Chemical Property of (9aR)-8-acetyl-1,3,7-trihydroxy-9a-methyl-9-oxodibenzofuran-4-carboxamide
Chemical Property:
- Vapor Pressure:3.61E-14mmHg at 25°C
- Boiling Point:582.5°Cat760mmHg
- Flash Point:306.1°C
- PSA：148.14000
- Density:1.7g/cm3
- LogP:1.59870
- Storage Temp.:?20°C
- Solubility.:chloroform: soluble1mg/mL
- XLogP3:0.9
- Hydrogen Bond Donor Count:4
- Hydrogen Bond Acceptor Count:7
- Rotatable Bond Count:2
- Exact Mass:331.06920175
- Heavy Atom Count:24
- Complexity:709
- Purity/Quality:
-
99% *data from raw suppliers
Cercosporamide *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:Xn
- Statements:
22
- MSDS Files:
-
SDS file from LookChem
Useful:
- Canonical SMILES:CC(=O)C1=C(C=C2C(C1=O)(C3=C(C=C(C(=C3O2)C(=O)N)O)O)C)O
- Isomeric SMILES:CC(=O)C1=C(C=C2[C@](C1=O)(C3=C(C=C(C(=C3O2)C(=O)N)O)O)C)O
-
Uses
Cercosporamide is a potent inhibitor of MAP-kinase interacting kinase-2 (Mnk2) and JAK3. Cercosporamide effectively inhibits eIF4E phosphorylation as well as inibitiing inhibits Pkc1. Cercosporamide displays antiproliferative and proapoptotic activity in cancer cells in vitro. Cercosporamide was originally identified as a host-selective phytotoxin and broad spectrum antifungal agent isolated from Cercosporidium henningsii. More recently, cercosporamide was shown to inhibit a cell wall integrity pathway mediated through a serine/threonine protein kinase, Pkc1, that is central to cell wall biosynthesis. It is both a potent (IC50<50nM) and selective inhibitor of Pkc1 kinase. Cercosporamide is a natural antifungal phytotoxin isolated from the Cercosporidium fungus, which infects the leaves of cassava plants. Its antifungal effect results from its selective 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.
