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Of the 2.4 million commercially available C2\u2010unsubstituted 1,3\u2010azole compounds, less than 1\u2009% are currently purchasable as their C2\u2010carboxylated derivatives, highlighting the substantial gap in compound availability. This availability gap leaves ample opportunities for exploring the synthetic accessibility and use of carboxylated azoles in bioactive compounds. In this study, we analyze and quantify the relevance of C2\u2010carboxylated 1,3\u2010azoles in small\u2010molecule research. An analysis of molecular databases such as ZINC, ChEMBL, COSMOS, and DrugBank identified relevant C2\u2010carboxylated 1,3\u2010azoles as anticoagulant and aroma\u2010giving compounds. Moreover, a pharmacophore analysis highlights promising pharmaceutical potential associated with C2\u2010carboxylated 1,3\u2010azoles, revealing the ATP\u2010sensitive inward rectifier potassium channel 1 (K<jats:sub>ATP<\/jats:sub>) and Kinesin\u2010like protein KIF18\u2005A as targets that can potentially be addressed with C2\u2010carboxylated 1,3\u2010azoles. Moreover, we identified several bioisosteres of C2\u2010carboxylated 1,3\u2010azoles. 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