We have developed a novel class of multivalent tubulin mimotopic VDAC-1 peptide like chemical inhibitor assembly by nano-chemical HA14-1 modifying scaffold, which is a Bcl-2 inhibitor discovered in previous scientific projects. Cell-penetrating VDAC1-based peptides were designed and screened to identify the most stable, short and apoptosis-inducing peptides toward CLL-derived lymphocytes revealing the potential of VDAC1-based peptides as an innovative and effective anti-CLL therapy. Multivalency is a design principle that can convert inhibitors with low affinity to ones with high avidity and/or biological “activity” gauged by some relevant parameter: (for example, values of IC50 the concentration of free ligand, often approximated as the total ligand, that reduces the experimental signal to 50% of its initial value). In addition, multivalent approaches can be effective in generating high-avidity ligands for proteins with multiple binding sites from low-affinity ligands. Multivalent ligands (primarily polyvalent ones) are especially well suited for inhibiting or augmenting interactions at biological surfaces (e. g., surfaces of bacteria, viruses, cells they can prevent adhesion of these surfaces to other surfaces by grafting polymers to the surfaces of viruses to prevent adhesion to cells). Computational docking, colchicine-tubulin competitive binding, and tubulin polymerization studies demonstrated that these compounds bind at the colchicine-binding site on tubulin and inhibit the formation of microtubules. The mode of action of the VDAC-1 peptides involves dysfunction of mitochondria energy production and apoptosis induction. In this study, we confine attention to the so called ligand-based target prediction machine learning peptide mimetic drug discovery approaches, commonly referred to as drug target fishing. These results demonstrate that the VDAC1 treating CLL peptides may assist target-fishing approaches that are currently ubiquitous in cheminformatics and can be essentially viewed as single-label peptidomimetic drug discovery schemes. Here, we have for the first time in silico discovered a Novel Class of VDAC1-peptide mimetic Tubulin targeted HA14-1-based multivalent chemical Inhibitor with Promising Anticancer Activities as novel pro-apoptotic annotated agent for B-cell chronic lymphocytic leukemia.