Structure Database (LMSD)

Common Name
Zearalenone
Systematic Name
(3S,11E)-14,16-Dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
Synonyms
  • Mycotoxin F2
LM ID
LMPK04000016
Formula
Exact Mass
Calculate m/z
318.146725
Status
Curated

Classification

Biological Context

Zearalenone is a mycotoxin that has been found in Fusarium and has estrogenic activities.1 It binds to human estrogen receptor α (ERα) and ERβ (IC50s = 9 and 5.8 nM, respectively).2 Zearalenone induces precocious development of mammary tissues in young female pigs and prepucial enlargement in young male pigs.3 Zearalenone (1.5-5 mg/kg of diet) induces hyperestrogenism in pigs. It also induces degeneration of meiotic chromatin in oocytes and reduces fertility in pigs when administered at a dose of 200 µg/kg.4 Zearalenone has been found as a contaminant in wheat, maize, and barley and livestock feeds.3,4

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Fusarium graminearum (#5518)
Sordariomycetes (#147550)
The structure of zearalenone,
Tetrahedron Letts, 1966
Fusarium graminearum (#5518)
Sordariomycetes (#147550)
Total synthesis of the macrolide, zearalenone.,
Tetrahedron, 1968
Pubmed ID: 5641272

String Representations

InChiKey (Click to copy)
MBMQEIFVQACCCH-QBODLPLBSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C12C=CCCCC(CCC[C@H](C)OC(=O)C1=C(O)C=C(O)C=2)=O

Other Databases

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 2
Aromatic Rings 1
Rotatable Bonds 0
Van der Waals Molecular Volume 312.45
Topological Polar Surface Area 85.90
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 3.87
Molar Refractivity 86.90

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Created at
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Updated at
3rd Apr 2025