Inflammation involves multiple processes in an organism, which respond to lesions related to harmful stimuli. After the stimuli by bacterial metabolites, such as the lipopolysaccharide, immune cells produce cytokines and pro-inflammatory biomarkers. Therefore, an alternative to attenuate this unbalanced organism status would be to inhibit the inflammatory cascade response. Vegetable food rich in polyphenols are correlated to health benefits in many studies, specially for their anti-inflammatory potential. Notwithstanding, the potential effects of bioactive compounds are determined by their bioavailability, which determines the liberation and solubility of these compounds during digestion for further absorption. Anthocyanins, a type of polyphenol, are found in several food and plants, especially in berries. Jaboticaba, also known as “Brazilian berry”, is a small fruit with a dark purple skin, normally discarded, which is rich in anthocyanins and phenolic acids. Despite jaboticaba peel health benefits being extensively reported in literature, the bioavailability and colonic biotransformation of its bioactive compounds is not always considered. Therefore, this study aims to investigate the anti-inflammatory potential of jaboticaba peel phenolic compounds and digestion metabolites through the in-silico screening with enzymes involved in the inflammatory cascade. 27 bioactive compounds and 18 enzymes have been retrieved from Pubchem database and Protein Data Bank, respectively. After the active site definition, molecular docking proceeded AutoDock v4.2 software. IKKa, COX1, P13K, myD88 and IRAK4 have been the most inhibited proteins. Cyanidin, in the chalcone form, generally required very low energy for binding, showing even a greater potential against COX-1 than well-known inhibitors (estimated free binding energy: -9,56). However, the chalcone form instability and higher binding energy of anthocyanins metabolites (from -5 to -3) have to be considered. On the other hand, ellagic acid biding energy is maintained or overcomed by its metabolites, especially urolithins, presenting low binding energies, down to -7,85 (urolithin A and P13K docking).