Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H24O5 |
| Molecular Weight | 320.3802 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1CCC[C@H](O)CCC\C=C\C2=C(C(O)=CC(O)=C2)C(=O)O1
InChI
InChIKey=FPQFYIAXQDXNOR-QDKLYSGJSA-N
InChI=1S/C18H24O5/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/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14+/m0/s1
| Molecular Formula | C18H24O5 |
| Molecular Weight | 320.3802 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| 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/21889607
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21889607
Zearalenone (ZEN) is a well-known mycotoxin present in numerous agricultural products. Humans and animals are therefore at a risk of exposure to zearalenone through consumption of contaminated food. After intake, ZEN is reduced to α- and β-zearalenol (α-ZEL and β-ZEL), zearalanone (ZAN), and α- and β-zearalanol (α-ZAL and β-ZAL). Zearalenone and its metabolites, including Alpha-zearalenol are full agonists for hERα and possess hAR-mediated antagonistic activity in PALM cells. Zearalenone and its derivatives have been shown to be carcinogenic, immunotoxic, and hepatonephrotoxic.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2930 |
0.06 nM [EC50] | ||
Target ID: CHEMBL1871 |
4.17 µM [IC50] | ||
Target ID: CHEMBL612557 |
|||
Target ID: P05106 Gene ID: 3690.0 Gene Symbol: ITGB3 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
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| Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. | 2001 May |
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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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| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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| Effects of environmental estrogenic chemicals on AP1 mediated transcription with estrogen receptors alpha and beta. | 2004 Jan |
|
| Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. | 2004 Jul |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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| ABCC1, ABCC2 and ABCC3 are implicated in the transepithelial transport of the myco-estrogen zearalenone and its major metabolites. | 2009 Oct 28 |
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| Aromatic hydroxylation and catechol formation: a novel metabolic pathway of the growth promotor zeranol. | 2010 Feb 15 |
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| In vitro toxicological effects of estrogenic mycotoxins on human placental cells: structure activity relationships. | 2012 Mar 15 |
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| Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. | 2012 Nov 19 |
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| Cellular mechanisms of the cytotoxic effects of the zearalenone metabolites α-zearalenol and β-zearalenol on RAW264.7 macrophages. | 2013 Apr |
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| Assessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays. | 2014 Dec |
|
| Affinity purification using recombinant PXR as a tool to characterize environmental ligands. | 2014 Feb |
|
| Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors. | 2014 Oct 1 |
|
| Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. | 2015 Feb |
|
| Activation of ER stress and apoptosis by α- and β-zearalenol in HCT116 cells, protective role of Quercetin. | 2016 Mar |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:50:58 GMT 2023
by
admin
on
Fri Dec 15 18:50:58 GMT 2023
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| Record UNII |
59D4EVJ5KC
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| Record Status |
Validated (UNII)
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| Record Version |
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5916-52-9
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NON-SPECIFIC STOICHIOMETRY | |||
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5284645
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DTXSID8022402
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alpha-Zearalenol
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C029659
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36455-72-8
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59D4EVJ5KC
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admin on Fri Dec 15 18:50:58 GMT 2023 , Edited by admin on Fri Dec 15 18:50:58 GMT 2023
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