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. 2024 Mar 13;14(12):8464–8480. doi: 10.1039/d3ra08871e

Fingerprint of the top 30 MACCS with high information gain.

Number MACCS fingerprints MACCS description IGa P_RBb (%) P_NRBc (%) Δ d (%) Ratee
1 MACCS_102 QO 0.1290 74.36 37.50 36.86 1.9829
2 MACCS_165 Ring 0.1037 58.97 82.50 −23.53 0.7148
3 MACCS_120 Heterocycle atom >1 (&…) 0.1020 56.41 65.00 −8.59 0.8679
4 MACCS_121 N heterocycle 0.1020 56.41 65.00 −8.59 0.8679
5 MACCS_105 A$A($A)$A 0.1005 5.13 20.00 −14.87 0.2564
6 MACCS_137 Heterocycle 0.0983 56.41 80.00 −23.59 0.7051
7 MACCS_163 6M ring 0.0952 43.59 65.00 −21.41 0.6706
8 MACCS_86 CH2QCH2 0.0809 74.36 57.50 16.86 1.2932
9 MACCS_83 QAAAA@1 0.0783 17.95 35.00 −17.05 0.5128
10 MACCS_141 CH3 >2 (&…) 0.0755 71.79 45.00 26.79 1.5954
11 MACCS_118 ACH2CH2A >1 0.0750 100.00 85.00 15.00 1.1765
12 MACCS_111 NACH2A 0.0703 74.36 57.50 16.86 1.2932
13 MACCS_48 OQ(O)O 0.0661 48.72 30.00 18.72 1.6239
14 MACCS_112 AA(A)(A)A 0.0644 23.08 30.00 −6.92 0.7692
15 MACCS_115 CH3ACH2A 0.0607 100.00 82.50 17.50 1.2121
16 MACCS_129 ACH2AACH2A 0.0492 92.31 75.00 17.31 1.2308
17 MACCS_146 O >2 0.0490 69.23 47.50 21.73 1.4575
18 MACCS_148 AQ(A)A 0.0479 87.18 82.50 4.68 1.0567
19 MACCS_108 CH3AAACH2A 0.0455 74.36 47.50 26.86 1.5655
20 MACCS_97 NAAAO 0.0439 15.38 40.00 −24.62 0.3846
21 MACCS_142 N >1 0.0371 58.97 45.00 13.97 1.3105
22 MACCS_98 QAAAAA@1 0.0336 35.90 42.50 −6.60 0.8446
23 MACCS_161 N 0.0317 89.74 80.00 9.74 1.1218
24 MACCS_159 O >1 0.0263 74.36 67.50 6.86 1.1016
25 MACCS_65 CN 0.0211 35.90 45.00 −9.10 0.7977
26 MACCS_139 OH 0.0210 7.69 15.00 −7.31 0.5128
27 MACCS_158 C–N 0.0201 74.36 72.50 1.86 1.0256
28 MACCS_80 NAAAN 0.0181 28.21 27.50 0.71 1.0256
29 MACCS_47 SAN 0.0137 74.36 70.00 4.36 1.0623
30 MACCS_138 QCH2A >1 (&…) 0.0125 100.00 95.00 5.00 1.0526
a

The value of information gain.

b

The proportion of compounds with strong wear resistance in which this MACCS descriptor appears.

c

The proportion of descriptors that appear in the general class of compounds with wear resistance.

d

The difference between p_RB (%) minus p_NRB (%), the frequency at which sub-structural fragments occur in the two classes of compounds.

e

The ratio of p_RB (%) to p_NRB (%); A can be any valid chemical element, Q is a hetero-atom (an atom other than carbon and hydrogen), and X is a halogen atom (F, Cl, Br, I); % denotes an aromatic bond, ! denotes the main chain or non-ring key, and $ denotes the ring key.