Topological descriptor

In the fields of chemical graph theory, molecular topology, and mathematical chemistry, a topological index also known as a connectivity index is a type of a molecular descriptor that is calculated based on the molecular graph of a chemical compound. Topological indices are numerical parameters of a graph which characterize its topology and are usually graph invariant. Topological indices are used for example in the development of quantitative structure-activity relationships (QSARs) in which the biological activity or other properties of molecules are correlated with their chemical structure.

Topological descriptors are derived from hydrogen-suppressed molecular graphs, in which the atoms are represented by vertices and the bonds by edges. The connections between the atoms can be described by various types of topological matrices (e.g., distance or adjacency matrices), which can be mathematically manipulated so as to derive a single number, usually known as graph invariant, graph-theoretical index or topological index. As a result, the topological index can be defined as two-dimensional descriptors that can be easily calculated from the molecular graphs, and do not depend on the way the graph is depicted or labeled and no need of energy minimization of the chemical structure.

The simplest topological indices do not recognize double bonds and atom types (C, N, O etc.) and ignore hydrogen atoms ("hydrogen suppressed") and defined for connected undirected molecular graphs only. More sophisticated topological indices also take into account the hybridization state of each of the atoms contained in the molecule. The Hosoya index is the first topological index recognized in chemical graph theory, and it is often referred to as "the" topological index. Other examples include the Wiener index, Randić’s molecular connectivity index, Balaban’s J index, and the TAU descriptors. The extended topochemical atom (ETA) indices have been developed based on refinement of TAU descriptors.

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