Filamentous fungi are known to be prolific producers of secondary metabolites, such as penicillin, lovastatin, and cyclosporine, and are an important resource for discovering small molecules of pharmaceutical and industrial value. Monascus spp. produced several well-known polyketides such as monacolin K, citrinin, and azaphilone pigments. Azaphilone pigments are a class of fungal metabolites characterized by a highly oxygenated pyrano-qunone bicyclic core and exhibiting a broad range of bioactivities. In this study, the orange pigments will be transformed into red pigments by replacing the oxygen moiety of orange pigments with various nitrogen-containing derivatives. The optimal side chain will be selected by using 3D QSAR approaches, such as pharmacophare development and molecular simulation. The amino acid and amino alcohol derivatives will be tested as the inhibitors of melanogenesis for novel cosmeceuticals.