Macrocyclic natural products with rotational symmetries were particularly challenging for chiral fingerprints. For instance, only MAP4C and MAP6C correctly identified the 136 possible stereoisomers of the cyclic peptide antibiotic quinaldopeptin (9) and the 2,080 stereoisomers of the cytotoxic macrocyclic depsipeptide onchidin (10), two natural product macrocycles with C2 symmetry. By contrast, the 528 stereoisomers of the C2 symmetrical antimicrobial macrocyclic peptide gramicidin S (11) were only distinguished by MAP6C. Furthermore, none of the chiral fingerprints tested was able to cope with the C3 symmetrical dodecadepsipeptide antibiotic valinomycin (12, 1,376 stereoisomers), the C4 symmetrical macrolide ionophore antibiotic nonactin (13, 16,456 stereoisomers), or the C7 symmetrical hepta-arginine cyclic peptide NP213 developed as antifungal agent (14, 20 stereoisomers). Note that all fingerprints were used with 2,048-bits, but that performance did not increase significantly when using much larger bit sizes or without MinHashing or folding. for structural formulae. b) N = number of stereocenters in the molecule. Sym. = rotational molecular symmetry for the molecule without chiral labels. c) Number of possible stereoisomers considering inversion of all chiral centers in the molecule and the internal symmetry, or number of sequence isomers (scrambled). The number of different fingerprint values for each fingerprint type is given in the following columns. All fingerprint were used with 2,048 bit size unless otherwise noted. d) all stereocenters in the molecule are considered. e) amino acids are scrambled, the N-terminal fatty acid and the branching Dab residue are maintained. f) only the α-carbon chirality of the scrambled residues was considered here, which corresponds to 512 stereoisomers per scrambled sequence. g) with 4,096 bits, only 135 different FP values are obtained with 2,048 bits due to a bit collision.