Abstract
The data have been obtained from the Heme Oxygenase Database (HemeOxDB) and refined according to the 2D-QSAR requirements. These data provide information about a set of more than 380 Heme Oxygenase-1 (HO-1) inhibitors. The development of the 2D-QSAR model has been undertaken with the use of CORAL software using SMILES, molecular graphs and hybrid descriptors (SMILES and graph together). The 2D-QSAR model regressions for HO-1 half maximal inhibitory concentration (IC50) expressed as pIC50 (pIC50=−LogIC50) are here included. The 2D-QSAR model was also employed to predict the HO-1 pIC50values of the FDA approved drugs that are herewith reported.
Keywords: Heme Oxygenase, 2D-QSAR, pIC50 prediction, FDA, CORAL
Specifications Table
| Subject area | Computational Chemistry |
| More specific subject area | Quantitative Structure-Activity Relationship (QSAR) modeling |
| Type of data | Table, figure |
| How data was acquired | Statistical modeling and online databases |
| Data format | Raw and analyzed |
| Experimental factors | The whole dataset consists of 382 HO-1 inhibitors which were randomly split and divided into training, invisible training, calibration, and validation sets. |
| Experimental features | The 2D-QSAR models have been developed using CORAL software. Chemical structure descriptors and pIC50 were used as variables. |
| Data source location | Department of Drug Sciences, Department of Mathematics and Computer Sciences, University of Catania, Italy |
| Data accessibility | With this article |
Value of the data
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•
HO-1 is a crucial enzyme involved in the catabolism of heme and overexpressed in a number of tumors with poor clinical outcome.
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•
2D-QSAR modeling data was generated to provide a method useful in finding or repurposing novel HO-1 inhibitors.
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The model has also been used to predict the HO-1 pIC50 for the FDA-approved drugs.
1. Data
HO-1 is a crucial enzyme involved in the regioselective catabolism of heme. Strongly induced upon stressful condition, HO-1 is recognized to fulfil crucial roles in cytoprotection and in the maintenance of endogenous homeostasis, playing a role in metabolic, cardiovascular, and pulmonary diseases [1], [2], [3]. Nevertheless, under adverse circumstances it has been demonstrated that aberrant levels of HO-1 may sustain cancerous diseases. Therefore, its inhibition is of interest in all such pathological conditions [4], [5], [6], [7]. QSAR models as well as other methods are regression, classification or statistical methods used in the chemical and biological sciences, helping in predicting variables or in understanding patterns [8], [9], [10], [11]. Data here reported provide information about a set of HO-1 inhibitors, recovered from the Heme Oxygenase Database (HemeOxDB) together with their pIC50 (−logIC50) [12]. These latter have been used in building up the first hybrid 2D-QSAR model embracing the all set of known HO-1 inhibitors. The model has also been used to predict the HO-1 pIC50 for the Food and Drug Administration approved drugs. These latter predicted HO-1 pIC50 data are also here reported.
2. Experimental design, materials and methods
2.1. Dataset preparation
The dataset consists of 382 HO-1 inhibitors which were randomly split three times and then divided into training (131 compounds), invisible training (131 compounds), calibration (60 compounds) sets for model development and a validation set (60 compounds) for invisible model validation. The three splits and four sets have been randomly generated, and their pIC50 minimum, maximum and middle are reported in Table 1.
Table 1.
Analysis of biological endpoints the HO-1 models (pIC50).
| Split | Set | Min | Max | Middle |
|---|---|---|---|---|
| Split 1 | Sub-training | 3.69 | 6.55 | 5.12 |
| Calibration | 3.41 | 7.22 | 5.31 | |
| Test | 4 | 6.62 | 5.31 | |
| Validation | 4 | 7.22 | 5.61 | |
| Split 2 | Sub-training | 3.41 | 7.22 | 5.31 |
| Calibration | 3.69 | 6.95 | 5.32 | |
| Test | 4 | 7.22 | 5.61 | |
| Validation | 3.98 | 6.56 | 5.27 | |
| Split 3 | Sub-training | 3.69 | 7.22 | 5.45 |
| Calibration | 3.41 | 7.22 | 5.31 | |
| Test | 4 | 6.95 | 5.47 | |
| Validation | 3.78 | 5.77 | 4.77 |
2.2. 2D-QSAR model development
2D-QSAR models have been developed with the use of the software CORAL [13], [14], [15]. Once the splits and sets were determined, nine models were developed and statistical quality recorded. Differences of these models consist in the way molecular structures have been depicted for the software process. Thus, in Table 2 regressions for the HO-1 pIC50 models using SMILES, molecular graphs and hybrid descriptors (SMILES and graph together) are reported. While in Table 3 is reported the statistical quality of models of the HO-1 pIC50.
Table 2.
Regression for the HO-1 pIC50 models.
| Model | Split | Regression equation |
|---|---|---|
| Hybrid | Split 1 | pIC50=0.0000163(±0.0147044)+0.0473151(±0.0001566)*DCW(0,41) |
| Split 2 | pIC50=−0.0264725(±0.0163573)+0.0471089(±0.0001704)*DCW(0,33) | |
| Split 3 | pIC50=0.0038812(±0.0212544)+0.0354836(±0.0001711)*DCW(2,30) | |
| SMILES | Split 1 | pIC50=1.7303408(±0.0126104)+0.0966933(±0.0004343)*DCW(0,36) |
| Split 2 | pIC50=2.1559955(±0.0115205)+0.0847448(±0.0004112*DCW(0,31) | |
| Split 3 | pIC50=2.2807230(±0.0150322)+0.0670793(±0.0004516)*DCW(2,30) | |
| Graph | Split 1 | pIC50=0.1566205(±0.0185526)+0.0603249(±0.0002615)*DCW(0,40) |
| Split 2 | pIC50=0.0038015(±0.0250024)+0.0618955(±0.0003421)*DCW(0,34) | |
| Split 3 | pIC50=−0.0000202(±0.0224837)+).0724072(±0.0003652)*DCW(2,70) |
Table 3.
Statistical quality for models of HO-1 pIC50.
| Model | Split | Set | T* | N* | n | r2 | q2 | s | Fcalc | F(0.05,1,n–2) | p-value |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Hybrid | Split 1 | Sub-training | 0 | 41 | 131 | 0.8085 | 0.8033 | 0.337 | 545 | 253.33 | 0.034 |
| Calibration | 131 | 0.8029 | 0.7971 | 0.390 | 526 | 253.33 | 0.035 | ||||
| Test | 60 | 0.8183 | 0.8053 | 0.381 | 261 | 252.12 | 0.049 | ||||
| Validation | 60 | 0.8291 | 0.398 | 281 | 252.12 | 0.047 | |||||
| Split 2 | Sub-training | 0 | 33 | 131 | 0.7782 | 0.7721 | 0.414 | 453 | 253.33 | 0.037 | |
| Calibration | 131 | 0.8187 | 0.8130 | 0.349 | 582 | 253.33 | 0.033 | ||||
| Test | 60 | 0.8888 | 0.8801 | 0.302 | 464 | 252.12 | 0.037 | ||||
| Validation | 60 | 0.7940 | 0.515 | 223 | 252.12 | 0.053 | |||||
| Split 3 | Sub-training | 2 | 30 | 131 | 0.7263 | 0.7177 | 0.427 | 342 | 253.33 | 0.043 | |
| Calibration | 131 | 0.7265 | 0.7192 | 0.438 | 343 | 253.33 | 0.043 | ||||
| Test | 60 | 0.8189 | 0.8037 | 0.502 | 262 | 252.12 | 0.049 | ||||
| Validation | 60 | 0.8204 | 0.562 | 265 | 252.12 | 0.049 | |||||
| SMILES | Split 1 | Sub-training | 131 | 0.6933 | 0.6849 | 0.427 | 292 | 253.33 | 0.047 | ||
| Calibration | 131 | 0.6590 | 0.6497 | 0.505 | 249 | 253.33 | 0.050 | ||||
| Test | 60 | 0.5008 | 0.4714 | 0.569 | 58 | 252.12 | 0.100 | ||||
| Validation | 60 | 0.6290 | 0.551 | 98 | 252.12 | 0.080 | |||||
| Split 2 | Sub-training | 131 | 0.6508 | 0.6415 | 0.520 | 240 | 253.33 | 0.051 | |||
| Calibration | 131 | 0.6883 | 0.6790 | 0.455 | 285 | 253.33 | 0.047 | ||||
| Test | 60 | 0.7593 | 0.7400 | 0.446 | 183 | 252.12 | 0.059 | ||||
| Validation | 60 | 0.4645 | 0.688 | 50 | 252.12 | 0.112 | |||||
| Split 3 | Sub-training | 131 | 0.6141 | 0.6010 | 0.507 | 205 | 253.33 | 0.057 | |||
| Calibration | 131 | 0.6096 | 0.5994 | 0.527 | 201 | 253.33 | 0.056 | ||||
| Test | 60 | 0.6697 | 0.6431 | 0.620 | 118 | 252.12 | 0.073 | ||||
| Validation | 60 | 0.5006 | 0.614 | 58 | 252.12 | 0.104 | |||||
| Graph | Split 1 | Sub-training | 0 | 40 | 131 | 0.7115 | 0.7035 | 0.414 | 318 | 253.33 | 0.047 |
| Calibration | 131 | 0.7077 | 0.6980 | 0.470 | 312 | 253.33 | 0.045 | ||||
| Test | 60 | 0.6839 | 0.6616 | 0.483 | 126 | 252.12 | 0.071 | ||||
| Validation | 60 | 0.6751 | 0.502 | 121 | 252.12 | 0.072 | |||||
| Split 2 | Sub-training | 0 | 34 | 131 | 0.6717 | 0.6613 | 0.504 | 264 | 253.33 | 0.049 | |
| Calibration | 131 | 0.7293 | 0.7209 | 0.444 | 348 | 253.33 | 0.043 | ||||
| Test | 60 | 0.7247 | 0.6941 | 0.452 | 153 | 252.12 | 0.064 | ||||
| Validation | 60 | 0.7021 | 0.543 | 137 | 252.12 | 0.068 | |||||
| Split 3 | Sub-training | 2 | 70 | 131 | 0.7336 | 0.7247 | 0.421 | 355 | 253.33 | 0.042 | |
| Calibration | 131 | 0.7336 | 0.7263 | 0.441 | 355 | 253.33 | 0.042 | ||||
| Test | 60 | 0.7070 | 0.6811 | 0.573 | 140 | 252.12 | 0.067 | ||||
| Validation | 60 | 0.5712 | 0.659 | 77 | 252.12 | 0.090 |
T* and N* are preferable values for the threshold and the number of epochs, respectively; n is the number of compounds in the set; r2 is the correlation coefficient; q2 is the cross-validated correlation coefficient; s is the root-mean-square error; F is the Fisher F ratio; F(0.05,1,n–2) is the 0.05-quantile of the Fisher's distribution F(1,n–2); p-value is the Fisher test's significance level.
