Table S1 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type A.
Skeleton A
No. / Ar / R / EC50() / Ref.1 / / H / 0.3 / 8
2* / / H / 1.7 / 8
3 / / H / 0.07 / 8
4* / / H / 0.4 / 8
5 / / H / 1.4 / 8
6 / / H / 0.03 / 8
7 / / H / 0.01 / 8
8 / / H / 0.1 / 8
9 / / H / 0.02 / 8
10 / / H / 0.01 / 8
11 / / H / 0.01 / 8
12* / / H / 0.03 / 8
13* / / H / 0.02 / 8
14 / / H / 0.01 / 8
15 / / Me / 0.02 / 8
* Test set
Table S2 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type B.
Skeleton B
No. / R / EC50() / Ref. / No. / R / EC50() / Ref.16 / / 0.03 / 8 / 17 / / 0.03 / 8
18 / / 0.08 / 8 / 18 / / 0.03 / 8
20* / / 0.004 / 8 / 21 / / 0.02 / 8
22 / / 0.02 / 8 / 23* / / 0.003 / 8
* Test set
Table S3 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type C.
Skeleton C
No. / R / R1 / EC50() / Ref.24 / / OMe / 0.06 / 8
25* / / OMe / 0.04 / 8
26 / / OMe / 0.01 / 8
27 / / OEt / 0.05 / 8
28 / / OEt / 0.05 / 8
29 / / OEt / 0.15 / 8
30 / / OEt / 0.02 / 8
31* / / OEt / 0.009 / 8
32 / / OEt / 0.02 / 8
33 / / OEt / 0.002 / 8
* Test set
Table S4 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type D.
Skeleton D
No. / R / EC50() / Ref. / No. / R / EC50() / Ref.34 / 4-Cl / 0.3 / 10 / 35 / 3-Cl / 0.32 / 10
36* / 2-Cl / 0.11 / 10 / 37 / H / 0.1 / 10
38* / 4-F / 0.2 / 10 / 39 / 3-F / 0.07 / 10
40 / 2-F / 0.1 / 10 / 41* / 4-CN / 1.2 / 10
42 / 3-CN / 0.6 / 10 / 43* / 4-NO2 / 3.8 / 10
44* / 3-NO2 / 0.9 / 10 / 45* / 4-Me / 0.06 / 10
46* / 4-OMe / 0.02 / 10
* Test Set
Table S5 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type E.
Skeleton E
No. / R / EC50() / Ref. / No. / R / EC50() / Ref.47 / Ph / 0.9 / 10 / 48 / 4-MePh / 1.9 / 10
49 / 4-MeOPh / 1.9 / 10 / 50 / 3-MeOPh / 0.6 / 10
51* / 2-MeOPh / 2.5 / 10 / 52 / 3,4-DiOMeOPh / 0.12 / 10
53 / 4-ClPh / 3.3 / 10 / 54* / 2-ClPh / 0.3 / 10
55 / 3-FPh / 0.2 / 10 / 56 / 2-FPh / 0.5 / 10
57 / 4-CF3Ph / 4.2 / 10 / 58 / 4-CNPh / 5.5 / 10
59* / 3-CNPh / 0.6 / 10 / 60 / 4-Pyridyl / 3.4 / 10
61 / trans-3-Pyridyl / 1.0 / 10 / 62 / cis-3-Pyridyl / 4.0 / 10
63 / 2-Pyridyl / 2.3 / 10
* Test set
Table S6 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type F
Skeleton F
No. / R / EC50() / Ref. / No. / R / EC50() / Ref.64 / Ph / 0.2 / 10 / 65 / 4-MePh / 0.14 / 10
66 / 4-MeOPh / 0.18 / 10 / 67 / 4-FPh / 0.34 / 10
68* / 2-FPh / 0.23 / 10 / 69 / (2-CO2Me)Ph / 0.13 / 10
70 / (2-CO2Et)Ph / 0.1 / 10 / 71 / (2-CO2iPr)Ph / 0.3 / 10
72 / (2-CONH2)Ph / 0.2 / 10 / 73 / (4-CONH2)Ph / 5 / 10
74* / (2-CONHEt)Ph / 0.2 / 10 / 75* / (2-SO2Me)Ph / 0.1 / 10
76* / (4-SO2Me)Ph / 1.9 / 10 / 77 / (2-SO2Me)Ph / 0.25 / 10
