RdScaffoldNetwork: The Scaffold Network Implementation in RDKit.

Abstract

We present an implementation of the scaffold network in the open source cheminformatics toolkit RDKit. Scaffold networks have been introduced in the literature as a powerful method to navigate and analyze large screening data sets in medicinal chemistry. Such a network can be created by iteratively applying predefined fragmentation rules to the investigated set of small molecules and by linking the produced fragments according to their descendence. This procedure results in a network graph, where the nodes correspond to the fragments and the edges correspond to the operations producing one fragment from another. In extension to the scaffold network implementations suggested in the literature, the presented implementation in RDKit allows an enhanced flexibility in terms of customizing the fragmentation rules and enables the inclusion of atom- and bond-generic scaffolds into the network. The output, providing node and edge information on the network, enables a simple and elegant navigation through the network, laying the basis to organize and better understand the data set being investigated.