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INTRODUCTION
Molecular descriptors are numerical values that characterize properties of molecules Examples:
Physicochemical properties (empirical) Values from algorithms, such as 2D fingerprints
Not likely to discriminate sufficiently when used alone Combined with other descriptors for best effect
Physicochemical Properties
Hydrophobicity
LogP the logarithm of the partition coefficient between n-octanol and water
ClogP (Leo and Hansch) based on small set of values from a small set of simple molecules
BioByte: http://www.biobyte.com/
Daylights MedChem Help page
http://www.daylight.com/dayhtml/databases/medchem/m edchem-help.html
Isolating carbon: one not doubly or triply bonded to a heteroatom
Molar Refractivity
MR = n2 1 MW -------- ----n2 + 2 d where n is the refractive index, d is density, and MW is molecular weight. Measures the steric bulk of a molecule.
Topological Indexes
Single-valued descriptors calculated from the 2D graph of the molecule Characterize structures according to size, degree of branching, and overall shape Example: Wiener Index counts the number of bonds between pairs of atoms and sums the distances between all pairs
Chi indexes introduces valence values to encode sigma, pi, and lone pair electrons
2D Fingerprints
Two types:
One based on a fragment dictionary
Each bit position corresponds to a specific substructure fragment Fragments that occur infrequently may be more useful
Atom-Pair Descriptors
Encode all pairs of atoms in a molecule Include the length of the shortest bond-bybond path between them Elemental type plus the number of nonhydrogen atoms and the number of bonding electrons
BCUT Descriptors
Designed to encode atomic properties that govern intermolecular interactions Used in diversity analysis Encode atomic charge, atomic polarizability, and atomic hydrogen bonding ability
Scaling (standardization): making sure that each descriptor has an equal chance of contributing to the overall analysis Correlations Reducing the dimensionality of a data set: Principal Components Analysis