azaspirene

naturalproductmech:mibig-a469ae857b MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKey	QLKGRMRPKQNCRR-XXPFWKOGSA-N
SMILES	CC\C=C\C=C\C1=C(C)C(=O)[C@@]2(O1)[C@@H](O)[C@](O)(CC1=CC=CC=C1)NC2=O
Stereochemistry	fully defined
Cross-references	npatlas:NPA06799

Filing pathway

Unclassified — 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 nrps, pks, 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 fumigatus Af293 NCBITaxon:330879	BGC_CHARACTERIZED	mibig:BGC0001037	PMID:25494235

Occurrences 1

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
Neosartorya NCBITaxon:36629	LOTUS	DOI:10.1021/OL020104+

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0001037	Aspergillus fumigatus Af293 NCBITaxon:330879	CLUSTER_DEMONSTRATED	genbank:CM000176.1

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.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 8 nodes, 8 edges

Partial experimental reconstitution, not a complete ordered pathway. Supplement sections2-5 specify Af293-derived cloning, N-FLAG/C-His6 PsoA, N-His6 PsoB/PsoF for bacterial protein purification, and a separate yeast PsoB/PsoG vector. Canonical entries are native reference examples, not verified full insert sequences. PsoG remains ungrounded. No transfer to pseurotin A/D, no direct PsoB catalytic assignment, and no inference of native essentiality. Primary starter preference takes precedence over the acetyl-starter statement in UniProt; that discrepant database statement is not adopted.

Subject	Predicate	Object	Evidence
PsoA (Af293 reference; tagged construct tested)	is_encoded_in_successful_reconstitution	Four-gene reconstitution in yeast BJ5464-NpgA	DOI:10.1021/ol503179v https://www.uniprot.org/uniprotkb/Q4WAZ9/entry reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Figure2a and supplement sections2/5: tested coexpression membership, not isolated-enzyme sufficiency or a physical complex. reference https://www.uniprot.org/uniprotkb/Q4WAZ9/entry evidence type CURATOR_INFERENCE retrieved on 2026-10-12 notes Selected Af293 native reference, not a deposited experimental construct: AFUA_8G00540, EAL85113.2, 4007 aa. Release2026_03 UniProt, spliced AAHF01000014.1 CDS and separately retrieved GenPept sequences agree exactly; coded_by coordinates, strand, start/stop, strain and taxon330879 checked. Protein-existence grades are not upgraded. The supplement names Af293 as cloning source; tags and assay hosts differ from the native context.
PsoB (Af293 reference)	is_encoded_in_successful_reconstitution	Four-gene reconstitution in yeast BJ5464-NpgA	DOI:10.1021/ol503179v https://www.uniprot.org/uniprotkb/Q4WAZ8/entry reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Figure2a and supplement sections2/5: tested coexpression membership, not isolated-enzyme sufficiency or a physical complex. reference https://www.uniprot.org/uniprotkb/Q4WAZ8/entry evidence type CURATOR_INFERENCE retrieved on 2026-10-12 notes Selected Af293 native reference, not a deposited experimental construct: AFUA_8G00530, EAL85114.1, 445 aa. Release2026_03 UniProt, spliced AAHF01000014.1 CDS and separately retrieved GenPept sequences agree exactly; coded_by coordinates, strand, start/stop, strain and taxon330879 checked. Protein-existence grades are not upgraded. The supplement names Af293 as cloning source; tags and assay hosts differ from the native context.
PsoF (Af293 reference)	is_encoded_in_successful_reconstitution	Four-gene reconstitution in yeast BJ5464-NpgA	DOI:10.1021/ol503179v https://www.uniprot.org/uniprotkb/Q4WAZ0/entry reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Figure2a and supplement sections2/5: tested coexpression membership, not isolated-enzyme sufficiency or a physical complex. reference https://www.uniprot.org/uniprotkb/Q4WAZ0/entry evidence type CURATOR_INFERENCE retrieved on 2026-10-12 notes Selected Af293 native reference, not a deposited experimental construct: AFUA_8G00440, EAL85122.1, 905 aa. Release2026_03 UniProt, spliced AAHF01000014.1 CDS and separately retrieved GenPept sequences agree exactly; coded_by coordinates, strand, start/stop, strain and taxon330879 checked. Protein-existence grades are not upgraded. The supplement names Af293 as cloning source; tags and assay hosts differ from the native context.
PsoG (Af293-derived construct; protein accession unresolved)	is_encoded_in_successful_reconstitution	Four-gene reconstitution in yeast BJ5464-NpgA	DOI:10.1021/ol503179v https://www.ncbi.nlm.nih.gov/nuccore/CM000176.1 reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Figure2a and supplement sections2/5: tested coexpression membership, not isolated-enzyme sufficiency or a physical complex. reference https://www.ncbi.nlm.nih.gov/nuccore/CM000176.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-12 notes TableS1 PsoG seg1f 3-prime sequence matches chromosome99604..99621 and reverse-strand WGS694118..694135, between annotated AFUA_8G00440/00460. Neither inspected nucleotide record annotates a CDS at that start. No deposited protein or exact assayed sequence was established. AFUA_8G00430/Q4WAY9/EAL85123.1 is a different157-aa locus and is not adopted. Three bounded current UniProt queries did not resolve PsoG; this is not global absence. Primer matching is not splice-model validation.
Four-gene reconstitution in yeast BJ5464-NpgA	produced_detected_product	Azaspirene	DOI:10.1021/ol503179v reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Figure2a: product matched an authentic standard by LC-MS; not proof that every enzyme is individually essential. snippet compared to the authentic standard
PsoA (Af293 reference; tagged construct tested)	catalyzes	PsoA starter selection in vitro	DOI:10.1021/ol503179v reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Figure2b and supplement FigureS4: purified PsoA starter assays; no complete azaspirene synthesis in vitro.
Propionyl-CoA	is_preferred_starter_in	PsoA starter selection in vitro	DOI:10.1021/ol503179v reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Competition experiment supports preference, not exclusive substrate use. Four malonyl-derived extensions were isotope-supported.
PsoG (Af293-derived construct; protein accession unresolved)	omission_changed_product_profile_in	Four-gene reconstitution in yeast BJ5464-NpgA	DOI:10.1021/ol503179v reference DOI:10.1021/ol503179v evidence type PRIMARY_EXPERIMENT retrieved on 2026-10-12 notes Without PsoG, peaks7/8 appeared. Their structures were not determined; the proposed hydroxylation is not a demonstrated purified-enzyme reaction.

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

Explore across X-Mech

AntibioticMech (azaspirene) ↗ MediaIngredientMech (naturalproductmech:mibig-a469ae857b) ↗ TaxonMech: Aspergillus fumigatus Af293 (NCBITaxon:330879) ↗ PathwayMech (mibig:BGC0001037) ↗

Open questions 1

curator-azaspirene-construct-and-pathway-limits — Which deposited experimental sequences resolve PsoG and the complete tagged constructs, and which intermediate-specific reactions are directly established?

Provenance

Source concept	Source	Version
BGC0001037	MIBIG	5

This page is generated from data/natural_products/unclassified/azaspirene.yaml, which is generated from the committed inventories. Neither is edited by hand.