Toward the Prediction of FBPase Inhibitory Activity Using Chemoinformatic Methods
Abstract
:1. Introduction
2. Results and Discussion
2.1. Descriptor Calculation and Preprocessing
2.2. Split of the Training and Test Sets
2.3. Set Parameters of GA-RF Algorithm
2.4. Statistical Results
2.5. Further Test for the External Prediction Power
2.6. Investigation of Parameter Turning on the GA-RF Model
2.7. Y-Randomization Check
2.8. Explanation of the Selected Descriptors
3. Experimental Section
3.1. Dataset
3.2. Descriptor Calculation
3.3. Computational Methods
3.4. Statistical Validation
4. Conclusions
Acknowledgments
References
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Name | Definition | Name | Definition |
---|---|---|---|
D004 | Number of 05-membered rings | D543 | Lowest eigenvalue from Burdex matrix weighted by van der Waals order-4 |
D016 | Number of double bonds | D545 | Lowest eigenvalue from Burdex matrix weighted by van der Waals order-6 |
D152 | Mean atomic polarizability scaled on carbon-SP3 | D547 | Lowest eigenvalue from Burdex matrix weighted by van der Waals order-8 |
D164 | Index of terminal vertex matrix | D557 | Lowest eigenvalue from Burden matrix weighted by polarizabilities order-2 |
D237 | Kier 3-path index | D561 | Lowest eigenvalue from Burden matrix weighted by polarizabilities order-6 |
D279 | Total information content order-4 index | D562 | Lowest eigenvalue from Burden matrix weighted by polarizabilities order-7 |
D309 | Sum eigenvalue weighted by mass distance matrix | D563 | Lowest eigenvalue from Burden matrix weighted by polarizabilities order-8 |
D455 | Geary topological structure autocorrelation length-1 weighted by atomic van der Waals volumes | D571 | Highest eigenvalue from Burden matrix weighted by masses order-8 |
D458 | Geary topological structure autocorrelation length-4 weighted by atomic van der Waals volumes | D582 | Highest eigenvalue from Burden matrix weighted by electronegativities Sanderson-scale order-3 |
D462 | Geary topological structure autocorrelation length-8 weighted by atomic van der Waals volumes | D589 | Highest eigenvalue from Burden matrix weighted by polarizabilities order-2 |
D465 | Geary topological structure autocorrelation length-3 weighted by atomic Sanderson electronegativities | D598 | Number of total tertiary carbon-SP3 |
D470 | Geary topological structure autocorrelation length-8 weighted by atomic Sanderson electronegativities | D647 | Number of group primary amines (aliphatic) |
D473 | Geary topological structure autocorrelation length-3 weighted by atomic polarizabilities | D715 | Number of group CH2R2 |
