GLYCOCHOLIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H43NO6
Molecular Weight	465.6227
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=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	465.6227
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 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27061917	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

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	16230354
Diastereomeric molecular recognition and binding behavior of bile acids by L/D-tryptophan-modified beta-cyclodextrins.	2005-10-28	16238298
Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles.	2005-10-03	16023752
mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man.	2005-10	16185316
Proapoptotic effect on normal and tumor intestinal cells of cytostatic drugs with enterohepatic organotropism.	2005-10	15985617
Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats.	2005-09-08	16145315
Bile salts inhibit growth and induce apoptosis of human esophageal cancer cell line.	2005-09-07	16127738
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.	2005-08-17	16101123
[Cholyl glycine (CG)].	2005-08	16149646
Octreotide induced prolongation of colonic transit increases faecal anaerobic bacteria, bile acid metabolising enzymes, and serum deoxycholic acid in patients with acromegaly.	2005-05	15831907
Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules.	2005-04-11	15778050
The influence of the ionic medium on the behaviour of sodium glycocholate and cholate aqueous solutions.	2005-04-02	15801173
High-speed digital imaging method for ciliary beat frequency measurement.	2005-04	15831215
Two common PFIC2 mutations are associated with the impaired membrane trafficking of BSEP/ABCB11.	2005-04	15791618
Stable ciliary activity in human nasal epithelial cells grown in a perfusion system.	2005-03-23	15725562
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	15720779
Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts.	2005-02	15714544
Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).	2005-02	15537867
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.	2005-01	15297262
Noninvasive methods to determine the critical micelle concentration of some bile acid salts.	2004-11-01	15464960
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s.	2004-10-01	15387580
Adsorption of bile acid by chitosan-orotic acid salt and its application as an oral preparation.	2004-10	15467231
Evaluation of different toxicity assays applied to proliferating cells and to stratified epithelium in relation to permeability enhancement with glycocholate.	2004-10	15251183
Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids.	2004-08-06	15281152
Functional assessment of bacterial colonization in patients with ileal pouch-anal anastomosis and Brooke ileostomy.	2004-08	15484354
Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging.	2004-07-01	15214790
[Study on relationship between serum cholylglycine and placental apoptosis in patients with intrahepatic cholestasis of pregnancy].	2004-07	15347465
Acid and bile salts induce DNA damage in human oesophageal cell lines.	2004-07	15215332
Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers.	2004-05	15069095
Metabolism and absorption enhancement of methionine enkephalin in human nasal epithelium.	2004-04	15165710
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy].	2004-04	15143715
Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin.	2004-04	14999743
Quantification of bile acids directly from plasma by MALDI-TOF-MS.	2004-03	14747894
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	14583090
[Effects of protease inhibitors on intestinal absorption of insulin].	2004-02	15127624
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction.	2004-01-13	14715004
Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats.	2004-01	14980001
Potential utility of various protease inhibitors for improving the intestinal absorption of insulin in rats.	2003-11	14713363
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.	2003-11	12842829
Steroid ring hydroxylation patterns govern cooperativity in human bile acid binding protein.	2003-10-14	14529265
Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor.	2003-10	14512880
Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection.	2003-08-08	12899981
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.	2003-08	12883481
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.	2003-07	12820155
Variation in plasma amino acid concentrations during a cycling competition.	2003-06	12853907
Protease inhibitors: synthesis of bacterial collagenase and matrix metalloproteinase inhibitors incorporating arylsulfonylureido and 5-dibenzo-suberenyl/suberyl moieties.	2003-05-15	12713832
Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH.	2003-04-01	12659967
Effect of sodium glycocholate on development of tolerance to Parthenium hysterophorus extracts.	2003-04	15255651
Quantification of bile acids directly from urine by MALDI-TOF-MS.	2003-03	12638043
[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis].	2003	14653242

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 `Mon Mar 31 17:53:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:01 GMT 2025`
Record UNII	G59NX3I3RT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHOLYLGLYCINE

Preferred Name

English

GLYCOCHOLIC ACID

Common Name

English

GLYCOCHOLIC ACID [MI]

Common Name

English

Glycocholic acid [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C843