U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of GLYCOCHOLIC ACID

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

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
Ileal mucosal bile acid absorption is increased in Cftr knockout mice.
2001
The lung as a route for systemic delivery of therapeutic proteins and peptides.
2001
Evaluation of insulin permeability and effects of absorption enhancers on its permeability by an in vitro pulmonary epithelial system using Xenopus pulmonary membrane.
2001 Apr
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Bile acid-induced rat hepatocyte apoptosis is inhibited by antioxidants and blockers of the mitochondrial permeability transition.
2001 Mar
Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1.
2001 May 18
Beneficial effects of glycocholic acid (GCA) on gut mucosal damage in bile duct ligated rats.
2001 Oct
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.
2001 Oct
Ocular tolerance of absorption enhancers in ophthalmic preparations.
2002
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
Solubilization of drugs by physiological mixtures of bile salts.
2002 Aug
Positively charged nanoparticles for improving the oral bioavailability of cyclosporin-A.
2002 Dec 5
On lead(II) glycocholate solubility.
2002 Jan-Feb
[Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy].
2002 Nov
Functional expression of the canalicular bile salt export pump of human liver.
2002 Nov
Ion conductors derived from biogenic amines, bile acids, and amino acids.
2002 Nov-Dec
[Maternal-fetal mixed lymphocyte culture in intrahepatic cholestasis of pregnancy].
2002 Sep
[Relationship between human leukocyte antigen-DRB1 allele gene polymorphism and intrahepatic cholestasis of pregnancy].
2002 Sep
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
Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection.
2003 Aug 8
Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10).
2003 Feb
Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.
2003 Jan 1
Variation in plasma amino acid concentrations during a cycling competition.
2003 Jun
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
[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
[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
[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
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
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
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
mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man.
2005 Oct
Diastereomeric molecular recognition and binding behavior of bile acids by L/D-tryptophan-modified beta-cyclodextrins.
2005 Oct 28
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 Dec 15 15:17:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:28 GMT 2023
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 [MI]
Common Name English
Glycocholic acid [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C843
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
LOINC 2100-6
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
CFR 21 CFR 862.1177
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
Code System Code Type Description
DAILYMED
G59NX3I3RT
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
PUBCHEM
10140
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
EVMPD
SUB22781
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
NCI_THESAURUS
C77849
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
CHEBI
17687
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID2047436
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
RXCUI
1426482
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB02691
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
MESH
D006000
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
SMS_ID
100000088797
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
WIKIPEDIA
GLYCOCHOLIC ACID
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
FDA UNII
G59NX3I3RT
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
CAS
475-31-0
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-494-9
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY
MERCK INDEX
m5799
Created by admin on Fri Dec 15 15:17:28 GMT 2023 , Edited by admin on Fri Dec 15 15:17:28 GMT 2023
PRIMARY Merck Index
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY