For peptides, we measured Jaccard distances between pairs of scrambled-sequence isomers versus pairs of stereoisomers with the same sequence for ln65 (7) and polymyxin B2 (1). For peptides, the degree of sequence similarity can also be measured by the Levenshtein distance, which represents the minimum number of mutations necessary to transform one sequence into another one, considering residue type changes, stereochemical inversions, insertions and deletions (Figure and Figure ). Jaccard distances generally increased with increasing Levensthein distances for all fingerprints. Similar to small molecules, distances between peptide stereoisomers were smaller than between sequence isomers only for chiral MAP fingerprints and APC. However, chiral ECFPs assigned larger distances to stereoisomers than to sequence isomers, which probably relates to their inability to distinguish many pairs of sequence isomers. For both ln65 (7) and polymyxin B2 (1), the lower Jaccard distances between stereoisomers compared to sequence isomers was well visible in TMAP representations of each dataset constructed using MAP4C as similarity measure (Figure ). In both cases, there was a complete separation between the 2,048/512 stereoisomers of the parent peptide and the 330/1,512 sequence isomers.