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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 of GLYCOCHOLIC ACID

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Observation on effect of danxiaoling in supplementary treatment of intrahepatic cholestasis in pregnancy].
2002 Feb
[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis].
2003
Effect of sodium glycocholate on development of tolerance to Parthenium hysterophorus extracts.
2003 Apr
Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH.
2003 Apr 1
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.
2003 Aug
Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection.
2003 Aug 8
Sodium glycocholate transport across Caco-2 cell monolayers, and the enhancement of mannitol transport relative to transepithelial electrical resistance.
2003 Feb 18
Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance.
2003 Feb 4
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.
2003 Jul
Quantification of bile acids directly from urine by MALDI-TOF-MS.
2003 Mar
Differential effects of metformin on bile salt absorption from the jejunum and ileum.
2003 Mar
Oral bile acids reduce bacterial overgrowth, bacterial translocation, and endotoxemia in cirrhotic rats.
2003 Mar
Effect of ursodeoxycholic acid on the impairment induced by maternal cholestasis in the rat placenta-maternal liver tandem excretory pathway.
2003 May
Protease inhibitors: synthesis of bacterial collagenase and matrix metalloproteinase inhibitors incorporating arylsulfonylureido and 5-dibenzo-suberenyl/suberyl moieties.
2003 May 15
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
Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor.
2003 Oct
Steroid ring hydroxylation patterns govern cooperativity in human bile acid binding protein.
2003 Oct 14
Metabolism and absorption enhancement of methionine enkephalin in human nasal epithelium.
2004 Apr
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy].
2004 Apr
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
[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
[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
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
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

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
  • Download
Name Type Language
GLYCOCHOLIC ACID
MI   WHO-DD  
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
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
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
CFR 21 CFR 862.1177
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
Code System Code Type Description
PUBCHEM
10140
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
PRIMARY
EVMPD
SUB22781
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
PRIMARY
NCI_THESAURUS
C77849
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
PRIMARY
EPA CompTox
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
PRIMARY
RXCUI
1426482
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB02691
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
PRIMARY
MESH
D006000
Created by admin on Fri Jun 25 21:24:55 UTC 2021 , Edited by admin on Fri Jun 25 21:24:55 UTC 2021
PRIMARY
WIKIPEDIA
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
PRIMARY
FDA UNII
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
PRIMARY
CAS
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
PRIMARY
ECHA (EC/EINECS)
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY