<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3657</id>
  <title>T3D3604</title>
  <common-name>Gliotoxin</common-name>
  <description>Gliotoxin is a sulfur-containing antibiotic produced by several species of fungi, some of which are pathogens of humans such as Aspergillus, and also by species of Trichoderma, and Penicillium. Gliotoxin possesses immunosuppressive properties as it may suppress and cause apoptosis  in certain types of cells of the immune system, including neutrophils, eosinophils, granulocytes, macrophages, and thymocytes. (L1941) </description>
  <cas>67-99-2</cas>
  <pubchem-id>6223</pubchem-id>
  <chemical-formula>C13H14N2O4S2</chemical-formula>
  <weight></weight>
  <appearance>White to light yellow solid.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density></density>
  <solubility></solubility>
  <specific-gravity></specific-gravity>
  <flash-point></flash-point>
  <vapour-pressure></vapour-pressure>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Gliotoxin possesses immunosuppressive properties as it may suppress and cause apoptosis  in certain types of cells of the immune system, including neutrophils, eosinophils, granulocytes, macrophages, and thymocytes. It also acts as an inhibitor of farnesyl transferase. Gliotoxin noncompetitively inhibits the chymotrypsin-like activity of the 20S proteasome and displays anti-inflammatory activity. It acts by blocking thiol groups in the cell membranes. Gliotoxin is also cytotoxic and causes neurite degeneration. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (L1941, A2951, A3014)</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Gliotoxin is a sulfur-containing antibiotic produced by several species of fungi, some of which are pathogens of humans such as Aspergillus, and also by species of Trichoderma, and Penicillium. Gliotoxin possesses immunosuppressive properties. (L1941) </use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Gliotoxin has immunosuppressive effects. It is also cytotoxic and causes neurite degeneration. (L1941, A2951)</health-effects>
  <symptoms></symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2009-11-13T22:01:12Z</created-at>
  <updated-at type="dateTime">2026-03-31T21:04:57Z</updated-at>
  <interacting-proteins></interacting-proteins>
  <wikipedia>http://en.wikipedia.org/wiki/Gliotoxin</wikipedia>
  <uniprot-id></uniprot-id>
  <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>CN1C(=O)C23CC4=CC=CC(O)C4N2C(=O)C1(CO)SS3</moldb-smiles>
  <moldb-formula>C13H14N2O4S2</moldb-formula>
  <moldb-inchi>InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3</moldb-inchi>
  <moldb-inchikey>FIVPIPIDMRVLAY-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">326.391</moldb-average-mass>
  <moldb-mono-mass type="decimal">326.039498326</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>5988</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>CHEM002580</chemdb-id>
  <dsstox-id>DTXSID60877179</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00011815</susdat-id>
  <iupac>7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0¹,⁹.0³,⁸]pentadeca-3,5-diene-10,14-dione</iupac>
</compound>
