LINGO-DOSM: lingo for descriptors of outline shape of molecules

Abstract

The linear notations are more compact than connection tables so they can be useful for storing and transmitting large number of chemical structures. Implicitly they contain the information needed to compute all kinds of molecular structures and, thus, molecular properties derived from these structures. In this DOSM is a new method of obtaining a rough description of 2D molecular structure from its 2D connection graph in the form of character string. Our method is based on the fragmentation of DOSM strings into overlapping substrings of a defined size that we call LINGO-DOSM. The integral set of LINGO-DOSM derived from a given DOSM string, LINGO-DOSM allows rigorous structure specification using very small and simple rule. In this paper, we study the possibility of using the textual descriptor for describing the 2D structure of the molecule. Simulated virtual screening experiments with the MDDR database show clearly the superiority of the LINGO-DOSM descriptor compared to many standard descriptors tested in this paper.