A more detailed explanation of the project can be found in our paper.

• Project Requirements
• Project Features and User Guide
  • Part 1
  • Part 2
  • Part 3.
  • part 4.
• Contact Us

We generated the relevant packages that the project relies on as requirements.txt files These packages can be installed directly in batches using CONDA:
conda install --yes --file requirements.txt

ase=3.18.0=pypi_0
bidict=0.18.3=pypi_0
dscribe=0.2.9=pypi_0
joblib=0.13.2=py36_0
matplotlib=3.1.2=pypi_0
molml=0.9.0=pypi_0
networkx=2.3=py_0
numpy=1.17.4=pypi_0
openbabel=3.0.0=py36h1360c68_0
pandas=0.25.0=py36hb3f55d8_0
pathlib=1.0.1=pypi_0
pickleshare=0.7.5=py36_0
pytorch=1.1.0=py3.6_cuda10.0.130_cudnn7.5.1_0
rdkit=2019.03.2=py36hb31dc5d_1
scikit-learn=0.22=pypi_0
scipy=1.2.1=pypi_0
seaborn=0.9.0=pypi_0
torch-cluster=1.4.2=pypi_0
torch-geometric=1.3.0=pypi_0
torch-scatter=1.3.1=pypi_0
torch-sparse=0.4.0=pypi_0
xgboost=0.90=pypi_0

• It is recommended to execute this project in a linux environment

Optimization of the molecular structure of reaction precursors (heterocyclic substrates and radicals) and calculation of their quantitative property data

1. Use quantum chemical software, such as Gaussian 09 or Gaussian 16, to obtain optimized structures at the level of B3LYP/6-311+G(2d, p).

2. Perform single point energy calculation based on the optimized structures and place it in a directory A (for example: ./Example/part_1/Sub/Ar). Calculation method, functional and basis set will be automatically corrected by the following scripts.
   - Tips:

   • In order to use the scripts for the property calculations, it is recommended that the input files are named in the following format.

     For heterocycles:     
         Ar_n-loc_n-c1-1sp.gjf (such as X4t-1-c1-1sp.gjf)  
         (Ar_n means the heterocycle's alias,
         loc_n means one of the atomic order number of the reaction site in heterocycle,
         c1 means the first conformation，
         and the sp suffix indicates that it is a single point calculation file.)
     For Radicals:       
         R_n-c1-1sp.gjf (such as CF3-c1-1sp.gjf)
     

   • For the extraction of local descriptors by scripts, please add the number of the target site atom of heteroarene (as in Gaussview or the order of the Cartesian coordinates) to the title line of the input file.

     For example:    
     in the fifth line of **./Example/part_1/Sub/Ar/X4t-1-c1-1sp.gjf**,    
     1 and 3 means the first and third atomic order number of the reaction    
     site in this heterocycle.   
     

     %nprocshared=28
     %mem=56GB
     #p aug-cc-pvtz m062x g09def

     X4t-1-c1-1stdsp 1 3

     0 1
     C         -1.42417300        2.11888500         0.00012700
     N         -0.21250800         2.61217900         -0.00003700
     C         0.80986200         1.72740500         -0.00011600
     C           0.71915500         0.34596500           0.00003400
     C         -0.61252800        -0.19945400           0.00007300
     ...

3. Copy the Descriptors_input_trans_new.py and Input_Make_NICS.py scripts from the ./ChemUtils/test folder to that directory A (for example: ./Example/part_1/Sub/Ar) and run them separately to get new Gaussian input files of a quantitative properties, which are placed in the Desc_gas_sp and NICS folders, respectively.In particular, for free radicals, there is no need to run the Input_Make_NICS.py script.

4. Submit files from these two folders to Gaussian Software for calculation and place the resulting output files in the same directory.

5. Copy get_PhysOrg.py to the Desc_gas_sp and NICS's parent directory A (for example: ./Example/part_1/Sub/Ar). Edit get_PhysOrg.py and change the folder absolute path of the project to the ChemUtils's parent folder (for example the folder absolute path of this tutorial file) in the third line, then save and close this file. Run it and therein will automatically generate the PhysOrg descriptor in the current directory in the phychem.csv file (for example: ./Example/part_1/Sub/Ar/Ar_phychem.csv).

• The purpose of rewriting the third line is to add the absolute path of the directory where ChemUtils is located to the python package search path

import os
import sys
sys.path.append("/mnt/G16/Scripts")

from ChemUtils.bin.PhysOrg import get_Pre_EQBV, get_Pre_PhysOrg
...

Get SOAP/FP descriptors based on SMILES

The operation in this part is to prepare descriptors for the SOAP/FP-XGB model based on SMILES input. One can skip this section if the SOAP/FP-XGB model prediction is not needed.

1. Generate the SMILES of the structures, and put it in smi (for example: ./Example/part_2/smi) folder, named Ar.smi and R.smi separately.
2. Copy the GetSOAPFromSMILES.py script from the ./ChemUtils/test folder to smi's parent folder (for example: ./Example/part_2) and run it to Generate 5 different 3D geometries by RDKit based on SMILES at MMFF94 level. The generated geometries will placed in Geometry (for example: ./Example/part_2/Geometry) folder and the descriprors of SOAP/FP will placed in SOAP (for example: ./Example/part_2/SOAP) folder.

All the required code has been provided in ChemUtils/test/GetSOAPFromSMILES.py
We also provide an example of this in the ./Example/part_2 folder.

Pre-test/pre-training preparation.

