Ilimaquinone
| Names | |
|---|---|
| Preferred IUPAC name
3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C22H30O4 | |
| Molar mass | 358.478 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
| |
Ilimaquinone is a bioactive marine natural product belonging to the class of sesquiterpene quinones. It was first isolated in 1979 from the marine sponge Hippospongia metachromia. Since then, it has also been identified in other marine sponges, including Dactylospongia elegans and Halichondria species. The compound features a 4,9-friedodrimane skeleton, containing four stereocenters, that is linked via a methyl bridge to a 2,5-dioxygenated benzoquinone.
Ilimaquinone has attracted interest in natural products and drug discovery research, owing to its diverse biological activities, which include antiproliferative, antiviral, and herbicidal effects. The originally reported structure of ilimaquinone contained an incorrect stereochemical assignment, which was revised in 1987 by Capon and colleagues through spectroscopic analysis.