A scaffold represents a core concept in medicinal chemistry and is the basis of most design and development efforts. Over time, certain scaffolds achieve "privileged" status, as they are recognized as being key to molecular functionality. Other scaffolds may go in the opposite direction whereby they receive decreasing attention over time. In this study we explored trends in scaffolds in terms of the properties of the compounds containing them with the goal of identifying scaffolds with increasing or decreasing trends. In particular, we considered popularity, bioactivity, and liabilities as the properties that were explored. We used data from ChEMBL_20, considering compounds reported between 1998 and 2014 and fit linear models to property <i>versus</i> time. In the talk we summarize the trends observed for 764 distinct scaffolds and in particular focus on a few “popular” (as revealed within our study) scaffolds. We assume that trends in activity could be used to highlight scaffolds of current interest within the medicinal chemistry community and the degree of interest being mapped to the steepness of the trend. We also explore the notion of popularity, using journal importance as a proxy for perceived popularity of a scaffold. Finally, we present an online tool that allows users to explore property trends for arbitrary scaffolds, based on ChEMBL data.

Scaffold histories: Visualizing temporal trends in scaffold properties

253rd National Meeting (2017)

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