ContaminantDB: Enterodiol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:47:56 UTC

Update Date

2026-04-05 16:32:45 UTC

Accession Number

CHEM002926

Identification

Common Name

Enterodiol

Class

Small Molecule

Description

Enterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye and wheat), seeds, nuts, legumes and vegetables. (1).

Contaminant Sources

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

Contaminant Type

Animal Toxin
Food Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Enterodiol	HMDB
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol	HMDB
Arbo 9	HMDB
[R-(R,r)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediol	HMDB
2,3-Bis(3'-hydroxybenzyl)butane-1,4-diol	HMDB
2,3-BHBBD	HMDB
2,3-Bis(3-hydroxybenzyl)butane-1,4-diol	HMDB
Enterodiol	HMDB

Chemical Formula

C₁₈H₂₂O₄

Average Molecular Mass

302.365 g/mol

Monoisotopic Mass

302.152 g/mol

CAS Registry Number

80226-00-2

IUPAC Name

Not Available

Traditional Name

(-)-enterodiol

SMILES

OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1

InChI Key

DWONJCNDULPHLV-HOTGVXAUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Dibenzylbutanediol lignans

Direct Parent

Dibenzylbutanediol lignans

Alternative Parents

Substituents

Dibenzylbutanediol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

lignan (CHEBI:81556 )

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	0.025 g/L	ALOGPS
logP	1.91	ALOGPS
logP	2.65	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.36 m³·mol⁻¹	ChemAxon
Polarizability	32.76 Å³	ChemAxon
Number of Rings	2	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-2950000000-4ed8a5eb8bfaabb7a263	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-004i-6520390000-6840ee48e5d508b92d94	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0900000000-6fd5b1caf0b11ab3dd17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-b01fb4b064e58a38e170	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-3900000000-4ed09c20e4a4fb3f3875	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0940000000-786ff272cb009339906f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0940000000-a340102680583cfc68f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0pb9-3900000000-aa3626a0e9a6776858b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0940000000-41e4cc9deb7aa9c799c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-179116fcc815df1446fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0290000000-fd222de6f034fee01c31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0ar3-2900000000-ee35613960c900d06fb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0290000000-2de3385ce84eba140c88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0900000000-9fba8f3772864b12ddbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-ebad5296a50b0dcf053a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0398000000-f09da6eee4bc76ff516a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0frj-0971000000-bce5b39682ed3570612f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05r9-0960000000-6920c1866fa29475fabc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0039000000-c4358f7b97aab38a1ecf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0096000000-fbf3e7cc759ef05d5425	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fdo-1690000000-046c3b836806f630a4ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0859000000-8fb5cc787a664fd76c34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0690-1950000000-7ae3b12589c277c0e377	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-2940000000-bfd4fbb4059ae278438f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0039000000-7d394202ae81237c33a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0393000000-63ea158a62162e087ae0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0r13-0890000000-72542e20683700bfc0c2	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

Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids.

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

HMDB0005056

FooDB ID

FDB021828

Phenol Explorer ID

Not Available

KNApSAcK ID

C00000702

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Mahalanabis, K. K.; Mumtax, M.; Snieckuz, V. Dimetalated tertiary succinamides. Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol. Tetrahedron Letters (1982), 23(39), 3975-8.

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.

3. Mahalanabis, K. K.; Mumtax, M.; Snieckuz, V. Dimetalated tertiary succinamides. Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol. Tetrahedron Letters (1982), 23(39), 3975-8.

4. Wang LQ: Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.

5. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510

Enterodiol (CHEM002926)

Structure for CHEM002926: Enterodiol