HU-331

HU-331 is a quinone anticarcinogenic drug synthesized from cannabidiol, a cannabinoid in the Cannabis sativa plant. It showed a great efficacy against oncogenic human cells. HU-331 does not cause arrest in cell cycle, cell apoptosis or caspase activation. HU-331 inhibits DNA topoisomerase II even at nanomolar concentrations, but has shown a negligible effect on the action of DNA topoisomerase I. The cannabinoid quinone HU-331 is a very specific inhibitor of topoisomerase II, compared with most known anticancer quinones. One of the main objectives of these studies is the development of a new quinone derived compound that produces anti-neoplastic activity while maintaining low toxicity at therapeutic doses.

HU-331
Names
Preferred IUPAC name
3-Hydroxy-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylcyclohexa-2,5-diene-1,4-dione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C21H28O3/c1-5-6-7-8-15-12-18(22)19(21(24)20(15)23)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,24H,2,5-10H2,1,3-4H3/t16-,17+/m0/s1 Y
    Key: WDXXEUARVHTWQF-DLBZAZTESA-N Y
SMILES
  • O=C\1C(\O)=C(/C(=O)/C=C/1CCCCC)[C@@H]2\C=C(/CC[C@H]2\C(=C)C)C
Properties
C21H28O3
Molar mass 328.445 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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