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aureothin

CHEBI:80024 EXACT SEEDED antibacterial

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 C-nitro compound that is (3Z)-3-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran which is substituted by a 6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl group at position 5. It is isolated from the soil bacterium, Streptomyces thioluteus and exhibits antitumor, antifungal, and insecticidal activities.

Structure

Standard InChIKeyGQKXCBCSVYJUMI-WACKOAQBSA-N
SMILES[H][C@]1(c2oc(OC)c(C)c(=O)c2C)C/C(=C/C(C)=C/c2ccc([N+](=O)[O-])cc2)CO1
Stereochemistryfully defined

Filing pathway

Polyketides — computed by NPClassifier npclassifier.gnps2.org@2026-10-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is 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.

TaxonBasisClusterEvidence
Streptomyces thioluteus
NCBITaxon:66431		 BGC_CHARACTERIZED mibig:BGC0000024 PMID:13174453, DOI:10.1021/ja102751h

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.

TaxonSourceReference
Streptomyces thioluteus
NCBITaxon:66431		 CHEBI https://www.ebi.ac.uk/chebi/CHEBI:80024

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0000024 Streptomyces thioluteus
NCBITaxon:66431 		CLUSTER_DEMONSTRATED genbank:AJ575648.1

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.

StepEnzymeReactionSubstrate → productEvidence
1 AurF 4-aminobenzoate N-oxygenase
UniProtKB:Q70KH9		 RHEA:58889 CHEBI:17836 → CHEBI:142863 DOI:10.1021/ja039328t

Step 1: AurF oxidizes 4-aminobenzoate to 4-nitrobenzoate, the nitroaryl starter unit used by the aureothin polyketide synthase.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (1 causal) 1 cited occurrence BIOSYNTHETIC LOCUS 1 gene cluster 1 curated pathway step NATURAL PRODUCT aureothin CHEBI:80024 Polyketides TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 5 graphs

Causal graph — biosynthesis 3 nodes, 2 edges

Partial Streptomyces thioluteus aureothin biosynthesis graph for AurF-catalyzed N-oxygenation of the nitroaryl starter unit.

SubjectPredicateObjectNotesEvidence
4-aminobenzoate is N-oxygenated by AurF
DOI:10.1021/ja039328t
  • reference
    DOI:10.1021/ja039328t
    evidence type
    PRIMARY_EXPERIMENT
    notes
    AurF catalyzes RHEA:58889 in aureothin biosynthesis.
AurF forms 4-nitrobenzoate This graph covers the starter-unit N-oxygenation step; downstream tailoring is represented separately where curated.
DOI:10.1021/ja039328t
  • reference
    DOI:10.1021/ja039328t
    evidence type
    PRIMARY_EXPERIMENT
    notes
    AurF catalyzes RHEA:58889 in aureothin biosynthesis.

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

Causal graph — biosynthesis 4 nodes, 3 edges

Native AurI reference and upstream pyrone methylation model. Q70KH3 is not an experimentally verified plasmid sequence. Paper-relative intermediates remain ungrounded; deoxyaureothin is not mature aureothin.

SubjectPredicateObjectNotesEvidence
aurI (AJ575648.1:28440-29132) encodes the native reference protein AurI Native Streptomyces thioluteus reference; not a host or construct accession.
https://www.ncbi.nlm.nih.gov/nuccore/AJ575648.1
https://www.uniprot.org/uniprotkb/Q70KH3/entry
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AJ575648.1
    evidence type
    DATABASE_ASSERTION
    notes
    AJ575648.1 CDS 28440..29132, forward strand, ATG start; GenPept CAE02607.1, 230 amino acids.
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH3/entry
    evidence type
    CURATOR_INFERENCE
    notes
    Full CDS translation equals the deposited translation, independent CAE02607.1 protein and reviewed Q70KH3 sequence. UniProt entry version 59, sequence version 1, retrieved 2026-10-07.
Demethylluteothin (iso-5, gamma-pyrone) is the gamma-pyrone substrate assigned to AurI Do not substitute the alpha-pyrone tautomer 5 for the depicted substrate iso-5.
https://www.uniprot.org/uniprotkb/Q70KH3/entry
DOI:10.1021/ja102751h
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH3/entry
    evidence type
    DATABASE_ASSERTION
    notes
    The reviewed entry assigns demethylluteothin methylation to AurI; its cited older biochemical paper was not newly read.
  • reference
    DOI:10.1021/ja102751h
    evidence type
    CURATOR_INFERENCE
    notes
    Figure 6 interpretation; not a purified-enzyme kinetic assay.
AurI is assigned the O-methylation forming Deoxyaureothin (6) Figure 6 model uses SAM and yields compound 6, before AurH-dependent maturation.
https://www.uniprot.org/uniprotkb/Q70KH3/entry
DOI:10.1021/ja102751h
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH3/entry
    evidence type
    DATABASE_ASSERTION
    notes
    The reviewed entry names luteothin/deoxyaureothin as the product.
  • reference
    DOI:10.1021/ja102751h
    evidence type
    CURATOR_INFERENCE
    notes
    Figure 6, p-nitrophenyl series. No mature-product formation is inferred here.

