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:CB5320664, eMolecules:2726126, Selleckchem:sn-38, ZINC000004099013
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SN-38 is an antineoplastic drug. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. SN38 is formed via hydrolysis of irinotecan by carboxylesterases and metabolized via glucuronidation by UGT1A1. The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecan toxicity, as it is then less easily excreted from the body in its SN-38 glucuronide form. SN-38 and its glucuronide are lost into the bile and intestines. It can cause the symptoms of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan.
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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)
S-sulfoglutathione (CHEBI:195386) 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 Types Sources
10577998 PubMed citation Europe PMC
1362956 PubMed citation Europe PMC
14988435 PubMed citation Europe PMC
16112416 PubMed citation Europe PMC
16316931 PubMed citation Europe PMC
16391576 PubMed citation Europe PMC
16404476 PubMed citation Europe PMC
16621738 PubMed citation Europe PMC
16650398 PubMed citation Europe PMC
16780237 PubMed citation Europe PMC
16877380 PubMed citation Europe PMC
17439666 PubMed citation Europe PMC
19580823 PubMed citation Europe PMC
4200890 PubMed citation Europe PMC
4745654 PubMed citation Europe PMC
8207209 PubMed citation Europe PMC
Last Modified
11 September 2023