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=C(C(O)=CC(O)=C2)C(=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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12828470 |
110.0 nM [EC50] | ||
Target ID: CHEMBL3746 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26798634 |
32.22 µM [IC50] | ||
Target ID: CHEMBL2093866 |
0.87 nM [EC50] | ||
Target ID: CHEMBL206 Sources: http://www.abcam.com/zearalenone-zea-ab142473.html |
56.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. | 1998 Oct |
|
Stimulation of alkaline phosphatase activity in Ishikawa cells induced by various phytoestrogens and synthetic estrogens. | 2002 Dec |
|
Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals. | 2002 Jan 15 |
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Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata. | 2003 Jun |
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Effects of zearalenone on mRNA expression and activity of cytochrome P450 1A1 and 1B1 in MCF-7 cells. | 2004 Jun |
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[Study on the transcriptional modulation of cytochrome P450 3A4 expression by zearalenone]. | 2004 Nov |
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Binding of xenoestrogens to the sex steroid-binding protein in plasma from Arctic charr (Salvelinus alpinus L.). | 2004 Oct |
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Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells. | 2005 Aug |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
The combination of deoxynivalenol and zearalenone at permitted feed concentrations causes serious physiological effects in young pigs. | 2008 Mar |
|
Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. | 2009 Apr 1 |
|
Comparative study of toxic effects of zearalenone and its two major metabolites alpha-zearalenol and beta-zearalenol on cultured human Caco-2 cells. | 2009 Jul-Aug |
|
Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry. | 2009 Jun |
|
Aromatic hydroxylation and catechol formation: a novel metabolic pathway of the growth promotor zeranol. | 2010 Feb 15 |
|
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. | 2010 Feb 15 |
|
Endocrine disrupting effects of zearalenone, alpha- and beta-zearalenol at the level of nuclear receptor binding and steroidogenesis. | 2011 Oct 10 |
|
Transgenerational toxicity of Zearalenone in pigs. | 2012 Aug |
|
In vivo effects of zearalenone on the expression of proteins involved in the detoxification of rat xenobiotics. | 2012 Feb |
|
Zearalenone exposure modulates the expression of ABC transporters and nuclear receptors in pregnant rats and fetal liver. | 2012 Jun 20 |
|
Individual and combined effects of Fusarium toxins on the mRNA expression of pro-inflammatory cytokines in swine jejunal epithelial cells. | 2013 Jul 18 |
|
Zearalenone induces apoptosis and cytoprotective autophagy in primary Leydig cells. | 2014 Apr 21 |
|
Hepatotoxic effects of mycotoxin combinations in mice. | 2014 Dec |
|
The influence of N-acetyl-l-cysteine on damage of porcine oocyte exposed to zearalenone in vitro. | 2015 Dec 1 |
|
Exposure to zearalenone mycotoxin alters in vitro porcine intestinal epithelial cells by differential gene expression. | 2015 Jan 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15664021
Rats: 0. 2 mg, 1 mg, or 2 mg daily for 3 consecutive days, sc injections
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21803136
In the H295R cells, cytotoxicity was observed in cells treated
with 100 uM concentration of Zearalenone. Zearalenone increased production of progesterone, estradiol, testosterone and cortisol hormones in the H295R steroidogenesis assay, with peak productions at 10 uM.
Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 15 15:12:10 GMT 2023
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Record UNII |
5W827M159J
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Record Status |
Validated (UNII)
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ZEARALENONE
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ACTIVE MOIETY |