patulin
CHEBI:74926 EXACT SEEDED antimicrobial unspecified
A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.
Structure
| Standard InChIKey | ZRWPUFFVAOMMNM-UHFFFAOYSA-N |
|---|---|
| SMILES | C1C=C2C(=CC(=O)O2)C(O1)O |
| Stereochemistry | undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers |
Filing pathway
Polyketides — 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 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 |
|---|---|---|---|
| Penicillium expansum NCBITaxon:27334 |
BGC_CHARACTERIZED | mibig:BGC0000120 | PMID:25120234 |
Occurrences 25
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 |
|---|---|---|
| Alternaria tenuissima NCBITaxon:119927 |
LOTUS | DOI:10.1021/JF00034A040 |
| Talaromyces diversus NCBITaxon:128434 |
LOTUS | DOI:10.1021/JF00034A040 |
| Talaromyces funiculosus NCBITaxon:128442 |
LOTUS | DOI:10.1021/JF00034A040 |
| Trichoderma virens NCBITaxon:1331945 |
LOTUS | DOI:10.1021/JF00034A040 |
| Heterobasidion annosum NCBITaxon:13563 |
LOTUS | DOI:10.1021/JF00034A040 |
| Aspergillus petrakii NCBITaxon:138280 |
LOTUS | DOI:10.1021/JF00034A040 |
| Thelonectria olida NCBITaxon:1576542 |
LOTUS | DOI:10.1021/JF00034A040 |
| Scopulariopsis flava NCBITaxon:186360 |
LOTUS | DOI:10.1021/JF00034A040 |
| Aspergillus cejpii NCBITaxon:1884262 |
LOTUS | DOI:10.1021/JF00034A040 |
| Corynascus sepedonium NCBITaxon:190048 |
LOTUS | DOI:10.1021/JF00034A040 |
| Amesia atrobrunnea NCBITaxon:1934350 |
LOTUS | DOI:10.1021/JF00034A040 |
| Cladorrhinum NCBITaxon:223374 |
LOTUS | DOI:10.1021/JF00034A040 |
| Calcarisporium arbuscula NCBITaxon:240499 |
LOTUS | DOI:10.1021/JF00034A040 |
| Acremonium sclerotigenum NCBITaxon:261921 |
LOTUS | DOI:10.1021/JF00034A040 |
| Ageratina calophylla NCBITaxon:2773065 |
LOTUS | DOI:10.1016/S0031-9422(00)84545-8 |
| Talaromyces trachyspermus NCBITaxon:28566 |
LOTUS | DOI:10.1021/JF00034A040 |
| Penicillium javanicum NCBITaxon:28578 |
LOTUS | DOI:10.1021/JF00034A040 |
| Talaromyces duclauxii NCBITaxon:29842 |
LOTUS | DOI:10.1021/JF00034A040 |
| Penicillium urticae NCBITaxon:29844 |
LOTUS | DOI:10.1128/AEM.45.6.1939-1942.1983 |
| Penicillium urticae NCBITaxon:29844 |
LOTUS | DOI:10.1139/M86-051 |
| Cylindrocarpon ianthothele NCBITaxon:303672 |
LOTUS | DOI:10.1021/JF00034A040 |
| Drechslera NCBITaxon:33198 |
LOTUS | DOI:10.1021/JF00034A040 |
| Purpureocillium lilacinum NCBITaxon:33203 |
LOTUS | DOI:10.1021/JF00034A040 |
| Penicillium hirsutum NCBITaxon:36648 |
LOTUS | DOI:10.1021/JF00034A040 |
| Penicillium aurantiogriseum NCBITaxon:36655 |
LOTUS | DOI:10.1021/JF00034A040 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000120 | Penicillium expansum NCBITaxon:27334 |
CLUSTER_DEMONSTRATED | genbank:KF899892.1 |
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.
Elsewhere in the fleet
- AntibioticMech — CHEBI:74926 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000120 | MIBIG | 5 |
| CHEBI:74926 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/patulin.yaml, which is generated from the committed inventories. Neither is edited by hand.