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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 22:56:58 UTC
Update Date2019-06-07 20:05:39 UTC
HMDB IDHMDB0006101
Secondary Accession Numbers
  • HMDB06101
Metabolite Identification
Common NameEnterolactone
DescriptionEnterolactone (CAS: 78473-71-9) is a mammalian lignan that has a similar biphenolic structure to lignans from plants. Lignans are compounds with estrogenic properties and are probably the most important source of phytoestrogens in western diets. Mammalian lignans are formed from precursors that are contained mainly in vegetables, whole grain products, and berries, via the action of intestinal microflora. Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol, and its glycosides. Secoisolariciresinol is converted to enterodiol which is subsequently converted to enterolactone as it passes through the colon. Matairesinol is converted directly to enterolactone. Enterolactone has been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of this antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men; however epidemiological evidence to date is conflicting (PMID: 16168401 , 12270221 , 11216511 , 12107024 ). Enterolactone is a biomarker for the consumption of soybeans and other soy products.
Structure
Data?1559937939
Synonyms
ValueSource
2,3-Bis(3'-hydroxybenzyl)butyrolactoneMeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomerMeSH
HPMFMeSH
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactoneMeSH
BHMDFMeSH
2,3-BHBBMeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomerMeSH
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanoneMeSH
(+)-EnterolactoneHMDB
(3S)-trans-EnterolactoneHMDB
(3S,4S)-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanoneHMDB
(3S,4S)-EnterolactoneHMDB
(±)-EnterolactoneHMDB
2,3-Bis(3’-hydroxybenzyl)butyrolactoneHMDB
EnterolactoneHMDB
trans-2,3-Bis(3-hydroxybenzyl)-γ-butyrolactoneHMDB
Chemical FormulaC18H18O4
Average Molecular Weight298.338
Monoisotopic Molecular Weight298.12050906
IUPAC Name(3S,4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
Traditional Nameenterolactone
CAS Registry Number185254-87-9
SMILES
OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=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/t14-,17+/m1/s1
InChI KeyHVDGDHBAMCBBLR-PBHICJAKSA-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.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

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 Solubility0.022 g/LALOGPS
logP3.2ALOGPS
logP3.61ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.71 m³·mol⁻¹ChemAxon
Polarizability30.94 ųChemAxon
Number of Rings3ChemAxon
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-2930000000-f09c9cac23beb829be13JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-642d4c8d3404bc3f1f38JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-0490000000-0fc8cabcfd095169a527JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-4930000000-03f5b31277825fdc664cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-c0857d2d2f364ae91560JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0190000000-f43dcd7ff2ab06e61ff1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-1950000000-316abee781de19a5a2baJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0091 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0113 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.014 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0013 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0041 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0151 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0202 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0207 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.022 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0225 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0137 +/- 0.0188 uMAdult (>18 years old)FemaleNormal details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected and Quantified0.0178 uMAdult (>18 years old)MaleNormal details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    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 Quantified0.169 +/- 0.189 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.118 +/- 0.115 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.880 +/- 1.387 umol/mmol creatinineAdult (>18 years old)Female
    Normal
    details
    UrineDetected and Quantified0.139 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
    UrineDetected and Quantified0.164 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.289 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.243 +/- 0.306 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified1.0700 +/- 0.880 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified1.593 +/- 1.773 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.0999 umol/mmol creatinineChildren (1 - 13 years old)FemaleNormal details
    UrineDetected and Quantified0.12 (0.01-1.94) umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified0.133 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.163 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.313 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.9333 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.71333 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.32 +/- 0.019 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.58 +/- 0.019 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.25 +/- 0.18 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.19 +/- 0.21 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.44 +/- 0.31 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.23 +/- 0.19 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.18 +/- 0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.092 +/- 0.092 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.11 +/- 0.072 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.208 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.310 +/- 0.412 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineDetected and Quantified0.0932 (0.0796-0.109) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
      • National Health a...
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineDetected and Quantified0.119 (0.0966-0.146) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
      • National Health a...
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1010 details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    UrineDetected and Quantified0.37 +/- 0.45 umol/mmol creatinineAdult (>18 years old)FemaleBreast cancer details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
    3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    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 IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDNot Available
    KNApSAcK IDC00000703
    Chemspider IDNot Available
    KEGG Compound IDC18165
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound114739
    PDB IDNot Available
    ChEBI ID81555
    References
    Synthesis ReferenceNot Available
    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. Boccardo F, Puntoni M, Guglielmini P, Rubagotti A: Enterolactone as a risk factor for breast cancer: a review of the published evidence. Clin Chim Acta. 2006 Mar;365(1-2):58-67. Epub 2005 Sep 15. [PubMed:16168401 ]
    3. Adlercreut H, Mazur W, Stumpf K, Kilkkinen A, Pietinen P, Hulten K, Hallmans G: Food containing phytoestrogens, and breast cancer. Biofactors. 2000;12(1-4):89-93. [PubMed:11216511 ]
    4. Adlercreutz H: Phyto-oestrogens and cancer. Lancet Oncol. 2002 Jun;3(6):364-73. [PubMed:12107024 ]
    5. 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 ]