CHEBI:10106 - zearalenone

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ChEBI Name zearalenone
ChEBI ID CHEBI:10106
Definition A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H22O5
Net Charge 0
Average Mass 318.36430
Monoisotopic Mass 318.14672
InChI InChI=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
InChIKey MBMQEIFVQACCCH-QBODLPLBSA-N
SMILES C[C@H]1CCCC(=O)CCC\C=C\c2cc(O)cc(O)c2C(=O)O1
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 (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 Sources
(-)-Zearalenone ChemIDplus
(10S)-Zearalenone ChemIDplus
(S)-(-)-Zearalenone ChemIDplus
(S)-Zearalenone ChemIDplus
(S-(E))-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione ChemIDplus
6-(10-Hydroxy-6-oxo-trans-1-undecenyl)-beta-resorcylic acid lactone ChemIDplus
trans-Zearalenone ChemIDplus
zearalenone UniProt
Manual Xrefs Databases
C00003025 KNApSAcK
C09981 KEGG COMPOUND
LMPK04000016 LIPID MAPS
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Registry Numbers Types Sources
17924-92-4 CAS Registry Number ChemIDplus
4875541 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17339071 PubMed citation Europe PMC
18027362 PubMed citation Europe PMC
18221829 PubMed citation Europe PMC
18280460 PubMed citation Europe PMC
18692541 PubMed citation Europe PMC
20654554 PubMed citation Europe PMC
38449531 PubMed citation Europe PMC
IND608145868 Agricola citation Europe PMC
Last Modified
18 March 2024