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

Causal graph — biosynthesis 7 nodes, 4 edges

Partial view of separate culture and complementation observations; connecting mechanistic edges are intentionally omitted because these experiments do not establish one continuous causal chain. Reported S. albus/pMZ02 triple-deficient background, not a native single-gene knockout. Complementation is retained at the reported pyrone class: no exact rescue-product assignment, verified complementation construct, mature-aureothin rescue or exclusion of polar effects. Supplementary material was not read.

SubjectPredicateObjectNotesEvidence
S. albus/pMZ02 without PNBA shows under the reported R2YE conditions No observed polyketide production Context-specific negative observation, not proof of inability in every condition.
DOI:10.1021/ja102751h
  • reference
    DOI:10.1021/ja102751h
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Main-text pyrone-mutant experiments, BioC passage 13.
    snippet
    no polyketide production was observed
S. albus/pMZ02 with PNBA yields in the reported culture Nordeoxyaureothin (5, alpha-pyrone) Precursor-feeding result; not evidence that AurI methylates the alpha tautomer.
DOI:10.1021/ja102751h
  • reference
    DOI:10.1021/ja102751h
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Main-text pyrone-mutant experiments, BioC passage 13.
AurI is the native gene-product reference associated with aurI complementation of the triple mutant Gene-label mapping only; no experimental plasmid sequence, tag or vector inferred.
https://www.uniprot.org/uniprotkb/Q70KH3/entry
DOI:10.1021/ja102751h
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH3/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Native aurI gene name and AJ575648/CAE02607.1 cross-reference.
  • reference
    DOI:10.1021/ja102751h
    evidence type
    CURATOR_INFERENCE
    notes
    Main text names aurI complementation, BioC passage 14.
aurI complementation of the triple mutant restores the reported Methylated gamma-pyrone formation Rescue sentence does not identify a unique complemented analogue.
DOI:10.1021/ja102751h
  • reference
    DOI:10.1021/ja102751h
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Main-text pyrone-mutant experiments, BioC passage 14.
    snippet
    restored the formation

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

Causal graph — biosynthesis 4 nodes, 3 edges

Native AurH reference and database-assigned aureothin maturation. Q70KH6 is not an experimentally verified plasmid sequence. The reviewed database assigns sequential hydroxylation and ring closure; this graph is not a newly inspected purified-enzyme assay. The precursor remains chemically ungrounded. No pMZ04 rescue claim is used.

SubjectPredicateObjectNotesEvidence
aurH (AJ575648.1:13938-15158) encodes the native reference protein AurH Native Streptomyces thioluteus reference; not a host or construct accession.
https://www.ncbi.nlm.nih.gov/nuccore/AJ575648.1
https://www.uniprot.org/uniprotkb/Q70KH6/entry
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AJ575648.1
    evidence type
    DATABASE_ASSERTION
    notes
    AJ575648.1 CDS 13938..15158, forward strand, ATG start; GenPept CAE02604.1, 406 amino acids.
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH6/entry
    evidence type
    CURATOR_INFERENCE
    notes
    Full CDS translation equals the deposited translation, independent CAE02604.1 protein and reviewed Q70KH6 sequence. UniProt entry version 98, sequence version 1, retrieved 2026-10-07.
Deoxyaureothin (luteothin) is the maturation substrate assigned to AurH Overall substrate assignment; not an experimental substrate-affinity measurement.
https://www.uniprot.org/uniprotkb/Q70KH6/entry
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH6/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Reviewed function and RHEA:58824 assign luteothin/deoxyaureothin as substrate. Older full primary papers were not newly read.
AurH is assigned the oxidative ring formation yielding aureothin Database annotation describes a (7R)-7-hydroxydeoxyaureothin intermediate followed by tetrahydrofuran formation. No exact intermediate structure or purified catalytic sufficiency is independently established here.
https://www.uniprot.org/uniprotkb/Q70KH6/entry
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH6/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Reviewed function and physiological RHEA:58825 name mature aureothin and explicitly cross-reference CHEBI:80024. This is not the unmethylated C21 reaction model in MITE0000190.

