<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3807</id>
  <title>T3D3753</title>
  <common-name>Butenolide</common-name>
  <description>Butenolide is a mycotoxin found in various species of fungi of the genus Fusarium. It can often be found in contaminated agricultural products. Butenolide had been implicated as the causative agent of a livestock mycotoxicosis called “fescue foot”, a peripheral vascular disorder occurring in cattle grazing on tall fescue grass. Butenolide is also one of the mycotoxins which have been considered as a suspected etiological factor for Kaschin-Beck disease (an endemic osteoarthropathy) and Keshan disease (an endemic cardiomyopathy), prevailing in some regions of China, and several studies have also indicated that butenolide can cause cartilage damage. (A3036, A3039)</description>
  <cas>16275-44-8</cas>
  <pubchem-id>27790</pubchem-id>
  <chemical-formula>C6H7NO3</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>Butenolide causes lipid peroxidation, disrupting the membrane lipid bilayer and causing damage to membrane protiens. It also induces production of reactive oxygen species by impairing the activities of complexes I–IV of the mitochondrial respiratory chain, especially in the liver, leading to oxidative stress. In addition, butenolide disrupts the cation gradient by inhibiting the activity of Ca2+/Mg2+-ATPase and Na+/K+-ATPase, likely either as a side effect of lipid peroxidation or by binding to the sulfhydryl groups in the active sites of these enzymes. (A3036, A3037)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity>LD50: 44 mg/kg (Intraperitoneal, Mouse) (A3038)
LD50: 275 mg/kg (Oral, Mouse) (A3038)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>Not listed by IARC.</carcinogenicity>
  <use-source>Butenolide is a mycotoxin found in various species of fungi of the genus Fusarium. It can often be found in contaminated agricultural products. (A3036)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Butenolide is cardiotoxic and hepatotoxic. Fusarium mycotoxins has been associated with both alimentary toxic aleukia, and esophageal cancer. Consumption of Fusarium mycotoxins-contaminated foodstuffs has also been considered as a suspected etiological factor for Kashin–Beck disease and Keshan disease. (A3036, A3039)</health-effects>
  <symptoms>Butenolide irritates the eyes and skin. It may also cause weight loss and growth retardation. (A3036, A3038)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-13T14:52:29Z</created-at>
  <updated-at type="dateTime">2026-04-06T11:39:00Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Butenolide</wikipedia>
  <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>CC(O)=NC1OC(=O)C=C1</moldb-smiles>
  <moldb-formula>C6H7NO3</moldb-formula>
  <moldb-inchi>InChI=1S/C6H7NO3/c1-4(8)7-5-2-3-6(9)10-5/h2-3,5H,1H3,(H,7,8)</moldb-inchi>
  <moldb-inchikey>HUSDLVGPEKVWAL-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">141.1247</moldb-average-mass>
  <moldb-mono-mass type="decimal">141.042593095</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>CHEM002721</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00122085</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>58.89</moldb-polar-surface-area>
  <moldb-refractivity>33.900299999999994</moldb-refractivity>
  <moldb-polarizability>12.990713637260011</moldb-polarizability>
  <moldb-rotatable-bond-count>1</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>5.564901124556345</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-0.8366488483879436</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>0.74</moldb-alogps-logp>
  <moldb-alogps-logs>-1.12</moldb-alogps-logs>
  <moldb-alogps-solubility>1.07e+01 g/l</moldb-alogps-solubility>
</compound>
