In summary, we have disclosed a direct electrochemical analysis and reaction of piperine and identified a series of chemically plausible metabolites. Furthermore, predictive modelling of piperine identified the most likely region of the molecule to undergo oxidation in the body. Analysis of the piperine metabolites binding pose within the active heme pocket of CYP3A4 revealed potential molecules that may lead to the inhibitive activity of piperine reported in the literature. Taken together, we have shown an approach that integrates computational docking, electrochemical reaction, and analytical techniques to predict the likelihood of metabolites in a challenging example. The CP-EDM technique may find use in a range of drug discovery endeavours to expedite the prediction and analytical aspects of drug metabolism.