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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
Structure of .BETA.-ZEARALENOL

SMILES

C[C@H]1CCC[C@@H](O)CCC\C=C\C2=C(C(O)=CC(O)=C2)C(=O)O1

InChI

InChIKey=FPQFYIAXQDXNOR-PMRAARRBSA-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

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27311894 | https://www.ncbi.nlm.nih.gov/pubmed/485136 | https://www.ncbi.nlm.nih.gov/pubmed/26335359 | https://www.ncbi.nlm.nih.gov/pubmed/26308051

β-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in Fusarium spp. β-Zearalenol is the β epimer of α-zearalenol and along with α-zearalenol is a major metabolite of zearalenone formed mainly in the liver but also to a lesser extent in the intestines during the first-pass metabolism. β-Zearalenol is about the same or slightly less potent as an estrogen relative to zearalenone. Contamination of grains by Fusarium species, notably maize, gives rise to high levels of zearalenol and is regarded as an important food quality issue for both human and animal health.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
11.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Synthesis and cytotoxic activities of semisynthetic zearalenone analogues.
2016 Aug 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Cytotoxicity assay against African green monkey kidney fibroblast (Vero) cells was performed in triplicate employing the colorimetric method. Cells were grown in culture flasks or, for experiments, multiwell plates (TPP, Winiger, Wohlen, Switzerland) in DMEM/F12 1:1 medium (Life Technologies, Basel, Swit-zerland) supplemented with 5% fetal calf serum (FCS) (Sera-Tech) and incubated at 37°C in a humidified 5% CO2 atmosphere. Twice a week, cells were detached by treat-ment with trypsin-EDTA (Life Technologies), counted, and subcultured at ratios between 1:5 and 1:20. Cell samples were counted in duplicate and viability was determined using the trypan blue exclusion method.
Name Type Language
.BETA.-ZEARALENOL
Common Name English
(3R,7R,11E)-7,14,16-TRIHYDROXY-3-METHYL-3,4,5,6,7,8,9,10-OCTAHYDRO-1H-2-BENZOXACYCLOTETRADECIN-1-ONE
Systematic Name English
(-)-.BETA.-ZEARALENOL
Common Name English
1H-2-BENZOXACYCLOTETRADECIN-1-ONE, 3,4,5,6,7,8,9,10-OCTAHYDRO-7,14,16-TRIHYDROXY-3-METHYL-, (3R,7R,11E)-
Systematic Name English
.BETA.-TRANS-ZEARALENOL
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID8022533
Created by admin on Sat Dec 16 00:26:34 GMT 2023 , Edited by admin on Sat Dec 16 00:26:34 GMT 2023
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WIKIPEDIA
beta-Zearalenol
Created by admin on Sat Dec 16 00:26:34 GMT 2023 , Edited by admin on Sat Dec 16 00:26:34 GMT 2023
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CAS
71030-11-0
Created by admin on Sat Dec 16 00:26:34 GMT 2023 , Edited by admin on Sat Dec 16 00:26:34 GMT 2023
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FDA UNII
35E809PP7O
Created by admin on Sat Dec 16 00:26:34 GMT 2023 , Edited by admin on Sat Dec 16 00:26:34 GMT 2023
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PUBCHEM
6437352
Created by admin on Sat Dec 16 00:26:34 GMT 2023 , Edited by admin on Sat Dec 16 00:26:34 GMT 2023
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