Derrubone

Derrubone
Names

IUPAC name 3-(1,3-Benzodioxol-5-yl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
Other names 5,7-Dihydroxy-3',4'-methylenedioxy-6-prenylisoflavone
Identifiers
CAS Number	22044-58-2^N
ChEMBL	ChEMBL412010^N
ChemSpider	4709237^N
Jmol interactive 3D	Image
PubChem	5810067
InChI 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
SMILES CC(=CCC1=C(C=C2C(=C1O)C(=O)C(=CO2)C3=CC4=C(C=C3)OCO4)O)C
Properties
Chemical formula	C₂₁H₁₈O₆
Molar mass	366.37 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

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

↑ 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: 365–74. doi:10.1039/J39690000365.
↑ 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.

Isoflavones and their glycosides

Isoflavones	Daidzein Genistein Irilone Orobol Pseudobaptigenin Anagyroidisoflavone A and B

O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin

Glycosides	Daidzin Genistin Iridin Ononin Puerarin Sophoricoside Tectoridin

Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone

Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone

Misc	Rotenoids

Synthetic	Ipriflavone

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