Serendipitous Discovery of a Novel Indole Derivative With Promising Multitarget Inhibitor and Its ADME Properties

ABSTRACT Ascidians are the source of biologically active indole‐based secondary metabolites with promising potential biomedical applications. Indole‐containing compounds often display cytotoxicity against cancer cell lines, making them valuable leads for anticancer drug discovery. Here, we unexpectedly discovered a novel indole derivative during the attempted synthesis of Herdmanine A. Promising multitarget interactions were discovered through spectroscopic characterization, followed by molecular docking against nine therapeutically relevant targets (including TB, AChE, HIV‐1 protease, EGFR, and COVID‐19 M pro ). Across these targets, TB target 1EVE showed the highest affinity (−9.6 kcal/mol). In silico ADME analysis predicted good absorption and drug‐like properties, supporting its potential as a lead compound. This serendipitous discovery highlights the potential of indole‐based analogues of marine metabolites as promising drug leads.