2.3. 2D-QSAR model settings for the best model [hybrid model split 1]
Fig. 1 shows a CORAL screenshot with settings for hybrid model split 1. While in Table 4, the complete list of SMILES and their distribution into the sub-training (+), calibration (−), test (#) and validation (*) sets for HO-1 pIC50 hybrid model split 1 is reported. These data may be prospectively used in finding novel models for HO-1 inhibition.
Fig. 1.
CORAL software validation method for the HO-1 pIC50 hybrid model [hybrid model split 1].
Table 4.
List of SMILES and their distribution into the sub-training (+), calibration (–), test (#) and validation (*) for hybrid model split 1.
| HemeOxDB_ID | SMILES | Exp pIC50 | |
|---|---|---|---|
| + | HemeOxDB131 | CSC[C@@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 5.046 |
| + | HemeOxDB306 | C(CC1(CN2C=NC(=C2)C2=CC=CC=C2)OCCO1)C1=CC=CC=C1 | 4 |
| + | HemeOxDB272 | COC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| + | HemeOxDB247 | BrC1=CC=CC(OCCCN2C=NC=N2)=C1 | 4 |
| + | HemeOxDB55 | C[C@@H]1CO[C@@](CCC2=CC=CC=C2)(CN2C=CN=C2)O1 | 5.699 |
| + | HemeOxDB20 | C(CC1(CN2C=CN=C2)OCCO1)C1=CC=CC=C1 | 6.155 |
| + | HemeOxDB81 | O=C(CN1C=NC=N1)C1=CC=C(CC2=CC=CC=C2)C=C1 | 5.569 |
| + | HemeOxDB34 | OC(CN1C=CN=C1)C1=CC=C(Cl)C=C1 | 5.924 |
| + | HemeOxDB162 | [O-][N+](=O)C1=CC=C(C=C1)C(=O)CN1C=NC=N1 | 4.717 |
| + | HemeOxDB59 | O=C(CN1C=CN=C1)C1=CC=C(C=C1)C1=CC=CC=C1 | 5.678 |
| + | HemeOxDB113 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC=CC(Br)=C3)O2)C=C1 | 5.301 |
| + | HemeOxDB185 | BrC1=CC=CC(OCCCCCCN2C=CN=C2)=C1 | 4.469 |
| + | HemeOxDB219 | O=C(CCN1C=CN=C1)C1=CC=CC=C1 | 4.102 |
| + | HemeOxDB107 | O=C(CN1C=CN=C1)C1=CC2=C(CCCC2)C=C1 | 5.398 |
| + | HemeOxDB197 | BrC1=CC=CC=C1CN1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4.377 |
| + | HemeOxDB196 | O=C(CCC1=CC=CC=C1)CN1C=NC(=C1C1=CC=CC=C1)C1=CC=CC=C1 | 4.398 |
| + | HemeOxDB99 | O=C(CCC1=CC=CC=C1)CN1C=CN=C1 | 5.398 |
| + | HemeOxDB91 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](COC3=CC=C(Br)C=C3)O2)C=C1 | 5.456 |
| + | HemeOxDB258 | CCCN1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4 |
| + | HemeOxDB369 | O=C(CCC1=CC=CC=C1)CN1N=NN=C1C1=CC=CC=C1 | 4 |
| + | HemeOxDB95 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CN=[N+]=[N-])O2)C=C1 | 5.444 |
| + | HemeOxDB122 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=C(Br)C=CC=C3)O2)C=C1 | 5.222 |
| + | HemeOxDB373 | O=C1C(CC2=C1C=CC=C2)N1C=CN=C1 | 4 |
| + | HemeOxDB125 | OC(CCC1=CC=CC=C1)CN1C=CN=C1 | 5.208 |
| + | HemeOxDB35 | FC[C@@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 5.921 |
| + | HemeOxDB23 | O=C(CN1C=NC=N1)C1=CC=C2C=CC=CC2=C1 | 6.155 |
| + | HemeOxDB261 | CSC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| + | HemeOxDB80 | BrC1=CC=C(C=C1)C(=O)CN1C=NC=N1 | 5.569 |
| + | HemeOxDB198 | IC1=CC=C(OCCCCCCN2C=CN=C2)C=C1 | 4.377 |
| + | HemeOxDB339 | COC1=CC=C(CCN2CCC(CC2)NC2=NC3=CC=CC=C3N2)C=C1 | 4 |
| + | HemeOxDB143 | C[C@H]1CO[C@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 4.921 |
| + | HemeOxDB233 | COC(=O)NC1=NC2=C(N1)C=CC(=C2)C(=O)C1=CC=C(F)C=C1 | 4 |
| + | HemeOxDB178 | [H]C1=CC2=C(OC(SCCCCN3C=CN=C3)=N2)C=C1 | 4.51 |
| + | HemeOxDB280 | IC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| + | HemeOxDB92 | C(CCC1=CC=CC=C1)CN1C=CN=C1 | 5.456 |
| + | HemeOxDB275 | C(C1CCCCC1)N1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4 |
| + | HemeOxDB377 | ON=C(N1C=CN=C1)C(=O)C1=CC=C(Cl)C=C1 | 3.987 |
| + | HemeOxDB157 | O=C(CN1C=NC=N1)C1=CC=C2OCCOC2=C1 | 4.745 |
| + | HemeOxDB187 | ClC1=CC2=C(SC(SCCCCCN3C=CN=C3)=N2)C=C1 | 4.44 |
| + | HemeOxDB330 | CN1C(NCCC2=CNC=N2)=NC2=CC=CC=C12 | 4 |
| + | HemeOxDB100 | ClC1=CC=C(C=C1)C(=O)CN1C=CN=C1 | 5.398 |
| + | HemeOxDB138 | ClC1=CC=C(CSC(CN2C=CN=C2)C2=CC=C(Cl)C=C2Cl)C=C1 | 4.959 |
| + | HemeOxDB43 | NC1=CC=CC(SC[C@@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)=C1 | 5.824 |
| + | HemeOxDB120 | ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C2=CC=C(Cl)C=C2Cl)C=C1 | 5.237 |
| + | HemeOxDB210 | ClC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C(Cl)=C1 | 4.208 |
| + | HemeOxDB358 | O=C(CCC1=CC=CC=C1)CN1C=CN=C1C1=CC=CC=C1 | 4 |
| + | HemeOxDB340 | CS(=O)(=O)C1=NC=CN1CC(=O)CCC1=CC=CC=C1 | 4 |
| + | HemeOxDB366 | O=C(CCC1=CC=CC=C1)CN1N=CC=N1 | 4 |
| + | HemeOxDB234 | O=C(NCCCN1C=CN=C1)C1=CC=CC=C1 | 4 |
| + | HemeOxDB50 | BrC1=CC(=CC=C1)C(=O)CN1C=NC=N1 | 5.745 |
| + | HemeOxDB16 | ClC1=CC=C(CCCCN2C=CN=C2)C=C1 | 6.301 |
| + | HemeOxDB379 | CCC(O)CN1C=CN=C1 | 3.883 |
| + | HemeOxDB164 | C[C@@H]1CO[C@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 4.699 |
| + | HemeOxDB308 | C(CC1(CN2N=CC=N2)OCCO1)C1=CC=CC=C1 | 4 |
| + | HemeOxDB365 | O=C(CCC1=CC=CC=C1)CN1N=C2C=CC=CC2=N1 | 4 |
| + | HemeOxDB154 | CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]1CO[C@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 4.77 |
| + | HemeOxDB278 | O=N(=O)C1=CC=CC(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=C1 | 4 |
| + | HemeOxDB352 | CSC1=NN=NN1CC(=O)CCC1=CC=CC=C1 | 4 |
| + | HemeOxDB248 | IC1=CC=C(OCCCN2C=CN=C2)C=C1 | 4 |
| + | HemeOxDB189 | NC1=CC(SC[C@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)=CC=C1 | 4.42 |
| + | HemeOxDB245 | [O-][N+](=O)C1=CC=C(OCCCN2C=CN=C2)C=C1 | 4 |
| + | HemeOxDB349 | CSC1=NN(CC(=O)CCC2=CC=CC=C2)C=N1 | 4 |
| + | HemeOxDB361 | O=C(CCC1=CC=CC=C1)CN1C=NC(C#N)=C1C#N | 4 |
| + | HemeOxDB132 | O=C(CCC1=CC=CC=C1)CN1C=NC(=N1)C1=CC=CC=C1 | 5.046 |
| + | HemeOxDB317 | CC1=NC=CN1CC(=O)CCC1=CC=C(Br)C=C1 | 4 |
| + | HemeOxDB133 | O=C(CCC1=CC=CC=C1)CN1N=CN=N1 | 5.018 |
| + | HemeOxDB282 | ClC1=CC(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=CC(Cl)=C1 | 4 |
| + | HemeOxDB363 | O=C(CCC1=CC=CC=C1)CN1C=NC2=CC=CC=C12 | 4 |
| + | HemeOxDB274 | O=N(=O)C1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| + | HemeOxDB148 | NC1=CC=C(SC[C@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 4.83 |
| + | HemeOxDB49 | OC1=CC=C(OC[C@@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.745 |
| + | HemeOxDB270 | BrC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| + | HemeOxDB37 | ClC1=C(Cl)C=C(C=C1)C(=O)CN1C=CN=C1 | 5.907 |
| + | HemeOxDB364 | O=C(CCC1=CC=CC=C1)CN1N=C(N=C1C1=CC=CC=C1)C1=CC=CC=C1 | 4 |
| + | HemeOxDB294 | COC(=O)NC1=NC2=CC(=CC=C2N1)C(=O)C1=CC=CC=C1 | 4 |
| + | HemeOxDB320 | CCN1CCN(CC1)C1=NC2=CC=CC=C2N1 | 4 |
| + | HemeOxDB76 | O=C(CCC1=CC=CC=C1)CN1C=NN=N1 | 5.585 |
| + | HemeOxDB295 | NCCC1=CN=CN1 | 4 |
| + | HemeOxDB163 | BrC1=CC=CC(OCCCCCN2C=NC=N2)=C1 | 4.699 |
| + | HemeOxDB304 | C(CC1(CN2C=CC=N2)OCCO1)C1=CC=CC=C1 | 4 |
| + | HemeOxDB61 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC=C(Br)C=C3)O2)C=C1 | 5.678 |
| + | HemeOxDB112 | C(C1=CC=CC=C1)C1=CC=C(C=C1)C1(CN2C=CN=C2)OCCO1 | 5.303 |
| + | HemeOxDB205 | CC(N1C=CN=C1)C(=O)C1=CC=CC=C1 | 4.31 |
| + | HemeOxDB38 | ClC1=C(Cl)C=C(C=C1)C(=O)CN1C=NC=N1 | 5.886 |
| + | HemeOxDB380 | C(N1C=NC=N1)C1(OCCO1)C1=CC=CC=C1 | 3.842 |
| + | HemeOxDB17 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](COC3=CC=CC=C3)O2)C=C1 | 6.229 |
| + | HemeOxDB375 | OC(CCC1=CC=CC=C1)CN1C=NC(=C1C1=CC=CC=C1)C1=CC=CC=C1 | 4 |
| + | HemeOxDB67 | C(N1C=CN=C1)C12CC3CC(CC(C3)C1)C2 | 5.658 |
| + | HemeOxDB172 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC=NC=C3)O2)C=C1 | 4.602 |
| + | HemeOxDB72 | O=C(CCC1=CC=CC=C1)CN1C=NC=N1 | 5.602 |
