A Molecular Fragment Database Generated through Simulated Sequential Single-Bond-Breaking

Abstract

We implemented a straightforward algorithm for generating a list of potential molecular fragments from a given molecule by simulating sequential fracturing of single bonds; we refer to this approach as the Simulated Sequential Single-Bond-Breaking (3S2B) algorithm. Applying the algorithm to a list of chemical structures, we generated a searchable database of molecular fragments. In this article, we describe the 3S2B algorithm and demonstrate three uses for the molecular fragment database: (i) to propose possible molecular structures for a given high (or low)-resolution mass value, (ii) to evaluate the quality of measured mass spectra for known compounds, and (iii) to propose possible identities for mass spectra of unknown compounds without a reference mass spectral database. An implementation of the 3S2B algorithm and command line interface for working with the molecular fragment database is available: https://github.com/EightBitAdder/3S2B-CLI.