Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:09 UTC
Update Date2021-09-14 15:41:20 UTC
HMDB IDHMDB0041824
Secondary Accession Numbers
  • HMDB41824
Metabolite Identification
Common Namealpha-Zearalenol
DescriptionAlpha-zearlenol is a nonsteroidal estrogen or mycoestrogen found in fungi belonging to the Fusarium genus including F. graminearum, F. culmorum, F. crookwellense, etc (PMID: 22095651 ), As a mycotoxin, alpha-zearalenol is a widely distributed compound that contaminates many crops, grains, and other commodities (PMID: 30830360 ). Alpha-zearalenol, is also a major hepatic metabolite of zearalenone (another mycotoxin). Zearalenone has two metabolites, alpha and beta zearalenol which are produced in the liver by 3α-hydroxisteroid dehydrogenase and 3β-hydroxisteroid dehydrogenase (PMID: 30830360 ). Like Alpha-zearlenol, zearalenone or F-2 mycotoxin is produced by certain Fusarium species. It causes infertility, abortion and other breeding problems in swine. Alpha-zearlenol is also produced synthetically and sold as Zeranol, which is used as an anabolic agent for cattle. Alpha-zearlenol exhibits strong growth-promoting properties, but its sale is restricted in Europe (PMID: 22095651 ). Alpha-zearalenol has three to four times the biological activity of zearalenone. Alpha-zearlenol contains a lactone ring in its structure and is structurally analogous to estrogen, thus it can bind to estrogen receptors, and causes hepatotoxic, hematotoxic, immunotoxic, genotoxic, teratogenic and carcinogenic effects on different animal species (PMID: 17045381 ).
Structure
Data?1563863706
Synonyms
ValueSource
trans-ZearalenolKegg
a-ZearalenolGenerator
Α-zearalenolGenerator
alpha-Zearalenol, (cis)-isomerHMDB
ZearalenolHMDB
beta-ZearalenolHMDB
(3R,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-oneHMDB
beta-trans-ZearalenolHMDB
(-)-beta-ZearalenolHMDB
3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-oneHMDB
Chemical FormulaC18H24O5
Average Molecular Weight320.3802
Monoisotopic Molecular Weight320.162373878
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
CAS Registry Number36455-72-8
SMILES
C[C@H]1CCC[C@H](O)CCC\C=C\C2=CC(O)=CC(O)=C2C(=O)O1
InChI Identifier
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
InChI KeyFPQFYIAXQDXNOR-QDKLYSGJSA-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
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+172.56930932474
DeepCCS[M-H]-170.21130932474
DeepCCS[M-2H]-204.21730932474
DeepCCS[M+Na]+179.97830932474
AllCCS[M+H]+179.932859911
AllCCS[M+H-H2O]+176.432859911
AllCCS[M+NH4]+183.132859911
AllCCS[M+Na]+184.132859911
AllCCS[M-H]-183.532859911
AllCCS[M+Na-2H]-184.032859911
AllCCS[M+HCOO]-184.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-ZearalenolC[C@H]1CCC[C@H](O)CCC\C=C\C2=CC(O)=CC(O)=C2C(=O)O13927.0Standard polar33892256
alpha-ZearalenolC[C@H]1CCC[C@H](O)CCC\C=C\C2=CC(O)=CC(O)=C2C(=O)O12845.5Standard non polar33892256
alpha-ZearalenolC[C@H]1CCC[C@H](O)CCC\C=C\C2=CC(O)=CC(O)=C2C(=O)O12882.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Zearalenol,1TMS,isomer #1C[C@H]1CCC[C@H](O[Si](C)(C)C)CCC/C=C/C2=CC(O)=CC(O)=C2C(=O)O12813.5Semi standard non polar33892256
alpha-Zearalenol,1TMS,isomer #2C[C@H]1CCC[C@H](O)CCC/C=C/C2=CC(O[Si](C)(C)C)=CC(O)=C2C(=O)O12855.2Semi standard non polar33892256
alpha-Zearalenol,1TMS,isomer #3C[C@H]1CCC[C@H](O)CCC/C=C/C2=CC(O)=CC(O[Si](C)(C)C)=C2C(=O)O12855.7Semi standard non polar33892256
alpha-Zearalenol,2TMS,isomer #1C[C@H]1CCC[C@H](O[Si](C)(C)C)CCC/C=C/C2=CC(O[Si](C)(C)C)=CC(O)=C2C(=O)O12870.5Semi standard non polar33892256
alpha-Zearalenol,2TMS,isomer #2C[C@H]1CCC[C@H](O[Si](C)(C)C)CCC/C=C/C2=CC(O)=CC(O[Si](C)(C)C)=C2C(=O)O12824.0Semi standard non polar33892256
alpha-Zearalenol,2TMS,isomer #3C[C@H]1CCC[C@H](O)CCC/C=C/C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O12879.0Semi standard non polar33892256
alpha-Zearalenol,3TMS,isomer #1C[C@H]1CCC[C@H](O[Si](C)(C)C)CCC/C=C/C2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O12907.5Semi standard non polar33892256
