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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-23 10:11:27 UTC
Update Date2019-07-23 05:46:42 UTC
HMDB IDHMDB0005056
Secondary Accession Numbers
  • HMDB05056
Metabolite Identification
Common 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.). Enterodiol is a biomarker for the consumption of soy beans and other soy products.
Structure
Data?1563860802
Synonyms
ValueSource
(-)-EnterodiolHMDB
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
Arbo 9HMDB
[R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
2,3-Bis(3'-hydroxybenzyl)butane-1,4-diolHMDB
2,3-BHBBDHMDB
2,3-Bis(3-hydroxybenzyl)butane-1,4-diolHMDB
EnterodiolHMDB
Chemical FormulaC18H22O4
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
IUPAC Name(2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
Traditional Name(-)-enterodiol
CAS Registry Number80226-00-2
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 KeyDWONJCNDULPHLV-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.
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 Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability32.76 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2950000000-4ed8a5eb8bfaabb7a263JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6520390000-6840ee48e5d508b92d94JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0398000000-f09da6eee4bc76ff516aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frj-0971000000-bce5b39682ed3570612fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r9-0960000000-6920c1866fa29475fabcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-c4358f7b97aab38a1ecfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0096000000-fbf3e7cc759ef05d5425JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdo-1690000000-046c3b836806f630a4edJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected and Quantified0.0014 uMAdult (>18 years old)BothNormal details
    BloodDetected and Quantified0.000992 uMAdult (>18 years old)FemaleNormal details
    BloodDetected and Quantified0.0015 uMAdult (>18 years old)FemaleNormal details
    BloodDetected and Quantified0.00152 uMAdult (>18 years old)FemaleNormal details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.01 (0.0 -0.3) umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified0.0733 +/-0.04 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.0533 +/- 0.0266 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.032 +/- 0.072 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.013 +/- 0.019 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.065 +/- 0.039 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.013 +/- 0.019 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.0065 +/- 0.019 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.00 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.0065 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.0247 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.0501 +/- 0.100 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
    UrineDetected and Quantified0.0140 (0.0120-0.0163) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
      • National Health a...
    details
    UrineDetected and Quantified0.0176 (0.0140-0.0222) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
      • National Health a...
    details
    UrineDetected and Quantified0.0373 +/- 0.0560 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.0240 +/- 0.0240 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.447 +/- 1.00667 umol/mmol creatinineAdult (>18 years old)Female
    Normal
    details
    UrineDetected and Quantified0.0108 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
    UrineDetected and Quantified0.0800 +/- 0.100 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.0833 +/- 0.229 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.133 +/- 0.220 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.0211 umol/mmol creatinineChildren (1 - 13 years old)FemaleNormal details
    UrineDetected and Quantified0.0258 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.0339 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.05 +/- 0.12 umol/mmol creatinineAdult (>18 years old)FemaleBreast cancer details
    Associated Disorders and Diseases
    Disease References
    Perillyl alcohol administration for cancer treatment
    1. Grace PB, Mistry NS, Carter MH, Leathem AJ, Teale P: High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS). J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jun 15;853(1-2):138-46. Epub 2007 Mar 18. [PubMed:17403619 ]
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021828
    KNApSAcK IDC00000702
    Chemspider ID102992
    KEGG Compound IDC18166
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkEnterodiol
    METLIN IDNot Available
    PubChem Compound115089
    PDB IDNot Available
    ChEBI ID544560
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceMahalanabis, 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
    1. Wang LQ: Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309. [PubMed:12270221 ]
    2. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]