D476 | Geary topological structure autocorrelation length-6 weighted by atomic polarizabilities | D719 | Number of group CH2RX |
D491 | Moran topological structure autocorrelation length-5 weighted by atomic van der Waals volumes | D729 | Number of group =CHR |
D492 | Moran topological structure autocorrelation length-6 weighted by atomic van der Waals volumes | D731 | Number of group =CHX |
D499 | Moran topological structure autocorrelation length-5 weighted by atomic Sanderson electronegativities | D746 | Number of group H attached to C0(sp3) no X attached to next C |
D506 | Moran topological structure autocorrelation length-4 weighted by atomic polarizabilities | D754 | Number of group O= |
D523 | Mean molecular topological order-3 charge index | D756 | Number of group Al-O-Ar or Ar-O-Ar or R-O-C=X |
D541 | Lowest eigenvalue from Burden matrix weighted by van der Waals order-2 | D775 | Hydrophilic factor index |
Model | Training Set | Test Set | ||||
---|---|---|---|---|---|---|
r2ncv | r2cv | RMSE | r2ts | r2pred | RMSE | |
GA-RF | 0.96 | 0.67 | 0.25 | 0.91 | 0.90 | 0.34 |
RF | 0.96 | 0.59 | 0.28 | 0.87 | 0.85 | 0.42 |
No. | R2 | Obs. pIC50 | GA-RF | RF | Ref. a | |||||
---|---|---|---|---|---|---|---|---|---|---|
1 | Me | 7.00 | 6.62 | 6.70 | [29] | |||||
2 * | Et | 6.40 | 6.20 | 6.25 | [29] | |||||
3 | vinyl | 5.92 | 5.99 | 6.05 | [29] | |||||
4 | CH2OH | 6.66 | 6.63 | 6.61 | [29] | |||||
5 * | H | 6.30 | 6.05 | 6.27 | [29] | |||||
6 | Cl | 6.74 | 6.61 | 6.64 | [29] | |||||
7 | Br | 7.10 | 6.85 | 6.89 | [29] | |||||
8 | SMe | 6.05 | 6.23 | 6.16 | [29] | |||||
9 | CN | 5.70 | 5.65 | 5.73 | [29] | |||||
10 * | NH2 | 7.60 | 7.38 | 7.20 | [29] | |||||
11 | NHMe | 6.00 | 5.95 | 6.08 | [29] | |||||
12 | NHAc | 5.00 | 5.69 | 5.66 | [29] | |||||
13 | CONH2 | 5.56 | 5.75 | 6.03 | [29] | |||||
14 * | CSNH2 | 6.30 | 6.38 | 6.39 | [29] | |||||
15 | Ph | 4.87 | 5.33 | 5.40 | [29] | |||||
16 * | 2-thienyl | 5.10 | 5.93 | 5.78 | [29] | |||||
17 | 3-pyridyl | 5.30 | 5.40 | 5.55 | [29] | |||||
No. | R5 | Obs. pIC50 | GA-RF | RF | Ref. a | |||||
18 | H | 6.35 | 6.38 | 6.42 | [29] | |||||
19 | Me | 6.92 | 6.84 | 6.80 | [29] | |||||
20 | HOCH2 | 6.30 | 6.73 | 6.55 | [29] | |||||
21 * | n-Pr | 7.52 | 7.29 | 7.13 | [29] | |||||
22 * | i-Pr | 7.55 | 7.04 | 7.01 | [29] | |||||
23 | CF3CH2 | 7.24 | 6.99 | 7.14 | [29] | |||||
24 | neopentyl | 7.92 | 7.58 | 7.51 | [29] | |||||
25 | cyclobutyl | 7.72 | 7.61 | 7.54 | [29] | |||||
26 * | cyclopentyl | 7.68 | 7.67 | 7.58 | [29] | |||||
27 | cyclohexyl | 8.00 | 7.80 | 7.83 | [29] | |||||
28 | cyclopropyl-CH2 | 7.70 | 7.62 | 7.53 | [29] | |||||
29 | cyclopentyl-CH2 | 7.74 | 7.36 | 7.44 | [29] | |||||
