<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3830</id>
  <title>T3D3776</title>
  <common-name>Sporidesmin</common-name>
  <description>Sporidesmin is a mycotoxin found in the spores of the fungus Pithomyces chartarum. It is a potent hepatotoxin and is known to cause pithomycotoxicosis (facial eczema, characterized by photosensitisation) in livestock. (A3095)

</description>
  <cas>1456-55-9</cas>
  <pubchem-id>99596</pubchem-id>
  <chemical-formula>C18H20ClN3O6S2</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point nil="true"/>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Sporidesmin and its reduced (dithiol) form undergo cyclic reduction/autoxidation reactions with glutathione and other thiols, generating toxic superoxide radicals, hydrogen peroxide, and hydroxy radicals. It targets the liver, causing pericholangitis and the occlusion of bile ducts, which leads to the accumulation of bile constitutents in the bloodstream. In livestock, this results in a build up of phylloerythrin, a photodyamic metabolite produced by the microbial degradation of chlorophyll in the rumen. High plasma levels of phylloerythrin cause the animals to become sensitive to sunlight. (A3097, A3098)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>Not listed by IARC.</carcinogenicity>
  <use-source>Sporidesmin is a mycotoxin found in the spores of the fungus Pithomyces chartarum. (A3095) </use-source>
  <min-risk-level nil="true"/>
  <health-effects>Sporidesmin is a potent hepatotoxin, causing liver damage from pericholangitis and the occlusion of bile
ducts, which results in the accumulation of bile constitutents in the bloodstream. This is known to lead to pithomycotoxicosis (facial eczema, characterized by photosensitisation) in livestock. Sporidesmin may also be carcinogenic in humans. (A3095, A3096) </health-effects>
  <symptoms>Sporidesmin causes diarrhea and lack of appetite. Pithomycotoxicosis is characterized by photosensitisation of the skin. (A3095)</symptoms>
  <treatment>Administration of zinc salts can protect against the effects of sporidesmin. Zinc forms a stable mercaptide with sporidesmin, preventing its autoxidation to toxic reactive oxygen species. (A3095)</treatment>
  <created-at type="dateTime">2010-05-27T19:14:43Z</created-at>
  <updated-at type="dateTime">2026-04-06T12:53:51Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <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>COC1=C2N(C)C3N4C(=O)C5(C)SSC4(C(O)C3(O)C2=CC(Cl)=C1OC)C(=O)N5C</moldb-smiles>
  <moldb-formula>C18H20ClN3O6S2</moldb-formula>
  <moldb-inchi>InChI=1S/C18H20ClN3O6S2/c1-16-14(24)22-13-17(26,12(23)18(22,30-29-16)15(25)21(16)3)7-6-8(19)10(27-4)11(28-5)9(7)20(13)2/h6,12-13,23,26H,1-5H3</moldb-inchi>
  <moldb-inchikey>QTONANGUNATZOU-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">473.951</moldb-average-mass>
  <moldb-mono-mass type="decimal">473.048204474</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id nil="true"/>
  <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>CHEM002740</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00124810</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>102.78000000000002</moldb-polar-surface-area>
  <moldb-refractivity>112.73439999999998</moldb-refractivity>
  <moldb-polarizability>45.00020869142949</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>7</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>11.876644139067661</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-3.905837756611427</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>1.73</moldb-alogps-logp>
  <moldb-alogps-logs>-2.06</moldb-alogps-logs>
  <moldb-alogps-solubility>4.16e+00 g/l</moldb-alogps-solubility>
</compound>