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

Causal graph — biosynthesis 6 nodes, 5 edges

Partial, derivative-specific whole-cell observations, not measurements on the mature aureothin owner or purified AurH kinetics. The native protein reference is associated by gene name, not by a verified construct sequence. Reported outcomes apply to the tested panel, not every alpha- or gamma-pyrone. Supplementary material was not read; no pMZ04 rescue or NorH grounding is used.

SubjectPredicateObjectNotesEvidence
AurH is the native gene-product reference associated with Reported S. lividans/pHJ110 analogue panel Protein-reference mapping only; no experimental plasmid sequence or tag inferred.
https://www.uniprot.org/uniprotkb/Q70KH6/entry
DOI:10.1021/ja102751h
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH6/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Native aurH gene name and AJ575648/CAE02604.1 cross-reference.
  • reference
    DOI:10.1021/ja102751h
    evidence type
    CURATOR_INFERENCE
    notes
    Main-text AurH biotransformation experiments, BioC passage 17; gene-label mapping, not experimental construct sequence verification.
Reported S. lividans/pHJ110 analogue panel shows the reported Formation of THF analogues 21-26 Passage 17 assigns deoxyaureonitrile 7, halogenated derivatives 8-11 and naphthoate 15 to corresponding products 21-26. HPLC-MS monitoring reported substrate disappearance; no rates, yields or universal specificity are inferred. Passage 22 characterizes new compounds, not every product anew.
DOI:10.1021/ja102751h
  • reference
    DOI:10.1021/ja102751h
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Main-text biotransformations, BioC passage 17; Figure 7 context.
    snippet
    complete disappearance of the starting material
AurH is the native gene-product reference associated with Reported alpha-pyrone 17 biotransformation Passage 17 names AurH; the exact host of this individual alpha-pyrone assay is not separately assigned beyond the reported whole-cell context.
https://www.uniprot.org/uniprotkb/Q70KH6/entry
DOI:10.1021/ja102751h
  • reference
    https://www.uniprot.org/uniprotkb/Q70KH6/entry
    evidence type
    DATABASE_ASSERTION
    notes
    Native aurH gene name and AJ575648/CAE02604.1 cross-reference.
  • reference
    DOI:10.1021/ja102751h
    evidence type
    CURATOR_INFERENCE
    notes
    Main-text AurH biotransformation experiments, BioC passage 17; gene-label mapping, not experimental construct sequence verification.
Reported alpha-pyrone 17 biotransformation produces the reported 7-Hydroxylated alpha-pyrone 20 Paper-relative compound identity remains ungrounded; not mature aureothin.
DOI:10.1021/ja102751h
  • reference
    DOI:10.1021/ja102751h
    evidence type
    PRIMARY_EXPERIMENT
    notes
    BioC passage 17 reports alpha-pyrone 17 to 7-hydroxy derivative 20; Figure 7 depicts the retained alpha-pyrone.
Reported alpha-pyrone 17 biotransformation shows the reported No observed alpha-pyrone heterocyclization Context-specific negative outcome for the tested substrate, not a universal proof of inactivity for all alpha-pyrones.
DOI:10.1021/ja102751h
  • reference
    DOI:10.1021/ja102751h
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Main-text biotransformations, BioC passage 17.
    snippet
    no heterocycle formation was observed

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

Elsewhere in the fleet

Explore across X-Mech

AntibioticMech (aureothin) ↗ MediaIngredientMech (CHEBI:80024) ↗ TaxonMech: Streptomyces thioluteus (NCBITaxon:66431) ↗ PathwayMech (mibig:BGC0000024) ↗

Provenance

Source conceptSourceVersion
BGC0000024MIBIG5
CHEBI:80024CHEBI3-star

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