hexadehydroastechrome

CHEBI:73878 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

An iron(III) hydroxamate that is astechrome in which the 3-methylbut-2-en-1-yl groups have been oxidised to 3-methylbuta-1,3-dien-1-yl groups. First isolated from Aspergillus fumigatus.

Structure

Standard InChIKey	QRPYQNLMWIGUCP-VMBSUALFSA-N
SMILES	C=C(/C=C/C1=CC=CC2=C1NC=C2CC(N3O[Fe](ON4C(CC5=CNC6=C5C=CC=C6/C=C/C(C)=C)=C(N=C(C4=O)C)OC)ON7C(CC8=CNC9=C8C=CC=C9/C=C/C(C)=C)=C(N=C(C7=O)C)OC)=C(N=C(C3=O)C)OC)C
Stereochemistry	fully defined

Filing pathway

Alkaloids — 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, 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:BGC0000372	PMID:25386169

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
Aspergillus fumigatus NCBITaxon:746128	LOTUS	DOI:10.3389/FMICB.2014.00530

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000372	Aspergillus fumigatus Af293 NCBITaxon:330879	CLUSTER_DEMONSTRATED	genbank:CM000171.1

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 12 nodes, 11 edges

Partial database-annotated assembly view, not an ordered experimental pathway. Five sequence-verified CEA10/A1163 protein references are distinct from the seeded Af293 producer and unresolved experimental alleles. HasE substrate timing remains alternative; tailoring order and exact intermediates are not fixed. Abstract contribution edges do not mean direct conversion to the final Fe(III) complex.

Subject	Predicate	Object	Evidence
HasD (CEA10/A1163 annotated reference)	annotated_to_catalyze	Tethered Trp-Ala assembly	https://www.uniprot.org/uniprotkb/B0XWK8/entry https://www.ncbi.nlm.nih.gov/protein/EDP52461.1 reference https://www.uniprot.org/uniprotkb/B0XWK8/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. NRPS annotation condenses tryptophan and alanine. No particular phosphopantetheinyl transferase is assigned. snippet condenses tryptophan and alanine reference https://www.ncbi.nlm.nih.gov/protein/EDP52461.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036270, taxon451804, versioned GenPept EDP52461.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.
Tethered Trp-Ala assembly	contributes_to_biosynthesis_of	hexadehydroastechrome	https://www.uniprot.org/uniprotkb/B0XWK8/entry reference https://www.uniprot.org/uniprotkb/B0XWK8/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The function is assigned to HAS biosynthesis. This abstract contribution edge does not assert a direct one-step conversion to the iron complex or an ordered complete pathway.
HasE (CEA10/A1163 annotated reference)	annotated_to_catalyze	C7 prenylation of tethered Trp or Trp-Ala	https://www.uniprot.org/uniprotkb/B0XWK7/entry https://www.ncbi.nlm.nih.gov/protein/EDP52460.1 reference https://www.uniprot.org/uniprotkb/B0XWK7/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The annotation leaves two alternatives: HasD-tethered tryptophan OR the tethered Trp-Ala dipeptide. No fixed timing or free-tryptophan assay kinetics is transferred to the native tethered route. snippet hasD-tethered tryptophan or the resulting tethered Trp-Ala dipeptid reference https://www.ncbi.nlm.nih.gov/protein/EDP52460.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036260, taxon451804, versioned GenPept EDP52460.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.
C7 prenylation of tethered Trp or Trp-Ala	contributes_to_biosynthesis_of	hexadehydroastechrome	https://www.uniprot.org/uniprotkb/B0XWK7/entry reference https://www.uniprot.org/uniprotkb/B0XWK7/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The function is assigned to HAS biosynthesis. This abstract contribution edge does not assert a direct one-step conversion to the iron complex or an ordered complete pathway.
HasH (CEA10/A1163 annotated reference)	annotated_to_catalyze	P450 tailoring of tethered intermediates	https://www.uniprot.org/uniprotkb/B0XWK4/entry https://www.ncbi.nlm.nih.gov/protein/EDP52457.1 reference https://www.uniprot.org/uniprotkb/B0XWK4/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. P450 annotation places HasH with HasC and HasG in tailoring toward the released O-methylated diketopiperazine ligand. The exact isolated substrate/product and reaction order are not resolved here. reference https://www.ncbi.nlm.nih.gov/protein/EDP52457.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036230, taxon451804, versioned GenPept EDP52457.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.
P450 tailoring of tethered intermediates	contributes_to_biosynthesis_of	hexadehydroastechrome	https://www.uniprot.org/uniprotkb/B0XWK4/entry reference https://www.uniprot.org/uniprotkb/B0XWK4/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The function is assigned to HAS biosynthesis. This abstract contribution edge does not assert a direct one-step conversion to the iron complex or an ordered complete pathway.
HasC (CEA10/A1163 annotated reference)	annotated_to_catalyze	O-methylation during ligand tailoring	https://www.uniprot.org/uniprotkb/B0XWK9/entry https://www.ncbi.nlm.nih.gov/protein/EDP52462.1 reference https://www.uniprot.org/uniprotkb/B0XWK9/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. O-methyltransferase annotation places HasC with HasH and HasG in tailoring toward the released O-methylated diketopiperazine ligand. No atom-specific methylation site or verified reaction order is asserted. reference https://www.ncbi.nlm.nih.gov/protein/EDP52462.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036280, taxon451804, versioned GenPept EDP52462.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.
O-methylation during ligand tailoring	contributes_to_biosynthesis_of	hexadehydroastechrome	https://www.uniprot.org/uniprotkb/B0XWK9/entry reference https://www.uniprot.org/uniprotkb/B0XWK9/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The function is assigned to HAS biosynthesis. This abstract contribution edge does not assert a direct one-step conversion to the iron complex or an ordered complete pathway.
HasG (CEA10/A1163 annotated reference)	annotated_to_catalyze	Prenyl-to-methylbutadienyl side-chain conversion	https://www.uniprot.org/uniprotkb/B0XWK5/entry https://www.ncbi.nlm.nih.gov/protein/EDP52458.1 reference https://www.uniprot.org/uniprotkb/B0XWK5/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The oxidoreductase is annotated to convert a prenyl side chain to a methylbutadienyl side chain. No purified assay, isolated substrate, or proven timing relative to ligand release is asserted. snippet methylbutadienyl side chain reference https://www.ncbi.nlm.nih.gov/protein/EDP52458.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036240, taxon451804, versioned GenPept EDP52458.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.
Prenyl-to-methylbutadienyl side-chain conversion	contributes_to_biosynthesis_of	hexadehydroastechrome	https://www.uniprot.org/uniprotkb/B0XWK5/entry reference https://www.uniprot.org/uniprotkb/B0XWK5/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The function is assigned to HAS biosynthesis. This abstract contribution edge does not assert a direct one-step conversion to the iron complex or an ordered complete pathway.
Three ligand molecules complex with Fe(III)	produces	hexadehydroastechrome	https://www.uniprot.org/uniprotkb/B0XWK8/entry reference https://www.uniprot.org/uniprotkb/B0XWK8/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The annotation describes assembly of three O-methylated diketopiperazine ligand molecules with Fe(III) to give HAS. No specific protein catalyst for complexation is assigned; this is not a protein trimer.