78 / 2-Thianolyl / 0.2 / 10 / 79* / 2-Thiophenyl / 0.15 / 10
80 / 3-Thiophenyl / 0.1 / 10 / 81 / 2-Imidazolyl / 0.5 / 10
82* / 2-Pyridyl / 0.8 / 10 / 83 / 3-Pyridyl / 0.4 / 10
84 / 4-Pyridyl / 0.9 / 10 / 85 / (2-CO2Me)-3-pyridyl / 0.04 / 10
86 / (2-CO2Et)-3-pyridyl / 0.02 / 10 / 87 / (2-Me)-3-pyridyl / 0.07 / 10
88 / (4-Me)-3-pyridyl / 0.15 / 10 / 89 / (2,4-diMe)-3-pyridyl / 0.05 / 10
90 / (4-MeO)-3-pyridyl / 0.03 / 10 / 91 / (4-EtO)-3-pyridyl / 0.02 / 10
92 / (4-MeO-2-Me)-3-pyridyl / 0.01 / 10 / 93 / (4-EtO-2-Me)-3-pyridyl / 0.03 / 10
* Test set
Table S7 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type G.
Skeleton G
No. / Ar / EC50() / Ref. / No. / Ar / EC50() / Ref.94 / / 4 / 14 / 95 / / 3 / 14
96* / / 7 / 14 / 97 / / 0.3 / 14
98* / / 0.05 / 14 / 99 / / 0.02 / 14
100 / / 0.18 / 14 / 101 / / 0.65 / 14
102* / / 0.045 / 14 / 103* / / 0.03 / 14
104 / / 0.05 / 14 / 105 / / 0.02 / 14
106 / / 1 / 14 / 107* / / 0.035 / 14
* Test set
Table S8 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type H.
Skeleton H
No. / R / EC50() / Ref. / No. / R / EC50() / Ref.108 / Ha / 0.2 / 14 / 109 / H / 0.13 / 14
110 / / 0.05 / 14 / 111 / / 0.1 / 14
112* / / 0.31 / 14 / 113 / / 0.16 / 14
114 / / 0.09 / 14 / 115 / / 0.06 / 14
116 / / 0.05 / 14 / 117 / / 0.25 / 14
118 / NHR=Me2 / 0.14 / 14 / 119 / NHR=Me2b / 13 / 14
120 / / 0.035 / 14 / 121 / / 0.035 / 14
122* / / 0.020 / 14 / 123 / / 0.04 / 14
124 / / 0.9 / 14 / 125 / / 0.26 / 14
126 / / 0.04 / 14 / 127* / / 0.03 / 14
128c / / 0.8 / 14 / 129d,* / / 0.7 / 14
130* / / 0.14 / 14 / 131* / / 0.1 / 14
132 / / 0.03 / 14 / 133 / / 0.03 / 14
134 / / 0.28 / 14 / 135 / / 0.33 / 14
136 / / 0.77 / 14 / 137* / / 4.5 / 14
138 / / 0.03 / 14 / 139 / / 0.006 / 14
140 / / 0.015 / 14 / 141 / / 0.03 / 14
142 / / 0.03 / 14 / 143 / / 0.015 / 14
144 / / 0.03 / 14
* Test set
aPyrimidine C-4=H
b Pyrimidine C-4=Et
c Enantiomer of 127
dPyrimidine C-4=cyclopropyl.
Table S9 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type I.
Skeleton I
No. / R / EC50() / Ref. / No. / R / EC50() / Ref.145* / / 0.016 / 16 / 146 / / 0.124 / 16
147 / / 0.052 / 16 / 148 / / 0.557 / 16
149 / / 0.008 / 15 / 150 / / 0.009 / 15
151* / / 0.125 / 15 / 152 / / 1.683 / 15
153* / / 0.168 / 15 / 154 / / 0.003 / 15
155 / / 0.001 / 15 / 156 / / 0.003 / 15
157 / / 0.012 / 15 / 158 / / 0.301 / 15
159 / / 0.007 / 15 / 160 / / 0.222 / 15
161 / / 6.204 / 15 / 162 / / 3.165 / 15
163 / / 0.114 / 15 / 164 / / 0.222 / 15
165* / / 0.017 / 15 / 166* / / 0.037 / 15
167 / / 0.017 / 15 / 168 / / 0.016 / 15
* Test set
Table S10 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type J.
