patulin (CHEBI:74926)

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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 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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C7H6O4

Net Charge

Average Mass

154.12010

Monoisotopic Mass

154.02661

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 .

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)

Incoming	patulin‒4-bromothiophenol adduct (CHEBI:189530) has functional parent patulin (CHEBI:74926) patulin‒4-bromothiophenol hapten (CHEBI:189533) has functional parent patulin (CHEBI:74926)

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
patulin	UniProt
patuline	ChemIDplus

Last Modified

21 January 2022