Milk Composition Database: Showing metabocard for Enterodiol (BMDB0005056)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:15:07 UTC

Update Date

2020-06-04 20:44:37 UTC

MCDB ID

BMDB0005056

Secondary Accession Numbers

BMDB05056

Metabolite Identification

Common Name

Enterodiol

Description

Enterodiol, also known as 2,3-BHBBD or arbo 9, belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Enterodiol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Enterodiol is a potentially toxic compound.

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 Weight

302.3649

Monoisotopic Molecular Weight

302.151809192

IUPAC Name

(2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

Traditional Name

(-)-enterodiol

CAS Registry Number

80226-00-2

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 )

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	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2950000000-4ed8a5eb8bfaabb7a263	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-004i-6520390000-6840ee48e5d508b92d94	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0900000000-6fd5b1caf0b11ab3dd17	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-b01fb4b064e58a38e170	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-3900000000-4ed09c20e4a4fb3f3875	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0940000000-786ff272cb009339906f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0940000000-a340102680583cfc68f0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0pb9-3900000000-aa3626a0e9a6776858b7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0940000000-41e4cc9deb7aa9c799c0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-179116fcc815df1446fe	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0290000000-fd222de6f034fee01c31	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0ar3-2900000000-ee35613960c900d06fb4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0290000000-2de3385ce84eba140c88	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0900000000-9fba8f3772864b12ddbb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-ebad5296a50b0dcf053a	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0398000000-f09da6eee4bc76ff516a	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0frj-0971000000-bce5b39682ed3570612f	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05r9-0960000000-6920c1866fa29475fabc	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0039000000-c4358f7b97aab38a1ecf	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0096000000-fbf3e7cc759ef05d5425	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fdo-1690000000-046c3b836806f630a4ed	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0859000000-8fb5cc787a664fd76c34	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0690-1950000000-7ae3b12589c277c0e377	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-2940000000-bfd4fbb4059ae278438f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0039000000-7d394202ae81237c33a9	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0393000000-63ea158a62162e087ae0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0r13-0890000000-72542e20683700bfc0c2	2021-09-24	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.232 uM	PMID: 18565930	details
Detected and Quantified	0.298 uM	PMID: 18565930	details
Detected and Quantified	0.43 uM	PMID: 18565930	details
Detected and Quantified	0.496 uM	PMID: 18565930	details
Detected and Quantified	0.00860 - 0.0132 uM	PMID: 19679050	details

External Links

HMDB ID

HMDB0005056

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterodiol

METLIN ID

Not Available

PubChem Compound

115089

PDB ID

Not Available

ChEBI ID

544560

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 Enterodiol (BMDB0005056)

Structure for BMDB0005056 (Enterodiol)