1. For test task, create a new folder named start with test_ such as test_sub in DataSet/raw folder to put all the required files in it. test_ is used to indicate that the data in this folder is used for testing and suffix of sub is used to distinguish between different test sets. In the next steps, you also need creat some necessary folders as needed.

2. The structure files related to aromatic heterocyclic precursors should be placed in test_sub/Ar/gjfs_and_logs and the structure files related to radical precursors should be placed in test_sub/R/gjfs_and_logs. These structure files are used to generate a range of other types of descriptors, such as ASCF, SOAP, Fingerprint, etc. Those descriptors could be used in model selection process.(for example: ./Example/part_4/Benchmark.ipynb)
   Those structure files could be available from the Desc_gas_sp folder in Part 1 with suffix of sp.gjf and sp.log.

3. PhysOrg descriptors file (Ar_phychem.csv and R_phychem.csv) should alse be placed in corresponding folder.(test_sub/Ar and test_sub/R)

4. We also need a label file TestSet_Label.csv which should be placed in test_sub to show the data set which chemical reaction combination information is included. The label file needs to be organized by the operator according to his needs, and it mainly records the transition state energy barrier information for training or testing, including heterocyclic aromatic aliases Ar_n, the number of the target site atom of heteroarene loc_n, radical aliases Radical_n and transition state energy barrier DG_TS information. For data that only needs to be predicted, DG_TS can be filled with 0.0. See examples (./DataSet/raw/test_sub/TestSet_Label.csv) for details.

   • The schema of the entire sub folder is as follows:

       -- DataSet/raw/test_sub
         |-- Ar  
         |  |-- gjfs_and_logs  
         |  |   |-- Ar1.gjf
         |  |   |-- Ar1.log 
         |  |   |-- ...   
         |  |-- Ar_phychem.csv  
         |-- R  
         |  |-- gjfs_and_logs  
         |  |   |-- R1.gjf
         |  |   |-- R1.log  
         |  |   |-- ...   
         |  |-- R_phychem.csv
         |-- TestSet_Label.csv
     

   • We have shown the location and contents of relevant documents in ./DataSet/raw/test_sub folder

   • It is worth noting that the information such as Ar_n, loc_n and Radical_n in the label file needs to be recorded in the precursor folders Ar and R as described in the previous steps.

5. Call the ReactionDataset and SelectivityDataset classes in ChemSelML.bin.ChemSelectivityDataset of this project, it will integrate all information in ./DataSet/raw/test_sub into one reaction database file ReactionDataset_ArR_test_sub.pt and chemical selectivity database file SelectivityDataset_ArR_test_sub.pt. These pt files includes various feature categories and target attributes needed for model training or testing. The generated file is located in a folder with the same name as test_sub under the ./Dataset/processed folder. See the example to generate this two file in the ./Example/part_4/PhysOrg-RF.ipynb file for details. Once these PT files are generated, they can be called multiple times.

    import numpy as np
    import pandas as pd
    import torch
   
    import os
    import sys
    # Add the absolute path of the directory where ChemSelML is located to the python package search path
    sys.path.append("/PyScripts/PyTorch.dir/Radical")
   
    from ChemSelML.bin.ChemSelectivityDataset import ReactionDataset, SelectivityDataset
   
    # '/PyScripts/PyTorch.dir/Radical/DataSet' corresponds to the "../DataSet" directory in this project.
    # mode corresponds to the folder name in "../DataSet/raw"
    dev2_ArR_dataset = ReactionDataset(root='/PyScripts/PyTorch.dir/Radical/DataSet', mode='dev_2')
    print(dev2_ArR_dataset,'\n')
    print(dev2_ArR_dataset.data,'\n')
   
    dev2_ArR_DDG_dataset = SelectivityDataset(root='/PyScripts/PyTorch.dir/Radical/DataSet', mode='dev_2')
    print(dev2_ArR_DDG_dataset,'\n')
    print(dev2_ArR_DDG_dataset.data,'\n')  
   

6. For training task, the created folder names should start with dev_ and followed by your own suffix identifier, such as dev_2 and label file should be named with TrainSet.csv. And the test_sub in the corresponding filename and directory path described in the previous steps will change to dec_2.

   • We provide the complete training set with the required files in the ./Dataset/processed/dev_2 folder and ./Dataset/raw/dev_2 folder

Model selection, training and testing

1. This project provides a model screening module ChemSelML.training.benchmark and a predictor training module ChemSelML.training.ChemSelPredictor. We show in detail the use of the model screening and predictor training functions in the ./Example/part_4 folder.
2. For model selection, we've put the relevant code in ./Example/part_4/Benchmark.ipynb.We have selected different regressors or classifiers according to the requirements to conduct 5-fold cross-validation tests on various combinations of features to compare the performance of each model.
3. And for model training and test case, we show in detail the training, saving, retuning, and prediction of the entire functional block of the PhysOrg-RF and SOAP/FP(MMFF84)-XGB models. It is easy for everyone to understand and use. We've put the relevant code in ./Example/part_4/PhysOrg-RF.ipynb and ./Example/part_4/SOAP/FP(MMFF84)-XGB.ipynb.

   • PS.

     We provide an output sample, which is placed in the example folder csv output file description:
     *DDG_Pred_ArR_site_sort*.csv: the transformation result of the predicted energy barrier difference of the model into the reference energy barrier result of each site.
     *DDG_Pred_site_vs_site*.csv: the predicted energy barrier difference of the model

Email: [email protected]; [email protected]