In the authors' collective experience, we have noticed how simple notions of exploited vectors can be a useful descriptor towards quantifying chemical diversity of a molecular series. Exploited vectors (EVs) are points of functionalization of a central scaffold, i.e. a subset of exit vectors of the scaffold that are functionalized. By identifying and analyzing these features, a quantitative, and importantly, objective, description of chemical diversity is ascertained. These descriptors are simple and easily interpretable by medicinal chemists, facilitating objective quantification of chemical diversity. Among them, we introduce the Exploited Vector Pattern (EVP) framework. EVPs uniquely characterize the various substitution patterns explored within a specific scaffold, i.e. an exhaustive list of different combinations of exit vectors that have been functionalized. This manuscript sets out how the EVP framework can be used throughout the medicinal chemistry optimization process. Firstly, we show that EVPs can be used to evaluate the progressibility of a molecular scaffold in the design of a bespoke fragment screening library. This application highlights the benefit of considering whether diverse chemical matter around each scaffold has been chemically explored and is readily available from commercial sources. By prioritising the range of available EVPs in a model fragment library design pipeline, rapid expansion of identified hit matter from fragment screens can be initiated by purchasing a diverse set of structurally related chemical matter.