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Showing Compound Enterodiol (FDB021828)

Record Information
Version1.0
Creation date2011-04-11 17:01:52 UTC
Update date2019-11-26 03:20:55 UTC
Primary IDFDB021828
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEnterodiol
DescriptionEnterodiol 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. (PMID: 12270221, J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.) [HMDB]. Enterodiol is a biomarker for the consumption of soy beans and other soy products.
CAS Number80226-00-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,3-Bis(3'-hydroxybenzyl)butane-1,4-diolHMDB
2,3-Bis(3-hydroxybenzyl)butane-1,4-diolMeSH
(-)-EnterodiolHMDB
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
[R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
Arbo 9HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP1.91ALOGPS
logP2.65ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.79ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity86.36 m³·mol⁻¹ChemAxon
Polarizability32.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H22O4
IUPAC name2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
InChI IdentifierInChI=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
InChI KeyDWONJCNDULPHLV-UHFFFAOYSA-N
Isomeric SMILESOCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC=CC(O)=C1
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
Classification
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.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassDibenzylbutanediol lignans
Direct ParentDibenzylbutanediol 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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MSEnterodiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1930000000-dc357c47c7a4c2221287Spectrum
    Predicted GC-MSEnterodiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEnterodiol, TBDMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0900000000-4635254ef028afadef7b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0900000000-3807f146b647a8154f922021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0009000000-49d3a24a4bfabda1ccb92021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0009000000-4887e5a3c5890adf19e62021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0900000000-5452f0f2a082d2e2d5c22021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0aor-0940000000-ab3333f258f65e2654442021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-0udi-0139000000-211581d50c893c6301a82021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0009000000-d9fa9fc29cfc79020ccd2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0139000000-b1afa28d2b20f9bb77bd2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0149000000-ddbea401fa15124e4b192021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0aor-0940000000-41e4cc9deb7aa9c799c02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0zfr-0960000000-34060980b28738b4f7122021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0zfr-0960000000-f646bc2901341aa101532021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0zfr-0960000000-d94a42aece1aaae3c17f2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0859000000-8fb5cc787a664fd76c342021-10-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0690-1950000000-7ae3b12589c277c0e3772021-10-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-2940000000-bfd4fbb4059ae278438f2021-10-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-7d394202ae81237c33a92021-10-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0393000000-63ea158a62162e087ae02021-10-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r13-0890000000-72542e20683700bfc0c22021-10-12View Spectrum
    NMRNot Available
    ChemSpider ID102992
    ChEMBL IDCHEMBL471076
    KEGG Compound IDC18166
    Pubchem Compound ID115089
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID1009
    DrugBank IDNot Available
    HMDB IDHMDB05056
    CRC / DFC (Dictionary of Food Compounds) IDHGS35-M:HGS35-M
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID1009
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference