IUPAC nomenclature chiral compounds

The chiral identity of a molecule is included in the nomenclature of inorganic compounds, and today s comprehensive system is based upon suggestions made in 1990 in IUPAC s Recommendations on Nomenclature of Inorganic Chemistry [84], and ACS s Inorganic Chemical Nomenclature [90]. The basis for the usage of stereochemical descriptors was laid by Brown [91,92], from which three types of chiral descriptor conventions were developed (i) Steering-wheel-convention [93], (ii) Skew-lines convention [94] and (iii) Oriented-skew-lines convention [95]. 

A special attention is given to stereochemistry, as some compounds are published without proper chirality representation even though the information is available, for example, for natural compounds and their derivatives. Furthermore, as illustrated in Fig. 13.2-8, compounds published in medicinal chemistry literature are often depicted in a human-readable format that is, structures are drawn in a format that chemists can interpret to reconstruct proper chirality. However, this format is not machine-readable , that is, cheminformatics software for 3D structural conversion, or for automatically generating IUPAC (International Union of Pure and Applied Chemistry) nomenclature, cannot perceive the stereo centers correctly... 

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