One chiral fingerprint to find them all

Table 1 Stereoisomer and scrambled sequence distinction task for selected natural products and peptides with multiple chiral centers and varying degrees of internal symmetry

Query^a)	N / Sym.^b)	Total^c)	MAP6C	MAP4C	MAP2C	APC	ECFP6C	ECFP4C
α-D-glucopyranose (2)	5 /–	32	32	32	32	11	32	32
Lactose (3)	10 / –	1,024	1,024	1,024	992	443	1,024	1,024
Trehalose (4)	10 / C₂	528	528	528	516	336	528	512
Validamycin A (5)	14 / –	16,384	16,384	16,384	16,384	7,657	16,384	16,384
Inositol (6)	6 / C_6v	9	9	9	9	1	1	1
ln65 (7)	11 / –	2,048	2,048	2,048	2,048	196	1,140	36
ln65 (scrambled)	11 / –	330	330	330	330	330	8	4
ln65 (dia × scrambled)	11 / –	675,840	675,840	675,840	675,840	90,217	38,500	144
R₉ (8)	9 / –	512	512	512	512	146	88	12
Polymyxin B2 (1)^d)	12 / –	4,096	4,096	4,096	4,096	2,500	4,096	1,536
PMB2 (scrambled)^e)	9 / –	1,512	1,512	1,512	1,512	1,512	861	75
PMB2 (dia × scrambled)^f)	9 / –	774,144	774,144	774,144	774,144	287,631	602,003	9,312
PMB2 (R, S or undefined)	12 / –	531,441	531,441	531,441	531,441	277,901	531,441	137,781
Quinaldopeptin (9)	8 / C₂	136	136^g)	136	134	64	132	90
Onchidin (10)	12 / C₂	2,080	2,080	2,080	2,064	469	1,760	810
Gramicidin S (11)	10 / C₂	528	528	504	334	25	448	243
Valinomycin (12)	12 / C₃	1,376	1,250	714	416	112	616	27
Nonactin (13)	16 / C₄	16,456	16,425	16,176	10,045	13,189	6,474	675
NP213 (14)	7 / C₇	20	7	13	17	13	5	3

^a)Name and nr. of molecule. See Fig. 4 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

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