Protein-tyrosine phosphatase 1B (PTP1B) is an attractive target for the treatment of type 2 diabetes. Oleanolic acid and its derivatives were found to be potent PTP1B inhibitors. In this study, we have performed QSAR studies followed by molecular docking. The docking study shows that most of the ligands can form hydrogen bonds with ARG24 and/or ARG254. Two quantitative structure activity relationships models have been constructed using different descriptors and the significance of these models is judged on the basis of correlation, Fischer F test, and quality factor (Q). It is believed that this study is helpful in the design of potent PTP1B inhibitors.