Table 1.

Comparison of frequency (in %) of FGs identified by checkmol [6] and by the presented algorithm

Functional group	Checkmol	This study	Functional group	Checkmol	This study
Secondary amide^a	33.34	33.21	Lactam	6.16	4.65
Alkyl aryl ether	28.27	28.93	Urea	5.94	4.49
Aryl chloride	18.13	18.17	Sec. aliphatic/aromatic amine	5.90	6.08
Tert. aliphatic amine	17.89	17.90	Sec. aliphatic amine	5.72	5.77
Tertiary amide^a	15.99	14.75	Prim. aromatic amine	5.50	5.52
Aryl fluoride	12.37	12.38	Carbonitrile	4.84	4.18
Oxoarene	11.61	13.64	Hydrazine derivative	4.45	4.32
Alcohol	11.64	10.23	Sec. aromatic amine	4.34	4.41
Sulfonamide	11.28	9.81	Prim. aliphatic amine	4.14	4.18
Tert. aliphatic/aromatic amine	10.90	10.96	Aryl bromide	4.02	4.03
Carboxylic acid	9.93	9.39	Primary amide	3.48	3.36
Phenol/hydroxyarene	9.52	9.58	Nitro compound	3.40	3.36
Dialkyl ether	8.65	9.42	Urethane	3.33	3.03
Alkene	8.63	4.46	Sulfone	2.98	2.89
Carboxlic acid ester	8.47	7.45	Diaryl ether	2.87	2.81
Ketone	7.82	5.31	Acetal	2.26	2.17
Thioether	7.51	7.52	Guanidine	2.21	1.59

^aIncluding lactames