beta-Zearalenol (CHEM003013)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-08-29 04:58:51 UTC
Update Date2026-04-06 17:12:08 UTC
Accession NumberCHEM003013
Identification
Common Namebeta-Zearalenol
ClassSmall Molecule
DescriptionBeta-zearalenol belongs to the family of Macrolides and Analogues. These are organic compounds containing a lactone ring of at least twelve members. The term 'macrolide' encompasses a diverse family of unrelated compounds with large macrolactam rings.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Fungal Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
beta-trans-ZearalenolKegg
b-trans-ZearalenolGenerator
Β-trans-zearalenolGenerator
b-ZearalenolGenerator
Β-zearalenolGenerator
alpha-Zearalenol, (cis)-isomerMeSH
(3R,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-oneMeSH
ZearalenolMeSH
3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-oneMeSH
alpha-ZearalenolMeSH
(-)-beta-ZearalenolMeSH
beta-ZearalenolMeSH
Chemical FormulaC18H24O5
Average Molecular Mass320.385 g/mol
Monoisotopic Mass320.162 g/mol
CAS Registry Number71030-11-0
IUPAC Name(3S,7S)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one
Traditional Nameβ-zearalenol
SMILES[H]\C1=C([H])/C2=CC(O)=CC(O)=C2C(=O)O[C@@]([H])(C)CCC[C@@]([H])(O)CCC1
InChI IdentifierInChI=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
InChI KeyFPQFYIAXQDXNOR-PMRAARRBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Dihydroxybenzoic acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP3.27ALOGPS
logP4.17ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.54ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.37 m³·mol⁻¹ChemAxon
Polarizability34.48 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0019000000-4e38670336b2fa219440Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-5489000000-c9486dc02bd2970e1610Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0900-7920000000-b32caa0abd80ca28eabeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-62edd83447cda917e4cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1119000000-9ed06dfe32fa5c630c0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-2390000000-eec44bc289fefe24387fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityMycotoxins, such as alpha-zearalenol (alpha-ZOL) and beta-zearalenol (beta-ZOL), as contaminants of animal food can impair fertility and can cause abnormal fetal development in farm animals. The addition of alpha- or beta-ZOL (7.5, 15 and 30 microM) to cultures stimulated with FSH (0.01 microg) or forskolin (10 microM) reduced progesterone synthesis and the levels of p450scc and 3beta-HSD transcripts in a dose-dependent manner (P<0.05). The enzymatic activity of 3beta-HSD and the abundance of p450scc protein were also reduced by these mycotoxins. The effects of mycotoxins on FSH receptor-dependent and receptor-independent pathways indicate that adenylate cyclase activity and/or regulatory pathways further downstream are targets of mycotoxin actions. The apparent dose-dependent reduction of p450scc and 3beta-HSD transcripts implies an effect of alpha- and beta-ZOL on transcriptional regulation of these enzymes. Testing the zearalenone derivatives, _- and _-ZOL, which is metabolised in the liver, as an examination of excretory products indicated a predominance of the _ epimer in pig and man. (1) Generally, alpha-zearalenol possess estrogenic potencies that are approximately 50% compared to that of E2, and their order of estrogenic potency (in both in vitro receptor competitive binding and in vivo induction of Vtg and Zr-proteins levels) is: alpha-zearalenol > beta-zearalenol. It has also been observed that mycotoxin alpha and beta zearalenol influence the apoptosis and proliferation of cultured granulosa cells from equine ovaries. (3) The mechanisms by which _-ZOL or _-ZOL mediates their cytotoxic effects appear to differ according to cell type and the exposed toxins. In evaluating the toxicity of _-ZOL and _-ZOL on RAW264.7 macrophages, _-ZOL not only more strongly reduced the viability of cells than did _-ZOL, but it also induced cell death mainly by apoptosis rather than necrosis. The zearalenone metabolites induced loss of mitochondrial membrane potential (MMP), mitochondrial changes in Bcl-2 and Bax proteins, and cytoplasmic release of cytochrome c and apoptosis-inducing factor (AIF). Use of an inhibitor specific to c-Jun N-terminal kinase (JNK), p38 kinase or p53, but not pan-caspase or caspase-8, decreased the toxin-induced generation of reactive oxygen species (ROS) and also attenuated the _-ZOL- or _-ZOL-induced decrease of cell viability. The activation of p53, JNK or p38 kinase by zearalenone metabolites is the main upstream signal required for the mitochondrial alteration of Bcl-2/Bax signaling pathways and intracellular ROS generation, while MMP loss and nuclear translocation of AIF are the critical downstream events for zearalenone metabolite-mediated apoptosis in macrophages. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBeta-Zearalenol
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6437352
Kegg Compound IDC14751
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available