In organic chemistry, the Cahn–Ingold–Prelog (CIP) sequence rules (also the CIP priority convention; named after Robert Sidney Cahn, Christopher Kelk Ingold, and Vladimir Prelog) are a standard process to completely and unequivocally name a stereoisomer of a molecule. The purpose of the CIP system is to assign an R or S descriptor to each stereocenter and an E or Z descriptor to each double bond so that the configuration of the entire molecule can be specified uniquely by including the descriptors in its systematic name. A molecule may contain any number of stereocenters and any number of double bonds, and each usually gives rise to two possible isomers. A molecule with an integer describing the number of stereocenters will usually have stereoisomers, and diastereomers each having an associated pair of enantiomers. The CIP sequence rules contribute to the precise naming of every stereoisomer of every organic molecule with all atoms of ligancy of fewer than 4 (but including ligancy of 6 as well, this term referring to the "number of neighboring atoms" bonded to a center).The "usually" has its basis in the fact that molecules with chiral centers nevertheless may have mirror planes of symmetry, e.g. meso compounds, that make some of the stereoisomers "degenerate" (identical), so that this mathematical expression overestimates the number. See Clayden, op. cit., p. 317.
