Brevianamide F (cyclo(L-Pro-L-Trp)) is a diketopiperazine metabolite isolated from a fermentation of Penicillium brevicompactum by Birch and co-workers in 1970. The structure of brevianamide F was elucidated by the same group two years later. Brevianamide F was subsequently reported as a metabolite common to a number of bacteria and fungi. It is therefore a useful standard for chemical and bioassay dereplication. Brevianamide F exhibits broad spectrum antibacterial activity and enhances the maturation of mammalian cells.