Aldose reductase (AR) is a crucial metabolic enzyme in the polyol pathway, responsible for converting glucose to sorbitol in tissues independently of insulin. This process is significantly accelerated in hyperglycemic conditions, leading to sorbitol accumu lation in tissues and resulting in microvascular complications. To discover new aldose reductase inhibitors, a group of naturally occurring compounds: seven Rhodanine (RH 1 to RH 7) and seven Rhodanine 3 acetic acid (RA 1 to RA 7) derivatives were investig ated through in silico analysis. Among all the compounds, RA 2 exhibited potent inhibitory activity against aldose reductase, with a binding affinity of 9.6 kcal/mol. Further molecular dynamics simulations and binding free energy calculations suggested th at RA 2 showed greater stability, flexibility, and binding energy. These findings suggest that RA 2 could be promising for treating diabetic complications, pending further in vitro and in vivo investigations.