| + | HemeOxDB161 | ClC1=CC=C(C=C1)C1(CN2C=CN=C2)OCCO1 | 4.721 |
| + | HemeOxDB232 | [O-][N+](=O)C1=CC=C(OCCCN2C=NC=N2)C=C1 | 4 |
| + | HemeOxDB286 | ClC1=CC2=C(SC(SCCCCN3C=CN=C3)=N2)C=C1 | 4 |
| + | HemeOxDB86 | C(CC12CC3CC(CC(C3)C1)C2)N1C=CN=C1 | 5.523 |
| + | HemeOxDB62 | FC(F)(F)C1=CC=C(SC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.678 |
| + | HemeOxDB381 | O=C(CCC1=CC=CC=C1)C[N+]1=CC=NC=C1 | 3.788 |
| + | HemeOxDB186 | ClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | 4.456 |
| + | HemeOxDB382 | C1CC(CCC1NC1=NC2=CC=CC=C2N1)C1=CN=CN1 | 3.699 |
| + | HemeOxDB127 | FC1=CC=C(COC(CN2C=CN=C2)C2=CC=C(CCC3=CC=CC=C3)C=C2)C=C1 | 5.155 |
| + | HemeOxDB173 | OC1=C(C=CC=C1)C(=O)CCN1C=CN=C1 | 4.602 |
| + | HemeOxDB31 | IC1=CC=C(OCCCCN2C=CN=C2)C=C1 | 6 |
| + | HemeOxDB289 | N1C=CN=C1 | 4 |
| + | HemeOxDB378 | COC(=O)NC1=NC2=C(N1)C=CC(=C2)S(=O)C1=CC=CC=C1 | 3.939 |
| + | HemeOxDB214 | C(CC1=CC=CC=C1)N1C=CN=C1 | 4.143 |
| + | HemeOxDB203 | OC(CCC1=CC=CC=C1)CN1C=CN=N1 | 4.357 |
| + | HemeOxDB362 | O=C(CCC1=CC=CC=C1)CN1C=NC=C1N(=O)=O | 4 |
| + | HemeOxDB212 | BrC1=CC=CC(OCCCN2C=CN=C2)=C1 | 4.161 |
| + | HemeOxDB69 | ClC1=CC=C(C(=O)CN2C=CN=C2)C(Cl)=C1 | 5.658 |
| + | HemeOxDB336 | COC(=O)SC1=NC=CN1CC(=O)CCC1=CC=CC=C1 | 4 |
| + | HemeOxDB130 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](COC3=CC=C(I)C=C3)O2)C=C1 | 5.046 |
| + | HemeOxDB242 | C(CCN1C=CN=C1)CN1C=CN=C1 | 4 |
| + | HemeOxDB58 | FC(F)(F)C1=CN=C(SC[C@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.678 |
| + | HemeOxDB284 | BrC1=CC=CC(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=C1 | 4 |
| + | HemeOxDB190 | BrC1=CC=C(C=C1)C1(CN2C=NC=N2)OCCO1 | 4.42 |
| + | HemeOxDB134 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CN3C=CN=C3)O2)C=C1 | 5 |
| + | HemeOxDB44 | BrC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)CN1C=CN=C1 | 5.824 |
| + | HemeOxDB13 | C(CCC1=CC=C(CCCC[N]2=CCN=C2)C=C1)CN1C=CN=C1 | 6.398 |
| + | HemeOxDB300 | BrC1=CC=C(CNCC2=CN=CC=C2)C=C1 | 4 |
| + | HemeOxDB119 | NC1=CC=C(SC[C@@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.237 |
| + | HemeOxDB9 | FC1=CC=C(OC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 6.553 |
| + | HemeOxDB327 | ClC1=CC=C(C=C1)C(/CN1C=CN=C1)=N/NC1=CC=CC=C1 | 4 |
| + | HemeOxDB353 | FC(F)(F)C(=O)N1C=CN=C1 | 4 |
| + | HemeOxDB273 | FC(F)(F)C1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| + | HemeOxDB26 | CC1=CC=C(C=C1)S(=O)(=O)C[C@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 6.097 |
| + | HemeOxDB97 | O=S(CCCN1C=CN=C1)C1=CC=CC=C1 | 5.432 |
| + | HemeOxDB311 | C1C2CC3CC1CC(C2)C3N1C=CN=C1 | 4 |
| + | HemeOxDB165 | ClC1=CC=C(CCC2(CN3C=CN=C3)OCCCO2)C=C1 | 4.699 |
| + | HemeOxDB305 | C(CC1(CN2C=CN=N2)OCCO1)C1=CC=CC=C1 | 4 |
| + | HemeOxDB228 | C(CCCN1C=CN=C1)CCN1C=CN=C1 | 4 |
| + | HemeOxDB180 | BrC1=CC=C(OCCCCN2C=CN=C2)C=C1 | 4.509 |
| + | HemeOxDB204 | O/N=C(/CN1C=CN=C1)C1=CC=C(Cl)C=C1 | 4.337 |
| – | HemeOxDB303 | BrC1=NN(CC(=O)CCC2=CC=CC=C2)C(Br)=N1 | 4 |
| – | HemeOxDB267 | ClC1=CC=CC=C1CN1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4 |
| – | HemeOxDB60 | BrC1=CC=CC(OCCCCN2C=CN=C2)=C1 | 5.678 |
| – | HemeOxDB201 | C(N1C=CN=C1)C1=CC=CC=C1 | 4.357 |
| – | HemeOxDB259 | C(N1CCCC1)C1=NC2=C(C=CC=C2)N1C(C1=CC=CC=C1)C1=CC=CC=C1 | 4 |
| – | HemeOxDB137 | OC(CCC1=CC=CC=C1)CN1C=NC=N1 | 4.991 |
| – | HemeOxDB254 | COC1=CC=C(CCN2CCC(CC2)NC2=NC3=C(C=CC=C3)N2CC2=CC=C(F)C=C2)C=C1 | 4 |
| – | HemeOxDB68 | ClC1=CC=C(C=C1)C(=O)CN1C=NC=N1 | 5.658 |
| – | HemeOxDB227 | ClC1=CC=C(CC[C@]2(CN3C=CN=C3)OC[C@@H](COC3=CC=C(C=C3)C34CC5CC(CC(C5)C3)C4)O2)C=C1 | 4 |
| – | HemeOxDB372 | O=C(NCCCN1C=CN=C1)NC1=CC=CC=C1 | 4 |
| – | HemeOxDB90 | ClC[C@@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 5.456 |
| – | HemeOxDB11 | NC1=CC=C(SC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 6.481 |
| – | HemeOxDB194 | NC1=CC=C(SC[C@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 4.398 |
| – | HemeOxDB268 | O=N(=O)C1=CC=CC=C1CN1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4 |
| – | HemeOxDB281 | C(CN1C(CN2CCCC2)=NC2=C1C=CC=C2)OC1=CC=CC=C1 | 4 |
| – | HemeOxDB337 | COC1=CC=C(CCN2CCC(CC2)NC2=NC3=C(C=C(C)C(C)=C3)N2CC2=CC=C(F)C=C2)C=C1 | 4 |
| – | HemeOxDB310 | C(CCNC1=NC2=CC=CC=C2N1)CCN1CCCCC1 | 4 |
| – | HemeOxDB238 | NC1=C(SC[C@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=CC=C1 | 4 |
| – | HemeOxDB88 | BrC1=CC=C(C=C1)C(=O)CN1C=CN=C1 | 5.495 |
| – | HemeOxDB223 | C(CCN1C=NC=N1)COC1=CC=CC=C1 | 4.036 |
| – | HemeOxDB199 | BrCC(=O)CCC1=CC=C(Br)C=C1 | 4.377 |
| – | HemeOxDB64 | ClC1=C(Cl)C(Cl)=C(C=C1)C(=O)CN1C=CN=C1 | 5.677 |
| – | HemeOxDB206 | BrC1=C(OCCCCN2C=CN=C2)C=CC=C1 | 4.276 |
| – | HemeOxDB156 | O=C1OC2=C(C=CC=C2)N1CCCCN1C=CN=C1 | 4.752 |
| – | HemeOxDB331 | COC(=O)C1=C(N(CC(=O)CCC2=CC=CC=C2)C=N1)C(=O)OC | 4 |
| – | HemeOxDB77 | C[C@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 5.585 |
| – | HemeOxDB213 | [H][C@@]12CCCC[C@]1([H])OC(CCC1=CC=C(Cl)C=C1)(CN1C=CN=C1)O2 | 4.161 |
| – | HemeOxDB251 | C1=CN(C=N1)C1=CC=CC=C1 | 4 |
| – | HemeOxDB220 | OC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1 | 4.097 |
| – | HemeOxDB65 | FC1=CC=C(SC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.658 |
| – | HemeOxDB175 | COC1=CC=C(OC[C@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 4.553 |
| – | HemeOxDB341 | CS(=O)(=O)C1=NC=NN1CC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB383 | OC1=CC=C(CCC(=O)CN2C=CN=C2)C=C1 | 3.418 |
| – | HemeOxDB357 | O=C(CCC1=CC=CC=C1)CN1C=CC=N1 | 4 |
| – | HemeOxDB169 | BrC1=CN(CCC(=O)CCC2=CC=CC=C2)C=N1 | 4.658 |
| – | HemeOxDB195 | CC(O)C(CC1=CC=C(Cl)C=C1)N1C=CN=C1 | 4.398 |
| – | HemeOxDB21 | COC1=CC=C(CCC(O)CN2C=CN=C2)C=C1 | 6.155 |
| – | HemeOxDB14 | CC(C)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=NC=N3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1 | 6.387 |
| – | HemeOxDB338 | COC1=CC=C(CCN2CCC(CC2)NC2=NC3=CC(Cl)=C(Cl)C=C3N2CC2=CC=C(F)C=C2)C=C1 | 4 |
| – | HemeOxDB46 | OC1=CC=C(SC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.799 |
| – | HemeOxDB155 | CC1=CC=C(C=C1)C(=O)CN1C=CN=C1 | 4.77 |
| – | HemeOxDB56 | OC(CCN1C=CN=C1)C12CC3CC(CC(C3)C1)C2 | 5.699 |
| – | HemeOxDB1 | OC(CCC1=CC=C(I)C=C1)CN1C=CN=C1 | 7.222 |
| – | HemeOxDB158 | ClC1=CC2=C(SC(SCCCN3C=CN=C3)=N2)C=C1 | 4.735 |
| – | HemeOxDB351 | CSC1=NN(CCC(=O)CCC2=CC=CC=C2)C=N1 | 4 |
| – | HemeOxDB321 | CCOC(=O)C1=NC=CN1CC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB250 | CSCCC(N)C(O)=O | 4 |
| – | HemeOxDB41 | NC1=CC=C(OC[C@@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.854 |
| – | HemeOxDB174 | O=C(CN1C=CN=C1)C1=CC=CC=C1 | 4.553 |
| – | HemeOxDB293 | FC1=CC=C(CN2C(NC3CCNCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| – | HemeOxDB177 | ClC1=CC(Cl)=C(C=C1)C1(CN2C=CN=C2)OCCO1 | 4.538 |
| – | HemeOxDB83 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC=C(Cl)C=C3)O2)C=C1 | 5.553 |
| – | HemeOxDB239 | NC(CC1=CN=CN1)C(O)=O | 4 |
| – | HemeOxDB257 | N#CC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| – | HemeOxDB360 | O=C(CCC1=CC=CC=C1)CN1C=NC(=N1)N(=O)=O | 4 |
| – | HemeOxDB128 | ClC1=C(Cl)C=C(C=C1)C1(CN2C=CN=C2)OCCO1 | 5.097 |
| – | HemeOxDB144 | BrC1=CC=C(C=C1)C1(CN2C=CN=C2)OCCO1 | 4.921 |
| – | HemeOxDB54 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](COC3=CC=C(C=C3)C3=CC=CC=C3)O2)C=C1 | 5.699 |
| – | HemeOxDB253 | CC1=NC=CN1 | 4 |
