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
The lung as a route for systemic delivery of therapeutic proteins and peptides.	2001	11686885
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	11305600
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.	2001 Apr 17	11292547
Nasal bioavailability of peptide T in rabbits: absorption enhancement by sodium glycocholate and glycofurol.	2001 Aug	11457652
Study of partition of nitrazepam in bile salt micelles and the role of lecithin.	2001 Feb	11272316
Enhanced efficiency of the placental barrier to cisplatin through binding to glycocholic acid.	2001 Jul-Aug	11724343
Bile acid-induced rat hepatocyte apoptosis is inhibited by antioxidants and blockers of the mitochondrial permeability transition.	2001 Mar	11230742
Analysis of the physicochemical interactions between Clostridium difficile toxins and cholestyramine using liquid chromatography with post-column derivatization.	2001 Mar 9	11257520
Ocular tolerance of absorption enhancers in ophthalmic preparations.	2002	12049486
Bile salt aggregates in the gas phase: an electrospray ionization mass spectrometric study.	2002 Apr 15	12007103
Nasal absorption enhancement strategies for therapeutic peptides: an in vitro study using cultured human nasal epithelium.	2002 Apr 26	11955816
Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition.	2002 Dec	12456554
Transport activity of human MRP3 expressed in Sf9 cells: comparative studies with rat MRP3.	2002 Jan	11837698
On lead(II) glycocholate solubility.	2002 Jan-Feb	11993267
Buccal transport of flecainide and sotalol: effect of a bile salt and ionization state.	2002 Jul 8	12086728
Drug metabolic activity of cultured hepatocytes can synchronize with bile acid concentration in the medium.	2002 Mar	11835266
Ion conductors derived from biogenic amines, bile acids, and amino acids.	2002 Nov-Dec	12440868
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
Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance.	2003 Feb 4	12569201
Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.	2003 Jan 1	12220224
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
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
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
[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
Evaluation of different toxicity assays applied to proliferating cells and to stratified epithelium in relation to permeability enhancement with glycocholate.	2004 Oct	15251183
High-speed digital imaging method for ciliary beat frequency measurement.	2005 Apr	15831215
[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
Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts.	2005 Feb	15714544
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 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

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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