10-fold SMILES augmentation was performed for each molecule, and the co-crystallization potential of the respective 12 API-coformer pairs was predicted with DeepCocrystal (Supporting Table ). For experimental validation, three categories of predictions were considered (Table ): (a) top-two high-certainty, positive prediction (adenine and caffeine), (b) top-two high-certainty, negative predictions (rosmarinic acid and riboflavin), and (c) two most uncertain predictions (theobromine and xanthine). Each selected pair was tested in the lab via well-established protocols, i.e., via grinding, liquid-assisted grinding, and slurry methods . The co-crystallization outcome was determined on the obtained powder samples, via infrared spectroscopy and solid-state nuclear magnetic resonance (see Materials and Methods).