CHEBI:16856 - glutathione

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ChEBI Name glutathione
ChEBI ID CHEBI:16856
Definition A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42873, CHEBI:43049, CHEBI:5437, CHEBI:12402, CHEBI:14327, CHEBI:24334
Supplier Information ChemicalBook:CB6320803, eMolecules:515159, MolPort-000-003-913, ZINC000003830891
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Glutathione (GSH, ) is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by reactive oxygen species such as free radicals, peroxides, lipid peroxides, and heavy metals. It is a tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and cysteine. The carboxyl group of the cysteine residue is attached by normal peptide linkage to glycine.
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Formula C10H17N3O6S
Net Charge 0
Average Mass 307.320
Monoisotopic Mass 307.08381
InChI InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
InChIKey RWSXRVCMGQZWBV-WDSKDSINSA-N
SMILES N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
skin lightening agent
Any cosmetic used to lighten the colour of skin by reducing the concentration of melanin.
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ChEBI Ontology
Outgoing glutathione (CHEBI:16856) has role Escherichia coli metabolite (CHEBI:76971)
glutathione (CHEBI:16856) has role antioxidant (CHEBI:22586)
glutathione (CHEBI:16856) has role cofactor (CHEBI:23357)
glutathione (CHEBI:16856) has role geroprotector (CHEBI:176497)
glutathione (CHEBI:16856) has role human metabolite (CHEBI:77746)
glutathione (CHEBI:16856) has role mouse metabolite (CHEBI:75771)
glutathione (CHEBI:16856) has role skin lightening agent (CHEBI:85046)
glutathione (CHEBI:16856) is a L-cysteine derivative (CHEBI:83824)
glutathione (CHEBI:16856) is a thiol (CHEBI:29256)
glutathione (CHEBI:16856) is a tripeptide (CHEBI:47923)
glutathione (CHEBI:16856) is conjugate acid of glutathionate(1−) (CHEBI:57925)
Incoming N-(4-oxoglutaryl)-L-cysteinylglycine (CHEBI:138934) has functional parent glutathione (CHEBI:16856)
S-(2,4-dinitrophenyl)glutathione (CHEBI:8927) has functional parent glutathione (CHEBI:16856)
S-(2-hydroxyethyl)glutathione (CHEBI:35896) has functional parent glutathione (CHEBI:16856)
S-acylglutathione (CHEBI:18126) has functional parent glutathione (CHEBI:16856)
S-sulfanylglutathione (CHEBI:52857) has functional parent glutathione (CHEBI:16856)
DON-10-glutathione (CHEBI:149452) has functional parent glutathione (CHEBI:16856)
eoxin C4 (CHEBI:63984) has functional parent glutathione (CHEBI:16856)
glutathione derivative (CHEBI:24337) has functional parent glutathione (CHEBI:16856)
phytochelatin (CHEBI:60836) has functional parent glutathione (CHEBI:16856)
glutathionate(1−) (CHEBI:57925) is conjugate base of glutathione (CHEBI:16856)
IUPAC Name
L-γ-glutamyl-L-cysteinylglycine
Synonyms Sources
5-L-Glutamyl-L-cysteinylglycine KEGG COMPOUND
gamma-L-Glutamyl-L-cysteinyl-glycine KEGG COMPOUND
Glutathione KEGG COMPOUND
Glutathione-SH HMDB
GSH KEGG COMPOUND
N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine KEGG COMPOUND
Reduced glutathione KEGG COMPOUND
Manual Xrefs Databases
111188 ChemSpider
1312 DrugCentral
C00001518 KNApSAcK
C00051 KEGG COMPOUND
D00014 KEGG DRUG
DB00143 DrugBank
FDB001498 FooDB
Glutathione Wikipedia
GLUTATHIONE MetaCyc
GSH PDBeChem
HMDB0000125 HMDB
View more database links
Registry Numbers Types Sources
1729812 Reaxys Registry Number Reaxys
70-18-8 CAS Registry Number KEGG COMPOUND
70-18-8 CAS Registry Number ChemIDplus
Citations
Shibamura A, Ikeda T, Nishikawa Y (2009)
A method for oral administration of hydrophilic substances to Caenorhabditis elegans: Effects of oral supplementation with antioxidants on the nematode lifespan.
