
|
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 Feb 1 |
|
Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats. | 2004 Jan |
|
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction. | 2004 Jan-Feb |
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[Study on relationship between serum cholylglycine and placental apoptosis in patients with intrahepatic cholestasis of pregnancy]. | 2004 Jul |
|
Acid and bile salts induce DNA damage in human oesophageal cell lines. | 2004 Jul |
|
Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging. | 2004 Jul 1 |
|
Quantification of bile acids directly from plasma by MALDI-TOF-MS. | 2004 Mar |
|
Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers. | 2004 May |
|
Noninvasive methods to determine the critical micelle concentration of some bile acid salts. | 2004 Nov 1 |
|
Adsorption of bile acid by chitosan-orotic acid salt and its application as an oral preparation. | 2004 Oct |
|
Evaluation of different toxicity assays applied to proliferating cells and to stratified epithelium in relation to permeability enhancement with glycocholate. | 2004 Oct |
|
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s. | 2004 Oct 1 |
|
High-speed digital imaging method for ciliary beat frequency measurement. | 2005 Apr |
|
Two common PFIC2 mutations are associated with the impaired membrane trafficking of BSEP/ABCB11. | 2005 Apr |
|
Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules. | 2005 Apr 11 |
|
[Cholyl glycine (CG)]. | 2005 Aug |
|
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 Dec 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 Feb |
|
Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts. | 2005 Feb |
|
Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11). | 2005 Feb |
|
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. | 2005 Jan |
|
The influence of the ionic medium on the behaviour of sodium glycocholate and cholate aqueous solutions. | 2005 Jan-Feb |
|
Stable ciliary activity in human nasal epithelial cells grown in a perfusion system. | 2005 Mar 23 |
|
Octreotide induced prolongation of colonic transit increases faecal anaerobic bacteria, bile acid metabolising enzymes, and serum deoxycholic acid in patients with acromegaly. | 2005 May |
|
mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man. | 2005 Oct |
|
Proapoptotic effect on normal and tumor intestinal cells of cytostatic drugs with enterohepatic organotropism. | 2005 Oct |
|
Diastereomeric molecular recognition and binding behavior of bile acids by L/D-tryptophan-modified beta-cyclodextrins. | 2005 Oct 28 |
|
Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles. | 2005 Oct 3 |
|
Bile salts inhibit growth and induce apoptosis of human esophageal cancer cell line. | 2005 Sep 7 |
|
Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats. | 2005 Sep-Oct |
|
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts. | 2005 Sep-Oct |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:24:55 UTC 2021
by
admin
on
Fri Jun 25 21:24:55 UTC 2021
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Record UNII |
G59NX3I3RT
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Record Status |
Validated (UNII)
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Record Version |
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-
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Name | Type | Language | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C843
Created by
admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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LOINC |
2100-6
Created by
admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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CFR |
21 CFR 862.1177
Created by
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Code System | Code | Type | Description | ||
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10140
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PRIMARY | |||
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SUB22781
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PRIMARY | |||
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C77849
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PRIMARY | |||
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475-31-0
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PRIMARY | |||
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1426482
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PRIMARY | RxNorm | ||
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DB02691
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PRIMARY | |||
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D006000
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PRIMARY | |||
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GLYCOCHOLIC ACID
Created by
admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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PRIMARY | |||
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G59NX3I3RT
Created by
admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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PRIMARY | |||
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475-31-0
Created by
admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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PRIMARY | |||
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207-494-9
Created by
admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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PRIMARY | |||
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M5799
Created by
admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |