Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H22O5 |
| Molecular Weight | 318.3643 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C2C(=O)O1
InChI
InChIKey=MBMQEIFVQACCCH-QBODLPLBSA-N
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
| Molecular Formula | C18H22O5 |
| Molecular Weight | 318.3643 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20002219 https://www.ncbi.nlm.nih.gov/pubmed/27481073
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20002219 https://www.ncbi.nlm.nih.gov/pubmed/27481073
Zearalenone (ZEN) is a toxic non-steroidal mycoestrogen produced by fungi that widely contaminate agricultural products, eliciting estrogenic responses by mimicking sex steroid hormones. Zearalenone is biosynthesised through a polyketide pathway by a variety of Fusarium fungi including Fusarium graminearum (Gibberella zeae), Fusarium culmorum, Fusarium equiseti, Fusarium crookwellense, Fusarium cerealis and Fusarium semitectum. Zearalenone and its derivatives share similar molecular mechanisms and activity with estrogens. They interact with the estrogen receptors (ERa and ERb) leading to functional and morphological changes in the reproductive system in both animals and humans. Zearalenone exposure is associated with the estrogenic syndrome and infertility in animals and premature thelarche and precocious puberty in girls. In animal models, it was found that prepubertal exposure to a low dose of Zearalenone, decreased breast cancer risk. When prepubertal rats were treated with 20 lg (1 mg ⁄ kg body weight) of Zearalenone, a significant reduction of both the incidence and multiplicity of DMBA-induced mammary tumours was noted. Zearalenone has been used to treat postmenopausal symptoms in women.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL242 |
110.0 nM [EC50] | ||
Target ID: CHEMBL3746 |
32.22 µM [IC50] | ||
Target ID: CHEMBL2093866 |
0.87 nM [EC50] | ||
Target ID: CHEMBL206 |
56.0 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The influence of N-acetyl-l-cysteine on damage of porcine oocyte exposed to zearalenone in vitro. | 2015-12-01 |
|
| Lycopene protects against acute zearalenone-induced oxidative, endocrine, inflammatory and reproductive damages in male mice. | 2015-03-25 |
|
| Exposure to zearalenone mycotoxin alters in vitro porcine intestinal epithelial cells by differential gene expression. | 2015-01-05 |
|
| Assessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays. | 2014-12 |
|
| Hepatotoxic effects of mycotoxin combinations in mice. | 2014-12 |
|
| Mitochondrial proteomic analysis reveals the molecular mechanisms underlying reproductive toxicity of zearalenone in MLTC-1 cells. | 2014-10-03 |
|
| Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors. | 2014-10-01 |
|
| Zearalenone inhibits testosterone biosynthesis in mouse Leydig cells via the crosstalk of estrogen receptor signaling and orphan nuclear receptor Nur77 expression. | 2014-06 |
|
| Effect of zearalenone on reproductive parameters and expression of selected testicular genes in mice. | 2014-06 |
|
| Modulation of mucin mRNA (MUC5AC and MUC5B) expression and protein production and secretion in Caco-2/HT29-MTX co-cultures following exposure to individual and combined Fusarium mycotoxins. | 2014-05 |
|
| Zearalenone induces apoptosis and cytoprotective autophagy in primary Leydig cells. | 2014-04-21 |
|
| Zearalenone induced toxicity in SHSY-5Y cells: The role of oxidative stress evidenced by N-acetyl cysteine. | 2014-03 |
|
| Neonatal exposure to zearalenone induces long term modulation of ABC transporter expression in testis. | 2013-08-09 |
|
| Effects of zearalenone on oxidative stress and inflammation in weanling piglets. | 2013-08 |
|
| Individual and combined effects of Fusarium toxins on the mRNA expression of pro-inflammatory cytokines in swine jejunal epithelial cells. | 2013-07-18 |
|
| Postweaning exposure to dietary zearalenone, a mycotoxin, promotes premature onset of puberty and disrupts early pregnancy events in female mice. | 2013-04 |
|
| In silico approach to evaluate molecular interaction between mycotoxins and the estrogen receptors ligand binding domain: a case study on zearalenone and its metabolites. | 2012-10-02 |
|
| Transgenerational toxicity of Zearalenone in pigs. | 2012-08 |
|
| Differential estrogenic actions of endocrine-disrupting chemicals bisphenol A, bisphenol AF, and zearalenone through estrogen receptor α and β in vitro. | 2012-07 |
|
| Zearalenone exposure modulates the expression of ABC transporters and nuclear receptors in pregnant rats and fetal liver. | 2012-06-20 |
|
| In vitro toxicological effects of estrogenic mycotoxins on human placental cells: structure activity relationships. | 2012-03-15 |
|
| In vivo effects of zearalenone on the expression of proteins involved in the detoxification of rat xenobiotics. | 2012-02 |
|
| Mycotoxin zearalenone induces AIF- and ROS-mediated cell death through p53- and MAPK-dependent signaling pathways in RAW264.7 macrophages. | 2011-12 |
|
| Effects of zearalenone and its derivatives on porcine immune response. | 2011-12 |
|
| Endocrine disrupting effects of zearalenone, alpha- and beta-zearalenol at the level of nuclear receptor binding and steroidogenesis. | 2011-10-10 |
|
| An In Vitro Cell Based Model for Assessing the Potential of Allergens to Release Mediators Through the Cross-linking of IgE. | 2010-07-27 |
|
| Aromatic hydroxylation and catechol formation: a novel metabolic pathway of the growth promotor zeranol. | 2010-02-15 |
|
| Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. | 2010-02-15 |
|
| Estrogenic in vitro assay on mouse embryonic Leydig cells. | 2010 |
|
| Comparative mechanisms of zearalenone and ochratoxin A toxicities on cultured HepG2 cells: is oxidative stress a common process? | 2009-12 |
|
| ABCC1, ABCC2 and ABCC3 are implicated in the transepithelial transport of the myco-estrogen zearalenone and its major metabolites. | 2009-10-28 |
|
| Induction of cells differentiation and ABC transporters expression by a myco-estrogen, zearalenone, in human choriocarcinoma cell line (BeWo). | 2009-09-19 |
|
| Comparative study of toxic effects of zearalenone and its two major metabolites alpha-zearalenol and beta-zearalenol on cultured human Caco-2 cells. | 2009-08-26 |
|
| Fusarial toxin-induced toxicity in cultured cells and in isolated mitochondria involves PTPC-dependent activation of the mitochondrial pathway of apoptosis. | 2009-08 |
|
| Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry. | 2009-06 |
|
| Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. | 2009-04-01 |
|
| Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress. | 2009-03-16 |
|
| Effects of Fusarium mycotoxins on steroid production by porcine granulosa cells. | 2008-08 |
|
| Effects of cyclopenta[c]phenanthrene and its derivatives on zona radiata protein, ERalpha, and CYP1A mRNA expression in liver of rainbow trout (Oncorhynchus mykiss Walbaum). | 2008-07-10 |
|
| Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008-04 |
|
| The combination of deoxynivalenol and zearalenone at permitted feed concentrations causes serious physiological effects in young pigs. | 2008-03 |
|
| Estrogenic effects in the immature rat uterus after dietary exposure to ethinylestradiol and zearalenone using a systems biology approach. | 2007-09 |
|
| Binding and activation of the seven-transmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. | 2006-12 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase. | 2006-10-01 |
|
| Toll-like receptor priming sensitizes macrophages to proinflammatory cytokine gene induction by deoxynivalenol and other toxicants. | 2006-08 |
|
| Molecular cloning of a novel type of rat cytoplasmic 17beta-hydroxysteroid dehydrogenase distinct from the type 5 isozyme. | 2006-06 |
|
| Estrogens modulate the gene expression of Wnt-7a in cultured endometrial adenocarcinoma cells. | 2006-04 |
|
| Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells. | 2005-08 |
|
| Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. | 1998-10 |
Sample Use Guides
Rats: 0. 2 mg, 1 mg, or 2 mg daily for 3 consecutive days, sc injections
Route of Administration:
Other
| Substance Class |
Chemical
Created
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admin
on
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Mon Mar 31 17:50:00 GMT 2025
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on
Mon Mar 31 17:50:00 GMT 2025
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| Record UNII |
5W827M159J
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| Record Status |
Validated (UNII)
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ZEARALENONE
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