| – | HemeOxDB265 | CC1=CC=CC(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=C1 | 4 |
| – | HemeOxDB335 | COC(=O)NC1=NC2=CC(=CC=C2N1)C(=O)C1=CC=CS1 | 4 |
| – | HemeOxDB87 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC#N)O2)C=C1 | 5.523 |
| – | HemeOxDB347 | CSC1=NC=CN1CCC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB183 | ClC1=CC=C(C=C1)C(=O)CCN1C=CN=C1 | 4.495 |
| – | HemeOxDB117 | NC1=CC=CC(SC[C@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)=C1 | 5.284 |
| – | HemeOxDB191 | COC1=CC=C(C=C1)C(=O)CN1C=CN=C1 | 4.409 |
| – | HemeOxDB208 | OC(CCC1=CC=CC=C1)CN1C=NN=N1 | 4.252 |
| – | HemeOxDB298 | BrC1=CC=C(C=C1)C(=O)CN=[N+]=[N-] | 4 |
| – | HemeOxDB332 | COC(=O)C1=CN(CC(=O)CCC2=CC=CC=C2)C=N1 | 4 |
| – | HemeOxDB376 | OC(CCC1=CC=CC=C1)CN1N=CN=N1 | 4 |
| – | HemeOxDB230 | BrC1=CC=CC(OCCCCN2C=NC=N2)=C1 | 4 |
| – | HemeOxDB101 | O=C(CN1C=CN=C1)C1=CC=C(CCC2=CC=CC=C2)C=C1 | 5.398 |
| – | HemeOxDB116 | FC1=CC=C(COC(CN2C=CN=C2)C2=CC=C(C=C2)C2=CC=C(Br)C=C2)C=C1 | 5.301 |
| – | HemeOxDB290 | CN1C=CN=C1 | 4 |
| – | HemeOxDB216 | O=C(CN1C=CN=C1)C1=CC=C2OCCOC2=C1 | 4.137 |
| – | HemeOxDB51 | BrC1=CC=C(CCC2(CN3C=CN=C3)OCCO2)C=C1 | 5.721 |
| – | HemeOxDB12 | BrC1=CC=C(CCC(=O)CN2C=NC=N2)C=C1 | 6.409 |
| – | HemeOxDB4 | OC(CCC1=CC=C(Br)C=C1)CN1C=CN=C1 | 6.854 |
| – | HemeOxDB279 | N#CC1=CC=CC=C1CN1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4 |
| – | HemeOxDB150 | ClC1=CC=C(COC(CN2C=CN=C2)C2=CC=C(Cl)C=C2Cl)C=C1 | 4.796 |
| – | HemeOxDB345 | CS(=O)(=O)C1=NN=NN1CCC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB297 | [O-][N+](=O)C1=NC=CN1CC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB10 | CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1 | 6.523 |
| – | HemeOxDB75 | O=C(CCN1C=NC=N1)CCC1=CC=CC=C1 | 5.602 |
| – | HemeOxDB147 | ClC1=CC=C(CC[C@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC4=C(C=CC=C4)C=C3)O2)C=C1 | 4.854 |
| – | HemeOxDB79 | FC1=CC=C(CCC(=O)CN2C=CN=C2)C=C1 | 5.569 |
| – | HemeOxDB33 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC=CC=C3)O2)C=C1 | 5.987 |
| – | HemeOxDB328 | ClC1=CC=C(C=C1)C(=O)CN1C=NN=C1 | 4 |
| – | HemeOxDB359 | O=C(CCC1=CC=CC=C1)CN1C=NC(=C1)N(=O)=O | 4 |
| – | HemeOxDB114 | O=C(CN1C=CN=C1)C1=CC=C(C=C1)C1CCCCC1 | 5.301 |
| – | HemeOxDB342 | CS(=O)(=O)C1=NC=NN1CCC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB73 | O=C(CN1C=CN=C1)C1=CC=C(C=C1)N(=O)=O | 5.602 |
| – | HemeOxDB367 | O=C(CCC1=CC=CC=C1)CN1N=NC(=N1)C1=CC=CC=C1 | 4 |
| – | HemeOxDB19 | ClC1=CC=C(CC[C@]2(CN3C=CN=C3)OC[C@@H](COC3=CC=C(C=C3)C#N)O2)C=C1 | 6.174 |
| – | HemeOxDB302 | BrC1=CN=CN1CCC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB63 | FC1=CC=C(C=C1)C(=O)CN1C=CN=C1 | 5.678 |
| – | HemeOxDB123 | CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 5.222 |
| – | HemeOxDB141 | OC[C@@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 4.921 |
| – | HemeOxDB277 | ClC1=C(Cl)C=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| – | HemeOxDB229 | CC(=O)NCCC1=CNC=N1 | 4 |
| – | HemeOxDB102 | NC1=CC=CC(SC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)=C1 | 5.398 |
| – | HemeOxDB264 | C(N1CCCC1)C1=NC2=C(C=CC=C2)N1CC1=CC2=C(C=CC=C2)C=C1 | 4 |
| – | HemeOxDB237 | CN(C)CCC(=O)C1=CC=C(Cl)C=C1 | 4 |
| – | HemeOxDB354 | FC1=CC=C(C=C1)C1=CC=NO1 | 4 |
| – | HemeOxDB159 | ClC1=CC(C(=O)CN2C=NC=N2)=C(Cl)C=C1 | 4.735 |
| – | HemeOxDB256 | C(N1CCCC1)C1=NC2=C(N1)C=CC=C2 | 4 |
| – | HemeOxDB241 | CC(C)C1=NC=CN1CC(=O)C1=CC=C(Br)C=C1 | 4 |
| – | HemeOxDB368 | O=C(CCC1=CC=CC=C1)CN1N=NC2=C1C=CC=C2 | 4 |
| – | HemeOxDB333 | COC(=O)C1=NC=NN1CC(=O)CCC1=CC=CC=C1 | 4 |
| – | HemeOxDB146 | C(CN1C=CN=C1)CC1=CC=CC=C1 | 4.854 |
| – | HemeOxDB78 | C(N1C=CN=C1)C1(OCCO1)C1=CC2=CC=CC=C2C=C1 | 5.58 |
| – | HemeOxDB57 | BrC1=CC=CC(=C1)C(=O)CN1C=CN=C1 | 5.686 |
| – | HemeOxDB312 | C1CC(CCN1)NC1=NC2=C(N1)C=CC=C2 | 4 |
| – | HemeOxDB32 | [H]C1=CC2=C(SC(SCCCCN3C=CN=C3)=N2)C=C1 | 6 |
| – | HemeOxDB324 | CCOC(=O)N1CCC(CC1)NC1=NC2=C(C=CC=C2)N1CC1=CC=C(F)C=C1 | 4 |
| – | HemeOxDB193 | [H]C1=CC2=C(SC(SCCCCCN3C=CN=C3)=N2)C=C1 | 4.4 |
| – | HemeOxDB103 | C(CCN1C=CN=C1)COC1=CC=CC=C1 | 5.398 |
| – | HemeOxDB291 | COC1=C2C(=O)[C@]3(OC2=C(Cl)C(OC)=C1)[C@H](C)CC(=O)C=C3OC | 4 |
| – | HemeOxDB283 | ClC1=CC=CC(Cl)=C1CN1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4 |
| – | HemeOxDB222 | O=C(CCC1=CC=CC=C1)CN1C=CN=N1 | 4.051 |
| – | HemeOxDB110 | ClC1=CC=C(CCC2(CN3C=CN=C3)SCCS2)C=C1 | 5.328 |
| – | HemeOxDB355 | NC1=NC2=C(N1)C=CC(OCCCCN1CCCCC1)=C2 | 4 |
| – | HemeOxDB288 | NC1=C(C=CC(Cl)=C1)C1=NN=NN1 | 4 |
| – | HemeOxDB28 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC4=C(C=CC=C4)C=C3)O2)C=C1 | 6.046 |
| – | HemeOxDB7 | BrC1=CC=C(CCCCN2C=CN=C2)C=C1 | 6.602 |
| – | HemeOxDB329 | ClC1=CC=C(OCCCCCNC2=NC3=CC=CC=C3N2)C=C1 | 4 |
| – | HemeOxDB129 | ClC1=CC=C(C=C1)C(/CN1C=CN=C1)=N/OCC1=CC=C(Br)C=C1 | 5.081 |
| – | HemeOxDB160 | O=S(CCCCN1C=CN=C1)C1=CC=CC=C1 | 4.734 |
| – | HemeOxDB27 | [H]C1=CC2=C(SC(SCCCN3C=CN=C3)=N2)C=C1 | 6.046 |
| – | HemeOxDB5 | OC(CN1C=CN=C1)C1=CC=C(CCC2=CC=CC=C2)C=C1 | 6.648 |
| – | HemeOxDB225 | CCCOC1=CC=C2NC(NC(=O)OC)=NC2=C1 | 4 |
| # | HemeOxDB142 | O=C(CN1C=CN=C1)NCC1=CC=CC=C1 | 4.921 |
| # | HemeOxDB66 | O=C(CN1C=CN=C1)C1=CC=CC2=CC=CC=C12 | 5.658 |
| # | HemeOxDB96 | IC1=CC=C(CCC2(CN3C=CN=C3)OCCO2)C=C1 | 5.432 |
| # | HemeOxDB167 | CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 4.678 |
| # | HemeOxDB39 | COC1=CC=C(OC[C@@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 5.876 |
| # | HemeOxDB89 | ClC1=CC=C(C=C1)C(CN1C=CN=C1)NCC1=CC=CC=C1 | 5.47 |
| # | HemeOxDB252 | COC1=CC=CC(=C1)C1=NN=NN1 | 4 |
| # | HemeOxDB151 | C(N1C=CN=C1)C1(OCCO1)C1=CC=C(C=C1)C1=CC=CC=C1 | 4.79 |
| # | HemeOxDB71 | C(CSC1=CC=CC=C1)CN1C=CN=C1 | 5.62 |
| # | HemeOxDB84 | C(CCN1C=CN=C1)CCC1=CC=CC=C1 | 5.553 |
| # | HemeOxDB6 | O=C(CN1C=NC=N1)C1=CC2=C(CCCC2)C=C1 | 6.62 |
| # | HemeOxDB226 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](COC3=CC=C(C=C3)C34CC5CC(CC(C5)C3)C4)O2)C=C1 | 4 |
| # | HemeOxDB40 | OC(CCC1=CC=C(F)C=C1)CN1C=CN=C1 | 5.854 |
| # | HemeOxDB109 | O=C(CN1C=CN=C1)C1=CC2=C(CCC2)C=C1 | 5.337 |
| # | HemeOxDB299 | BrC1=CC=C(CCC(=O)CN2C=NC3=CC=CC=C23)C=C1 | 4 |
| # | HemeOxDB249 | C(OC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1)C1=CC=CC=C1 | 4 |
| # | HemeOxDB350 | CSC1=NN(CC(=O)CCC2=CC=CC=C2)N=N1 | 4 |
| # | HemeOxDB149 | OC(CCC1=CC=CC=C1)CN1C=NC(=C1)C1=CC=CC=C1 | 4.824 |
| # | HemeOxDB104 | BrC1=CC(=CC=C1)C1(CN2C=CN=C2)OCCO1 | 5.398 |
| # | HemeOxDB246 | [O-][N+](=O)C1=CC=C(OCCCCN2C=NC=N2)C=C1 | 4 |
| # | HemeOxDB326 | ClC1=C(Cl)N(CC(=O)CCC2=CC=CC=C2)C=N1 | 4 |
| # | HemeOxDB356 | O=C(C1CC1)C1=CC=C(C=C1)N1C=CN=C1 | 4 |
| # | HemeOxDB325 | CCOC(=O)N1CCC(CC1)NC1=NC2=C(N1)C=CC=C2 | 4 |
| # | HemeOxDB217 | IC1=CC=C(OCCCN2C=NC=N2)C=C1 | 4.125 |
| # | HemeOxDB53 | O=C(CN1C=CN=C1)C1=CC=C(CC2=CC=CC=C2)C=C1 | 5.701 |
| # | HemeOxDB276 | ClC1=C(Cl)C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=CC=C1 | 4 |
| # | HemeOxDB29 | FC1=CC=C(COC(CCC2=CC=C(Cl)C=C2)CN2C=CN=C2)C=C1 | 6.046 |
| # | HemeOxDB136 | BrC1=CC=C(OCCCCCCN2C=CN=C2)C=C1 | 5 |
| # | HemeOxDB313 | CC(=O)C(CC1=CC=C(Cl)C=C1)N1C=CN=C1 | 4 |
| # | HemeOxDB25 | O=C(CN1C=NC=N1)C1=CC=CC2=CC=CC=C12 | 6.102 |
| # | HemeOxDB243 | CCC(COC(C)=O)N1C=CN=C1 | 4 |
| # | HemeOxDB184 | O=C(CCC1=CC=CC=C1)CN1C=NC(=C1)C1=CC=CC=C1 | 4.495 |
| # | HemeOxDB318 | CC1=NC=CN1CC(=O)CCC1=CC=CC=C1 | 4 |
