15-acetyldeoxynivalenol

CHEBI:146194 EXACT SEEDED

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

A trichothecene mycotoxin that is deoxynivalenol acetylated on the oxygen at C-15. A skin and eye irritant, along with its 3-acetyl regioisomer and its parent deoxynivalenol it is considered among the most commonly and widely distributed cereal contaminants.

Structure

Standard InChIKey	IDGRYIRJIFKTAN-HTJQZXIKSA-N
SMILES	CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]3(C[C@H]([C@H]([C@@]34CO4)O2)O)C)COC(=O)C
Stereochemistry	fully defined
Cross-references	pubchem:10382483, chembl:CHEMBL468823

Filing pathway

Terpenoids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is terpene, from MIBiG.

Producer organisms 2

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

Taxon	Basis	Cluster	Evidence
Fusarium graminearum PH-1 NCBITaxon:229533	BGC_CHARACTERIZED	mibig:BGC0002176	DOI:10.1074/jbc.m109.045047
Fusarium graminearum NCBITaxon:5518	SOURCE_ASSERTION	mibig:BGC0001277	DOI:10.1128/aem.68.6.2959-2964.2002

Occurrences 4

Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.

Taxon	Source	Reference
Fusarium culmorum NCBITaxon:5516	LOTUS	DOI:10.1128/AEM.56.10.3047-3051.1990
Fusarium graminearum NCBITaxon:5518	LOTUS	DOI:10.1007/BF00597600
Fusarium graminearum NCBITaxon:5518	LOTUS	DOI:10.1007/BF00598566
Fusarium graminearum NCBITaxon:5518	LOTUS	DOI:10.1016/0031-9422(89)85014-9

Biosynthetic gene clusters 2

Accession	Host	Locus evidence	Genome
mibig:BGC0002176	Fusarium graminearum PH-1 NCBITaxon:229533	CLUSTER_DEMONSTRATED	genbank:CM000574.1
mibig:BGC0001277	Fusarium graminearum NCBITaxon:5518	CLUSTER_UNSTATED	genbank:AF359361.3

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Reaction	Substrate → product	Evidence
1	Tri8 UniProtKB:Q9C1B2		ungrounded → CHEBI:146194	DOI:10.1128/AEM.68.6.2959-2964.2002

Step 1: Fusarium graminearum Tri8 is represented as the C-3 esterase proposed to deacetylate 3,15-diacetyldeoxynivalenol to the exact 15-acetyldeoxynivalenol product. The 3,15-diacetylated precursor accumulated in Tri8-disrupted Fusarium graminearum, but it is not represented by a local exact chemical CURIE, so only the exact product is recorded on this pathway step.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Partial Fusarium graminearum graph for the Tri8-catalyzed C-3 deacetylation proposed to complete 15-acetyldeoxynivalenol biosynthesis.

Subject	Predicate	Object	Evidence
3,15-diacetyldeoxynivalenol	is deacetylated by	Tri8	DOI:10.1128/AEM.68.6.2959-2964.2002 https://www.uniprot.org/uniprotkb/Q9C1B2 https://www.ncbi.nlm.nih.gov/nuccore/AF359361.3 https://www.ncbi.nlm.nih.gov/protein/AAK33086.1 reference DOI:10.1128/AEM.68.6.2959-2964.2002 evidence type PRIMARY_EXPERIMENT snippet Tri8 encodes an esterase responsible for deacetylation at C-3 notes McCormick and Alexander disrupted Tri8 in Fusarium graminearum Z3639, observed loss of 15-acetyldeoxynivalenol biosynthesis with accumulation of C-3-acetylated trichothecenes including 3,15-diacetyldeoxynivalenol, and confirmed Tri8 C-3 deacetylase activity with yeast-expression and cell-free feeding experiments. reference https://www.uniprot.org/uniprotkb/Q9C1B2 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:Q9C1B2 resolves Fusarium graminearum Tri8, names the Gibberella zeae/Fusarium graminearum organism, cites DOI:10.1128/AEM.68.6.2959-2964.2002, and cross-references EMBL AF359361 to GenPept AAK33086.1. reference https://www.ncbi.nlm.nih.gov/nuccore/AF359361.3 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes GenBank AF359361.3 is the Fusarium graminearum trichothecene biosynthetic cluster; its TRI8 coding sequence maps to protein AAK33086.1. reference https://www.ncbi.nlm.nih.gov/protein/AAK33086.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept AAK33086.1 is the AF359361.3 TRI8 coding sequence cross-referenced by UniProtKB:Q9C1B2.
Tri8	catalyzes	trichothecene C-3 deacetylation	DOI:10.1128/AEM.68.6.2959-2964.2002 https://www.uniprot.org/uniprotkb/Q9C1B2 reference DOI:10.1128/AEM.68.6.2959-2964.2002 evidence type PRIMARY_EXPERIMENT snippet Tri8 encodes an esterase responsible for deacetylation at C-3 notes McCormick and Alexander disrupted Tri8 in Fusarium graminearum Z3639, observed loss of 15-acetyldeoxynivalenol biosynthesis with accumulation of C-3-acetylated trichothecenes including 3,15-diacetyldeoxynivalenol, and confirmed Tri8 C-3 deacetylase activity with yeast-expression and cell-free feeding experiments. reference https://www.uniprot.org/uniprotkb/Q9C1B2 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:Q9C1B2 resolves Fusarium graminearum Tri8, names the Gibberella zeae/Fusarium graminearum organism, cites DOI:10.1128/AEM.68.6.2959-2964.2002, and cross-references EMBL AF359361 to GenPept AAK33086.1.
trichothecene C-3 deacetylation	produces	15-acetyldeoxynivalenol	DOI:10.1128/AEM.68.6.2959-2964.2002 reference DOI:10.1128/AEM.68.6.2959-2964.2002 evidence type PRIMARY_EXPERIMENT snippet Tri8 encodes an esterase responsible for deacetylation at C-3 notes McCormick and Alexander disrupted Tri8 in Fusarium graminearum Z3639, observed loss of 15-acetyldeoxynivalenol biosynthesis with accumulation of C-3-acetylated trichothecenes including 3,15-diacetyldeoxynivalenol, and confirmed Tri8 C-3 deacetylase activity with yeast-expression and cell-free feeding experiments.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Explore across X-Mech

AntibioticMech (15-acetyldeoxynivalenol) ↗ MediaIngredientMech (CHEBI:146194) ↗ TaxonMech: Fusarium graminearum PH-1 (NCBITaxon:229533) ↗ TaxonMech: Fusarium graminearum (NCBITaxon:5518) ↗ PathwayMech (mibig:BGC0002176) ↗ PathwayMech (mibig:BGC0001277) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0001277, BGC0002176. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0002176	MIBIG	3
BGC0001277	MIBIG	4
CHEBI:146194	CHEBI	3-star

This page is generated from data/natural_products/terpenoids/15-acetyldeoxynivalenol.yaml, which is generated from the committed inventories. Neither is edited by hand.