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Bioisosteric replacement is a standard technique that is used in medicinal chemistry to design analogs of bioactive molecules with similar biological activity and with additional improved characteristics. Successful application of this technique relies on a good knowledge of physicochemical properties of common organic substituents and an efficient way to navigate their space. In this study the properties of the most common substituents present in bioactive molecules are analysed and a freely-available web tool https://bit.ly/craigplot that allows visualization, analysis and selection of bioisosteric substituents is presented.
Peter Ertl (Tue,) studied this question.