| # | HemeOxDB322 | CCOC(=O)CC1=NN(CC(=O)CCC2=CC=CC=C2)N=N1 | 4 |
| # | HemeOxDB145 | C(CC1(CN2C=NC=N2)OCCO1)C1=CC=CC=C1 | 4.886 |
| # | HemeOxDB346 | CSC1=NC=CN1CC(=O)CCC1=CC=CC=C1 | 4 |
| # | HemeOxDB319 | CCCC(=O)N1C=CN=C1 | 4 |
| # | HemeOxDB244 | C(COC1=CC=CC=C1)CN1C=NC=N1 | 4 |
| # | HemeOxDB74 | NC1=C(SC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=CC=C1 | 5.602 |
| # | HemeOxDB153 | [H]C1=CC2=C(OC(SCCCN3C=CN=C3)=N2)C=C1 | 4.772 |
| # | HemeOxDB108 | ClC1=CC(Cl)=C(C=C1)C(=O)CN1C=NC=N1 | 5.387 |
| # | HemeOxDB236 | C(N1CCCC1)C1=NC2=C(C=CC=C2)N1CC1=CC=CC=C1 | 4 |
| # | HemeOxDB85 | O=C(CN1C=CN=C1)C12CC3CC(CC(C3)C1)C2 | 5.523 |
| # | HemeOxDB36 | C(CCN1C=CN=C1)CSC1=CC=CC=C1 | 5.921 |
| # | HemeOxDB105 | C(CN1C=CN=C1)SCC1=CC=CC=C1 | 5.398 |
| # | HemeOxDB211 | ClC1=CC=C(C=C1)C1(CN2C=NC=N2)OCCO1 | 4.163 |
| # | HemeOxDB70 | COC1=CC=C(CCC(=O)CN2C=CN=C2)C=C1 | 5.658 |
| # | HemeOxDB370 | O=C(CCN1C=CC=N1)CCC1=CC=CC=C1 | 4 |
| # | HemeOxDB202 | IC1=CC=C(OCCCCCN2C=CN=C2)C=C1 | 4.357 |
| # | HemeOxDB181 | C(N1C=CN=C1)C1(OCCO1)C1=CC=CC=C1 | 4.509 |
| # | HemeOxDB139 | O=C(CN1C=CN=C1)C1=CC=C(OCC2=CC=CC=C2)C=C1 | 4.959 |
| # | HemeOxDB314 | CC(=O)C(CC1=CC=CC=C1)N1C=NC=N1 | 4 |
| # | HemeOxDB323 | CCOC(=O)CC1=NN=NN1CC(=O)CCC1=CC=CC=C1 | 4 |
| # | HemeOxDB135 | OC(CN1C=CN=C1)C1=CC=C(C=C1)N(=O)=O | 5 |
| # | HemeOxDB126 | ClC1=CC=C(Cl)C(=C1)C(=O)CN1C=CN=C1 | 5.18 |
| # | HemeOxDB235 | CCCSC1=CC2=C(NC(NC(=O)OC)=N2)C=C1 | 4 |
| # | HemeOxDB24 | O=C(CN1C=NC=N1)C1=CC=C(C=C1)C1=CC=CC=C1 | 6.131 |
| # | HemeOxDB18 | C[C@@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 6.222 |
| # | HemeOxDB82 | ClC1=CC=C(CCC2(CN3C=CN=C3)OCCO2)C=C1 | 5.553 |
| # | HemeOxDB292 | COC1=CC=C(CCN2CCC(CC2)NC2=NC3=CC=CC=C3N2CC2=CC=CC=C2)C=C1 | 4 |
| * | HemeOxDB348 | CSC1=NC=NN1CC(=O)CCC1=CC=CC=C1 | 4 |
| * | HemeOxDB287 | COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2 | 4 |
| * | HemeOxDB271 | CC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| * | HemeOxDB118 | ClC1=CC=C(C(CN2C=CN=C2)OCC2=C(Cl)C=CC=C2Cl)C(Cl)=C1 | 5.252 |
| * | HemeOxDB98 | FC1=CC=C(CCC2(CN3C=CN=C3)OCCO2)C=C1 | 5.42 |
| * | HemeOxDB266 | N#CC1=CC=CC(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=C1 | 4 |
| * | HemeOxDB106 | IC1=CC=C(C=C1)C(=O)CN1C=CN=C1 | 5.398 |
| * | HemeOxDB121 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3=CC=C(C=C3)N(=O)=O)O2)C=C1 | 5.222 |
| * | HemeOxDB115 | NC1=CC=CC=C1SC[C@@H]1CO[C@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 5.301 |
| * | HemeOxDB296 | CCCCN1C=CN=C1 | 4 |
| * | HemeOxDB170 | O=C(CCN1C=CN=C1)/C=C/C1=CC=CC=C1 | 4.638 |
| * | HemeOxDB371 | O=C(CN1C=CN=C1)C1=CC=CS1 | 4 |
| * | HemeOxDB111 | ClC1=CC=C(CCC(=O)CN2C=CN=C2)C=C1 | 5.328 |
| * | HemeOxDB45 | O=C(CCCC1=CC=CC=C1)CN1C=CN=C1 | 5.824 |
| * | HemeOxDB168 | NC[C@H]1CO[C@@](CCC2=CC=CC=C2)(CN2C=CN=C2)O1 | 4.678 |
| * | HemeOxDB192 | C(CC1(CN2C=NN=N2)OCCO1)C1=CC=CC=C1 | 4.409 |
| * | HemeOxDB93 | O=C(CCN1C=CN=C1)C12CC3CC(CC(C3)C1)C2 | 5.456 |
| * | HemeOxDB188 | IC1=CC=C(OCCCCN2C=NC=N2)C=C1 | 4.42 |
| * | HemeOxDB224 | ClC1=CC=C(Cl)C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=C1 | 4.018 |
| * | HemeOxDB215 | C(CC1(CN2N=CN=N2)OCCO1)C1=CC=CC=C1 | 4.143 |
| * | HemeOxDB231 | ClC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| * | HemeOxDB171 | O=C(C(N1C=CN=C1)C1=CC=CC=C1)C1=CC=CC=C1 | 4.62 |
| * | HemeOxDB334 | COC(=O)C1=NN(CC(=O)CCC2=CC=CC=C2)C=N1 | 4 |
| * | HemeOxDB307 | C(CC1(CN2C=NC(=C2C2=CC=CC=C2)C2=CC=CC=C2)OCCO1)C1=CC=CC=C1 | 4 |
| * | HemeOxDB182 | C(CN1C=CN=C1)OCC1=CC=CC=C1 | 4.495 |
| * | HemeOxDB124 | C(CN1C=CN=C1)SC1=CC=CC=C1 | 5.222 |
| * | HemeOxDB140 | O=C(CN1C=NC=N1)C1=CC=CC=C1 | 4.924 |
| * | HemeOxDB343 | CS(=O)(=O)C1=NN(CC(=O)CCC2=CC=CC=C2)C=N1 | 4 |
| * | HemeOxDB221 | NC1=C(SC[C@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=CC=C1 | 4.06 |
| * | HemeOxDB316 | CC(C)(N1C=CN=C1)C(=O)C1=CC=CC=C1 | 4 |
| * | HemeOxDB374 | O=C1C(CC2=CC=CC=C12)N1C=CN=C1 | 4 |
| * | HemeOxDB240 | NCC(=O)C1=CC=C(Br)C=C1 | 4 |
| * | HemeOxDB269 | ClC1=CC=CC(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)=C1 | 4 |
| * | HemeOxDB209 | C(CN1C=CN=C1)OC1=CC=CC=C1 | 4.215 |
| * | HemeOxDB52 | O=C(CN1C=CN=C1)C1=CC=C2C=CC=CC2=C1 | 5.721 |
| * | HemeOxDB48 | COC[C@@H]1CO[C@@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 5.762 |
| * | HemeOxDB218 | CC1=CC=CC=C1CN1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4.119 |
| * | HemeOxDB22 | COC1=CC=C(SC[C@@H]2CO[C@@](CCC3=CC=C(Cl)C=C3)(CN3C=CN=C3)O2)C=C1 | 6.155 |
| * | HemeOxDB262 | FC1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| * | HemeOxDB2 | OC(CN1C=CN=C1)C1=CC=C(C=C1)C1=CC=C(Br)C=C1 | 7.222 |
| * | HemeOxDB3 | IC1=CC=C(CCC(=O)CN2C=CN=C2)C=C1 | 6.959 |
| * | HemeOxDB8 | O=C(CC(C1=CC=CC=C1)C1=CC=CC=C1)CN1C=CN=C1 | 6.569 |
| * | HemeOxDB94 | C(N1C=NC=N1)C1(OCCO1)C1=CC2=CC=CC=C2C=C1 | 5.446 |
| * | HemeOxDB47 | BrC1=CC=C(CCC(=O)CN2C=CN=C2)C=C1 | 5.77 |
| * | HemeOxDB166 | NC[C@H]1CO[C@](CCC2=CC=C(Cl)C=C2)(CN2C=CN=C2)O1 | 4.678 |
| * | HemeOxDB263 | C(CC1=CC=CC=C1)N1C(CN2CCCC2)=NC2=C1C=CC=C2 | 4 |
| * | HemeOxDB152 | O=C1SC2=C(C=CC=C2)N1CCCN1C=CN=C1 | 4.78 |
| * | HemeOxDB301 | BrC1=CN(CC(=O)CCC2=CC=CC=C2)C=N1 | 4 |
| * | HemeOxDB285 | N1C=NC2=CC=CC=C12 | 4 |
| * | HemeOxDB309 | C(CC1=CC=CS1)N1C=CN=C1 | 4 |
| * | HemeOxDB315 | CC(=O)CCC1=CC=C(Br)C=C1 | 4 |
| * | HemeOxDB30 | ClC1=CC=C(CC[C@@]2(CN3C=CN=C3)OC[C@@H](CSC3CCCCC3)O2)C=C1 | 6.027 |
| * | HemeOxDB200 | BrC1=CC=CC(OCCCCCN2C=CN=C2)=C1 | 4.371 |
| * | HemeOxDB15 | OC(CCC1=CC=C(Cl)C=C1)CN1C=CN=C1 | 6.301 |
| * | HemeOxDB176 | O=C(CCN1C=CN=C1)CCC1=CC=CC=C1 | 4.553 |
| * | HemeOxDB344 | CS(=O)(=O)C1=NN(CCC(=O)CCC2=CC=CC=C2)N=N1 | 4 |
| * | HemeOxDB207 | COC(=O)C1=CN=CN1CC(=O)CCC1=CC=CC=C1 | 4.26 |
| * | HemeOxDB255 | OC(=O)CN1C=CN=C1 | 4 |
| * | HemeOxDB260 | CC(C)C1=CC=C(CN2C(CN3CCCC3)=NC3=C2C=CC=C3)C=C1 | 4 |
| * | HemeOxDB179 | C(COC1=CC=CC=C1)CN1C=CN=C1 | 4.509 |
2.4. QSAR hybrid model split 1 validation
The endpoints of the FDA-approved drugs were determined in order to additionally validate the model. The whole set composed of 1428 drugs was refined in order to remove quaternary ammonium salts, and compounds with too long SMILES (not elaborated by CORAL), and compounds containing atoms not enumerated in the model (Al, Fe, Gd, etc.). Overall, the whole set was reduced to 1376 compounds and these were evaluated with hybrid model resulting from split 1. Over 1376 compounds, 995 have been defined as outliers by the model since they fall outside the domain of applicability. Table 5 reports the SMILES and predicted HO-1 pIC50 for these FDA approved drugs evaluated with the hybrid model split 1.
Table 5.
List of SMILES and predicted pIC50 of the FDA-approved drugs.
| Calc pIC50 | |
|---|---|
| CCC1=C(C)CN(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC2CCC(C)CC2)C1=O | 7.657 |
| COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(=O)OC1=CC2=C(CCC2)C=C1 | 7.3445 |
| CC(C)C1CC[C@@H](CC1)C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O | 6.7911 |
| OC(=O)C(CC(=O)N1CC2CCCCC2C1)CC1=CC=CC=C1 | 6.7525 |
| CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C | 6.7024 |
| CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCCC2C1 | 6.5387 |
| COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 | 6.28 |
