U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ZEARALENONE

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

HIDE SMILES / InChI

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

Description
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.

CNS Activity

Curator's Comment: In rat, zearalenone is carried into the brain through the blood-brain barrier and binds with the estrogen receptors of both the hypothalamus and hypophysis

Approval Year

TargetsConditions

Conditions

PubMed

PubMed

TitleDatePubMed
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
Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata.
2003 Jun
Effects of zearalenone on mRNA expression and activity of cytochrome P450 1A1 and 1B1 in MCF-7 cells.
2004 Jun
[Study on the transcriptional modulation of cytochrome P450 3A4 expression by zearalenone].
2004 Nov
Binding of xenoestrogens to the sex steroid-binding protein in plasma from Arctic charr (Salvelinus alpinus L.).
2004 Oct
Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells.
2005 Aug
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
Patents

Sample Use Guides

Rats: 0. 2 mg, 1 mg, or 2 mg daily for 3 consecutive days, sc injections
Route of Administration: Other
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
by admin
on Fri Dec 15 15:12:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:10 GMT 2023
Record UNII
5W827M159J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZEARALENONE
HSDB   MI  
Common Name English
COMPD F-2
Code English
MYCOTOXIN F2
Common Name English
ZEARALENONE [MI]
Common Name English
6-(10-HYDROXY-6-OXO-TRANS-1-UNDECENYL) BETA RESORCYCLIC ACID-MU-LACTONE
Common Name English
MYCOTOXIN F-2
Common Name English
ZENONE
Common Name English
FES
Common Name English
1H-2-BENZOXACYCLOTETRADECIN-1,7(8H)-DIONE, 3,4,5,6,9,10-HEXAHYDRO-14,16-DIHYDROXY-3-METHYL-, (3S,11E)-
Systematic Name English
ZEARALENONE [HSDB]
Common Name English
(S)-(-)-ZEARALENONE
Common Name English
Code System Code Type Description
PUBCHEM
5281576
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID0021460
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
MERCK INDEX
m11584
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
ZEARALENONE
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
MESH
D015025
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
CHEBI
10106
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
HSDB
4208
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
CAS
17924-92-4
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
FDA UNII
5W827M159J
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
241-864-0
Created by admin on Fri Dec 15 15:12:10 GMT 2023 , Edited by admin on Fri Dec 15 15:12:10 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY