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
Nasal bioavailability of peptide T in rabbits: absorption enhancement by sodium glycocholate and glycofurol.	2001 Aug	11457652
MRP subfamily transporters and resistance to anticancer agents.	2001 Dec	11804191
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
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.	2001 Oct	11680582
Solubilization of drugs by physiological mixtures of bile salts.	2002 Aug	12240947
Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition.	2002 Dec	12456554
Drug metabolic activity of cultured hepatocytes can synchronize with bile acid concentration in the medium.	2002 Mar	11835266
Colesevelam hydrochloride.	2002 May 15	12040732
[Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy].	2002 Nov	12487922
Ion conductors derived from biogenic amines, bile acids, and amino acids.	2002 Nov-Dec	12440868
[Relationship between human leukocyte antigen-DRB1 allele gene polymorphism and intrahepatic cholestasis of pregnancy].	2002 Sep	12411009
[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis].	2003	14653242
Differential effects of metformin on bile salt absorption from the jejunum and ileum.	2003 Mar	12630937
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
Functional assessment of bacterial colonization in patients with ileal pouch-anal anastomosis and Brooke ileostomy.	2004 Aug	15484354
Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids.	2004 Aug 6	15281152
Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats.	2004 Jan	14980001
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.	2005 Jan	15297262
Stable ciliary activity in human nasal epithelial cells grown in a perfusion system.	2005 Mar 23	15725562
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 `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