Skeleton J
No. / R1 / R2 / EC50() / Ref.169 / Me / H / 0.016 / 15
170 / Et / H / 0.016 / 15
171 / Pr / H / 0.020 / 15
172 / i-Pr / H / 0.026 / 15
173* / / H / 0.026 / 15
174 / Cyclobutyl / H / 0.016 / 15
175 / Cyclopropyl / H / 0.060 / 15
176 / / H / 0.059 / 15
177 / / H / 0.034 / 15
178 / NH2 / H / 0.037 / 15
179 / H / Me / 0.038 / 15
180 / Me / Me / 0.043 / 15
181* / Et / Me / 0.264 / 15
182 / Cyclopropyl / Me / 0.703 / 15
183* / Et / Et / 0.069 / 15
* Test set
Table S11 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type K.
Skeleton K
No. / Y / R / EC50() / Ref.184* / H / / 0.020 / 13
185 / H / / 0.030 / 13
186* / H / / 0.050 / 13
187* / Me / / 0.020 / 13
188 / Me / / 0.020 / 13
189* / Me / / 0.020 / 13
* Test set
Table S12 Chemical structures and biological activities of the HCV replication inhibitors with skeleton type L.
Skeleton L
No. / Z / R / EC50() / Ref.190 / Et / / 0.005 / 13
191* / Et / / 0.010 / 13
192 / = / / 0.004 / 13
193 / = / / 0.007 / 13
194 / CH2OMe / / 0.002 / 13
195* / CH2OMe / / 0.003 / 13
* Test set
Table S13Chemical structures and biological activities of the HCV replication inhibitors with skeleton type M.
Skeleton M
No. / R / EC50() / Ref. / No. / R / EC50() / Ref.196 / / 0.040 / 13 / 197 / / 0.050 / 13
198 / = / 0.090 / 13 / 199 / / 0.020 / 13
200* / / 0.020 / 13 / 201 / / 0.004 / 13
202* / / 0.008 / 13 / 203 / / 0.020 / 13
204 / / 0.004 / 13 / 205 / / 0.180 / 13
206* / / 0.010 / 13 / 207 / / 0.130 / 13
208 / / 0.020 / 13
* Test set
Table S14Chemical structures and biological activities of the HCV replication inhibitors.
No. / Structure / EC50() / Ref. / No. / Structure / EC50() / Ref.209* / / 0.030 / 15 / 210 / / 0.030 / 15
211 / / 0.020 / 13
* Test set
Table S15 The experimental and predicted EC50 values of training and test sets
CoMFA / CoMSIANo. / pEC50,exp. / pEC50,pred. / REa / pEC50,pred. / REa
1 / 6.52 / 7.21 / -0.69 / 6.72 / -0.20
2* / 5.77 / 6.40 / -0.63 / 5.94 / -0.17
3 / 7.15 / 6.54 / 0.62 / 7.06 / 0.09
4* / 6.40 / 6.39 / 0.01 / 6.68 / -0.27
5 / 5.85 / 5.87 / -0.02 / 5.65 / 0.20
6 / 7.52 / 6.49 / 1.03 / 7.45 / 0.07
7 / 8.00 / 6.95 / 1.05 / 7.97 / 0.03
8 / 7.00 / 6.60 / 0.40 / 7.33 / -0.33
9 / 7.7 / 7.17 / 0.53 / 7.59 / 0.11
10 / 8.00 / 7.25 / 0.75 / 8.13 / -0.13
11 / 8.00 / 7.42 / 0.58 / 7.64 / 0.36
12* / 7.52 / 7.39 / 0.13 / 7.72 / -0.20
13* / 7.70 / 7.54 / 0.16 / 7.68 / 0.02
14 / 8.00 / 7.39 / 0.61 / 7.83 / 0.17
15 / 7.70 / 7.64 / 0.06 / 7.80 / -0.10
16 / 7.52 / 7.32 / 0.20 / 7.35 / 0.17
17 / 7.52 / 8.17 / -0.65 / 7.72 / -0.20
18 / 7.10 / 7.37 / -0.27 / 7.10 / 0.00
19 / 7.52 / 8.05 / -0.53 / 7.50 / 0.02
20* / 8.40 / 8.16 / 0.24 / 8.14 / 0.26
21 / 7.70 / 7.78 / -0.08 / 7.85 / -0.15
22 / 7.70 / 8.24 / -0.54 / 7.62 / 0.08
23* / 8.52 / 7.28 / 1.24 / 7.88 / 0.64
24 / 7.22 / 7.52 / -0.30 / 7.26 / -0.04
25* / 7.40 / 7.87 / -0.47 / 7.48 / -0.08
26 / 8.00 / 8.63 / -0.63 / 8.15 / -0.15
27 / 7.30 / 7.67 / -0.37 / 7.45 / -0.15
28 / 7.30 / 7.91 / -0.61 / 7.17 / 0.13
29 / 6.82 / 7.21 / -0.39 / 6.77 / 0.05
30 / 7.70 / 8.33 / -0.63 / 7.83 / -0.13
31* / 7.05 / 7.94 / -0.89 / 7.42 / -0.37
32 / 7.70 / 8.02 / -0.32 / 7.73 / -0.03
33 / 8.70 / 8.58 / 0.12 / 8.57 / 0.13
34 / 6.52 / 6.11 / 0.41 / 6.34 / 0.18
35 / 6.49 / 6.64 / -0.15 / 6.83 / -0.34
36* / 6.96 / 6.69 / 0.27 / 6.79 / 0.17
37 / 7.00 / 6.38 / 0.62 / 6.83 / 0.17
38* / 6.70 / 6.30 / 0.40 / 6.61 / 0.09
39 / 7.15 / 6.41 / 0.74 / 6.69 / 0.46
To be continued
No. / CoMFA / CoMSIApEC50,exp. / pEC50,pred. / REa / pEC50,pred. / REa
40 / 7.00 / 6.41 / 0.59 / 6.90 / 0.10
41* / 5.92 / 6.06 / -0.14 / 6.25 / -0.33
42 / 6.22 / 6.38 / -0.16 / 6.28 / -0.06
43* / 5.42 / 6.14 / -0.72 / 5.54 / -0.12
44* / 6.05 / 5.99 / 0.06 / 6.15 / -0.10
45* / 7.22 / 6.53 / 0.69 / 7.04 / 0.18
46* / 7.70 / 6.67 / 1.03 / 7.81 / -0.11
47 / 6.05 / 5.96 / 0.09 / 6.03 / 0.02
48 / 5.72 / 6.03 / -0.31 / 5.99 / -0.27
49 / 5.72 / 5.96 / -0.24 / 5.77 / -0.05
50 / 6.22 / 6.01 / 0.21 / 6.10 / 0.12
51* / 5.60 / 6.14 / -0.54 / 5.55 / 0.05
52 / 6.92 / 6.28 / 0.64 / 6.76 / 0.16
53 / 5.48 / 5.85 / -0.37 / 5.65 / -0.17
54* / 6.52 / 6.39 / 0.13 / 6.77 / -0.25
55 / 6.70 / 6.31 / 0.39 / 6.69 / 0.01
56 / 6.30 / 5.99 / 0.31 / 5.91 / 0.39
57 / 5.38 / 6.21 / -0.83 / 5.50 / -0.12
58 / 5.26 / 5.88 / -0.62 / 5.06 / 0.20
59* / 6.22 / 6.10 / 0.12 / 6.00 / 0.22
60 / 5.47 / 6.08 / -0.61 / 5.79 / -0.32
61 / 6.00 / 6.03 / -0.03 / 5.99 / 0.01
62 / 5.40 / 6.48 / -1.08 / 5.28 / 0.12
63 / 5.64 / 6.19 / -0.55 / 5.71 / -0.07
64 / 6.70 / 6.51 / 0.19 / 6.95 / -0.25
