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<compound>
  <id type="integer">2234</id>
  <title>T3D2230</title>
  <common-name>2,3,4,6,7-Pentabromodibenzofuran</common-name>
  <description>2,3,4,6,7-Pentabromodibenzofuran belongs to the dibenzofurans, a subclass of benzofurans within the organic compounds. With an average molecular weight of 562.67 g/mol, 2,3,4,6,7-Pentabromodibenzofuran is a heavy molecule. This exogenous compound has the formula C12H3Br5O and exists as a solid at room temperature. It is classified as an organoheterocyclic compound. Recorded protein targets 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>124388-77-8</cas>
  <pubchem-id>153905</pubchem-id>
  <chemical-formula>C12H3Br5O</chemical-formula>
  <weight>557.610080</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>No indication of carcinogenicity (not listed by IARC). (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>EYES: irrigate opened eyes for several minutes under running water.
      
INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.
      
SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention.
      
INHALATION: supply fresh air. If required provide artificial respiration.</treatment>
  <created-at type="dateTime">2009-06-24T20:57:59Z</created-at>
  <updated-at type="dateTime">2026-08-18T21:10:13Z</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>2,3,4,6,7-Pentabromodibenzofuran</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>BrC1=CC=C2C3=CC(Br)=C(Br)C(Br)=C3OC2=C1Br</moldb-smiles>
  <moldb-formula>C12H3Br5O</moldb-formula>
  <moldb-inchi>InChI=1S/C12H3Br5O/c13-6-2-1-4-5-3-7(14)8(15)10(17)12(5)18-11(4)9(6)16/h1-3H</moldb-inchi>
  <moldb-inchikey>DOMLPUMLHHUETA-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">562.672</moldb-average-mass>
  <moldb-mono-mass type="decimal">557.610077953</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>6.8</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>135645</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>CHEM001944</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00121079</susdat-id>
  <iupac>2,3,4,6,7-pentabromodibenzofuran</iupac>
  <moldb-polar-surface-area>13.14</moldb-polar-surface-area>
  <moldb-refractivity>89.3408</moldb-refractivity>
  <moldb-polarizability>35.88104398268624</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>-4.301703431950195</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>6.67</moldb-alogps-logp>
  <moldb-alogps-logs>-5.03</moldb-alogps-logs>
  <moldb-alogps-solubility>5.20e-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>CED0159405</sync-id>
  <structure-inchikey>DOMLPUMLHHUETA-UHFFFAOYSA-N</structure-inchikey>
  <structure-fingerprint>40000200000000010000000000000000000000000000000000000000000000000000000000120008000000000000000000000000002000000000000000000000000800000000000000000800000000000000000000000004000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000001040000000000000000000000000000000040000080000000000000000002000000000800000000000000000000000200800000100000000000000000000000004000200000000000000000000000000000040000000000000000000000000000000000000004000</structure-fingerprint>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:25Z</structure-indexed-at>
</compound>
