CHEBI:74926 - patulin

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ChEBI Name patulin
ChEBI ID CHEBI:74926
Definition A furopyran and lactone that is 2H-pyran-3(6H)-ylidene)acetic acid which is syubstituted 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C7H6O4
Net Charge 0
Average Mass 154.12010
Monoisotopic Mass 154.027
InChI InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
InChIKey ZRWPUFFVAOMMNM-UHFFFAOYSA-N
SMILES OC1OCC=C2OC(=O)C=C12
Roles Classification
Biological Role(s): Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
mycotoxin
Poisonous substance produced by fungi.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
View more via ChEBI Ontology
ChEBI Ontology
Outgoing patulin (CHEBI:74926) has role Aspergillus metabolite (CHEBI:76956)
patulin (CHEBI:74926) has role Penicillium metabolite (CHEBI:76964)
patulin (CHEBI:74926) has role antimicrobial agent (CHEBI:33281)
patulin (CHEBI:74926) has role carcinogenic agent (CHEBI:50903)
patulin (CHEBI:74926) has role mutagen (CHEBI:25435)
patulin (CHEBI:74926) has role mycotoxin (CHEBI:25442)
patulin (CHEBI:74926) is a γ-lactone (CHEBI:37581)
patulin (CHEBI:74926) is a furopyran (CHEBI:74927)
patulin (CHEBI:74926) is a lactol (CHEBI:38131)
IUPAC Name
4-hydroxy-4H-furo[3,2-c]pyran-2(6H)-one
Synonyms Sources
(2,4-dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone ChemIDplus
(2,4-dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactone ChemIDplus
4,6-dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-one ChemIDplus
clavacin ChemIDplus
clavatin ChemIDplus
claviform ChemIDplus
claviformin ChemIDplus
expansin ChemIDplus
expansine ChemIDplus
mycoin C3 ChemIDplus
mycoine C3 ChemIDplus
PAT ChEBI
patuline ChemIDplus
Manual Xrefs Databases
C00024000 KNApSAcK
C16748 KEGG COMPOUND
HMDB0034299 HMDB
Patulin Wikipedia
US2417584 Patent
View more database links
Registry Numbers Types Sources
149-29-1 CAS Registry Number KEGG COMPOUND
149-29-1 CAS Registry Number ChemIDplus
149675 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21656641 PubMed citation Europe PMC
22410236 PubMed citation Europe PMC
22988003 PubMed citation Europe PMC
23192667 PubMed citation Europe PMC
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23729413 PubMed citation Europe PMC
23813870 PubMed citation Europe PMC
23870868 PubMed citation Europe PMC
Last Modified
01 October 2014