<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3782</id>
  <title>T3D3728</title>
  <common-name>Alternariol methyl ether</common-name>
  <description>Alternariol methyl ether is an altertoxin, which is a mycotoxin of Alternaria fungi. Altertoxins are important contaminants in cereals, vegetables, and fruits, as well as in the ground, on wood or walls. Studies have shown altertoxins to be toxic, genotoxic, mutagenic, and carcinogenic. In particular, they have been associated with esophageal cancer in humans. (A2977, A2979)</description>
  <cas>23452-05-3</cas>
  <pubchem-id>5360741</pubchem-id>
  <chemical-formula>C15H12O5</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>Alternariol methyl ether has been shown to have genotoxic and mutagenic properties. It has demonstrated DNA-damaging activities such as single-strand and double-strand DNA breaks, DNA-intercalating, and DNA cross-linking, as well as induction of DNA repair synthesis and inhibition of DNA replication. These effects are thought to be at least partially due to its ability to bind to the DNA minor groove with high affinity, which inhibits the activity of DNA-acting enzymes such as topoisomerase.  (A2977, A2978, A2979)</mechanism-of-toxicity>
  <metabolism>Alternariol methyl ether is metabolized by microsomes in the liver, preferentially at aromatic positions. It is also demethylated to alternariol. The products of aromatic hydroxylation are either catechols or hydroquinones, which may form reactive semiquinones and quinones or undergo redox cycling. (A2981)</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>Not listed by IARC.</carcinogenicity>
  <use-source>Alternariol methyl ether is an altertoxin, which is a mycotoxin of Alternaria fungi. Altertoxins are important contaminants in cereals, vegetables, and fruits, as well as in the ground, on wood or walls. (A2977, A2979)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Altertoxins have been shown to be toxic, genotoxic, mutagenic, and carcinogenic. In particular, they have been associated with esophageal cancer in humans. (A2977, A2979)</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-04T17:21:10Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:27Z</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=CC(O)=C2C(=O)OC3=C(C(C)=CC(O)=C3)C2=C1</moldb-smiles>
  <moldb-formula>C15H12O5</moldb-formula>
  <moldb-inchi>InChI=1S/C15H12O5/c1-7-3-8(16)4-12-13(7)10-5-9(19-2)6-11(17)14(10)15(18)20-12/h3-6,16-17H,1-2H3</moldb-inchi>
  <moldb-inchikey>InChIKey=LCSDQFNUYFTXMT-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">272.2528</moldb-average-mass>
  <moldb-mono-mass type="decimal">272.068473494</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL483526</chembl-id>
  <chemspider-id>4514573</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"/>
</compound>
