Genomic and chemical analysis has revealed that numerous species of filamentous cyanobacteria harbor complex secondary metabolisms tailored to their particular ecological niche. The metabolomic analysis of strains and environmental samples from benthic cyanobacterial mats (BCMs) from coral reefs has the potential to expand the library of marine cyanobacteria-derived natural products. In this study, cyanobacterial strains were obtained from phytobenthos collected from coral reefs in Abrolhos, Brazil and Ishigaki, Japan. Phylogenetic analysis of isolates shows high similarity to previously described members of benthic mats and also suggests the geographic expansion of the Adonisia lineage. Chemical analysis by untargeted liquid chromatography-high resolution mass spectrometry and data processing via MZmine and FBMN-GNPS confirmed the presence of a wide diversity of secondary metabolites. In addition, similarity analysis applying the newly developed tool DBsimilarity indicated the broad coverage of various biosynthetic and chemical classes of compounds previously reported for cyanobacteria. This report is one of the first applications of untargeted metabolomics workflow and similarity network construction for groups of marine filamentous cyanobacteria isolated from benthic mats on corals reefs.