30 | cyclohexyl-CH2 | 7.23 | 7.18 | 7.08 | [29] | |||||
31 | PhCH2 | 6.82 | 6.85 | 6.82 | [29] | |||||
32 * | morpholinyl-CH2 | 6.25 | 6.16 | 6.45 | [29] | |||||
No. | R5 | Obs. pIC50 | GA-RF | RF | Ref.a | |||||
33 | Cl | 7.15 | 7.03 | 6.97 | [29] | |||||
34 * | Br | 7.30 | 6.99 | 6.88 | [29] | |||||
35 * | I | 7.00 | 6.87 | 6.36 | [29] | |||||
36 | 1-morpholinyl | 7.80 | 7.09 | 7.29 | [29] | |||||
37 | EtS | 7.48 | 7.32 | 7.24 | [29] | |||||
38 * | n-PrS | 7.80 | 7.21 | 7.03 | [29] | |||||
39 | i-PrS | 7.62 | 7.50 | 7.46 | [29] | |||||
40 | t-BuS | 7.62 | 7.52 | 7.53 | [29] | |||||
41 * | PhS | 6.52 | 6.70 | 6.58 | [29] | |||||
42 | CONMe2 | 5.77 | 5.94 | 6.22 | [29] | |||||
43 | CO2Et | 7.85 | 7.55 | 7.48 | [29] | |||||
44 | CO2Bn | 7.82 | 7.25 | 7.43 | [29] | |||||
45 | n-PrSO | 6.07 | 6.56 | 6.45 | [29] | |||||
46 * | Ph | 7.85 | 7.68 | 7.64 | [29] | |||||
47 * | 2-MeO-Ph | 7.37 | 7.51 | 7.52 | [29] | |||||
48 | 3-MeO-Ph | 7.68 | 7.60 | 7.62 | [29] | |||||
49 | 4-MeO-Ph | 7.66 | 7.61 | 7.64 | [29] | |||||
50 * | 4-MeS-Ph | 7.68 | 7.41 | 7.40 | [29] | |||||
51 | 4-t-Bu-Ph | 7.06 | 7.21 | 7.10 | [29] | |||||
52 * | 4-MeO2C-Ph | 7.85 | 7.48 | 7.36 | [29] | |||||
53 | 4-F-Ph | 7.80 | 7.71 | 7.68 | [29] | |||||
54 | 4-Cl-Ph | 7.89 | 7.76 | 7.75 | [29] | |||||
55 | 4-Ac-Ph | 7.49 | 7.45 | 7.48 | [29] | |||||
56 | 4-MeSO2-Ph | 7.39 | 7.30 | 7.00 | [29] | |||||
57 * | 4-Ph-Ph | 7.47 | 7.31 | 7.23 | [29] | |||||
58 | 2-nathphyl | 7.92 | 7.66 | 7.61 | [29] | |||||
59 | 2-furanyl | 7.40 | 7.12 | 7.22 | [29] | |||||
60 * | 2-thienyl | 7.36 | 7.17 | 7.20 | [29] | |||||
No. | [linker] | R5 | Obs. pIC50 | GA-RF | RF | Ref. a | ||||
61 | 2,5-furanyl | H | 5.00 | 5.41 | 5.78 | [29] | ||||
62 | -CH2OCO- | n-Pr | 7.30 | 6.90 | 6.92 | [29] | ||||
63* | -CH2NHCO- | 2-thienyl | 6.02 | 6.42 | 6.69 | [29] | ||||
64 | 2,6-pyridyl | H | 5.70 | 5.74 | 5.94 | [29] | ||||
65 | 1,3-phenyl | H | 5.89 | 6.06 | 6.01 | [29] | ||||
66 * | 1,3-phenyl-(6-Me) | n-Pr | 6.87 | 6.71 | 6.39 | [29] | ||||
67 * | 1,3-phenyl-(6-OMe) | i-Pr | 6.68 | 7.05 | 6.89 | [29] | ||||
68 * | 1,3-phenyl-(6-F) | Ph | 7.10 | 7.42 | 7.27 | [29] | ||||
No. | R5 | Obs. pIC50 | GA-RF | RF | Ref. a | |||||
69 * | i-Bu | 6.92 | 6.38 | 6.13 | [30] | |||||
70 | H | 5.00 | 5.60 | 5.43 | [30] | |||||
71 | Allyl | 6.85 | 6.70 | 6.51 | [30] | |||||
72 | n-Bu | 6.77 | 6.64 | 6.54 | [30] | |||||
73* | n-Pentyl | 6.68 | 6.54 | 6.35 | [30] | |||||
74 | -CH2-cyclohexyl | 6.49 | 6.24 | 6.29 | [30] | |||||
75 | Ph | 6.80 | 6.78 | 6.80 | [30] | |||||
76 | Bn | 6.05 | 6.23 | 6.12 | [30] | |||||
77 | -CH2-(2-thienyl) | 6.59 | 6.47 | 6.59 | [30] | |||||
78 | n-PrS | 7.15 | 6.97 | 6.91 | [30] | |||||
