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Drug Design, Molecular Descriptors in

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Encyclopedia of Complexity and Systems Science

Definition of the Subject

Empirical observations of association between chemical structures and their physical, chemical, or biological properties have a longhistory [1], but the real development of mathematical correlations started in the 20th century. Forphysico‐chemical properties, topological indices and their applications were first published by Wiener in 1947 followed soon by Platt and Hosoya, aswill be shown later. Quantitative structure‐activity relationships (QSARs) have 1962 as official birthdates with the connection between Hammettsubstituent constants, lipophilicity, and biological activities, as will be discussed below.

The huge development in analytical and synthetic methods, leading to combinatorial chemistry, high‐throughput screening, and virtual screening(ligand- or structure‐based) on one hand, and on the other hand to the progress in computational hardware and software that allows the processing ofmillions of virtual structure libraries, have made it possible to...

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Abbreviations

ADMET :

Absorption, distribution, metabolism, excretion, and toxicity, five factors which determine whether a compound with favorable features resulting from a computer‐assisted drug design will also be a useful medicinal drug.

Local vertex invariant (LOVI):

A number associated with a vertex of a molecular graph. It does not depend on the arbitrary numerical labeling of vertices.

Molecular descriptor:

A mathematical entity (either a number, or a set of numbers characterizing substituents or molecular fragments) associated with a chemical structure, allowing quantitative manipulations of such structures (correlations with properties, clustering, ordering or partial ordering, determination of similarity or dissimilarity). Constitutional isomerism is associated with topological indices or other two‐dimensional descriptors, whereas stereoisomerism requires three‐dimensional descriptors.

Molecular graph:

Constitutional chemical formula representing atoms by points (vertices) and covalent bonds by lines (edges). Hydrogen atoms are usually omitted (in hydrogen‐depleted graphs) and carbon atoms are not shown explicitly, but other atoms are assigned weights according to the nature of the heteroatom. Multiple bonds are shown explicitly in multigraphs.

Pharmacophore:

A set of chemical features that determine the biological activity.

Quantitative structure‐activity relationship (QSAR):

Mathematical correlation (e. g. a mono- or multi‐parametric equation) between a physical or a chemical property and molecular descriptor(s).

Receptor:

Physiological macromolecule (usually a protein, but sometimes DNA or RNA), also called target, to which a drug (ligand) binds.

Quantitative structure‐property relationship (QSPR):

Mathematical correlation (e. g. a mono- or multi‐parametric equation) between a biological property and molecular descriptor(s).

Quantitative structure‐toxicity relationship (QSTR ):

Mathematical correlation (e. g. a mono- or multi‐parametric equation) between toxicologic properties and molecular descriptor(s).

Topological index (TI) :

A number characterizing a molecular constitutional graph, resulting from mathematical operations on the LOVIs, or edges/vertices of the graph.

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  1. Texas A&M University, Galveston, USA

    Alexandru T. Balaban

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  1. Alexandru T. Balaban
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  1. RAMTECH LIMITED, 122 Escalle Lane, Larkspur, CA, 94939, USA

    Robert A. Meyers Ph. D. (Editor-in-Chief) (Editor-in-Chief)

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© 2009 Springer-Verlag

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Balaban, A.T. (2009). Drug Design, Molecular Descriptors in. In: Meyers, R. (eds) Encyclopedia of Complexity and Systems Science. Springer, New York, NY. https://doi.org/10.1007/978-0-387-30440-3_136

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