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A new pseudo\u2010NP design principle is described, i.e., the combination of NP\u2010fragments by transformations that are not part of current biosynthesis pathways. A collection of indofulvin pseudo\u2010NPs is obtained from 2\u2010hydroxyethyl\u2010indoles and ketones derived from the fragment\u2010sized NP griseofulvin by means of an iso\u2010oxa\u2010Pictet\u2010Spengler reaction. Cheminformatic analysis indicates that the indofulvins reside in an area of chemical space sparsely covered by NPs, drugs, and drug\u2010like compounds and they may combine favorable properties of these compound classes. 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