Based on the prioritization suggested by the similarity algorithm, the interactions of DHPPIQ 2-aldehyde adducts with cholinesterases (ChEs) and other Alzheimer’s disease (AD)-related targets (i.e., β-amyloid aggregation and monoamine oxidases) were evaluated, which led us to identify some DHPPIQ derivatives as hits of prospective multitarget-directed ligands (MTDLs) for this fatal neurodegenerative disorder. This evidence concerns the gene BCHE and early-onset autosomal dominant Alzheimer disease.