79 | i-PrS | 6.96 | 7.01 | 7.02 | [30] | |||||
80 * | t-BuS | 6.92 | 6.64 | 7.05 | [30] | |||||
81 | PhS | 5.40 | 5.79 | 6.08 | [30] | |||||
82 | -CO2Me | 7.17 | 7.06 | 6.70 | [30] | |||||
83 * | -CO2Et | 7.42 | 7.10 | 6.85 | [30] | |||||
84 | -CO2Pr-i | 7.40 | 7.13 | 7.14 | [30] | |||||
85 | -CO2Bn | 7.07 | 6.95 | 6.91 | [30] | |||||
86 | -COSEt | 7.52 | 7.23 | 7.20 | [30] | |||||
87 | -COBu-t | 6.07 | 6.10 | 6.22 | [30] | |||||
No. | R2 | Obs. pIC50 | GA-RF | RF | Ref. a | |||||
88 | Me | 6.22 | 6.24 | 6.14 | [30] | |||||
89 | HO | 5.00 | 5.48 | 5.43 | [30] | |||||
90 * | H | 5.72 | 5.87 | 5.80 | [30] | |||||
91 | Me2N- | 5.68 | 5.61 | 5.54 | [30] | |||||
92* | i-Pr- | 5.66 | 5.79 | 5.78 | [30] | |||||
93 | MeHN- | 5.37 | 5.55 | 5.62 | [30] | |||||
94 | Et | 6.02 | 6.09 | 5.94 | [30] | |||||
95 * | EtHN- | 5.00 | 5.43 | 5.68 | [30] | |||||
96 | vinyl | 5.17 | 5.49 | 5.54 | [30] | |||||
No. | R2 | R5 | Obs. pIC50 | GA-RF | RF | Ref. a | ||||
97 | H2N- | H | 5.15 | 5.50 | 5.43 | [30] | ||||
98 * | H2N- | Me | 6.38 | 6.19 | 5.72 | [30] | ||||
99 | H2N- | Et | 6.42 | 6.39 | 6.17 | [30] | ||||
100 * | H2N- | n-Pr | 6.55 | 6.46 | 6.08 | [30] | ||||
101 * | H2N- | i-Pr | 6.24 | 6.36 | 6.19 | [30] | ||||
102 * | H2N- | n-Bu | 6.60 | 6.32 | 5.98 | [30] | ||||
103 * | H2N- | n-Pent | 6.46 | 6.30 | 6.10 | [30] | ||||
104 | Me | CF3 | 5.00 | 5.45 | 5.54 | [30] | ||||
105 | H | Ph | 5.00 | 5.35 | 5.45 | [30] | ||||
No. | X | Y | Q | R2 | R5 | Obs. pIC50 | GA-RF | RF | Ref. a | |
106 | NH | O | PO3H2 | NH2 | iBu | 5.30 | 5.55 | 5.47 | [31] | |
107 | S | O | PO3H2 | H | H | 5.26 | 5.58 | 5.56 | [31] | |
108 | CH=CH | O | PO3H2 | NH2 | Ph | 7.38 | 6.95 | 6.87 | [31] | |
No. | R8 | R′ | Obs. pIC50 | GA-RF | RF | Ref. a | ||||
109 * | -NH(CH2)2PO3H2 | OH | 4.00 | 4.36 | 4.62 | [32] | ||||
110 * | -NH(CH2)2OPO3H2 | OH | 3.85 | 4.27 | 4.56 | [32] | ||||
111 | -NH(CH2)2PO3H2 | H | 4.00 | 4.27 | 4.44 | [32] | ||||
No. | [linker] | R9 | Obs. pIC50 | GA-RF | RF | Ref. a | ||||
112 | -NH(CH2)2- | Bn | 4.04 | 4.20 | 4.26 | [32] | ||||
113 * | -NH(CH2)2- | Ph(CH2)2- | 4.00 | 4.14 | 4.20 | [32] | ||||
114 | -NH(CH2)2- | 2-naphthyl-CH2- | 4.46 | 4.35 | 4.42 | [32] | ||||
115 * | -CONHCH2- | Ph(CH2)2- | 4.00 | 4.19 | 4.50 | [32] | ||||
116 | -(CH2)3- | Ph(CH2)2- | 4.00 | 4.04 | 4.16 | [32] | ||||
117 * | -CH=CHCH2- | Ph(CH2)2- | 4.00 | 4.19 | 4.28 | [32] | ||||
118 | -S(CH2)2- | Ph(CH2)2- | 3.84 | 4.03 | 4.29 | [32] | ||||
119 * | -CH2OCH2- | Ph(CH2)2- | 4.64 | 4.09 | 4.38 | [32] | ||||
120 | -2,5-furanyl- | Ph(CH2)2- | 5.30 | 4.95 | 4.95 | [32] | ||||
121 | -2,5-thienyl- | Ph(CH2)2- | 4.32 | 4.55 | 4.71 | [32] | ||||
