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
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 |
|---|---|---|
| Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. | 1998 Oct |
|
| Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
|
| Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. | 2001 May |
|
| Stimulation of alkaline phosphatase activity in Ishikawa cells induced by various phytoestrogens and synthetic estrogens. | 2002 Dec |
|
| Interaction of estrogen mimics, singly and in combination, with plasma sex steroid-binding proteins in rainbow trout (Oncorhynchus mykiss). | 2002 Feb |
|
| Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals. | 2002 Jan 15 |
|
| Estrogen mimics bind with similar affinity and specificity to the hepatic estrogen receptor in Atlantic salmon (Salmo salar) and rainbow trout (Oncorhynchus mykiss). | 2002 Mar |
|
| Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata. | 2003 Jun |
|
| Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals. | 2003 Mar |
|
| Induction of vitellogenin synthesis in an Atlantic salmon (Salmo salar) hepatocyte culture: a sensitive in vitro bioassay for the oestrogenic and anti-oestrogenic activity of chemicals. | 2003 Sep-Oct |
|
| Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. | 2004 Jan 9 |
|
| Molecular cloning of a novel type of rat cytoplasmic 17beta-hydroxysteroid dehydrogenase distinct from the type 5 isozyme. | 2006 Jun |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Estrogenic effects in the immature rat uterus after dietary exposure to ethinylestradiol and zearalenone using a systems biology approach. | 2007 Sep |
|
| Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. | 2009 Apr 1 |
|
| Fusarial toxin-induced toxicity in cultured cells and in isolated mitochondria involves PTPC-dependent activation of the mitochondrial pathway of apoptosis. | 2009 Aug |
|
| 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 |
|
| Induction of cells differentiation and ABC transporters expression by a myco-estrogen, zearalenone, in human choriocarcinoma cell line (BeWo). | 2009 Sep 19 |
|
| Aromatic hydroxylation and catechol formation: a novel metabolic pathway of the growth promotor zeranol. | 2010 Feb 15 |
|
| Endocrine disrupting effects of zearalenone, alpha- and beta-zearalenol at the level of nuclear receptor binding and steroidogenesis. | 2011 Oct 10 |
|
| Differential estrogenic actions of endocrine-disrupting chemicals bisphenol A, bisphenol AF, and zearalenone through estrogen receptor α and β in vitro. | 2012 Jul |
|
| Zearalenone exposure modulates the expression of ABC transporters and nuclear receptors in pregnant rats and fetal liver. | 2012 Jun 20 |
|
| 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 Oct 2 |
|
| Effects of zearalenone on oxidative stress and inflammation in weanling piglets. | 2013 Aug |
|
| Neonatal exposure to zearalenone induces long term modulation of ABC transporter expression in testis. | 2013 Aug 9 |
|
| Individual and combined effects of Fusarium toxins on the mRNA expression of pro-inflammatory cytokines in swine jejunal epithelial cells. | 2013 Jul 18 |
|
| Effect of zearalenone on reproductive parameters and expression of selected testicular genes in mice. | 2014 Jun |
|
| 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 May |
|
| Lycopene protects against acute zearalenone-induced oxidative, endocrine, inflammatory and reproductive damages in male mice. | 2015 Mar 25 |
Sample Use Guides
Rats: 0. 2 mg, 1 mg, or 2 mg daily for 3 consecutive days, sc injections
Route of Administration:
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5281576
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DTXSID0021460
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m11584
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ZEARALENONE
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241-864-0
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ACTIVE MOIETY
METABOLITE (PARENT)
