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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
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
Effects of zearalenone on mRNA expression and activity of cytochrome P450 1A1 and 1B1 in MCF-7 cells.
2004 Jun
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
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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:12:10 UTC 2023
Record UNII
5W827M159J
Record Status Validated (UNII)
Record Version
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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 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID0021460
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
MERCK INDEX
m11584
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
ZEARALENONE
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
MESH
D015025
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
CHEBI
10106
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
HSDB
4208
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
CAS
17924-92-4
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
FDA UNII
5W827M159J
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
241-864-0
Created by admin on Fri Dec 15 15:12:10 UTC 2023 , Edited by admin on Fri Dec 15 15:12:10 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY