Since endophytes have been acknowledged as synthesizers of diverse natural metabolites, these reliable sources has received significant attention by contributing a substantial role in drug discovery. Pilot studies from Dr. Jisha MS’s laboratory have isolated a potent mycoendophyte from surface sterilized root segments of Withania somnifera. Based on its phylogenetic analysis using a polyphasic approach, this isolate was identified as a taxonomically novel species named as Penicillium setosum sp.nov. One of her research scholar, Ms. Sherin Varghese has explored this discovery to new heights by bringing further developments in this field. By using two dimensional analytical techniques like Ultra Performance Liquid Chromatography coupled to Quadrapole Time – of – Flight Mass Spectrometry (UPLC – Q – ToF – MS) and Gas Chromatography – Mass Spectrometry (GC – MS), she has executed the chemotaxonomic profiling of Penicillium setosum sp.nov. The results revealed that P. setosum could synthesize a mass array of bioactive compounds endowed with multifunctional biological activities. The bioactive compounds comprehended diketopiperazines (Cyclo (L-Pro L-Val) and Cyclo (leucyl prolyl)), sesquiterpenes (Dihydroartemisinate), imidazole derivatives (Etomidate), polyketides (Patulin), anthocyanidins (Diosmetinidin), flavonoids (Quercetin and its derivatives), tannins (n-Octyl gallate), Salicylate etc. These compounds harbored varied biological activities such as antimicrobial, antioxidant, anti inflammatory and anticancer activities. Studies on the antibacterial efficacy of the active fraction of P. setosum revealed that Quercetin and its derivatives displayed significant antibacterial activity with the minimum inhibitory concentration of 8µg/ml against E.coli and Staphylococcus aureus. In silico docking studies to predict the anticancer potential of these compounds have revealed that Diosmetinidin (-10.01kcal/mol) could effectively interact with the selected target receptor FLT3 receptor of human responsible for acute myeloid leukemia. n-Octyl gallate (-7.4kcal/mol) and Quercetin acetate (-7.2kcal/mol) could interact with Human Androgen Receptor responsible for prostate cancer. Hence, these novel discoveries have uncovered the fact that Penicillium setosum sp.nov isolated from Withania somnifera can be deemed as an authentic source for novel bioactive metabolites that have extraordinary potential for developing them into successful pharmaceutical agents.