Showing metabocard for Enterolactone (BMDB0006101)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:09 UTC
Update Date2020-06-04 20:50:53 UTC
MCDB ID BMDB0006101
Secondary Accession Numbers
  • BMDB06101
Metabolite Identification
Common NameEnterolactone
DescriptionEnterolactone, also known as HPMF or 2,3-BHBB, belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Enterolactone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Enterolactone is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
HPMFMeSH
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactoneMeSH
2,3-BHBBMeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomerMeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactoneMeSH
BHMDFMeSH
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanoneMeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomerMeSH
(+/-)-enterolactoneChEMBL, HMDB
dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanoneHMDB
EnterolactoneMeSH
Chemical FormulaC18H18O4
Average Molecular Weight298.3331
Monoisotopic Molecular Weight298.120509064
IUPAC Name3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
Traditional NameHPMF
CAS Registry Number76543-15-2
SMILES
OC1=CC=CC(CC2COC(=O)C2CC2=CC(O)=CC=C2)=C1
InChI Identifier
InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2
InChI KeyHVDGDHBAMCBBLR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.2ALOGPS
logP3.61ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.71 m³·mol⁻¹ChemAxon
Polarizability30.77 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2930000000-324d2f99f3a80a9100172017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2936200000-90d0a08c212a572a564a2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-642d4c8d3404bc3f1f382016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-0490000000-0fc8cabcfd095169a5272016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-4930000000-03f5b31277825fdc664c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-c0857d2d2f364ae915602016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0190000000-f43dcd7ff2ab06e61ff12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-1950000000-316abee781de19a5a2ba2016-08-03View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified91 uM details
Detected and Quantified72 uM details
Detected and Quantified130 uM details
Detected and Quantified91 uM details
Detected and Quantified0.0369 - 0.0825 uM details
HMDB IDHMDB0006101
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnterolactone
METLIN IDNot Available
PubChem Compound123917
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
  2. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]