The druggability of the Schiff bases and dithiocarbamate derivatives of chitosan was examined; the oral bioavailability and bioactivity of all these molecules against selected drug targets were investigated, as well as ADME/Tox studies were conducted. It was observed that the Lipinski's rule of five was satisfied by all the molecules. The Schiff bases and dithiocarbamate derivatives of chitosan also show good bioactivity score for protease and enzyme inhibition. The ADME/Tox studies conducted show that almost all the derivatives are free from toxicity risks, except citral- and sulfur-containing derivatives. Substitution of the -SH group by -NH2 gives better positive results in toxicology studies. From this study, it has been observed that these molecules exhibit fairly good drug score and are orally viable molecules. The mechanism driving their bioactivity might be chelation of chitosan and its derivatives with essential metal ions. Chitosan and the derivatives studied can serve as good lead molecules for further research.