| COC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C | 6.2556 |
| CCCN(CCC)CCC1=C2CC(=O)NC2=CC=C1 | 6.061 |
| CC(C)NCC(O)COC1=CC=C(CCOCC2CC2)C=C1 | 5.948 |
| CCCCCCCCCCCCCCCCCCCCCCO | 5.9243 |
| O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1 | 5.8772 |
| CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O | 5.8503 |
| FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1C(=O)NC2=CC=CC=C12)C1=CC=C(F)C=C1 | 5.8017 |
| COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC | 5.701 |
| COC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC | 5.6809 |
| CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1 | 5.6401 |
| NC(=N)C1=CC=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1 | 5.6056 |
| CCC1(CCC(C)C)C(=O)NC(=O)NC1=O | 5.4584 |
| CN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C2 | 5.4311 |
| CC(C)CC1=CC=C(C=C1)C(C)C(O)=O | 5.4135 |
| CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1 | 5.3913 |
| CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C | 5.3834 |
| CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O | 5.3733 |
| CN1N=C(C(=O)NC2CC3CCCC(C2)N3C)C2=CC=CC=C12 | 5.3389 |
| CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C1=CC=CC=C1 | 5.3217 |
| CC(C)COCC(CN(CC1=CC=CC=C1)C1=CC=CC=C1)N1CCCC1 | 5.2783 |
| CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O | 5.2659 |
| CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 | 5.2609 |
| CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C1=CC=CC=C1 | 5.2472 |
| OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O | 5.2426 |
| CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 | 5.167 |
| ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1 | 5.1454 |
| CC1=CC=C(C=C1)C(=O)C1=CC(=C(O)C(O)=C1)[N+]([O-])=O | 5.092 |
| COC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C | 5.0598 |
| CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 | 5.0534 |
| CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 | 4.9973 |
| N[C@@H](CC1=CN=CN1)C(O)=O | 4.9548 |
| CN(CC1=CC=C(C=C1)C(C)(C)C)CC1=CC=CC2=CC=CC=C12 | 4.9507 |
| COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 | 4.9426 |
| CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1 | 4.9373 |
| CCCCC1(CC)C(=O)NC(=O)NC1=O | 4.9305 |
| CCCN(CCC1=CC=CS1)C1CCC2=C(C1)C=CC=C2O | 4.9178 |
| CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O | 4.9138 |
| CO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC | 4.9129 |
| NC(=N)N1CCC2=CC=CC=C2C1 | 4.8682 |
| ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1 | 4.8625 |
| CC1=CN=C(C=N1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 | 4.861 |
| N[C@@H](CC1=CC=CC=C1)C(O)=O | 4.8219 |
| CN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C12 | 4.8123 |
| COC1=CC(C(O)C(C)N)=C(OC)C=C1 | 4.7948 |
| COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N(C)CCCNC(=O)C1CCCO1 | 4.7908 |
| CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O | 4.7818 |
| FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)N1C(=O)NC2=CC=CC=C12 | 4.7367 |
| COC1=CC=C(C=C1)C(=O)NC1=CC=CC=C1CCC1CCCCN1C | 4.7264 |
| O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2 | 4.7135 |
| CN1CCC[C@@H]1CCO[C@](C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1 | 4.7082 |
| C(C(C1CCCCC1)C1CCCCC1)C1CCCCN1 | 4.6999 |
| CC1=CC(=O)N(O)C(=C1)C1CCCCC1 | 4.6909 |
| CCCC(=O)O[C@H](COC(=O)CC)COP(O)(=O)OC[C@H](N)C(O)=O | 4.671 |
| CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1 | 4.6597 |
| COC1=CC2=C(C=CC=C2CCNC(C)=O)C=C1 | 4.6382 |
| CC(C)NCC(O)C1=CC(O)=C(O)C=C1 | 4.6327 |
| ClC1=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=CS1 | 4.6304 |
| CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1 | 4.6169 |
| CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O | 4.6135 |
| COC1=CC2=C(NC=C2CCNC(C)=O)C=C1 | 4.5993 |
| CC[C@@H](N1CCCC1=O)C(N)=O | 4.5956 |
| CC(C)NCC(O)COC1=CC=CC=C1CC=C | 4.5892 |
| COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1CCCO1 | 4.5855 |
| CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O | 4.5747 |
| N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O | 4.5676 |
| COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1 | 4.5607 |
| COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1 | 4.559 |
| CC(C)NCC(O)COC1=CC=CC2=CC=CC=C12 | 4.5575 |
| NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1 | 4.5554 |
| CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O | 4.5553 |
| CCN(CC)CCCN(C1CC2=CC=CC=C2C1)C1=CC=CC=C1 | 4.5518 |
| N[C@@H](CCC(O)=O)C(O)=O | 4.5412 |
| O=C(NC1=CC2=C(C=C1)C(=O)C=C(O2)C1=NNN=N1)C1=CC=C(OCCCCC2=CC=CC=C2)C=C1 | 4.5399 |
| COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2 | 4.5388 |
| CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1 | 4.5281 |
| CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1 | 4.5246 |
| CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O | 4.5244 |
| CC(C)(N)CC1=CC=CC=C1 | 4.519 |
| CN1CCCC(CC2C3=CC=CC=C3SC3=CC=CC=C23)C1 | 4.5063 |
| C(C1=NCCN1)C1=CC=CC2=CC=CC=C12 | 4.5059 |
| COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C1=CC=CC=C1 | 4.4965 |
| CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC | 4.4815 |
| CC(N)CC1=CC=CC=C1 | 4.4686 |
| CC(CCC1=CC=CC=C1)NCC(O)C1=CC(C(N)=O)=C(O)C=C1 | 4.46 |
| COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 | 4.4456 |
| CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC | 4.438 |
| CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(O)C=CC(C)=C1)C(C)C | 4.4327 |
| C[C@H](C1=CNC=N1)C1=C(C)C(C)=CC=C1 | 4.4282 |
| CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 | 4.4149 |
| CCN1C(=O)NC(C1=O)C1=CC=CC=C1 | 4.411 |
| CCOC(=O)C1(CCN(CCC2=CC=C(N)C=C2)CC1)C1=CC=CC=C1 | 4.3966 |
| CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 | 4.395 |
| CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 | 4.3921 |
| O=C(CCCC1=CC=CC=C1)OCC(COC(=O)CCCC1=CC=CC=C1)OC(=O)CCCC1=CC=CC=C1 | 4.3813 |
| COC1=CC=C(C=C1)C(Cl)=C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1 | 4.3799 |
| OC(=O)CCC1=NC(=C(O1)C1=CC=CC=C1)C1=CC=CC=C1 | 4.3619 |
| ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl | 4.3605 |
| CC1=C(OC2=C(C=CC=C2C(=O)OCCN2CCCCC2)C1=O)C1=CC=CC=C1 | 4.3556 |
| CC(C)NCC(O)COC1=CC=CC=C1OCC=C | 4.3528 |
| CCCCOC1=C(N)C=CC(=C1)C(=O)OCCN(CC)CC | 4.3329 |
| CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 | 4.3306 |
| CCC(NC(C)C)C(O)C1=CC(O)=C(O)C=C1 | 4.3301 |
| C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O | 4.2933 |
| CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12 | 4.2886 |
| CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 | 4.2868 |
| COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1 | 4.2712 |
| CCCC(CCC)C(O)=O | 4.2703 |
| N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O | 4.2604 |
| CC=C(C(=CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1 | 4.2578 |
| CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1 | 4.2572 |
| CN1C(=O)CC(C1=O)C1=CC=CC=C1 | 4.2564 |
| CCC1(CC)C(=O)NC(=O)N(C)C1=O | 4.2557 |
| CC(COC1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1 | 4.2525 |
| C1=CN(C=N1)C(C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 | 4.2453 |
| CCC(C)C1(CC=C)C(=O)NC(=O)NC1=O | 4.2429 |
| CNC(C)CCC=C(C)C | 4.2383 |
| CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O | 4.232 |
| CCOC(=O)N1C=CN(C)C1=S | 4.2193 |
| CCCC(C)C1(CC)C(=O)NC(=O)NC1=O | 4.2154 |
| CCCSC1=CC2=C(C=C1)N=C(NC(=O)OC)N2 | 4.2147 |
| OC(=O)CCCC1=CC=C(C=C1)N(CCCl)CCCl | 4.1857 |
| CN(C)CCC(C1=CC=CC=C1)C1=CC=CC=N1 | 4.1779 |
| FC1=CC=C(C=C1)N1C=C(C2CCN(CCN3CCNC3=O)CC2)C2=C1C=CC(Cl)=C2 | 4.1777 |
| NC1=C2CCCCC2=NC2=CC=CC=C12 | 4.1688 |
| CC(C)NCC(O)C1=CC(O)=CC(O)=C1 | 4.1666 |
| CC(=O)OCC(=O)NCCCOC1=CC=CC(CN2CCCCC2)=C1 | 4.1621 |
| CCCCCCCCCCCCOCCO | 4.1454 |
| CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC | 4.1434 |
| CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1 | 4.1393 |
| COCCOC1=CN=C(NS(=O)(=O)C2=CC=CC=C2)N=C1 | 4.129 |
| CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C | 4.128 |
| CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1 | 4.1273 |
| CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1 | 4.1235 |
| CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1 | 4.1159 |
| CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 | 4.1151 |
| O=C1N=CN=C2NNC=C12 | 4.1095 |
| COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O | 4.1047 |
| CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1 | 4.0987 |
| N1C2=CC=CC=C2N=C1C1=CSC=N1 | 4.0878 |
| COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1 | 4.0859 |
| NC1=C2NC=NC2=NC=N1 | 4.0841 |
| CCC(C)C1(CC)C(=O)NC(=O)NC1=O | 4.0792 |
| [O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O | 4.0755 |
| CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1 | 4.0695 |
| COC1=C(OC)C=C(CCNCC(O)COC2=CC=CC(C)=C2)C=C1 | 4.0662 |
| CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1 | 4.0599 |
| NC1=CC=C(C=C1)C(=O)NCC(O)=O | 4.0555 |
| CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1 | 4.055 |
| CN[C@@H](C)CC1=CC=CC=C1 | 4.0441 |
| COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1 | 4.0407 |
| CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I | 4.0284 |
| C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1 | 4.0265 |
| NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1 | 4.0196 |
| CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1 | 4.0159 |
| CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O | 4.0115 |
| NC1=CC(Cl)=C(NC2=NCCN2)C(Cl)=C1 | 3.9983 |
| NC1=NC(N)=C2N=C(C(N)=NC2=N1)C1=CC=CC=C1 | 3.9959 |
| OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O | 3.9916 |
| ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1 | 3.9883 |
| ClC1=CC=C(S1)C(=O)NC[C@H]1CN(C(=O)O1)C1=CC=C(C=C1)N1CCOCC1=O | 3.9842 |
| CC(CCC1=CC=C(O)C=C1)NCCC1=CC(O)=C(O)C=C1 | 3.9783 |
| S=C1N=CNC2=C1NC=N2 | 3.9627 |
| COC1=CC=C(CCN2CCC(CC2)NC2=NC3=CC=CC=C3N2CC2=CC=C(F)C=C2)C=C1 | 3.9599 |
| CC(C)NCC(O)COC1=C(C)C(C)=C(OC(C)=O)C(C)=C1 | 3.9588 |
| C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1 | 3.9578 |
| NC1=NC(=S)C2=C(N1)N=CN2 | 3.9538 |
| CC(C)C[C@H](N)C(O)=O | 3.9532 |
| CC(C)NC(=O)NS(=O)(=O)C1=C(NC2=CC=CC(C)=C2)C=CN=C1 | 3.9437 |
| CN1C=NC2=C1C(=O)NC(=O)N2C | 3.9378 |
| OC(=O)CCCN1CCC(CC1)OC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1 | 3.937 |
| CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C | 3.9279 |
| C[C@H](N)CC1=CC=CC=C1 | 3.9224 |
| C(C=CC1=CC=CC=C1)N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1 | 3.9128 |
| NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N1 | 3.9055 |
| C(C1=NCCN1)C1=CC=CC=C1 | 3.8771 |
| CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1 | 3.87 |
| N[C@@H]1CONC1=O | 3.8665 |
| CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1 | 3.8642 |
| OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2 | 3.8597 |
| COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1 | 3.852 |
| BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12 | 3.8374 |
| CCN(CC)CCOC(=O)C1(CCCCC1)C1CCCCC1 | 3.8337 |
| CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 | 3.8223 |
| CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1 | 3.8159 |
| CN1CCCC1C1=CN=CC=C1 | 3.8105 |
| CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1 | 3.8102 |
| CC(C)(C)C1=CC=C(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)C=C1 | 3.8053 |
| C1CN2C[C@@H](N=C2S1)C1=CC=CC=C1 | 3.7974 |
| CCCC1=NC2=C(C=C(C=C2C)C2=NC3=CC=CC=C3N2C)N1CC1=CC=C(C=C1)C1=CC=CC=C1C(O)=O | 3.7869 |
| CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=N1 | 3.7777 |
| NC12CC3CC(CC(C3)C1)C2 | 3.7696 |
| CCOC(=O)C1(CCN(C)CC1)C1=CC=CC=C1 | 3.768 |
| ClC1=CC=CC(Cl)=C1NC1=NCCN1 | 3.7435 |
| CN(C)CCN(CC1=CC=C(Cl)C=C1)C1=CC=CC=N1 | 3.7364 |
| CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1 | 3.7274 |
| CCSC1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1 | 3.7204 |
| CCC1=C(C(N)=NC(N)=N1)C1=CC=C(Cl)C=C1 | 3.7158 |
| CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C1=CC=C(Cl)C=C1 | 3.7 |
| CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 | 3.683 |
| COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O | 3.6757 |
| CCCN1C2=C(NC=N2)C(=O)NC1=O | 3.6597 |
| OC(=O)CCCCC1CCSS1 | 3.6596 |
| NC1=CC(O)=C(C=C1)C(O)=O | 3.6575 |
| CCN(C(=O)C=CC)C1=CC=CC=C1C | 3.6561 |
| CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1 | 3.6541 |
| OC(CCN1CCCC1)(C1CCCCC1)C1=CC=CC=C1 | 3.6539 |
| OC(=O)CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O | 3.6529 |
| CC(N)C(=O)NC1=C(C)C=CC=C1C | 3.6507 |
| CC(C)C1(CC=C)C(=O)NC(=O)NC1=O | 3.6424 |
| O[C@@H]1CNC(C1)C(O)=O | 3.6252 |
| OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C1=CC=C(Cl)C=C1 | 3.6228 |
| CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC | 3.6183 |
| CNC(C)CC1CCCCC1 | 3.6151 |
| CN1CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C2 | 3.6081 |
| NC(CCC(O)=O)C=C | 3.5995 |
| CC1=CC(OCC2CNC(=O)O2)=CC(C)=C1 | 3.5949 |
| NC(=O)C1=CC=CC=C1O | 3.5896 |
| CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1 | 3.5827 |
| CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1 | 3.5725 |
| CCN(CC)C(=O)N1CCN(C)CC1 | 3.5702 |
| CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 | 3.5675 |
| CCN1CCCC1CNC(=O)C1=C(OC)C=CC(=C1)S(N)(=O)=O | 3.5621 |
| ClC1=CC2=C(OC(=O)N2)C=C1 | 3.5614 |
| CCN(CC1=CC=NC=C1)C(=O)C(CO)C1=CC=CC=C1 | 3.5501 |
| O=C1N(C2CCC(=O)NC2=O)C(=O)C2=CC=CC=C12 | 3.5307 |
| CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O | 3.5243 |
| CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1 | 3.5195 |
| CC1CC(CC(C)(C)C1)OC(=O)C(O)C1=CC=CC=C1 | 3.5093 |
| OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1 | 3.4952 |
| CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC | 3.4926 |
| CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1 | 3.4886 |
| COC(=O)C(C1CCCCN1)C1=CC=CC=C1 | 3.488 |
| CCCN[C@H]1CCC2=C(C1)SC(N)=N2 | 3.4868 |
| FC1=CC=C(C=C1)C(N1CCN(CC1)C1=NC(NCC=C)=NC(NCC=C)=N1)C1=CC=C(F)C=C1 | 3.4866 |
| CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C | 3.468 |
| COC1=CC=C(CN(CCN(C)C)C2=NC=CC=C2)C=C1 | 3.4624 |
| CC(=O)OC1=CC=CC=C1C(O)=O | 3.455 |
| OC(=O)CCCCCCCC(O)=O | 3.4544 |
| CN1C(=O)OC(C)(C)C1=O | 3.45 |
| CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C | 3.4483 |
| OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O | 3.4432 |
| CCC1(C)OC(=O)N(C)C1=O | 3.4358 |
| CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1 | 3.4185 |
| CC1=CC(=O)C2=CC=CC=C2C1=O | 3.406 |
| CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2 | 3.392 |
| O=C(OCC1=CC=CC=C1)C1=CC=CC=C1 | 3.3773 |
| CC1=CC(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)=CC=C1 | 3.3751 |
