Molecular and pharmacokinetic properties prediction is important determinant in the current drug development process. In this study, molecular and pharmacokinetic properties of phenoxy acids and their derivatives are theoretically predicted using in silico tools to determine how synthetic modifications such as branching, amidation, esterification, heterocyclic groups, and hydrazide group change the structural and pharmacokinetic properties with respect to the parent phenoxy acid. From the results it was observed that phenoxy acid possess good central nervous system (CNS) permeability compared to the acid derivatives. It could also be further predicted that conversion of phenoxy acid to functional derivatives leads to molecules with good pharmacokinetic profile. Based upon these theoretical predictions, it can be concluded that various chemical modifications of phenoxy acid moiety furnish promising derivatives with good pharmacokinetic profile and oral bioavailability.