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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H42NO5.Na
Molecular Weight 471.6051
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM GLYCODEOXYCHOLATE

SMILES

[Na+].C[C@H](CCC(=O)NCC([O-])=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

InChI

InChIKey=VMSNAUAEKXEYGP-YEUHZSMFSA-M
InChI=1S/C26H43NO5.Na/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);/q;+1/p-1/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-;/m1./s1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C26H42NO5
Molecular Weight 448.6154
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter.
1998 Jan
Acute pancreatitis and bacterial translocation.
2001 May
Glutathione depletion with L-buthionine-(S,R)-sulfoximine demonstrates deleterious effects in acute pancreatitis of the rat.
2002 Aug
Pancreatic capillary blood flow in an improved model of necrotizing pancreatitis in the rat.
2002 Aug
cAMP inhibits bile acid-induced apoptosis by blocking caspase activation and cytochrome c release.
2002 Sep
Effects of heparin in experimental models of acute pancreatitis and post-ERCP pancreatitis.
2004 Feb
Degradation and inactivation of plasma tumor necrosis factor-alpha by pancreatic proteases in experimental acute pancreatitis.
2005
Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts.
2005 Feb
Effects of N-acetylcysteine on acute necrotizing pancreatitis in rats.
2005 May-Jun
Composition of aqueous solutions containing sodium glycocholate and glycodeoxycholate.
2005 Nov-Dec
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.
2005 Sep-Oct
Effects of omega-3 fatty acids on acute necrotizing pancreatitis in rats.
2006
MMP-9 in serum correlates with the development of pulmonary complications in experimental acute pancreatitis.
2006
Characterization of fasted-state human intestinal fluids collected from duodenum and jejunum.
2006 Aug
Vectorial transport of unconjugated and conjugated bile salts by monolayers of LLC-PK1 cells doubly transfected with human NTCP and BSEP or with rat Ntcp and Bsep.
2006 Mar
Effects of the probiotic agent Saccharomyces Boulardii on the DNA damage in acute necrotizing pancreatitis induced rats.
2007 Aug
Effects of octreotide in acute hemorrhagic necrotizing pancreatitis in rats.
2007 Nov
Complexation of tauro- and glyco-conjugated bile salts with three neutral beta-CDs studied by ACE.
2007 Oct
Determination of intralumenal individual bile acids by HPLC with charged aerosol detection.
2008 Dec
Protective effects and anti-inflammatory pathways of exogenous calcitonin gene-related peptide in severe necrotizing pancreatitis.
2009
Probiotics prevent intestinal barrier dysfunction in acute pancreatitis in rats via induction of ileal mucosal glutathione biosynthesis.
2009
Capsaicin reduces tissue damage in experimental acute pancreatitis.
2009 Aug
Thermodynamics and structure of inclusion compounds of tauro- and glyco-conjugated bile salts and beta-cyclodextrin.
2009 Jul 7
Use of correction factors in mobility shift affinity capillary electrophoresis for weak analyte-ligand interactions.
2009 May
Loss of organic anion transporting polypeptide 1a1 increases deoxycholic acid absorption in mice by increasing intestinal permeability.
2011 Dec
Patents

Patents

WO2015067947A1
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:15:47 GMT 2025
Edited
by admin
on Mon Mar 31 22:15:47 GMT 2025
Record UNII
6W76V75MT1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
J286.892J
Preferred Name English
SODIUM GLYCODEOXYCHOLATE
Common Name English
SODIUM (((3.ALPHA.,5.BETA.,12.ALPHA.,20R)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)ACETATE
Systematic Name English
SODIUM N-((3ALPHA,5BETA,12ALPHA)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINOACETATE
Systematic Name English
GLYCINE, N-((3.ALPHA.,5.BETA.,12.ALPHA.)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)-, MONOSODIUM SALT
Systematic Name English
SODIUM GLYCYLDEOXYCHOLATE
Common Name English
N-(3.ALPHA.,12.ALPHA.-DIHYDROXY-24-OXO-5.BETA.-CHOLAN-24-YL)GLYCINE SODIUM SALT
Systematic Name English
(3.ALPHA.,12.ALPHA.-DIHYDROXY-24-OXO-5.BETA.-CHOLAN-24-YLAMINO)ACETIC ACID SODIUM SALT
Systematic Name English
GLYCINE, N-((3.ALPHA.,5.BETA.,12.ALPHA.)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)-, SODIUM SALT (1:1)
Systematic Name English
2-((4R)-4-((1S,2S,11S,16S,5R,7R,10R,14R,15R)-5,16-DIHYDROXY-2,15-DIMETHYLTETRA CYCLO(8.7.0.0(2,7).0(11,15))HEPTADEC-14-YL)PENTANOYLAMINO)ACETIC ACID, SODIUM SALT
Systematic Name English
GLYCODEOXYCHOLIC ACID, SODIUM SALT
Common Name English
N-((3ALPHA,5BETA,12ALPHA)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINOACETATE
Systematic Name English
N-(2-OXO-2-(SODIOOXY)ETHYL)-3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLANE-24-AMIDE
Systematic Name English
SODIUM 2-(((4R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-DIHYDROXY-10,13-DIMETHYL-2,3,4,5,6,7,8,9,11,12,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA(A)PHENANTHREN-17-YL)PENTANOYL)AMINO)ACETATE
Systematic Name English
3.ALPHA.,12.ALPHA.-DIHYDROXY-24-(((SODIOOXYCARBONYL)METHYL)AMINO)-5.BETA.-CHOLAN-24-ONE
Systematic Name English
GLYCINE, N-(3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLAN-24-OYL)-, MONOSODIUM SALT
Systematic Name English
Code System Code Type Description
FDA UNII
6W76V75MT1
Created by admin on Mon Mar 31 22:15:47 GMT 2025 , Edited by admin on Mon Mar 31 22:15:47 GMT 2025
PRIMARY
CAS
16409-34-0
Created by admin on Mon Mar 31 22:15:47 GMT 2025 , Edited by admin on Mon Mar 31 22:15:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
240-455-4
Created by admin on Mon Mar 31 22:15:47 GMT 2025 , Edited by admin on Mon Mar 31 22:15:47 GMT 2025
PRIMARY
PUBCHEM
23688465
Created by admin on Mon Mar 31 22:15:47 GMT 2025 , Edited by admin on Mon Mar 31 22:15:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID30936904
Created by admin on Mon Mar 31 22:15:47 GMT 2025 , Edited by admin on Mon Mar 31 22:15:47 GMT 2025
PRIMARY
Related Record Type Details
Structure of GLYCODEOXYCHOLIC ACID
PARENT -> SALT/SOLVATE
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