The 7-methoxy-2-(3,4-dimethoxyphenyl)-1-benzofuran- 5-carbaldehyde was synthesized by known literature method (Wittig reaction approach) from vanillin. To deduce the anticancer and antibacterial activity of the 7 -methoxy-2- (3,4-dimethoxyphenyl)-1-benzofuran-5-carbaldehyde, it is docked with different biomarkers of cancer ce ll and bacteria. Grid was generated for each oncoproteins by specifying the active site amino acids. The bind ing model of best scoring analogue with each protein was assesse d from their G-scores and disclosed by docking anal ysis using the XP visualizer tool. An analysis of the receptor -ligand interaction studies revealed that 7-methoxy -2-(3,4- dimethoxyphenyl)-1-benzofuran-5-carbaldehyde is mos t active against 3LAU (Arora 2 kinase) and 1VOM (Dictyostelium myosin) biomarkers and have the feat ures to prove themselves as anticancer drugs. The C ramer rules of toxicity predicts the toxicological hazard (when administered orally) from the molecular stru cture. It shows that it is class III toxic compound. Also stereoche mistry and molecular parameters are studied by usin g Avogadro’s software. Both MB and MTT assay shows that, 7-metho xy-2-(3,4-dimethoxyphenyl)-1-benzofuran-5-carbaldeh yde is strong cytotoxic against (A-459) human lung cell li ne than (MCF-07) breast cancer cell line.