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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H43NO5
Molecular Weight 449.6233
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCODEOXYCHOLIC ACID

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[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=WVULKSPCQVQLCU-BUXLTGKBSA-N
InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1

HIDE SMILES / InChI
Glycodeoxycholic acid (GDCA), a bile acid, is formed in the liver from chenodeoxycholate and glycine. GDCA was one of twenty-five plasma metabolites, which were significantly different among asthma and healthy controls. Besides, GDCA was elevated in patients with acetaminophen-induced acute liver failure (AALF) and was significantly increased in non-surviving AALF patients compared with survivors. Thus GDCA level could serve as a prognostic biomarker for AALF patients.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter.
1998 Jan
Bioadhesive starch microspheres and absorption enhancing agents act synergistically to enhance the nasal absorption of polypeptides.
2001 Jul 3
Examination of the solubilization of drugs by bile salt micelles.
2002 Aug
Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor.
2003 Oct
The isolated perfused liver response to a 'second hit' of portal endotoxin during severe acute pancreatitis.
2005
1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media.
2005 Oct
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.
2005 Sep-Oct
Effects of subtotal colectomy on bacterial translocation during experimental acute pancreatitis.
2006 Jan
Single-step analysis of individual conjugated bile acids in human bile using 1H NMR spectroscopy.
2006 Jun
Effects of the probiotic agent Saccharomyces Boulardii on the DNA damage in acute necrotizing pancreatitis induced rats.
2007 Aug
Effects of enalaprilat on acute necrotizing pancreatitis in rats.
2007 Dec
Complexation of tauro- and glyco-conjugated bile salts with three neutral beta-CDs studied by ACE.
2007 Oct
Design and in vitro characterization of buccoadhesive drug delivery system of insulin.
2008 Jan
Probiotics enhance pancreatic glutathione biosynthesis and reduce oxidative stress in experimental acute pancreatitis.
2008 Nov
Effect of platelet-activating factor antagonist WEB 2086 on microcirculatory disorders in acute experimental pancreatitis of graded severity.
2009 Jan
Sodium glycodeoxycholate and glycocholate mixed aggregates in gas and solution phases.
2009 May 21
Glycodeoxycholic acid levels as prognostic biomarker in acetaminophen-induced acute liver failure patients.
2014 Dec
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Glycodeoxycholic acid (GDCA) can induce the increase of MDA and decrease of fluidity of hepatocyte membrane, and finally cause hepatocyte injury. In the presence of GDCA (final concentration of 250 mumol/L), the concentration of hepatocyte MDA of GDCA increased significantly (P < 0.001) and membrane fluidity decreased (P < 0.02) after culture of 1 or 4 hours. ALT was directly related to MDA and fluorescence polarization (P), r was 0.945 and 0.986, respectively.
Name Type Language
GLYCODEOXYCHOLIC ACID
Common Name English
GLYCINE, N-((3.ALPHA.,5.BETA.,12.ALPHA.)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)-
Systematic Name English
DEOXYCHOLYLGLYCINE
Common Name English
DEOXYGLYCOCHOLIC ACID
Common Name English
GLYCODESOXYCHOLIC ACID
Common Name English
GLYCYLDEOXYCHOLIC ACID
Common Name English
GLYCINE, N-(3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLAN-24-OYL)-
Systematic Name English
3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLANIC ACID-24-GLYCINE
Common Name English
Classification Tree Code System Code
LOINC 2202-0
Created by admin on Sat Dec 16 09:04:24 GMT 2023 , Edited by admin on Sat Dec 16 09:04:24 GMT 2023
Code System Code Type Description
WIKIPEDIA
Glycodeoxycholic acid
Created by admin on Sat Dec 16 09:04:24 GMT 2023 , Edited by admin on Sat Dec 16 09:04:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID80957422
Created by admin on Sat Dec 16 09:04:24 GMT 2023 , Edited by admin on Sat Dec 16 09:04:24 GMT 2023
PRIMARY
PUBCHEM
3035026
Created by admin on Sat Dec 16 09:04:24 GMT 2023 , Edited by admin on Sat Dec 16 09:04:24 GMT 2023
PRIMARY
CAS
360-65-6
Created by admin on Sat Dec 16 09:04:24 GMT 2023 , Edited by admin on Sat Dec 16 09:04:24 GMT 2023
PRIMARY
FDA UNII
DS124M0828
Created by admin on Sat Dec 16 09:04:24 GMT 2023 , Edited by admin on Sat Dec 16 09:04:24 GMT 2023
PRIMARY
CHEBI
27471
Created by admin on Sat Dec 16 09:04:24 GMT 2023 , Edited by admin on Sat Dec 16 09:04:24 GMT 2023
PRIMARY