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
3D model of Zearalenone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
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
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
Admin
Created at
-
Updated at
3rd Apr 2025