alpha-Zearalenol,1TBDMS,isomer #1C[C@H]1CCC[C@H](O[Si](C)(C)C(C)(C)C)CCC/C=C/C2=CC(O)=CC(O)=C2C(=O)O13035.6Semi standard non polar33892256
alpha-Zearalenol,1TBDMS,isomer #2C[C@H]1CCC[C@H](O)CCC/C=C/C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C(=O)O13082.3Semi standard non polar33892256
alpha-Zearalenol,1TBDMS,isomer #3C[C@H]1CCC[C@H](O)CCC/C=C/C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13068.8Semi standard non polar33892256
alpha-Zearalenol,2TBDMS,isomer #1C[C@H]1CCC[C@H](O[Si](C)(C)C(C)(C)C)CCC/C=C/C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C(=O)O13323.4Semi standard non polar33892256
alpha-Zearalenol,2TBDMS,isomer #2C[C@H]1CCC[C@H](O[Si](C)(C)C(C)(C)C)CCC/C=C/C2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13275.6Semi standard non polar33892256
alpha-Zearalenol,2TBDMS,isomer #3C[C@H]1CCC[C@H](O)CCC/C=C/C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13320.9Semi standard non polar33892256
alpha-Zearalenol,3TBDMS,isomer #1C[C@H]1CCC[C@H](O[Si](C)(C)C(C)(C)C)CCC/C=C/C2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13560.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Zearalenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0049000000-a87e9d1011a2491c8ddb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Zearalenol GC-MS (3 TMS) - 70eV, Positivesplash10-0229-8500950000-f4d3c9bdf8d5f08d6cad2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Zearalenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 10V, Positive-QTOFsplash10-0uk9-0019000000-4e38670336b2fa2194402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 20V, Positive-QTOFsplash10-0uk9-5489000000-c9486dc02bd2970e16102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 40V, Positive-QTOFsplash10-0900-7920000000-b32caa0abd80ca28eabe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 10V, Negative-QTOFsplash10-014i-0019000000-62edd83447cda917e4cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 20V, Negative-QTOFsplash10-0gb9-1119000000-9ed06dfe32fa5c630c0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 40V, Negative-QTOFsplash10-052b-2390000000-eec44bc289fefe24387f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 10V, Negative-QTOFsplash10-014i-0009000000-116f24373daa24d943ea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 20V, Negative-QTOFsplash10-0udi-0009000000-65d407b0c8387d27535d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 40V, Negative-QTOFsplash10-0006-8091000000-fdac99a2354a0b46e9cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 10V, Positive-QTOFsplash10-0udi-0009000000-ab0d3e9427f8c52160012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 20V, Positive-QTOFsplash10-0udi-0009000000-930d5de96dccc6bd3e832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Zearalenol 40V, Positive-QTOFsplash10-0pb9-1092000000-12d134b2e63ea616dcd92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111671
KNApSAcK IDNot Available
Chemspider ID4447689
KEGG Compound IDC14750
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-Zearalenol
METLIN IDNot Available
PubChem Compound5284645
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thevis M, Fussholler G, Schanzer W: Zeranol: doping offence or mycotoxin? A case-related study. Drug Test Anal. 2011 Nov-Dec;3(11-12):777-83. doi: 10.1002/dta.352. Epub 2011 Nov 17. [PubMed:22095651 ]
  2. Nittoli AC, Costantini S, Sorice A, Capone F, Ciarcia R, Marzocco S, Budillon A, Severino L: Effects of alpha-zearalenol on the metabolome of two breast cancer cell lines by 1H-NMR approach. Metabolomics. 2018 Feb 14;14(3):33. doi: 10.1007/s11306-018-1330-3. [PubMed:30830360 ]
  3. Zinedine A, Soriano JM, Molto JC, Manes J: Review on the toxicity, occurrence, metabolism, detoxification, regulations and intake of zearalenone: an oestrogenic mycotoxin. Food Chem Toxicol. 2007 Jan;45(1):1-18. doi: 10.1016/j.fct.2006.07.030. Epub 2006 Aug 30. [PubMed:17045381 ]