<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3123</id>
  <title>T3D3081</title>
  <common-name>(-)-Gossypol</common-name>
  <description>(-)-Gossypol is found in fats and oils. (-)-Gossypol is a constituent of Gossypium hirsutum (cotton).

(-)-gossypol has been shown to exhibit anti-tumor, anti-cancer and anti-proliferative functions (A7832, A7833, A7834).</description>
  <cas>90141-22-3</cas>
  <pubchem-id>3503</pubchem-id>
  <chemical-formula>C30H30O8</chemical-formula>
  <weight>518.194070</weight>
  <appearance>White powder.</appearance>
  <melting-point>178 - 183°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (ingestion) (L1817) ; dermal (L1817)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Gossypol may cause apoptosis via the regulation of Bax and Bcl-2 proteins. It is also an inhibitor of calcineurin and protein kinases C, and has been shown to bind calmodulin. (L1239)</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>Gossypol is a plant toxin found in the cotton plant (genus Gossypium, family Malvaceae). Among other things, it has been tested as a male oral contraceptive in China. In addition to its contraceptive properties, gossypol has also long been known to possess anti-malarial properties. (L1239)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Gossypol may cause low potassium levels and thus causes temporary paralysis. (L1239)</health-effects>
  <symptoms>Symptoms of gossypol poisoning include fatigue, muscle weakness, and at its most extreme, paralysis.  (L1239)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-23T18:26:07Z</created-at>
  <updated-at type="dateTime">2026-04-14T19:16:03Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07667</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>25520</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Gossypol</stitch-id>
  <drugbank-id>DB13044</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>CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C</moldb-smiles>
  <moldb-formula>C30H30O8</moldb-formula>
  <moldb-inchi>InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3</moldb-inchi>
  <moldb-inchikey>QBKSWRVVCFFDOT-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">518.5544</moldb-average-mass>
  <moldb-mono-mass type="decimal">518.194067936</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB40723</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>3383</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 nil="true"/>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002418</chemdb-id>
  <dsstox-id>DTXSID5023110</dsstox-id>
  <toxcast-id>23110</toxcast-id>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde</iupac>
</compound>
