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<compound>
  <id type="integer">2143</id>
  <title>T3D2139</title>
  <common-name>1,2,3,4,6,8,9-Heptachlorodibenzofuran</common-name>
  <description>1,2,3,4,6,8,9-Heptachlorodibenzofuran belongs to the dibenzofurans, a subclass of benzofurans within the organic compounds. This exogenous organoheterocyclic compound has the formula C12HCl7O and an average molecular weight of 409.31 g/mol. At room temperature, it exists as a solid. Recorded protein targets for this compound include the transient receptor potential cation channel subfamily A member 1 (TRPA1) and the aryl hydrocarbon receptor (AHR). Binding to the aryl hydrocarbon receptor increases its ability to activate transcription in the XRE promoter region, which alters the expression of several genes.</description>
  <cas>69698-58-4</cas>
  <pubchem-id>50611</pubchem-id>
  <chemical-formula>C12HCl7O</chemical-formula>
  <weight>405.784710</weight>
  <appearance>Colorless crystals.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Inhalation (L952) ; dermal (L952) ; oral (L952)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.</mechanism-of-toxicity>
  <metabolism>No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>CDFs are created from production of coal tar and during incineration. They are used as insecticides, in the production of PVC, and in industrial bleaching. (L952)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in  people who ingested CDFs. (L952)</health-effects>
  <symptoms>Skin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-06-24T20:57:44Z</created-at>
  <updated-at type="dateTime">2026-08-18T22:15:30Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>1,2,3,4,6,8,9-Heptachlorodibenzofuran</stitch-id>
  <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>ClC1=C2OC3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=C(Cl)C(Cl)=C1</moldb-smiles>
  <moldb-formula>C12HCl7O</moldb-formula>
  <moldb-inchi>InChI=1S/C12HCl7O/c13-2-1-3(14)11-4(6(2)15)5-7(16)8(17)9(18)10(19)12(5)20-11/h1H</moldb-inchi>
  <moldb-inchikey>BADFHCOLISGRRW-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">409.307</moldb-average-mass>
  <moldb-mono-mass type="decimal">405.784708603</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>7.6</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>45874</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></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM001867</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00120306</susdat-id>
  <iupac>1,2,3,4,6,8,9-heptachlorodibenzofuran</iupac>
  <moldb-polar-surface-area>13.14</moldb-polar-surface-area>
  <moldb-refractivity>84.86039999999998</moldb-refractivity>
  <moldb-polarizability>34.03411209177651</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>0</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>-4.234735129337839</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>7.63</moldb-alogps-logp>
  <moldb-alogps-logs>-5.58</moldb-alogps-logs>
  <moldb-alogps-solubility>1.09e-03 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organoheterocyclic compounds</superklass>
  <klass>Benzofurans</klass>
  <subklass>Dibenzofurans</subklass>
  <paper-count type="integer">0</paper-count>
  <sync-id>CED0061930</sync-id>
  <structure-inchikey>BADFHCOLISGRRW-UHFFFAOYSA-N</structure-inchikey>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:22Z</structure-indexed-at>
</compound>
