ContaminantDB: Enterolactone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (28)XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:48:01 UTC

Update Date

2026-04-05 16:32:49 UTC

Accession Number

CHEM002927

Identification

Common Name

Enterolactone

Class

Small Molecule

Description

Enterolactone (C18H18O4) is an exogenous organic compound with an average molecular weight of 298.33 g/mol. It exists as a solid at room temperature. Enterolactone belongs to the tetrahydrofuran lignans, a subclass of furanoid lignans within the organic compounds. This compound is produced in the colon via the action of bacteria on matairesinol and its glycosides, as well as secoisolariciresinol. While matairesinol is converted directly to enterolactone, secoisolariciresinol is first converted to enterodiol before becoming enterolactone as it passes through the colon. Enterolactone has been shown to possess weakly estrogenic and antiestrogenic activities. It has been suggested that the high production of this mammalian lignan in the gut may protect against prostate cancer in men and breast cancer in women, although epidemiological evidence is conflicting. Recorded protein targets for enterolactone include the translocator protein (TSPO), the estrogen receptor (ESR1), and nuclear receptor subfamily 1 group I member 2 (NR1I2).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Ester
Ether
Food Toxin
Industrial/Workplace Toxin
Mammal Toxin
Metabolite
Natural Compound
Organic Compound

Chemical 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 Mass

298.333 g/mol

Monoisotopic Mass

298.121 g/mol

CAS Registry Number

76543-15-2

IUPAC Name

Not Available

Traditional Name

HPMF

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

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

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

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol and its glycosides.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0006101

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Enterolactone

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

123917

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Link

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.

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.

Enterolactone (CHEM002927)

Structure for CHEM002927: Enterolactone