In the analysis of molecular similarity and chirality of enantiomers performed in this paper, we introduce a new local similarity index based on the Hirshfeld partitioning. In the framework of conceptual density functional theory and considering the enantiomers of the halomethane CHFClBr and of the amino acids alanine and leucine, this index is used to investigate the dissimilarity of chiral molecules. Furthermore, we illustrate Mezey's holographic electron density theorem.