gliotoxin

CHEBI:5385 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:35489 CHEBI:35489
CHEBI:38163 CHEBI:38163
CHEBI:46761 CHEBI:46761
CHEBI:64130 CHEBI:64130

Chemical structure

Computed structure properties
Molecular formula	C13H14N2O4S2
Charge	0
Average mass	326.399 Da
Monoisotopic mass	326.0395 Da
Source	ChEBI
InChIKey	FIVPIPIDMRVLAY-RBJBARPLSA-N

SMILES

[H][C@]12C(=CC=C[C@@H]1O)C[C@]13SS[C@](CO)(C(=O)N21)N(C)C3=O

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

Also called

(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 (EXACT_SYNONYM)— chebi
Aspergillin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:67-99-2
kegg.compound:C10595
knapsack:C00002340
ppdb:2793
reaxys:50675
wikipedia.en:Gliotoxin

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:35718 CHEBI:35718

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:5385`	gliotoxin	`antibioticmech:chebi-10e4f030da`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.