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

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCC(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	465.6227
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 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
Ocular tolerance of absorption enhancers in ophthalmic preparations.	2002	12049486
Carriers involved in targeting the cytostatic bile acid-cisplatin derivatives cis-diammine-chloro-cholylglycinate-platinum(II) and cis-diammine-bisursodeoxycholate-platinum(II) toward liver cells.	2002 Apr	11901224
Bile salt aggregates in the gas phase: an electrospray ionization mass spectrometric study.	2002 Apr 15	12007103
Examination of the solubilization of drugs by bile salt micelles.	2002 Aug	12115803
Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition.	2002 Dec	12456554
[Observation on effect of danxiaoling in supplementary treatment of intrahepatic cholestasis in pregnancy].	2002 Feb	12585148
Nasal glucagon delivery using microcrystalline cellulose in healthy volunteers.	2002 Feb 21	11897411
Buccal transport of flecainide and sotalol: effect of a bile salt and ionization state.	2002 Jul 8	12086728
Colesevelam hydrochloride.	2002 May 15	12040732
Ion conductors derived from biogenic amines, bile acids, and amino acids.	2002 Nov-Dec	12440868
[Maternal-fetal mixed lymphocyte culture in intrahepatic cholestasis of pregnancy].	2002 Sep	12411010
[Relationship between human leukocyte antigen-DRB1 allele gene polymorphism and intrahepatic cholestasis of pregnancy].	2002 Sep	12411009
A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test.	2002 Sep	12231118
[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis].	2003	14653242
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
Substitution of Trp1242 of TM17 alters substrate specificity of human multidrug resistance protein 3.	2003 Feb	12388190
Sodium glycocholate transport across Caco-2 cell monolayers, and the enhancement of mannitol transport relative to transepithelial electrical resistance.	2003 Feb 18	12550793
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.	2003 Jul	12820155
Quantification of bile acids directly from urine by MALDI-TOF-MS.	2003 Mar	12638043
Differential effects of metformin on bile salt absorption from the jejunum and ileum.	2003 Mar	12630937
Oral bile acids reduce bacterial overgrowth, bacterial translocation, and endotoxemia in cirrhotic rats.	2003 Mar	12601352
Effect of ursodeoxycholic acid on the impairment induced by maternal cholestasis in the rat placenta-maternal liver tandem excretory pathway.	2003 May	12606635
Potential utility of various protease inhibitors for improving the intestinal absorption of insulin in rats.	2003 Nov	14713363
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
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
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
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
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
mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man.	2005 Oct	16185316
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

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 `Wed Jul 05 22:48:37 UTC 2023` Edited by `admin` on `Wed Jul 05 22:48:37 UTC 2023`
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 [MI]

Common Name

English

Glycocholic acid [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C843