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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:42:00 UTC
Update Date2019-07-23 06:35:07 UTC
HMDB IDHMDB0041838
Secondary Accession Numbers
  • HMDB41838
Metabolite Identification
Common Namebeta-Zearalenol
Descriptionbeta-Zearalenol, also known as β-zearalenol, 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. β-Zearalenol is about the same or slightly less potent as an estrogen relative to zearalenone. It 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 first-pass metabolism. β-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in Fusarium spp. beta-Zearalenol is an extremely weak basic (essentially neutral) compound (based on its pKa). beta-Zearalenol is a potentially toxic compound. A relatively high proportion of α-zearalenol is formed from zearalenone compared to β-zearalenol in humans.
Structure
Data?1563863707
Synonyms
ValueSource
b-ZearalenolGenerator
Β-zearalenolGenerator
beta-trans-ZearalenolHMDB
(3R,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-oneMeSH
alpha-Zearalenol, (cis)-isomerMeSH
ZearalenolMeSH
(-)-beta-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
Chemical FormulaC18H24O5
Average Molecular Weight320.3802
Monoisotopic Molecular Weight320.162373878
IUPAC Name(3R,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one
Traditional Name(3R,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-2-benzoxacyclotetradecin-1-one
CAS Registry Number71030-11-0
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-/m1/s1
InChI KeyFPQFYIAXQDXNOR-SXIUOJOQSA-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 DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Polarizability35.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0049000000-a87e9d1011a2491c8ddbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0229-8500950000-f4d3c9bdf8d5f08d6cadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0009000000-7c4b0f54561fc9fb00efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0019000000-0ddc6b67266db6bf948dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9i-0091000000-c9b5c6dadc302f064937Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-4c7a5b7c318ba756101eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-238b579c178c4fdd9caeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uml-0093000000-e779329162fb1416b22aSpectrum
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5908979
KEGG Compound IDC14751
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBeta-Zearalenol
METLIN IDNot Available
PubChem Compound13932155
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available