65 / 6.85 / 6.64 / 0.21 / 7.03 / -0.18
66 / 6.74 / 6.47 / 0.27 / 6.53 / 0.21
67 / 6.47 / 6.61 / -0.14 / 6.33 / 0.14
68* / 6.64 / 6.67 / -0.03 / 6.54 / 0.10
69 / 6.89 / 6.86 / 0.03 / 6.74 / 0.15
70 / 7.00 / 7.28 / -0.28 / 7.04 / -0.04
71 / 6.52 / 7.04 / -0.52 / 6.70 / -0.18
72 / 6.70 / 7.10 / -0.40 / 6.71 / -0.01
73 / 5.30 / 5.93 / -0.63 / 5.37 / -0.07
74* / 6.70 / 7.37 / -0.67 / 6.89 / -0.19
75* / 7.00 / 7.14 / -0.14 / 7.50 / -0.50
76* / 5.72 / 6.25 / -0.53 / 5.79 / -0.07
77 / 6.60 / 6.42 / 0.19 / 6.43 / 0.17
78 / 6.70 / 6.26 / 0.44 / 6.68 / 0.02
79* / 6.82 / 6.78 / 0.04 / 7.11 / -0.29
To be continued
CoMFA / CoMSIANo. / pEC50,exp. / pEC50,pred. / REa / pEC50,pred. / REa
80 / 7.00 / 6.63 / 0.37 / 6.84 / 0.16
81 / 5.72 / 6.62 / -0.32 / 6.60 / -0.30
82* / 6.10 / 6.38 / -0.28 / 6.49 / -0.39
83 / 6.40 / 6.89 / -0.49 / 6.55 / -0.15
84 / 6.05 / 6.61 / -0.56 / 6.41 / -0.36
85 / 7.40 / 6.83 / 0.57 / 7.58 / -0.18
86 / 7.70 / 7.03 / 0.67 / 7.63 / 0.07
87 / 7.15 / 6.81 / 0.34 / 6.90 / 0.25
88 / 6.82 / 6.91 / -0.09 / 6.70 / 0.12
89 / 7.30 / 7.25 / 0.05 / 7.50 / -0.20
90 / 7.52 / 7.28 / 0.24 / 7.63 / -0.11
91 / 7.70 / 7.34 / 0.37 / 7.64 / 0.06
92 / 8.00 / 7.56 / 0.44 / 7.97 / 0.03
93 / 7.52 / 6.95 / 0.57 / 7.80 / -0.28
94 / 5.40 / 6.25 / -0.85 / 5.87 / -0.47
95 / 5.52 / 5.69 / -0.17 / 5.43 / 0.09
96* / 5.15 / 6.15 / -0.99 / 5.70 / -0.55
97 / 6.52 / 6.75 / -0.23 / 6.45 / 0.07
98* / 7.30 / 6.26 / 1.04 / 7.12 / 0.18
99 / 7.70 / 7.10 / -0.60 / 7.70 / 0.00
100 / 6.74 / 7.11 / -0.37 / 6.68 / 0.06
101 / 6.19 / 6.56 / -0.37 / 6.07 / 0.12
102* / 7.35 / 7.14 / 0.21 / 7.22 / 0.13
103* / 7.52 / 7.19 / 0.33 / 7.55 / -0.03
104 / 7.30 / 7.16 / 0.14 / 7.47 / -0.17
105 / 7.70 / 7.29 / 0.41 / 7.68 / 0.024
106 / 6.00 / 6.85 / -0.85 / 5.97 / 0.032
107* / 7.46 / 7.32 / 0.14 / 7.71 / -0.25
108 / 6.70 / 6.63 / 0.07 / 6.91 / -0.21
109 / 6.89 / 6.72 / 0.17 / 6.86 / 0.03
110 / 7.30 / 7.15 / 0.15 / 6.97 / 0.33
111 / 7.00 / 7.21 / -0.21 / 7.03 / -0.03
112* / 6.51 / 6.89 / -0.38 / 6.90 / -0.39
113 / 6.80 / 6.74 / 0.06 / 6.87 / -0.07
114 / 7.05 / 6.96 / 0.09 / 7.05 / 0.00
115 / 7.22 / 7.53 / -0.31 / 7.12 / 0.10
116 / 7.30 / 7.48 / -0.18 / 7.36 / -0.06
117 / 6.60 / 7.29 / -0.69 / 6.62 / -0.02
118 / 6.85 / 6.74 / 0.11 / 6.90 / -0.05
To be continued
CoMFA / CoMSIANo. / pEC50,exp. / pEC50,pred. / REa / pEC50,pred. / REa
119 / 4.89 / 6.66 / -1.77 / 4.96 / -0.07
120 / 7.46 / 7.46 / 0.00 / 7.61 / -0.15
121 / 7.46 / 7.46 / 0.00 / 7.48 / -0.02
122* / 7.70 / 6.95 / 0.76 / 7.83 / -0.13
123 / 7.40 / 7.48 / -0.08 / 7.33 / 0.07
124 / 6.05 / 7.48 / -1.43 / 6.23 / -0.18
125 / 6.59 / 6.56 / 0.03 / 6.59 / 0
126 / 7.40 / 7.51 / -0.11 / 7.34 / 0.06
127* / 7.52 / 7.26 / 0.26 / 7.32 / 0.20
128 / 6.10 / 6.83 / -0.73 / 6.26 / -0.16
129* / 6.15 / 6.15 / 0.00 / 6.44 / -0.29
130* / 6.85 / 7.08 / -0.23 / 7.13 / -0.28
131* / 7.00 / 7.32 / -0.32 / 7.11 / -0.11
132 / 7.52 / 7.46 / 0.06 / 7.56 / -0.04
133 / 7.52 / 7.63 / -0.11 / 7.29 / 0.23
134 / 6.55 / 7.30 / -0.75 / 6.60 / -0.04
135 / 6.48 / 6.89 / -0.41 / 6.43 / 0.05
136 / 6.11 / 7.01 / -0.90 / 6.11 / 0.00
137* / 5.35 / 6.67 / -1.32 / 5.63 / -0.28
138 / 7.52 / 7.60 / -0.08 / 7.44 / 0.08
139 / 8.22 / 7.23 / 0.99 / 8.21 / 0.01
140 / 7.82 / 6.90 / 0.93 / 7.85 / -0.03
141 / 7.52 / 7.64 / -0.12 / 7.51 / 0.01
142 / 7.52 / 7.71 / -0.19 / 7.35 / 0.17
143 / 7.82 / 7.64 / 0.18 / 7.66 / 0.16
144 / 7.52 / 7.58 / -0.06 / 7.64 / -0.12
145* / 7.80 / 7.17 / 0.63 / 8.14 / -0.34
146 / 6.91 / 6.83 / 0.08 / 6.91 / 0.00
147 / 7.28 / 6.84 / 0.44 / 7.11 / 0.17
148 / 6.25 / 6.97 / -0.72 / 6.31 / -0.05
149 / 8.10 / 6.66 / 1.44 / 8.18 / -0.08
150 / 8.05 / 6.72 / 1.33 / 7.91 / 0.14
151* / 6.90 / 6.99 / -0.09 / 7.43 / -0.53
152 / 5.77 / 6.68 / -0.91 / 5.73 / 0.04
153* / 6.77 / 6.87 / -0.10 / 7.21 / -0.44
154 / 8.52 / 7.53 / 0.99 / 8.54 / -0.02
155 / 9.00 / 7.47 / 1.53 / 8.72 / 0.28
156 / 8.52 / 7.65 / 0.87 / 8.38 / 0.14
157 / 7.92 / 7.72 / 0.20 / 7.96 / -0.04
158 / 6.52 / 7.34 / -0.82 / 6.75 / -0.23
To be continued
CoMFA / CoMSIANO. / pEC50,exp. / pEC50,pred. / REa / pEC50,pred. / REa
159 / 8.15 / 7.37 / 0.78 / 7.88 / 0.27
160 / 6.65 / 6.02 / 0.64 / 6.62 / 0.03
161 / 5.21 / 6.24 / -1.03 / 5.33 / -0.12
162 / 5.50 / 7.36 / -1.86 / 5.59 / -0.09
163 / 6.94 / 6.90 / 0.05 / 6.92 / 0.02
164 / 6.65 / 7.18 / -0.52 / 6.60 / 0.05
165* / 7.77 / 7.45 / 0.32 / 8.23 / -0.46
166* / 7.43 / 7.48 / -0.05 / 7.79 / -0.36
167 / 7.77 / 7.46 / 0.31 / 7.49 / 0.28
168 / 7.80 / 7.40 / 0.40 / 7.67 / 0.13
169 / 7.80 / 7.55 / 0.25 / 7.66 / 0.14