| CCN(CC)CC(=O)NC1=C(C)C=CC=C1C | 3.3688 |
| CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1 | 3.3675 |
| OC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C1 | 3.3635 |
| O=C(C1CCCCC1)N1CC2N(CCC3=CC=CC=C23)C(=O)C1 | 3.3627 |
| CCCNC(C)C(=O)NC1=CC=CC=C1C | 3.3422 |
| CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1 | 3.3392 |
| CC(C)C1=CC=CC(C(C)C)=C1O | 3.3379 |
| COC1=CC=CC=C1OCC(O)CN1CCN(CC(=O)NC2=C(C)C=CC=C2C)CC1 | 3.3373 |
| CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C | 3.3366 |
| CCC1(C)CC(=O)NC1=O | 3.3363 |
| [O-][N+](=O)C1=CC=C(O1)C=NN1CCOC1=O | 3.3153 |
| OC(=O)C1=CC=CC=C1O | 3.3147 |
| CC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C1 | 3.3142 |
| CN1C2=C(NC=N2)C(=O)N(C)C1=O | 3.3104 |
| OC(=O)[C@@H]1CCCN1 | 3.3103 |
| CCCCC1=NN(CC2=CN=C(C=C2)C2=CC=CC=C2C2=NNN=N2)C(CCCC)=N1 | 3.3095 |
| CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 | 3.3078 |
| CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C | 3.307 |
| CC(N)C12CC3CC(CC(C3)C1)C2 | 3.2932 |
| CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1 | 3.2863 |
| CN1C=CNC1=S | 3.2765 |
| CC(CC1=CC=C(O)C=C1)NCC(O)C1=CC(O)=CC(O)=C1 | 3.2612 |
| CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1 | 3.2558 |
| CC1=NC=C(N1CCO)[N+]([O-])=O | 3.2451 |
| OC(CCN1CCCCC1)(C1CCCCC1)C1=CC=CC=C1 | 3.2362 |
| CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1 | 3.2288 |
| CSC1=CC=C(C=C1)C(=O)C1=C(C)NC(=O)N1 | 3.227 |
| CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1C | 3.2248 |
| OC(CCN1CCCCC1)(C1CCCC1)C1=CC=CC=C1 | 3.2185 |
| NC1=CC=NC=C1 | 3.2158 |
| CC1=CNN=C1 | 3.1896 |
| COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1COC2=CC=CC=C2O1 | 3.1822 |
| CCC1=NC=CC(=C1)C(N)=S | 3.1661 |
| CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 | 3.166 |
| COC1=CC=C(CC(C)NCC(O)C2=CC(NC=O)=C(O)C=C2)C=C1 | 3.165 |
| CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1 | 3.1551 |
| CSC1=CC2=C(SC3=CC=CC=C3N2CCC2CCCCN2C)C=C1 | 3.1429 |
| N[C@@H]1CC1C1=CC=CC=C1 | 3.136 |
| C[C@H](N)C(O)=O | 3.1245 |
| OC(=O)P(O)(O)=O | 3.1094 |
| CCN(CC)C(C)C(=O)C1=CC=CC=C1 | 3.1013 |
| CNC1(C)C2CCC(C2)C1(C)C | 3.1002 |
| OCCCC([O-])=O | 3.0886 |
| CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1 | 3.0855 |
| CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1 | 3.0848 |
| OC(=O)CCC(O)=O | 3.0847 |
| CCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C1 | 3.0826 |
| CN1C(=O)CC(C)(C1=O)C1=CC=CC=C1 | 3.0796 |
| CCC1(CC)C(=O)NCC(C)C1=O | 3.0788 |
| CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1 | 3.0748 |
| CC(C)[C@H](N)C(O)=O | 3.0747 |
| CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 | 3.073 |
| NC1=NC(N)=C(N=N1)C1=C(Cl)C(Cl)=CC=C1 | 3.0561 |
| OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl | 3.0542 |
| NC1=CC(=NC(N)=[N+]1[O-])N1CCCCC1 | 3.052 |
| CN1CCN2C(C1)C1=CC=CC=C1CC1=CC=CC=C21 | 3.0512 |
| OC(CCCN1CCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1 | 3.0364 |
| O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1 | 3.0293 |
| CCC1(CCC(=O)NC1=O)C1=CC=C(N)C=C1 | 3.0264 |
| CCC1C2=CC(OC)=C(OC)C=C2C(=NN=C1C)C1=CC(OC)=C(OC)C=C1 | 3.0217 |
| OCC(O)COC1=CC=C(Cl)C=C1 | 3.021 |
| CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1 | 3.014 |
| COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1 | 3.0046 |
| CN1N(C(=O)C=C1C)C1=CC=CC=C1 | 2.9964 |
| NC1=CC(C(O)=O)=C(O)C=C1 | 2.9921 |
| CCOC(=O)NC1=C(N)C=C(NCC2=CC=C(F)C=C2)C=C1 | 2.9857 |
| ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1 | 2.984 |
| OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2 | 2.9785 |
| CCOC(=O)C1=CC=C(N)C=C1 | 2.9674 |
| NC1=NC(=O)C2=C(N1)N(COCCO)C=N2 | 2.9585 |
| ClC1=C(NC2=NCCN2)C2=NSN=C2C=C1 | 2.9531 |
| CC(=O)NC1=CC=C(O)C=C1 | 2.9383 |
| CN(C)CCOC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1 | 2.933 |
| ClC1=CC=C(C=C1)C(=O)NCCN1CCOCC1 | 2.9176 |
| CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C | 2.908 |
| CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 | 2.8934 |
| O[Bi]1OC(=O)C2=CC=CC=C2O1 | 2.8838 |
| CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1 | 2.8838 |
| NCC1(CC(O)=O)CCCCC1 | 2.8533 |
| OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1 | 2.8411 |
| CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1 | 2.8189 |
| CC[C@H](C)[C@H](N)C(O)=O | 2.7924 |
| CN1CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C1 | 2.7413 |
| CC(C)NC1=C(N=CC=C1)N1CCN(CC1)C(=O)C1=CC2=C(N1)C=CC(NS(C)(=O)=O)=C2 | 2.7251 |
| CCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C1 | 2.7218 |
| OC1=CC=CC=C1 | 2.7195 |
| NC(=O)C1=NC=CN=C1 | 2.7092 |
| ClC1=CC=C2N=C3NC(=O)CN3CC2=C1Cl | 2.6664 |
| CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1 | 2.665 |
| OC1=CC=C(OCC2=CC=CC=C2)C=C1 | 2.6436 |
| NC1=CC=C(C=C1)S(N)(=O)=O | 2.5847 |
| CCCC1=CC(=O)NC(=S)N1 | 2.5686 |
| CC(C)(C(=O)C1=CN=CC=C1)C1=CN=CC=C1 | 2.5476 |
| OC(=O)C1=CN=CC=C1 | 2.5144 |
| CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1 | 2.4741 |
| CCCOC1=C(C=C(C=C1)S(=O)(=O)NCCC1CCCN1C)C1=NC(=O)C2=C(N1)C(CCC)=NN2C | 2.4651 |
| NC1=CC=CC2=C1CN(C1CCC(=O)NC1=O)C2=O | 2.4402 |
| CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1 | 2.4091 |
| CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1 | 2.3858 |
| CCC1(CCC(=O)NC1=O)C1=CC=CC=C1 | 2.3774 |
| OCC1=CC=CC=C1 | 2.3389 |
| CC1=CC=CC=C1N1CCN(CCC2=NN=C3CCCCN23)CC1 | 2.3216 |
| NC1=CC(=CNC1=O)C1=CC=NC=C1 | 2.314 |
| C1CNCCN1 | 2.304 |
| CC(=O)C(O)=O | 2.1885 |
| OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 | 2.1507 |
| CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC | 2.1161 |
| CC1=CC(=NN=C1NCCN1CCOCC1)C1=CC=CC=C1 | 2.0988 |
| COC1=C2OC(=O)C=CC2=CC2=C1OC=C2 | 2.0963 |
| OC1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2 | 2.0811 |
| CC([O-])=O | 2.0735 |
| CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC | 2.0558 |
| CC(C)C1=C(OCC2=NCCN2)C=C(C)C=C1 | 1.9714 |
| CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 | 1.9135 |
| OC(=O)C1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2 | 1.9133 |
| CC(=O)NC[C@H]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC1 | 1.9014 |
| CC1=NS(=O)(=O)C2=C(N1)C=CC(Cl)=C2 | 1.8688 |
| CC1C(OCCN1C)C1=CC=CC=C1 | 1.8681 |
| [O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1 | 1.8203 |
| CC(=O)NO | 1.728 |
| CC1NCCOC1C1=CC=CC=C1 | 1.6547 |
| CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1 | 1.5526 |
| CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2 | 1.5024 |
| CN1C=CC(=O)C(O)=C1C | 1.4429 |
| BrC1=CC2=C(NC(=O)CN=C2C2=CC=CC=N2)C=C1 | 1.3273 |
| CC1=CC=CN2C(=O)C(=CN=C12)C1=NNN=N1 | 1.1747 |
| C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 | 1.0795 |
Acknowledgements
This work was supported by Research Funding from University of Catania (FIR) 2014 project code 108D20. Free academic licenses from ChemAxon and OpenEye Scientific Software for their suites of programs are gratefully acknowledged.
Footnotes
Transparency document
Transparency document associated with this article can be found in the online version at http://dx.doi.org/10.1016/j.dib.2017.09.036.
Contributor Information
Emanuele Amata, Email: eamata@unict.it.
Valeria Pittalà, Email: vpittala@unict.it.
Transparency document. Supplementary material
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