In the current analysis, we identified 8902 ring systems, 3853 were only present in NAPROC-13 NPs, 2973 were only present in UNPD-A, and 438 were only present in FDA-approved drugs. The major overlapping set was between NAPROC-13 and UNPD-A, as expected, with 1504 ring systems. Between UNPD-A and FDA-approved drugs, there is an overlap of 229 ring systems, and between NAPROC-13 and FDA-approved drugs of 109 ring systems. Finally, 102 ring systems are shared among the three databases The predominant ring system in NP databases under study is the chromone (1-benzopyran-4-one) core, which serves as the structural foundation for flavonoids. Flavonoids, abundant in plants, play pivotal roles in essential metabolic pathways and have been linked to various biological activities, notably their antioxidant properties. Remarkably, this ring system is also prevalent among FDA-approved drug structures. Additionally, both NP databases exhibit a significant presence of diverse steroid-type cores, which are well-documented for their wide-ranging bioactivities. In their most frequent ring systems, UNPD-A exhibits nitrogen-containing ring systems in limited quantities, while NAPROC-13 lacks such structures entirely. Contrastingly, both databases include oxygencontaining ring systems. These characteristics align with the typical patterns observed in natural products and contrast with synthetic compounds like FDA-approved drugs. Conversely, UNPD-A displays a marked abundance of quinone-type cores, a feature notably absent in NAPROC-13. Quinones are intriguing NPs known for their dual nature, possessing both beneficial and potentially toxic effects in humans. This characteristic positions quinones as a promising area for ongoing and future investigations into their therapeutic potential and safety profile. 54