CHEBI:5385 - gliotoxin

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ChEBI Name gliotoxin
ChEBI ID CHEBI:5385
Definition A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C13H14N2O4S2
Net Charge 0
Average Mass 326.39100
Monoisotopic Mass 326.039
InChI InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
InChIKey FIVPIPIDMRVLAY-RBJBARPLSA-N
SMILES [H][C@@]12[C@@H](O)C=CC=C1C[C@@]13SS[C@@](CO)(N(C)C1=O)C(=O)N23
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): mycotoxin
Poisonous substance produced by fungi.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
EC 2.5.1.58 (protein farnesyltransferase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein farnesyltransferase (EC 2.5.1.58), one of the three enzymes in the prenyltransferase group.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
proteasome inhibitor
A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing gliotoxin (CHEBI:5385) has role antifungal agent (CHEBI:35718)
gliotoxin (CHEBI:5385) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
gliotoxin (CHEBI:5385) has role immunosuppressive agent (CHEBI:35705)
gliotoxin (CHEBI:5385) has role mycotoxin (CHEBI:25442)
gliotoxin (CHEBI:5385) has role proteasome inhibitor (CHEBI:52726)
gliotoxin (CHEBI:5385) is a dipeptide (CHEBI:46761)
gliotoxin (CHEBI:5385) is a organic disulfide (CHEBI:35489)
gliotoxin (CHEBI:5385) is a organic heterotetracyclic compound (CHEBI:38163)
gliotoxin (CHEBI:5385) is a pyrazinoindole (CHEBI:64130)
IUPAC Name
(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Synonym Source
Aspergillin ChemIDplus
Manual Xrefs Databases
2793 PPDB
C00002340 KNApSAcK
C10595 KEGG COMPOUND
Gliotoxin Wikipedia
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Registry Numbers Types Sources
50675 Reaxys Registry Number Reaxys
50675 Beilstein Registry Number ChemIDplus
67-99-2 CAS Registry Number KEGG COMPOUND
67-99-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16020669 PubMed citation Europe PMC
23832115 PubMed citation Europe PMC
24368570 PubMed citation Europe PMC
24847038 PubMed citation Europe PMC
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25494483 PubMed citation Europe PMC
25766143 PubMed citation Europe PMC
25816130 PubMed citation Europe PMC
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Last Modified
06 July 2015