No. | R8 | Obs. pIC50 | GA-RF | RF | Ref. a | |||||
122 * | -(CH2)2-OPO(OH)2 | 4.40 | 4.13 | 4.21 | [32] | |||||
123 | -2,5-furanyl-SO3H | 3.82 | 4.43 | 4.50 | [32] | |||||
No. | R2 | R | R9 | Obs. pIC50 | GA-RF | RF | Ref. a | |||
124 | H | -N(Me)2 | -(CH2)2Ph | 3.60 | 4.11 | 4.17 | [32] | |||
125 | H | -NHMe | -(CH2)2Ph | 4.30 | 4.46 | 4.41 | [32] | |||
126 | H | Cl | -(CH2)2Ph | 4.30 | 4.61 | 4.59 | [32] | |||
127 | H | -NH2 | -CH2CH(Ph)2 | 4.15 | 4.31 | 4.47 | [32] | |||
128 | H | -NH2 | -(CH2)2(cyclohexyl) | 5.85 | 5.54 | 5.54 | [32] | |||
129 | H | -NH2 | -(CH2)(2-naphthyl) | 5.48 | 5.22 | 5.19 | [32] | |||
130 | H | -NH2 | cyclopropyl | 5.82 | 5.70 | 5.78 | [32] | |||
131 | H | -NH2 | cyclopentyl | 5.70 | 5.69 | 5.76 | [32] | |||
132 | H | -NH2 | Et | 5.74 | 5.65 | 5.76 | [32] | |||
133 | H | -NH2 | isobutyl | 5.82 | 5.81 | 5.82 | [32] | |||
134 | H | -NH2 | neopentyl | 6.10 | 5.87 | 5.87 | [32] | |||
135 * | -SMe | -NH2 | isobutyl | 6.15 | 5.52 | 5.42 | [32] | |||
136 | -SO2Me | -NH2 | isobutyl | 4.55 | 4.95 | 4.99 | [32] | |||
No. | R2 | R9 | [linker] | Obs. pIC50 | GA-RF | RF | Ref. a | |||
137 * | H | -CH2C(Me)2CH2OH | 2,5-furanyl | 5.35 | 5.52 | 5.40 | [32] | |||
138 | H | -CH2C(Me)2CH2Cl | 2,5-furanyl | 6.05 | 5.83 | 5.91 | [32] | |||
139 * | H | -CH2C(Me)2CMe3 | 2,5-furanyl | 5.80 | 5.66 | 5.67 | [32] | |||
140 * | H | -CH(Me)CMe3 | 2,5-furanyl | 5.30 | 5.72 | 5.74 | [32] | |||
141 | -NH2 | -CH2CMe3 | 2,5-furanyl | 5.26 | 5.27 | 5.27 | [32] | |||
142 * | -SMe | -CH2CMe3 | 2,5-furanyl | 5.96 | 5.54 | 5.42 | [32] | |||
143 * | H | -CH2CMe3 | 2,5-(3,4-di-Cl)furanyl | 4.89 | 5.56 | 5.42 | [32] | |||
No. | R | Obs. pIC50 | GA-RF | RF | Ref. a | |||||
144 * | Me | 5.22 | 5.49 | 5.70 | [33] | |||||
145 | Et | 5.65 | 5.80 | 5.88 | [33] | |||||
146 | nPr | 5.96 | 6.00 | 6.03 | [33] | |||||
147 * | iBu | 5.82 | 5.91 | 6.00 | [33] | |||||
148 | cycllopropyl-CH2- | 6.10 | 6.03 | 6.02 | [33] | |||||
149 | cyclobutyl-CH2- | 6.10 | 6.04 | 6.01 | [33] | |||||
150 | cyclopentyl-CH2- | 5.82 | 5.87 | 5.81 | [33] | |||||
151 | cyclohexyl-CH2- | 5.60 | 5.64 | 5.63 | [33] | |||||
152 | cycloheptyl-CH2- | 5.49 | 5.57 | 5.64 | [33] | |||||
153 | norbornyl | 6.00 | 5.94 | 5.85 | [33] | |||||
154 * | benzyl | 5.30 | 5.72 | 5.70 | [33] | |||||
155 | 4-tBu-benzyl | 5.02 | 5.26 | 5.34 | [33] | |||||
156 | 4-CF3-benzyl | 5.15 | 5.50 | 5.51 | [33] | |||||
157 | 4-Ph-benzyl | 5.60 | 5.63 | 5.59 | [33] | |||||
158 * | 3-furanyl-CH2- | 5.38 | 5.74 | 5.68 | [33] | |||||
159 * | 3-HO-benzyl | 5.73 | 5.87 | 5.75 | [33] | |||||
160 * | 3-thienyl-CH2- | 5.40 | 6.02 | 6.08 | [33] | |||||
No. | R1 | R5 | R7 | Obs. pIC50 | GA-RF | RF | Ref. a | |||
