Bovine Metabolome Database: Showing metabocard for Enterolactone (BMDB0006101)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:20:09 UTC

Update Date

2020-06-04 20:50:53 UTC

BMDB ID

BMDB0006101

Secondary Accession Numbers

BMDB06101

Metabolite Identification

Common Name

Enterolactone

Description

Enterolactone, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
HPMF	MeSH
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone	MeSH
2,3-BHBB	MeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomer	MeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone	MeSH
BHMDF	MeSH
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone	MeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer	MeSH
(+/-)-enterolactone	ChEMBL, HMDB
dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanone	HMDB
Enterolactone	MeSH

Chemical Formula

C₁₈H₁₈O₄

Average Molecular Weight

298.3331

Monoisotopic Molecular Weight

298.120509064

IUPAC Name

3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

Traditional Name

HPMF

CAS Registry Number

76543-15-2

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 Key

HVDGDHBAMCBBLR-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.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.2	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.71 m³·mol⁻¹	ChemAxon
Polarizability	30.77 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2930000000-324d2f99f3a80a910017	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-2936200000-90d0a08c212a572a564a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0190000000-642d4c8d3404bc3f1f38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5a-0490000000-0fc8cabcfd095169a527	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-4930000000-03f5b31277825fdc664c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-c0857d2d2f364ae91560	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0190000000-f43dcd7ff2ab06e61ff1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-1950000000-316abee781de19a5a2ba	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected and Quantified	0.0369 - 0.0825 uM	Not Specified	Not Specified	Normal	PMID: 19679050	details
Milk	Detected and Quantified	90.503 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	72.402 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	130.056 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	90.503 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0006101

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterolactone

METLIN ID

Not Available

PubChem Compound

123917

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]

Showing metabocard for Enterolactone (BMDB0006101)

Structure for BMDB0006101 (Enterolactone)