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 |
|
Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
|
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 |
|
Mycotoxins in root extracts of American and Asian ginseng bind estrogen receptors alpha and beta. | 2004 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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The unusual binding properties of the third distinct teleost estrogen receptor subtype ERbetaa are accompanied by highly conserved amino acid changes in the ligand binding domain. | 2004 Jun |
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Binding and activation of the seven-transmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. | 2006 Dec |
|
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. | 2009 Apr 1 |
|
Comparative mechanisms of zearalenone and ochratoxin A toxicities on cultured HepG2 cells: is oxidative stress a common process? | 2009 Dec |
|
Mycotoxin zearalenone induces AIF- and ROS-mediated cell death through p53- and MAPK-dependent signaling pathways in RAW264.7 macrophages. | 2011 Dec |
|
Effects of zearalenone and its derivatives on porcine immune response. | 2011 Dec |
|
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 |
|
In vitro toxicological effects of estrogenic mycotoxins on human placental cells: structure activity relationships. | 2012 Mar 15 |
|
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 |
|
Hepatotoxic effects of mycotoxin combinations in mice. | 2014 Dec |
|
Zearalenone inhibits testosterone biosynthesis in mouse Leydig cells via the crosstalk of estrogen receptor signaling and orphan nuclear receptor Nur77 expression. | 2014 Jun |
|
Effect of zearalenone on reproductive parameters and expression of selected testicular genes in mice. | 2014 Jun |
|
Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors. | 2014 Oct 1 |
|
The influence of N-acetyl-l-cysteine on damage of porcine oocyte exposed to zearalenone in vitro. | 2015 Dec 1 |
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
on
Edited
Fri Dec 15 15:12:10 UTC 2023
by
admin
on
Fri Dec 15 15:12:10 UTC 2023
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Record UNII |
5W827M159J
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Record Status |
Validated (UNII)
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m11584
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ZEARALENONE
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