In this study, a data set of 34 pyrrolidine-based organocatalysts applicable on asymmetric aldol reaction were considered. The data set was subjected to Density Functional Theory(DFT) optimization using BLY3P/6-31G* modeland Quantitative Structure-Property Relatisonship(QSPR) calculation. From the optimization and calculation, several electronic, topological and stereochemical-based descriptors were generated which led to the development of five regression models. The best model (Model one), with R2= 0.84 and Rext=0.88, was used to adjust theprolinestructure for finding new catalyst candidates A simulation reaction was carried out in which the candidate catalyst was applied over asymmetric aldol reaction between acetone and 4-nitrobenzaldehyde in an acetone medium. A plausible mechanism of the reaction was developed using HOMO-LUMO energies calculated using density functional theory at 6-31G*/B3LYP level of theory. From the itemized elementary steps, the fourth step was identified as the rate-determining step, with the highest activation energy of 54.20 kJmol-1.The mechanism was used to derive the rate law from which the overall rate constant was calculated and found to be 0.787 M-1 s-1. The simulation reaction was also conducted on the same reaction catalyzed by proline and themechanism was developed. New mechanistic steps that followed the previously reported iminium-enamine route of typical class 1 aldolase enzymes were proposed in greater detail. From the elementary steps, the first step which involves a bimolecular collision of acetone and proline was considered as the rate-determining step, having the highest activation energy of 59.07 kJmol-1. The mechanism was used to develop the rate law from which the overall rate constant was calculated and found to be 4.04Ã—10âˆ’8ð‘‘ð‘š3ð‘€ð‘œð‘™âˆ’1ð‘ âˆ’1. The new mechanistic insights and the explicit computation of the rate constant further improved the kinetic knowledge of the reaction.