Derrubone
Names
IUPAC name
5,7-Dihydroxy-6-(3-methylbut-2-en-1-yl)-3′,4′-[methylenebis(oxy)]isoflavone
Systematic IUPAC name
3-(2H-1,3-Benzodioxol-5-yl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-1-benzopyran-4-one
Other names
5,7-Dihydroxy-3',4'-methylenedioxy-6-prenylisoflavone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C21H18O6/c1-11(2)3-5-13-15(22)8-18-19(20(13)23)21(24)14(9-25-18)12-4-6-16-17(7-12)27-10-26-16/h3-4,6-9,22-23H,5,10H2,1-2H3 ☒N
    Key: FTBGFGQPUMCUSC-UHFFFAOYSA-N ☒N
  • InChI=1/C21H18O6/c1-11(2)3-5-13-15(22)8-18-19(20(13)23)21(24)14(9-25-18)12-4-6-16-17(7-12)27-10-26-16/h3-4,6-9,22-23H,5,10H2,1-2H3
    Key: FTBGFGQPUMCUSC-UHFFFAOYAI
  • CC(=CCC1=C(C=C2C(=C1O)C(=O)C(=CO2)C3=CC4=C(C=C3)OCO4)O)C
Properties
C21H18O6
Molar mass 366.369 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Derrubone is a prenylated isoflavone, a type of flavonoid. It was originally isolated from the Indian tree Derris robusta.[1] Recent research indicates that it acts as an inhibitor of Hsp90 to its function as a chaperone protein.[2]

References

  1. ^ East AJ, Ollis WD, Wheeler RE (1969). "Natural occurrence of 3-aryl-4-hydroxycoumarins. Part I. Phytochemical examination of Derris robusta(roxb.) benth". J. Chem. Soc. C. 3 (3): 365–74. doi:10.1039/J39690000365.
  2. ^ Hadden MK, Galam L, Gestwicki JE, Matts RL, Blagg BS (December 2007). "Derrubone, an inhibitor of the Hsp90 protein folding machinery". J. Nat. Prod. 70 (12): 2014–8. doi:10.1021/np070190s. PMID 18020309.


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