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

Causal graph — biosynthesis 5 nodes, 3 edges

Partial database-annotated view of cluster regulation and transporter requirement. Links between gene-expression regulation and transporter-dependent production are intentionally omitted because their mediation is not established here. CEA10/A1163 reference accessions are not assigned to experimental alleles. HasA positive regulation is not direct promoter binding, HasB requirement is not an identified transport reaction, and the HasF null regulatory finding applies only to tested growth conditions.

Subject	Predicate	Object	Evidence
HasA (CEA10/A1163 annotated reference)	annotated_positive_regulator_of	HAS biosynthetic-gene expression	https://www.uniprot.org/uniprotkb/B0XWT0/entry https://www.ncbi.nlm.nih.gov/protein/EDP52464.1 reference https://www.uniprot.org/uniprotkb/B0XWT0/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. Positive regulation is a database annotation; direct DNA contact, promoter targets and mediation are not established here. reference https://www.ncbi.nlm.nih.gov/protein/EDP52464.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036300, taxon451804, versioned GenPept EDP52464.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.
HasB (CEA10/A1163 annotated reference)	annotated_required_for	HAS production	https://www.uniprot.org/uniprotkb/B0XWL0/entry https://www.ncbi.nlm.nih.gov/protein/EDP52463.1 reference https://www.uniprot.org/uniprotkb/B0XWL0/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The MFS-type transporter is annotated as required for production. No transported substrate, compartment, transport direction, or direct efflux of HAS is asserted; this is not universal essentiality. reference https://www.ncbi.nlm.nih.gov/protein/EDP52463.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036290, taxon451804, versioned GenPept EDP52463.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.
HasF (CEA10/A1163 annotated reference)	not_observed_to_regulate_under_tested_conditions	HAS biosynthetic-gene expression	https://www.uniprot.org/uniprotkb/B0XWK6/entry https://www.ncbi.nlm.nih.gov/protein/EDP52459.1 reference https://www.uniprot.org/uniprotkb/B0XWK6/entry evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Inspected UniProt FUNCTION annotation, citing PMID23360537; its primary paper was not retrieved. DATABASE_ASSERTION, not a directly inspected experiment. CEA10/A1163 reference is not equated to the Af293 producer or an experimental allele. The annotation explicitly reports no regulation under the tested growth conditions. The disruption annotation likewise reports no effect on production in tested laboratory conditions; neither establishes universal dispensability. Exact assay strain and conditions were not independently verified. snippet at least under the growth conditions tested reference https://www.ncbi.nlm.nih.gov/protein/EDP52459.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-12 notes Identity only: A1163 AFUB_036250, taxon451804, versioned GenPept EDP52459.1 matches reviewed UniProt and the complete spliced CDS on DS499596.1, including start/stop and strand. Sequence agreement does not establish functional activity or the experimental allele.

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

Explore across X-Mech

AntibioticMech (hexadehydroastechrome) ↗ MediaIngredientMech (CHEBI:73878) ↗ TaxonMech: Aspergillus fumigatus Af293 (NCBITaxon:330879) ↗ PathwayMech (mibig:BGC0000372) ↗

Open questions 1

curator-has-cluster-reference-and-mechanism-limits — Which experimental alleles, substrate timings and conditions establish the HAS assembly and regulatory mechanism?

Provenance

Source concept	Source	Version
BGC0000372	MIBIG	5
CHEBI:73878	CHEBI	3-star

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