This study investigates how grapevines (Vitis vinifera L.) respond to shading induced by artificial nets, focusing on physiological and metabolic changes. Through a multidisciplinary approach, grapevines’ adaptations to shading are presented via biochemical analyses and hyperspectral data that are then combined with systems biology techniques. In the study, conducted in a ‘Moscatel Galego Branco’ vineyard in Portugal’s Douro Wine Region during post-veraison, shading was applied and predawn leaf water potential (Ψpd) was then measured to assess water stress. Biochemical analyses and hyperspectral data were integrated to explore adaptations to shading, revealing higher chlorophyll levels (chlorophyll a-b 117.39% higher) and increased Reactive Oxygen Species (ROS) levels in unshaded vines (52.10% higher). Using a self-learning artificial intelligence algorithm (SL-AI), simulations highlighted ROS’s role in stress response and accurately predicted chlorophyll a (R2: 0.92, MAPE: 24.39%), chlorophyll b (R2: 0.96, MAPE: 17.61%), and ROS levels (R2: 0.76, MAPE: 52.17%). In silico simulations employing flux balance analysis (FBA) elucidated distinct metabolic phenotypes between shaded and unshaded vines across cellular compartments. Integrating these findings provides a systems biology approach for understanding grapevine responses to environmental stressors. The leveraging of advanced omics technologies and precise metabolic models holds immense potential for untangling grapevine metabolism and optimizing viticultural practices for enhanced productivity and quality.