<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3814</id>
  <title>T3D3760</title>
  <common-name>Fumagillin</common-name>
  <description>Fumagillin is a mycotoxin found in the fungus Aspergillus fumigatus. It is an antimicrobial agent and amebicide that has been used in the treatment of microsporidiosis and other infections, especially in immunodeficient patients. It also has been investigated as a angiogenesis inhibitor in the treatment of cancer. Since fumagillin is often used to treat microsporidiosis in bees, it can be found as a contaminant in honey. (L1966, A3058)</description>
  <cas>23110-15-8</cas>
  <pubchem-id>6436022</pubchem-id>
  <chemical-formula>C26H34O7</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>Fumagillin blocks blood vessel formation (angiogenesis) by inhibiting the enzyme methionine aminopeptidase 2. This prevents angiogenesis by arresting endothelial cells in the G1 phase of the cell cycle. Inhibition of angiogenesis can suppress tumor growth and metastasis. Methionine aminopeptidase 2 inhibition also blocks Wnt signaling, which plays a critical role in development, cell differentiation, and tumorigenesis. (A3059, A3060)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Fumagillin is a mycotoxin found in the fungus Aspergillus fumigatus. It is an antimicrobial agent and amebicide that has been used in the treatment of microsporidiosis and other infections, especially in immunodeficient patients. It also has been investigated as a angiogenesis inhibitor in the treatment of cancer. Since fumagillin is often used to treat microsporidiosis in bees, it can be found as a contaminant in honey. (L1966, A3058)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Fumagillin can be genotoxic, clastogenic, and cytotoxic. It may also cause thrombocytopenia, neutropenia and hyperlipasaemia. (A3058, A3061, A3062)</health-effects>
  <symptoms>Fumagillin may cause abdominal cramps, vomiting, and diarrhea. (A3062)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-19T15:34:28Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:30Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Fumagillin</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>DB02640</drugbank-id>
  <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>COC1C(CCC2(CO2)C1C1(C)OC1CC=C(C)C)OC(=O)C=CC=CC=CC=CC(O)=O</moldb-smiles>
  <moldb-formula>C26H34O7</moldb-formula>
  <moldb-inchi>InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+</moldb-inchi>
  <moldb-inchikey>InChIKey=NGGMYCMLYOUNGM-HCNIIHBUSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">458.544</moldb-average-mass>
  <moldb-mono-mass type="decimal">458.230453442</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>&lt;p&gt;Peterson, M.H., Goldstein, A.W. and Denison, F.W. Jr.; U.S. Patent 2,803,586; August 20, 1957; assigned to Abbott Laboratories.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
