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Table 1 Substituents clustered according to their root atoms

From: Craig plot 2.0: an interactive navigation in the substituent bioisosteric space

R

%

R—level2

%

Attached to (%), the * represents any extension

R–C

48.1

R–C–C

9.0

N, n (36), C (29), O (16), c (10), X (4), C(=O)* (4)

  

R–C(–C)–C

4.9

C (39), N, n (37), c (11), O (8), C(=O)* (5), X (1)

  

R–C(=O)–N

3.9

C (50), c(34), N, n (13), O (2), C(=O)* (1)

  

R–C(=O)–C

3.7

N, n (76), c (9), O (9), C (6)

  

R–C–c

2.9

N, n (42), C (34), O (10), c (5), C(=O)* (4), X (4)

  

R–C–N

2.8

c (52), C (33), C(=O)* 14

  

R–C(–C)–N

2.4

C(=O)* (53), C (32), c (15)

  

R–C(=O)-c

2.0

N, n (74), C (12), O (7), c (7)

  

R–C(–C)-O

1.7

C (69), c (12), N, n (9), C(=O)* (6), O (4)

  

R–C =C

1.4

c (43), C(=O)* (40), C (12), N, n (3), X (2)

  

R–C(–C)–c

1.2

N, n (71), C (11), c (6), O (6), C(=O)* (5)

  

R–C–C–O

1.0

C (64), c (20). C(=O)* (14)

R–c

20.6

R–c(:c):c

10.9

C (42), N, n (21), c (18), C(=O)* (8) O (6), X (5)

  

R–c(:n):c

5.2

C (30), N, n (28), c (22), C(=O)* (13), O (4), X (3)

  

R–c(:n):n

1.9

c (31), C (25), N, n (24), X (15), C(=O)* (4), O (2)

R–N

19.6

R–N–C

8.7

C(=O)* (34), C (34), c (32)

  

R–N(–C)–C

4.7

C (42), c (33), C(=O)* (25)

  

R-N–c

3.1

C(=O)* (58), c (28), C (13)

R–O

6.1

R–O–C

4.0

c (70), C(=O)* (17), C (14)

  

R–O–c

1.8

C (54), c (41), C(=O)* (5)

R–S

3.2

R–S–C

1.0

c (69), C (30)

R–n

2.0

R–n(:c):c

1.1

C (71), c (28), C(=O)* (1)

  1. The substituent substructures are shown in SMILES-like notation (atoms in uppercase are aliphatic, in lowercase aromatic, colon is an aromatic bond and the comma between atomic symbols a logical OR). Only substituent classes with more than 1% frequency are shown