Mechanisms of ageing and development 130, 652-655 [PubMed:19580823]
[show Abstract]
Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG (2007)
Growth control of the eukaryote cell: a systems biology study in yeast.
Journal of biology 6, 4 [PubMed:17439666]
[show Abstract]
Czeczot H, Scibior D, Skrzycki M, Podsiad M (2006)
Glutathione and GSH-dependent enzymes in patients with liver cirrhosis and hepatocellular carcinoma.
Acta biochimica Polonica 53, 237-242 [PubMed:16404476]
[show Abstract]
Djurhuus R, Segadal K, Svardal AM (2006)
Glutathione in blood cells decreases without DNA breaks after a simulated saturation dive to 250 msw.
Aviation, space, and environmental medicine 77, 597-604 [PubMed:16780237]
[show Abstract]
Calvo-Marzal P, Chumbimuni-Torres KY, Höehr NF, Kubota LT (2006)
Determination of glutathione in hemolysed erythrocyte with amperometric sensor based on TTF-TCNQ.
Clinica chimica acta; international journal of clinical chemistry 371, 152-158 [PubMed:16650398]
[show Abstract]
Schulpis KH, Papassotiriou I, Parthimos T, Tsakiris T, Tsakiris S (2006)
The effect of L-cysteine and glutathione on inhibition of Na+, K+-ATPase activity by aspartame metabolites in human erythrocyte membrane.
European journal of clinical nutrition 60, 593-597 [PubMed:16391576]
[show Abstract]
Iwasaki Y, Hoshi M, Ito R, Saito K, Nakazawa H (2006)
Analysis of glutathione and glutathione disulfide in human saliva using hydrophilic interaction chromatography with mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 839, 74-79 [PubMed:16621738]
[show Abstract]
Briz O, Romero MR, Martinez-Becerra P, Macias RI, Perez MJ, Jimenez F, San Martin FG, Marin JJ (2006)
OATP8/1B3-mediated cotransport of bile acids and glutathione: an export pathway for organic anions from hepatocytes?
The Journal of biological chemistry 281, 30326-30335 [PubMed:16877380]
[show Abstract]
Kaynar H, Meral M, Turhan H, Keles M, Celik G, Akcay F (2005)
Glutathione peroxidase, glutathione-S-transferase, catalase, xanthine oxidase, Cu-Zn superoxide dismutase activities, total glutathione, nitric oxide, and malondialdehyde levels in erythrocytes of patients with small cell and non-small cell lung cancer.
Cancer letters 227, 133-139 [PubMed:16112416]
[show Abstract]
Sohlenius-Sternbeck AK, Schmidt S (2005)
Impaired glutathione-conjugating capacity by cryopreserved human and rat hepatocytes.
Xenobiotica; the fate of foreign compounds in biological systems 35, 727-736 [PubMed:16316931]
[show Abstract]
Wu G, Fang YZ, Yang S, Lupton JR, Turner ND (2004)
Glutathione metabolism and its implications for health.
The Journal of nutrition 134, 489-492 [PubMed:14988435]
[show Abstract]
Morrison JA, Jacobsen DW, Sprecher DL, Robinson K, Khoury P, Daniels SR (1999)
Serum glutathione in adolescent males predicts parental coronary heart disease.
Circulation 100, 2244-2247 [PubMed:10577998]
[show Abstract]
Yim CY, Hibbs JB, McGregor JR, Galinsky RE, Samlowski WE (1994)
Use of N-acetyl cysteine to increase intracellular glutathione during the induction of antitumor responses by IL-2.
Journal of immunology (Baltimore, Md. : 1950) 152, 5796-5805 [PubMed:8207209]
[show Abstract]
Witschi A, Reddy S, Stofer B, Lauterburg BH (1992)
The systemic availability of oral glutathione.
European journal of clinical pharmacology 43, 667-669 [PubMed:1362956]
[show Abstract]
Uotila L (1973)
Purification and characterization of S-2-hydroxyacylglutathione hydrolase (glyoxalase II) from human liver.
Biochemistry 12, 3944-3951 [PubMed:4745654]
Uotila L (1973)
Preparation and assay of glutathione thiol esters. Survey of human liver glutathione thiol esterases.
Biochemistry 12, 3938-3943 [PubMed:4200890]
Last Modified
11 October 2021