161 * | iBu | Et | H | 5.60 | 5.86 | 5.87 | [33] | |||
162 | iBu | nPr | H | 5.52 | 5.69 | 5.66 | [33] | |||
163 * | iBu | MeO | H | 6.15 | 6.41 | 6.25 | [33] | |||
164 | iBu | OH | H | 6.30 | 6.23 | 6.24 | [33] | |||
165 | iBu | Cl | H | 6.70 | 6.52 | 6.56 | [33] | |||
166 | iBu | H | Cl | 6.05 | 6.19 | 6.11 | [33] | |||
167 | iBu | Br | H | 6.40 | 6.32 | 6.29 | [33] | |||
168 * | iBu | H | Br | 6.40 | 6.21 | 6.14 | [33] | |||
169 * | iBu | F | H | 7.00 | 6.56 | 6.47 | [33] | |||
170 * | (Et)2CHCH2- | F | H | 6.82 | 6.83 | 6.57 | [33] | |||
171 | (Et)2CH- | F | H | 6.07 | 6.42 | 6.38 | [33] | |||
172 * | cPr-CH2- | F | H | 7.26 | 6.54 | 6.53 | [33] | |||
No. | R5 | R6 | R7 | Obs. pIC50 | GA-RF | RF | Ref. a | |||
173 | Br | H | Br | 6.00 | 6.09 | 6.03 | [33] | |||
174 | Cl | H | Cl | 6.35 | 6.34 | 6.30 | [33] | |||
175 * | F | H | Cl | 7.00 | 6.77 | 6.67 | [33] | |||
176 | F | H | Br | 6.89 | 6.75 | 6.67 | [33] | |||
177 | F | Cl | H | 6.65 | 6.66 | 6.59 | [33] | |||
178 | Br | Cl | Cl | 5.00 | 5.53 | 5.60 | [33] | |||
179 * | F | H | vinyl | 6.55 | 6.90 | 6.94 | [33] | |||
180 | F | H | cPr | 7.22 | 7.08 | 7.10 | [33] | |||
No. | R7 | Obs. pIC50 | GA-RF | RF | Ref. a | |||||
181 * | Ph | 7.05 | 6.79 | 6.83 | [33] | |||||
182 | 4-F-Ph | 6.74 | 6.74 | 6.75 | [33] | |||||
183 | 4-Cl-Ph | 7.05 | 6.94 | 6.81 | [33] | |||||
184 | Et | 7.26 | 7.07 | 7.06 | [33] | |||||
185 | nPr | 7.00 | 6.99 | 7.02 | [33] | |||||
186 | tBu(CH2)2- | 6.68 | 6.70 | 6.67 | [33] | |||||
187 | (Me)2CH(CH2)3- | 7.00 | 6.92 | 6.99 | [33] | |||||
188 | HO(CH2)3- | 7.10 | 6.97 | 7.05 | [33] | |||||
189 | (Me)2N(CH2)3- | 7.26 | 6.72 | 6.73 | [33] | |||||
190 * | Cl(CH2)4- | 7.15 | 6.74 | 6.78 | [33] |
Model | r2ts | r2pred | r2o | (r2ts − r2o)/r2ts | k | r2m |
---|---|---|---|---|---|---|
GA-RF | 0.91 | 0.90 | 0.90 | 0.01 | 1.01 | 0.83 |
RF | 0.87 | 0.85 | 0.85 | 0.02 | 1.01 | 0.76 |
© 2012 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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Hao, M.; Zhang, S.; Qiu, J. Toward the Prediction of FBPase Inhibitory Activity Using Chemoinformatic Methods. Int. J. Mol. Sci. 2012, 13, 7015-7037. https://doi.org/10.3390/ijms13067015
Hao M, Zhang S, Qiu J. Toward the Prediction of FBPase Inhibitory Activity Using Chemoinformatic Methods. International Journal of Molecular Sciences. 2012; 13(6):7015-7037. https://doi.org/10.3390/ijms13067015
Chicago/Turabian StyleHao, Ming, Shuwei Zhang, and Jieshan Qiu. 2012. "Toward the Prediction of FBPase Inhibitory Activity Using Chemoinformatic Methods" International Journal of Molecular Sciences 13, no. 6: 7015-7037. https://doi.org/10.3390/ijms13067015