(9aS)-8-Acetyl-9,9a-dihydro-1,3,7-trihydroxy-9a-methyl-9-oxo-4-dibenzofurancarboxamide

ChEBI: A member of the class of dibenzofurans that is a potent broad spectrum antifungal agent isolated from the fungus Cercosporidium henningsii.

Cercosporamide is a member of the class of dibenzofurans that is a potent broad spectrum antifungal agent isolated from the fungus Cercosporidium henningsii. It has a role as an antifungal agent, a phytotoxin, a fungal metabolite and an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor. It is a member of dibenzofurans, a polyphenol, a monocarboxylic acid amide and a methyl ketone.

Cercosporamide is a natural antifungal phytotoxin isolated from the Cercosporidium fungus, which infects the leaves of cassava plants. Its antifungal effect results from itsselective and potent inhibition of fungal PKC-like 1 kinases (Pkc1), which are central to cell wall integrity (IC50 = 25 nM for Candida Pkc1). Cercosporamide less effectively inhibits human PKC isoforms PKCα, β, and γ (IC50s = 1.02, 0.35, and 5.8 μM, respectively), an action linked to lowering of plasma glucose in hyperglycemic mice. However, it potently inhibits MAPK-interacting kinases Mnk1 and Mnk2 (IC50 = 115 and 11 nM, respectively), reducing protein translation in cancer cells. Cercosporamide is orally bioavailable.

Molecular Weight:331.28
XLogP3:0.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:331.06920175
Monoisotopic Mass:331.06920175
Topological Polar Surface Area:147
Heavy Atom Count:24
Complexity:709
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes