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. 2019 Dec 11;11:78. doi: 10.1186/s13321-019-0401-4

Table 2.

The top 10 most used R groups from approved drugs

R group SMILES Occurrence (%) Both top 10
Methyl *C 23.6 O
Hydroxy *O 18.2 O
Chloro *Cl 6.4 O
Amino *N 5.1
Methoxy *OC 5.0 O
Carboxy *C(=O)O 3.9 O
Fluoro *F 2.9 O
Ethyl *CC 2.2
Hydroxymethyl *CO 1.7
Trifulromethyl *C(F)(F)F 1.0 O