﻿AbstractDuring a mycological survey of the Democratic Republic of the Congo, a fungal specimen that morphologically resembled the American speciesHypoxylonpapillatumwas encountered. A polyphasic approach including morphological and chemotaxonomic together with a multigene phylogenetic study (ITS, LSU,tub2, andrpb2) ofHypoxylonspp. and representatives of related genera revealed that this strain represents a new species of theHypoxylaceae. However, the multi-locus phylogenetic inference indicated that the new fungus clustered withH.papillatumin a separate clade from the other species ofHypoxylon. Studies by ultrahigh performance liquid chromatography coupled to diode array detection and ion mobility tandem mass spectrometry (UHPLC-DAD-IM-MS/MS) were carried out on the stromatal extracts. In particular, the MS/MS spectra of the major stromatal metabolites of these species indicated the production of hitherto unreported azaphilone pigments with a similar core scaffold to the cohaerin-type metabolites, which are exclusively found in theHypoxylaceae. Based on these results, the new genusParahypoxylonis introduced herein. Aside fromP.papillatum, the genus also includesP.ruwenzoriensesp. nov., which clustered together with the type species within a basal clade of theHypoxylaceaetogether with its sister genusDurotheca.