170 / 7.70 / 7.56 / 0.14 / 7.68 / 0.02
171 / 7.70 / 7.52 / 0.18 / 7.64 / 0.06
172 / 7.59 / 7.75 / -0.16 / 7.72 / -0.13
173* / 7.59 / 7.78 / -0.19 / 7.64 / -0.05
174 / 7.80 / 7.60 / 0.20 / 7.78 / 0.02
175 / 7.22 / 7.05 / 0.18 / 7.35 / -0.13
176 / 7.23 / 7.51 / -0.28 / 7.11 / 0.12
177 / 7.47 / 7.54 / -0.07 / 7.40 / 0.07
178 / 7.43 / 7.59 / -0.16 / 7.35 / 0.08
179 / 7.42 / 7.44 / -0.02 / 7.68 / -0.26
180 / 7.37 / 7.60 / -0.23 / 7.74 / -0.37
181* / 6.58 / 6.53 / 0.05 / 6.81 / -0.23
182 / 6.15 / 6.68 / -0.53 / 6.21 / -0.05
183* / 7.16 / 7.04 / 0.12 / 6.78 / 0.38
184* / 7.70 / 7.57 / 0.13 / 7.59 / 0.11
185 / 7.52 / 7.72 / -0.20 / 7.57 / -0.05
186* / 7.30 / 7.50 / -0.20 / 7.76 / -0.46
187* / 7.70 / 7.69 / 0.01 / 7.63 / 0.07
188 / 7.70 / 7.82 / -0.12 / 7.56 / 0.14
189* / 7.70 / 6.69 / 0.01 / 7.73 / -0.02
190 / 8.30 / 7.73 / 0.57 / 8.06 / 0.24
191* / 8.00 / 7.93 / 0.08 / 7.70 / 0.30
192 / 8.40 / 7.74 / 0.66 / 8.36 / 0.04
193 / 8.15 / 7.67 / 0.48 / 8.33 / -0.18
194 / 8.70 / 7.81 / 0.89 / 8.93 / -0.23
195* / 8.52 / 7.89 / 0.63 / 8.76 / -0.24
196 / 7.40 / 7.23 / 0.18 / 7.66 / -0.26
197 / 7.30 / 6.99 / 0.31 / 7.30 / 0.00
198 / 7.05 / 7.18 / -0.13 / 6.98 / 0.07
To be continued
CoMFA / CoMSIANO. / pEC50,exp. / pEC50,pred. / REa / pEC50,pred. / REa
199 / 7.70 / 7.69 / 0.01 / 7.50 / 0.20
200* / 7.70 / 7.64 / 0.06 / 7.79 / -0.09
201 / 8.40 / 8.01 / 0.39 / 8.54 / -0.14
202* / 8.10 / 7.28 / 0.82 / 7.63 / 0.47
203 / 7.70 / 7.79 / -0.09 / 7.89 / -0.19
204 / 8.40 / 7.90 / 0.50 / 8.58 / -0.18
205 / 6.74 / 7.25 / -0.51 / 6.61 / 0.12
206* / 8.00 / 7.57 / 0.43 / 7.98 / 0.016
207 / 6.89 / 6.56 / 0.33 / 6.77 / 0.12
208 / 7.70 / 7.78 / -0.08 / 7.67 / 0.03
209* / 7.52 / 7.19 / 0.33 / 7.59 / -0.07
210 / 7.52 / 7.23 / 0.29 / 7.47 / 0.05
211 / 7.70 / 7.45 / 0.25 / 7.46 / 0.24
* Test set
RE, relative error
Table S16Pharmacophore models and their statistic parameters
MODEL / SIZE / HITS / SCORE / TOLERANCE / DMEANMODEL_047 / 8 / 35 / 3.3993 / 0.2500 / 3.5855
MODEL_041 / 8 / 35 / 3.3993 / 0.2500 / 3.5855
MODEL_013 / 8 / 35 / 3.3985 / 0.2500 / 3.5826
MODEL_009 / 8 / 35 / 3.3985 / 0.2500 / 3.5826
MODEL_036 / 8 / 35 / 3.3967 / 0.2500 / 3.5760
MODEL_030 / 8 / 35 / 3.3967 / 0.2500 / 3.5760
MODEL_003 / 8 / 35 / 3.3397 / 0.2500 / 3.3821
