The isolation and structure elucidation of indolotryptoline alkaloid xenocladoniamide F (8) from a cladoniamide heterologous production system is reported. The structure of 8 is determined by NMR and X-ray crystallography. Relative to the parent cladoniamides, 8 lacks any remnant of an N-methylsuccinimide ring. This pentacyclic alkaloid is the most minimal indolotryptoline natural product yet reported. © 2013 Elsevier Ltd. All rights reserved.