aculene D

CHEBI:155910 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 sesquiterpenoid that is (3aR)-4,7,8,8a-tetrahydroazulen-1(3aH)-one substituted by an ethyl, methyl, hydroxy and methyl groups at positions 3, 6, 8S, and 8aR, respectively. It is a fungal metabolite isolated from Penicillium sp. SCS-KFD08 and Aspergillus aculeatus.

Structure

Standard InChIKey	IIQOUDJDCRTCJY-MBNYWOFBSA-N
SMILES	CCC1=CC(=O)[C@@]2([C@@H]1CC=C(C[C@@H]2O)C)C
Stereochemistry	fully defined
Cross-references	pubchem:146672910

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 1

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
Aspergillus aculeatus ATCC 16872 NCBITaxon:690307	BGC_CHARACTERIZED	mibig:BGC0002225	PMID:31618514

Occurrences 3

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
Penicillium sp. SCS-KFD08 NCBITaxon:1808020	CHEBI	PMID:27709333
Aspergillus aculeatus NCBITaxon:5053	LOTUS	DOI:10.3390/MOLECULES190810898
Aspergillus aculeatus NCBITaxon:5053	CHEBI	PMID:25068785

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002225	Aspergillus aculeatus ATCC 16872 NCBITaxon:690307	CLUSTER_DEMONSTRATED	genbank:KV878977.1

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	AneA aculene D dioxygenase UniProtKB:A0A1L9WUX8	RHEA:65112	CHEBI:155910 + CHEBI:16810 + CHEBI:15379 → CHEBI:155912 + CHEBI:30031 + CHEBI:16526 + CHEBI:15377	DOI:10.1002/anie.201910200

Step 1: AneA introduces the 5,6-alkene into aculene D to form aculene C; RHEA:65112 grounds the full 2-oxoglutarate- and O2-dependent dioxygenase reaction.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Aspergillus aculeatus ATCC 16872 BGC0002225 2-oxoglutarate-dependent dioxygenase AneA desaturates aculene D between C-5 and C-6 to form aculene C.

Subject	Predicate	Object	Notes	Evidence
aculene D	is desaturated by	AneA aculene D dioxygenase	AneA desaturates aculene D between C5 and C6.	DOI:10.1002/anie.201910200 DOI:10.1039/D1NP00074H https://mibig.secondarymetabolites.org/repository/BGC0002225.3/BGC0002225.gbk https://www.uniprot.org/uniprotkb/A0A1L9WUX8 https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv reference DOI:10.1002/anie.201910200 evidence type PRIMARY_EXPERIMENT snippet characterized the biosynthetic pathway based on gene inactivation, feeding experiments, and heterologous reconstitution notes Lee et al. identified the Aspergillus aculeatus aculene biosynthetic gene cluster, inactivated aneA, and used Saccharomyces cerevisiae and Aspergillus oryzae heterologous reconstitution to connect AneA to 5,6-desaturation of aculene D into aculene C. reference DOI:10.1039/D1NP00074H evidence type REVIEW snippet the unsaturation is catalyzed by AneA notes Wang et al. summarize Lee et al.'s aneA deletion phenotype and place AneA after A. oryzae reconstitution of AneC/F/D/G to aculene D in the published aculene A-C pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0002225.3/BGC0002225.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0002225.3 maps the A. aculeatus ATCC 16872 KV878977 aculene region to CDS OJJ99912.1 at locus ASPACDRAFT_119783. reference https://www.uniprot.org/uniprotkb/A0A1L9WUX8 evidence type DATABASE_ASSERTION snippet The dioxygenase aneA converts aculene D into aculene C retrieved on 2026-09-30 notes Reviewed UniProtKB:A0A1L9WUX8 is the 298 aa A. aculeatus ATCC 16872 Dioxygenase aneA, cross-references KV878977 protein OJJ99912.1, and annotates RHEA:65112 from PMID:31618514. reference https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes The Rhea Swiss-Prot mapping links UniProtKB:A0A1L9WUX8 to RHEA:65112, the aculene D 2-oxoglutarate-dependent desaturation reaction.
AneA aculene D dioxygenase	forms	aculene C	The AneA dioxygenase reaction yields aculene C from aculene D.	DOI:10.1002/anie.201910200 DOI:10.1039/D1NP00074H https://mibig.secondarymetabolites.org/repository/BGC0002225.3/BGC0002225.gbk https://www.uniprot.org/uniprotkb/A0A1L9WUX8 https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv reference DOI:10.1002/anie.201910200 evidence type PRIMARY_EXPERIMENT snippet characterized the biosynthetic pathway based on gene inactivation, feeding experiments, and heterologous reconstitution notes Lee et al. identified the Aspergillus aculeatus aculene biosynthetic gene cluster, inactivated aneA, and used Saccharomyces cerevisiae and Aspergillus oryzae heterologous reconstitution to connect AneA to 5,6-desaturation of aculene D into aculene C. reference DOI:10.1039/D1NP00074H evidence type REVIEW snippet the unsaturation is catalyzed by AneA notes Wang et al. summarize Lee et al.'s aneA deletion phenotype and place AneA after A. oryzae reconstitution of AneC/F/D/G to aculene D in the published aculene A-C pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0002225.3/BGC0002225.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0002225.3 maps the A. aculeatus ATCC 16872 KV878977 aculene region to CDS OJJ99912.1 at locus ASPACDRAFT_119783. reference https://www.uniprot.org/uniprotkb/A0A1L9WUX8 evidence type DATABASE_ASSERTION snippet The dioxygenase aneA converts aculene D into aculene C retrieved on 2026-09-30 notes Reviewed UniProtKB:A0A1L9WUX8 is the 298 aa A. aculeatus ATCC 16872 Dioxygenase aneA, cross-references KV878977 protein OJJ99912.1, and annotates RHEA:65112 from PMID:31618514. reference https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes The Rhea Swiss-Prot mapping links UniProtKB:A0A1L9WUX8 to RHEA:65112, the aculene D 2-oxoglutarate-dependent desaturation reaction.

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

Explore across X-Mech

AntibioticMech (aculene D) ↗ MediaIngredientMech (CHEBI:155910) ↗ TaxonMech: Aspergillus aculeatus ATCC 16872 (NCBITaxon:690307) ↗ PathwayMech (mibig:BGC0002225) ↗

Provenance

Source concept	Source	Version
BGC0002225	MIBIG	3
CHEBI:155910	CHEBI	3-star

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