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Table 2 The top 10 most used R groups from approved drugs

From: IntelliPatent: a web-based intelligent system for fast chemical patent claim drafting

R groupSMILESOccurrence (%)Both top 10
Methyl*C23.6O
Hydroxy*O18.2O
Chloro*Cl6.4O
Amino*N5.1 
Methoxy*OC5.0O
Carboxy*C(=O)O3.9O
Fluoro*F2.9O
Ethyl*CC2.2 
Hydroxymethyl*CO1.7 
Trifulromethyl*C(F)(F)F1.0O