glycochenodeoxycholic acid (CHEBI:36274)

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CHEBI:36274 - glycochenodeoxycholic acid

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ChEBI Name	glycochenodeoxycholic acid

ChEBI ID	CHEBI:36274

Definition	A bile acid glycine conjugate having 3α,7α-dihydroxy-5β-cholan-24-oyl as the bile acid component.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:5463, CHEBI:41520, CHEBI:3591

Supplier Information	eMolecules:1939099, ZINC000003914812

Download	Molfile XML SDF

more structures >>

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reading 75 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

75 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Wikipedia	License
Glycochenodeoxycholic acid is a bile salt formed in the liver from chenodeoxycholic acid and glycine, usually found as the sodium salt. It acts as a detergent to solubilize fats for absorption.
Read full article at Wikipedia

Formula

C26H43NO5

Net Charge

Average Mass

449.62336

Monoisotopic Mass

449.31412

InChI

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

InChIKey

GHCZAUBVMUEKKP-GYPHWSFCSA-N

SMILES

[H][C@@]12C[C@H](O)CC[C@]1(C)[C@@]1([H])CC[C@]3(C)[C@]([H])(CC[C@@]3([H])[C@]1([H])[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	glycochenodeoxycholic acid (CHEBI:36274) has functional parent chenodeoxycholic acid (CHEBI:16755) glycochenodeoxycholic acid (CHEBI:36274) has role human metabolite (CHEBI:77746) glycochenodeoxycholic acid (CHEBI:36274) is a bile acid glycine conjugate (CHEBI:36255) glycochenodeoxycholic acid (CHEBI:36274) is conjugate acid of glycochenodeoxycholate (CHEBI:36252)

Incoming	glycocholic acid (CHEBI:17687) has functional parent glycochenodeoxycholic acid (CHEBI:36274) sulfoglycochenodeoxycholic acid (CHEBI:72733) has functional parent glycochenodeoxycholic acid (CHEBI:36274) glycochenodeoxycholate (CHEBI:36252) is conjugate base of glycochenodeoxycholic acid (CHEBI:36274)

IUPAC Names

[(3α,7α-dihydroxy-24-oxo-5β-cholan-24-yl)amino]acetic acid

N-(3α,7α-dihydroxy-5β-cholan-24-oyl)glycine

Synonyms	Sources
chenodeoxycholylglycine	ChemIDplus
Chenodeoxyglycocholate	KEGG COMPOUND
chenodeoxyglycocholic acid	ChEBI
GCDCA	ChEBI
glycine chenodeoxycholate	ChemIDplus
Glycochenodeoxycholate	KEGG COMPOUND
GLYCOCHENODEOXYCHOLIC ACID	PDBeChem
Glycochenodeoxycholic acid	KEGG COMPOUND

Manual Xrefs	Databases
C05466	KEGG COMPOUND
CHO	PDBeChem
DB02123	DrugBank
Glycochenodeoxycholic_acid	Wikipedia
GLYCOCHENODEOXYCHOLIC_ACID	MetaCyc
HMDB0006898	HMDB
View more database links

Registry Numbers	Types	Sources
3226177	Beilstein Registry Number	Beilstein
3226177	Reaxys Registry Number	Reaxys
640-79-9	CAS Registry Number	ChemIDplus

Citations

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Xiao JF, Varghese RS, Zhou B, Nezami Ranjbar MR, Zhao Y, Tsai TH, Di Poto C, Wang J, Goerlitz D, Luo Y, Cheema AK, Sarhan N, Soliman H, Tadesse MG, Ziada DH, Ressom HW (2012)
LC-MS based serum metabolomics for identification of hepatocellular carcinoma biomarkers in Egyptian cohort.
Journal of proteome research 11, 5914-5923 [PubMed:23078175]
[show Abstract]
Although hepatocellular carcinoma (HCC) has been subjected to continuous investigation and its symptoms are well-known, early stage diagnosis of this disease remains difficult and the survival rate after diagnosis is typically very low (3-5%). Early and accurate detection of metabolic changes in the sera of patients with liver cirrhosis can help improve the prognosis of HCC and lead to a better understanding of its mechanism at the molecular level, thus providing patients with in-time treatment of the disease. In this study, we compared metabolite levels in sera of 40 HCC patients and 49 cirrhosis patients from Egypt by using ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometer (UPLC-QTOF MS). Following data preprocessing, the most relevant ions in distinguishing HCC cases from cirrhotic controls are selected by statistical methods. Putative metabolite identifications for these ions are obtained through mass-based database search. The identities of some of the putative identifications are verified by comparing their MS/MS fragmentation patterns and retention times with those from authentic compounds. Finally, the serum samples are reanalyzed for quantitation of selected metabolites as candidate biomarkers of HCC. This quantitation was performed using isotope dilution by selected reaction monitoring (SRM) on a triple quadrupole linear ion trap (QqQLIT) coupled to UPLC. Statistical analysis of the UPLC-QTOF data identified 274 monoisotopic ion masses with statistically significant differences in ion intensities between HCC cases and cirrhotic controls. Putative identifications were obtained for 158 ions by mass based search against databases. We verified the identities of selected putative identifications including glycholic acid (GCA), glycodeoxycholic acid (GDCA), 3β, 6β-dihydroxy-5β-cholan-24-oic acid, oleoyl carnitine, and Phe-Phe. SRM-based quantitation confirmed significant differences between HCC and cirrhotic controls in metabolite levels of bile acid metabolites, long chain carnitines and small peptide. Our study provides useful insight into appropriate experimental design and computational methods for serum biomarker discovery using LC-MS/MS based metabolomics. This study has led to the identification of candidate biomarkers with significant changes in metabolite levels between HCC cases and cirrhotic controls. This is the first MS-based metabolic biomarker discovery study on Egyptian subjects that led to the identification of candidate metabolites that discriminate early stage HCC from patients with liver cirrhosis.

Last Modified

21 January 2016

CHEBI:36274 - glycochenodeoxycholic acid

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