Non-coding RNAs account for up to 80 % of the human genome.1 It has become increasingly clear that non-coding RNAs play a diverse and critical role in many important cellular functions.2 Although modulation of non-coding RNAs using small molecules has been demonstrated to be a promising therapeutic strategy, the structure-interaction relationships of RNA targeting small molecules remain largely unexplored.3 We hereby present a fragment-based drug discovery approach where NMR identified hits were validated and ranked by SPR, and binding poses were modelled using NOESY data in combination with molecular docking to evaluate and elaborate fragment hits against a theophylline aptamer model system. The methods used in this study have the potential to be applied to a variety of novel RNA targets.