<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3822</id>
  <title>T3D3768</title>
  <common-name>Luteoskyrin</common-name>
  <description>Luteoskyrin is a mycotoxin produced by the fungus Penicillium islandicum. It is known to be a storage mold contaminant of rice and has been shown to be hepatotoxic and hepatocarcinogenic. (A3069, A3070)</description>
  <cas>21884-44-6</cas>
  <pubchem-id>30840</pubchem-id>
  <chemical-formula>C30H22O12</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>Luteoskyrin is hepatotoxic. It is thought that this is a result of its metabolic reduction to the semiquinone radical catalyzed by NADPH-dependent cytochrome reductases in the liver, leading to the generation of active oxygen species in redox systems. This causes the induction of lipid peroxidation, hepatocellular membrane damage, and elevation of serum transaminase activities, resultin in liver injuries. Luteoskyrin is also hepatocarcinogenic, possibly a result of its ability to induce DNA fragmentation. It is able to bind to DNA, forming chelate-complexes with nucleic acids and select metal ions. Luteoskyrin inhibits the replication, transcription and repair of DNA, which is at least partially because it inhibits RNA polymerase and ribonuclease H. (A2955, A3042, A3070, A3071, A3072)</mechanism-of-toxicity>
  <metabolism>Luteoskyrin accumulates selectively in the liver, with minor distribution to the serum and kidneys. In the liver it is reduced to its semiquinone radical by NADPH-dependent cytochrome reductases. (A3070,A3071)</metabolism>
  <toxicity nil="true"/>
  <lethaldose>145 mg/kg subcutaneously and 221 mg/kg orally in mice. (A3069)</lethaldose>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>Luteoskyrin is a mycotoxin produced by the fungus Penicillium islandicum. It is known to be a storage mold contaminant of rice. (A3069)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Luteoskyrin is hepatotoxic and hepatocarcinogenic, causing hepatic disorders such as liver
cirrhosis and liver tumors. (A3069, A3070)</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-21T14:46:10Z</created-at>
  <updated-at type="dateTime">2026-04-03T17:45:28Z</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>CC1=CC(O)=C2C(O)=C3C(=O)C4C(O)C5C6C(O)C(C(=O)C7=C(O)C8=C(O)C=C(C)C(O)=C8C(=O)C467)C35C(=O)C2=C1O</moldb-smiles>
  <moldb-formula>C30H22O12</moldb-formula>
  <moldb-inchi>InChI=1S/C30H22O12/c1-5-3-7(31)9-11(19(5)33)27(41)29-13-14-24(38)17(29)26(40)16-22(36)10-8(32)4-6(2)20(34)12(10)28(42)30(14,16)18(23(13)37)25(39)15(29)21(9)35/h3-4,13-14,17-18,23-24,31-38H,1-2H3</moldb-inchi>
  <moldb-inchikey>FAZDYVMEXQHRLI-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">574.4885</moldb-average-mass>
  <moldb-mono-mass type="decimal">574.111126168</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>28613</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>CHEM002735</chemdb-id>
  <dsstox-id>DTXSID0020787</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00026980</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>230.11999999999995</moldb-polar-surface-area>
  <moldb-refractivity>143.68880000000001</moldb-refractivity>
  <moldb-polarizability>54.87610768349246</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>12</moldb-acceptor-count>
  <moldb-donor-count>8</moldb-donor-count>
  <moldb-pka-strongest-acidic>5.566740446371182</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-4.338395485455224</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-2</moldb-physiological-charge>
  <moldb-number-of-rings>8</moldb-number-of-rings>
  <moldb-alogps-logp>1.74</moldb-alogps-logp>
  <moldb-alogps-logs>-2.50</moldb-alogps-logs>
  <moldb-alogps-solubility>1.84e+00 g/l</moldb-alogps-solubility>
</compound>
