Protein-ligand interactions account for numerous controllable metabolic processes in the body. Due to their high specificity, proteins, such as enzymes, are prime targets for drug-induced modulations of metabolic intermediates to effect the desired physiological responses. For instance, the enzyme 3- hydroxy-3-methylglutaryl-CoA reductase (HMGR), an enzyme responsible for a committed step in cholesterol biosynthesis, is targeted by inhibitors called ‘statins’ to reduce LDL cholesterol levels in the blood, a hallmark of cardiovascular diseases (CVD). In a previous study conducted by Saludes, et al. at University of San Agustin CND3, pineapple fruit was found to contain the small molecule ligand N1,N10-diferuloylspermidine that inhibited HMGR and lipase activities in vitro. This proposed study, therefore, aims to validate the inhibitory mechanism of action of N1,N10-diferuloylspermidine at the molecular level. This goal will be achieved using two approaches: (1) in silico molecular docking tools and (2) solution state NMR spectroscopy. The information derived from the above strategies shall provide insights on the structural motifs responsible for the ligand binding to the target enzymes. This knowledge shall, in turn, stimulate rational drug designs geared towards HMGR and lipase inhibition for the benefit of Filipinos who suffer from CVDs.