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<compound>
  <id type="integer">4020</id>
  <title>T3D3966</title>
  <common-name>Enterodiol</common-name>
  <description>Enterodiol belongs to the dibenzylbutanediol lignans, a subclass of dibenzylbutane lignans within the organic compounds. This exogenous compound has the formula C18H22O4 and an average molecular weight of 302.36 g/mol. At room temperature, it exists as a solid.</description>
  <cas>80226-00-2</cas>
  <pubchem-id>115089</pubchem-id>
  <chemical-formula>C18H22O4</chemical-formula>
  <weight>302.4</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>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.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T04:47:56Z</created-at>
  <updated-at type="dateTime">2026-08-20T00:51:08Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C18166</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>544560</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1</moldb-smiles>
  <moldb-formula>C18H22O4</moldb-formula>
  <moldb-inchi>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</moldb-inchi>
  <moldb-inchikey>DWONJCNDULPHLV-HOTGVXAUSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">302.3649</moldb-average-mass>
  <moldb-mono-mass type="decimal">302.151809192</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.6</logp>
  <hmdb-id>HMDB05056</hmdb-id>
  <chembl-id>CHEMBL471076</chembl-id>
  <chemspider-id>102992</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <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. </synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002926</chemdb-id>
  <dsstox-id>DTXSID0047876</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00076968</susdat-id>
  <iupac>(2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol</iupac>
  <moldb-polar-surface-area>80.92</moldb-polar-surface-area>
  <moldb-refractivity>86.36060000000002</moldb-refractivity>
  <moldb-polarizability>32.76260824205408</moldb-polarizability>
  <moldb-rotatable-bond-count>7</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>9.793418141582793</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.603209181436301</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>1.91</moldb-alogps-logp>
  <moldb-alogps-logs>-4.09</moldb-alogps-logs>
  <moldb-alogps-solubility>2.47e-02 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Lignans, neolignans and related compounds</superklass>
  <klass>Dibenzylbutane lignans</klass>
  <subklass>Dibenzylbutanediol lignans</subklass>
  <paper-count type="integer">1107</paper-count>
  <sync-id>CED0008275</sync-id>
  <structure-inchikey>DWONJCNDULPHLV-HOTGVXAUSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:01:02Z</structure-indexed-at>
</compound>
