To obtain a preliminary insight into the carbonic anhydrase inhibitory potentials of our randomly sketched synthetically feasible 3-substituted coumarins, we investigated their molecular similarity to all the compounds in the ChEMBL-28 database. The upstream stage of this pharmacology prediction approach was performed using DataWarrior 5.5.0, where ChEMBL compounds of ≥70% similarity (based on the FragFp descriptor) to our 3-substituted coumarins were retrieved, then the SkeletonSpheres descriptor was calculated for the whole chemical library (Figure ). These chemical data were then channeled to a custom R 4.1.2 pipeline to enable a more flexible downstream analysis process, which culminated with a Fisher's exact test to enrich the biological annotations retrieved from ChEMBL. The output information of the downstream analysis (Table ) was indeed successful in illuminating our decisions along the rest of the study. The data points were spatially organized on the map using the rubber band scaling algorithm of DataWarrior.