Showing metabocard for Enterolactone (LMDB00470)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:50:33 UTC
Update Date2016-07-19 23:04:19 UTC
LmdbLMDB00470
Secondary Accession NumbersNone
Metabolite Identification
Common NameEnterolactone
DescriptionEnterolactone is a mammalian lignan that have a similar biphenolic structure to lignans from plants. Lignans are compounds with estrogenic properties and are probably the most important source of phytoestrogens in western diets. Mammalian lignans are formed from precursors that are contained mainly in vegetables, whole grain products and berries, via action of intestinal microflora. Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol and its glycosides. Secoisolariciresinol is converted to enterodiol which is subsequently converted to enterolactone as it passes through the colon. Matairesinol is converted directly to enterolactone. Enterolactone have been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of this antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men; however epidemiological evidence to date is conflicting. (PMID: 16168401 , 12270221 , 11216511 , 12107024 ).
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2930000000-324d2f99f3a80a910017Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2936200000-90d0a08c212a572a564aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-642d4c8d3404bc3f1f38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-0490000000-0fc8cabcfd095169a527Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-4930000000-03f5b31277825fdc664cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-c0857d2d2f364ae91560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0190000000-f43dcd7ff2ab06e61ff1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-1950000000-316abee781de19a5a2baSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected and Quantified6.7 - 989.1 uMNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0006101
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEnterolactone
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID123917
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boccardo F, Puntoni M, Guglielmini P, Rubagotti A: Enterolactone as a risk factor for breast cancer: a review of the published evidence. Clin Chim Acta. 2006 Mar;365(1-2):58-67. Epub 2005 Sep 15. [16168401 ]
  2. Wang LQ: Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309. [12270221 ]
  3. Adlercreut H, Mazur W, Stumpf K, Kilkkinen A, Pietinen P, Hulten K, Hallmans G: Food containing phytoestrogens, and breast cancer. Biofactors. 2000;12(1-4):89-93. [11216511 ]
  4. Adlercreutz H: Phyto-oestrogens and cancer. Lancet Oncol. 2002 Jun;3(6):364-73. [12107024 ]