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CHEBI:10106 - zearalenone

ChEBI IDCHEBI:10106
ChEBI Namezearalenone
Stars
DefinitionA macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.
Last Modified18 March 2024
DownloadsMolfile
FormulaC18H22O5
Net Charge0
Average Mass318.369
Monoisotopic Mass318.14672
SMILESC[C@H]1CCCC(=O)CCC/C=C/c2cc(O)cc(O)c2C(=O)O1
InChIInChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+/t12-/m0/s1
InChIKeyMBMQEIFVQACCCH-QBODLPLBSA-N
Roles Classification
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
mycoestrogen  Any compound produced by a fungus that happens to have estrogenic activity.
ChEBI Ontology
Outgoing Relation(s)
zearalenone (CHEBI:10106) has role fungal metabolite (CHEBI:76946)
zearalenone (CHEBI:10106) has role mycoestrogen (CHEBI:76990)
zearalenone (CHEBI:10106) is a macrolide (CHEBI:25106)
zearalenone (CHEBI:10106) is a resorcinols (CHEBI:33572)
Incoming Relation(s)
(S,E)-2,4-dihydroxy-6-(10-hydroxy-6-oxoundec-1-en-1-yl)benzoate (CHEBI:229751) has functional parent zearalenone (CHEBI:10106)
zearalenone hapten ZEo (CHEBI:191182) has functional parent zearalenone (CHEBI:10106)
zearalenone hapten ZEp (CHEBI:191183) has functional parent zearalenone (CHEBI:10106)
IUPAC Name 
(3S,11E)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
Synonyms  Source
(S)-ZearalenoneChemIDplus
(-)-ZearalenoneChemIDplus
trans-ZearalenoneChemIDplus
(10S)-ZearalenoneChemIDplus
6-(10-Hydroxy-6-oxo-trans-1-undecenyl)-beta-resorcylic acid lactoneChemIDplus
(S)-(-)-ZearalenoneChemIDplus
UniProt Name  Source
zearalenoneUniProt
Manual XrefsDatabases
C09981KEGG COMPOUND
LMPK04000016LIPID MAPS
C00003025KNApSAcK
Registry NumbersSources
Reaxys:4875541Reaxys
CAS:17924-92-4KEGG COMPOUND
CAS:17924-92-4ChemIDplus
Citations