GLYCOCHOLIC ACID

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

Structure Search

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

HIDE SMILES / InChI

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

Description
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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatocellular carcinoma 78 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27061917	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis].	2003	14653242
Effect of sodium glycocholate on development of tolerance to Parthenium hysterophorus extracts.	2003 Apr	15255651
Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH.	2003 Apr 1	12659967
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.	2003 Aug	12883481
Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection.	2003 Aug 8	12899981
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.	2003 Jul	12820155
Variation in plasma amino acid concentrations during a cycling competition.	2003 Jun	12853907
Quantification of bile acids directly from urine by MALDI-TOF-MS.	2003 Mar	12638043
Protease inhibitors: synthesis of bacterial collagenase and matrix metalloproteinase inhibitors incorporating arylsulfonylureido and 5-dibenzo-suberenyl/suberyl moieties.	2003 May 15	12713832
Potential utility of various protease inhibitors for improving the intestinal absorption of insulin in rats.	2003 Nov	14713363
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.	2003 Nov	12842829
Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor.	2003 Oct	14512880
Steroid ring hydroxylation patterns govern cooperativity in human bile acid binding protein.	2003 Oct 14	14529265
Metabolism and absorption enhancement of methionine enkephalin in human nasal epithelium.	2004 Apr	15165710
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy].	2004 Apr	15143715
Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin.	2004 Apr	14999743
Functional assessment of bacterial colonization in patients with ileal pouch-anal anastomosis and Brooke ileostomy.	2004 Aug	15484354
Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids.	2004 Aug 6	15281152
[Effects of protease inhibitors on intestinal absorption of insulin].	2004 Feb	15127624
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	14583090
Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats.	2004 Jan	14980001
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction.	2004 Jan-Feb	14715004
[Study on relationship between serum cholylglycine and placental apoptosis in patients with intrahepatic cholestasis of pregnancy].	2004 Jul	15347465
Acid and bile salts induce DNA damage in human oesophageal cell lines.	2004 Jul	15215332
Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging.	2004 Jul 1	15214790
Quantification of bile acids directly from plasma by MALDI-TOF-MS.	2004 Mar	14747894
Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers.	2004 May	15069095
Noninvasive methods to determine the critical micelle concentration of some bile acid salts.	2004 Nov 1	15464960
Adsorption of bile acid by chitosan-orotic acid salt and its application as an oral preparation.	2004 Oct	15467231
Evaluation of different toxicity assays applied to proliferating cells and to stratified epithelium in relation to permeability enhancement with glycocholate.	2004 Oct	15251183
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s.	2004 Oct 1	15387580
High-speed digital imaging method for ciliary beat frequency measurement.	2005 Apr	15831215
Two common PFIC2 mutations are associated with the impaired membrane trafficking of BSEP/ABCB11.	2005 Apr	15791618
Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules.	2005 Apr 11	15778050
[Cholyl glycine (CG)].	2005 Aug	16149646
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	16230354
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	15720779
Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts.	2005 Feb	15714544
Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).	2005 Feb	15537867
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.	2005 Jan	15297262
The influence of the ionic medium on the behaviour of sodium glycocholate and cholate aqueous solutions.	2005 Jan-Feb	15801173
Stable ciliary activity in human nasal epithelial cells grown in a perfusion system.	2005 Mar 23	15725562
Octreotide induced prolongation of colonic transit increases faecal anaerobic bacteria, bile acid metabolising enzymes, and serum deoxycholic acid in patients with acromegaly.	2005 May	15831907
mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man.	2005 Oct	16185316
Proapoptotic effect on normal and tumor intestinal cells of cytostatic drugs with enterohepatic organotropism.	2005 Oct	15985617
Diastereomeric molecular recognition and binding behavior of bile acids by L/D-tryptophan-modified beta-cyclodextrins.	2005 Oct 28	16238298
Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles.	2005 Oct 3	16023752
Bile salts inhibit growth and induce apoptosis of human esophageal cancer cell line.	2005 Sep 7	16127738
Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats.	2005 Sep-Oct	16145315
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.	2005 Sep-Oct	16101123

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:24:55 UTC 2021` Edited by `admin` on `Fri Jun 25 21:24:55 UTC 2021`
Record UNII	G59NX3I3RT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLYCOCHOLIC ACID

Common Name

English

CHOLYLGLYCINE

Common Name

English

GLYCOCHOLIC ACID [WHO-DD]

Common Name

English

GLYCOCHOLIC ACID [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C843