MODEL_001 / 8 / 35 / 3.3396 / 0.2500 / 3.3818
MODEL_042 / 8 / 35 / 2.8277 / 0.2500 / 3.3429
MODEL_010 / 8 / 35 / 2.8257 / 0.2500 / 3.3368
MODEL_031 / 8 / 35 / 2.8237 / 0.2500 / 3.3306
MODEL_037 / 8 / 35 / 2.5359 / 0.2500 / 4.1659
MODEL_038 / 8 / 35 / 2.5359 / 0.2500 / 4.1659
MODEL_005 / 8 / 35 / 2.5347 / 0.2500 / 4.1601
MODEL_006 / 8 / 35 / 2.5347 / 0.2500 / 4.1601
MODEL_026 / 8 / 35 / 2.5323 / 0.2500 / 4.1479
MODEL_027 / 8 / 35 / 2.5323 / 0.2500 / 4.1479
MODEL_039 / 8 / 35 / 2.0172 / 0.2500 / 4.0610
MODEL_007 / 8 / 35 / 2.0166 / 0.2500 / 4.0580
MODEL_028 / 8 / 35 / 2.0136 / 0.2500 / 4.0437
MODEL_040 / 8 / 35 / 2.0073 / 0.2500 / 4.0137
MODEL_008 / 8 / 35 / 2.0060 / 0.2500 / 4.0079
MODEL_029 / 8 / 35 / 2.0037 / 0.2500 / 3.9973
MODEL_045 / 8 / 35 / 1.9768 / 0.2500 / 3.8759
MODEL_012 / 8 / 35 / 1.9755 / 0.2500 / 3.8701
MODEL_034 / 8 / 35 / 1.9724 / 0.2500 / 3.8570
MODEL_043 / 8 / 35 / 1.9500 / 0.2500 / 3.7623
MODEL_011 / 8 / 35 / 1.9494 / 0.2500 / 3.7601
MODEL_032 / 8 / 35 / 1.9469 / 0.2500 / 3.7498
MODEL_044 / 8 / 35 / 1.8812 / 0.2500 / 3.5013
MODEL_033 / 8 / 35 / 1.8798 / 0.2500 / 3.4963
MODEL_004 / 8 / 35 / 1.8232 / 0.2500 / 3.3113
MODEL_002 / 8 / 35 / 1.8232 / 0.2500 / 3.3111
MODEL_046 / 8 / 35 / 1.8178 / 0.2500 / 3.2948
MODEL_035 / 8 / 35 / 1.8178 / 0.2500 / 3.2946
MODEL_048 / 8 / 35 / 1.0852 / 0.2500 / 4.2336
MODEL_025 / 7 / 35 / 3.1899 / 0.2500 / 2.9787
MODEL_023 / 7 / 35 / 2.2497 / 0.2500 / 3.1175
MODEL_020 / 7 / 35 / 1.8454 / 0.2500 / 3.3809
MODEL_024 / 7 / 35 / 1.6010 / 0.2500 / 2.7781
MODEL_014 / 7 / 35 / 1.5539 / 0.2500 / 4.2010
MODEL_019 / 7 / 35 / 1.0249 / 0.2500 / 3.9180
To be continued
MODEL / SIZE / HITS / SCORE / TOLERANCE / DMEANMODEL_015 / 7 / 35 / 0.9417 / 0.2500 / 3.5489
MODEL_022 / 7 / 35 / 0.9226 / 0.2500 / 3.4734
MODEL_021 / 7 / 35 / 0.9122 / 0.2500 / 3.4338
MODEL_018 / 7 / 35 / 0.8777 / 0.2500 / 3.3091
MODEL_017 / 7 / 35 / 0.8519 / 0.2500 / 3.2222
MODEL_016 / 7 / 35 / 0.8400 / 0.2500 / 3.1837
SIZE, number of features in the model;
HITS, number of molecules that match during the search;
SCORE, an overall measure of fit and of overlap volume for entire collection of structures;
TOLERANCE, initial tolerance setting;
DMEAN, average inter-point distance.