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CHEBI:74926 - patulin

Default Structure
ChEBI IDCHEBI:74926
ChEBI Namepatulin
Stars
DefinitionA 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.
Last Modified21 January 2022
SubmitterGareth Owen
DownloadsMolfile
FormulaC7H6O4
Net Charge0
Average Mass154.121
Monoisotopic Mass154.02661
SMILESO=C1C=C2C(=CCOC2O)O1
InChIInChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
InChIKeyZRWPUFFVAOMMNM-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
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.
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.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
ChEBI Ontology
Outgoing Relation(s)
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 furopyran (CHEBI:74927)
patulin (CHEBI:74926) is a lactol (CHEBI:38131)
patulin (CHEBI:74926) is a γ-lactone (CHEBI:37581)
Incoming Relation(s)
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  Source
(2,4-dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactoneChemIDplus
(2,4-dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid-3,4-lactoneChemIDplus
4,6-dihydro-4-hydroxy-2H-furo(3,2-c)pyran-2-oneChemIDplus
clavacinChemIDplus
clavatinChemIDplus
claviformChemIDplus
UniProt Name  Source
patulinUniProt
Manual XrefsDatabases
C00024000KNApSAcK
C16748KEGG COMPOUND
HMDB0034299HMDB
PatulinWikipedia
US2417584Patent
Registry NumbersSources
Reaxys:149675Reaxys
CAS:149-29-1ChemIDplus
CAS:149-29-1KEGG COMPOUND
Citations