alpha-Zearalenol (T3D4052)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 04:58:39 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4052
Identification
Common Namealpha-Zearalenol
ClassSmall Molecule
DescriptionAlpha-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.
Compound Type
  • Ester
  • Ether
  • Fungal Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
a-Zearalenol
trans-Zearalenol
α-Zearalenol
Chemical FormulaC18H24O5
Average Molecular Mass320.380 g/mol
Monoisotopic Mass320.162 g/mol
CAS Registry Number36455-72-8
IUPAC Name(3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one
Traditional Namezeranol
SMILES[H]\C1=C([H])/C2=CC(O)=CC(O)=C2C(=O)O[C@@]([H])(C)CCC[C@]([H])(O)CCC1
InChI IdentifierInChI=1/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+/s2
InChI KeyInChIKey=FPQFYIAXQDXNOR-GWCUECQRNA-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
LogPNot 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
Polarizability34.47 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0049000000-a87e9d1011a2491c8ddb2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0229-8500950000-f4d3c9bdf8d5f08d6cad2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0019000000-4e38670336b2fa2194402016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-5489000000-c9486dc02bd2970e16102016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0900-7920000000-b32caa0abd80ca28eabe2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-62edd83447cda917e4cb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1119000000-9ed06dfe32fa5c630c0a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-2390000000-eec44bc289fefe24387f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-116f24373daa24d943ea2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-65d407b0c8387d27535d2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8091000000-fdac99a2354a0b46e9cb2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-ab0d3e9427f8c52160012021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-930d5de96dccc6bd3e832021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-1092000000-12d134b2e63ea616dcd92021-09-24View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41824
PubChem Compound ID5284645
ChEMBL IDNot Available
ChemSpider ID4447689
KEGG IDC14750
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Tiemann U, Tomek W, Schneider F, Vanselow J: Effects of the mycotoxins alpha- and beta-zearalenol on regulation of progesterone synthesis in cultured granulosa cells from porcine ovaries. Reprod Toxicol. 2003 Nov-Dec;17(6):673-81. [14613819 ]
  2. Lu J, Yu JY, Lim SS, Son YO, Kim DH, Lee SA, Shi X, Lee JC: Cellular mechanisms of the cytotoxic effects of the zearalenone metabolites alpha-zearalenol and beta-zearalenol on RAW264.7 macrophages. Toxicol In Vitro. 2013 Apr;27(3):1007-17. doi: 10.1016/j.tiv.2013.01.011. Epub 2013 Jan 31. [23376438 ]
  3. wikigenes [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available