UPPER is a cheminformatics toolkit for featurizing molecules and building quantitative structure-property relationships (QSPRs) for physicochemical properties. This molecular representation is supplied as input to linear and nonlinear learning algorithms.
Phase transitions such as melting and boiling characterize a material's interaction with its environment. Properties such as transition temperature can influence whether a material is suitable for a given application. Examples of phase-driven applications include drug development, melt-casting explosives, or energy harvesting materials. However, a well-known difficulty of materials discovery is that chemical synthesis is costly and time consuming. Therefore, identifying potential candidates may proceed a long and arduous synthesis task. A priori knowledge of transition temperatures would limit the chemical space of candidate compounds, expediting discovery.
Predicting physicochemical properties has long been the work of linear regression-based QSPRs. These models have had success but are often limited by their inability to find nonlinear mappings from easy-to-derive descriptors. Recently, there has been a strong interest in applying the tools of data science to chemistry. Nonlinear machine learning (ML) algorithms have made their presence from the atomic scale to the continuum. This work builds on these modern-day predictive tools for transition temperatures. Specifically, this code featurizes compounds using group-constitutive and geometrical descriptors, previously shown to map to enthalpy and entropy--two thermodynamic quantities that drive phase transitions. The descriptors originate from the work of Yalkowsky and coworkers J. Pharm. 103:2710-2723, 2014, known as UPPER (Unified Physicochemical Property Estimation Relationships). A notable advantage of UPPER is that descriptors are derived purely from a compound's SMILES string. Thus, besides relatively simple structural characteristics such as connectivity and hybridization, there are no high-level or numerically intensive calculations necessary. This molecular representation can be supplied as input to learning algorithms. The code currently supports ridge regression and eXtreme Gradient Boosting (XGBoost). While it is generally a challenge to train models to limited experimental data, we find that UPPER's concise set of domain-specific descriptors, combined with nonlinear ML algorithms, provide an appealing framework for predicting transition enthalpies, entropies, and temperatures in a diverse set of compounds.
conda env create -f environment.yml
conda activate upperSee examples folder. Edit params.py for the desired tasks.
Set construct_fp to True.
procedure_params = {'construct_fp': True,
'multiprocessing': False, # cv for multiple models
'model': 'xgb',
'train': False,
'predict': False,
'hyperparametrize': False, # and trains
'feature_reduction': False,
}Set path to dataset (data_path), name of column with SMILES (smiles_name), and where to save featurization (fp_path).
fp_params = {'data_path': '/path/to/data/example.csv',
'smiles_name': 'SMILES',
'labels': {'groups': ['X', 'Y', 'YY', 'YYY', 'YYYY', 'YYYYY', 'Z', 'ZZ', 'YZ', 'YYZ', 'YYYZ', '', 'RG', 'AR', 'BR2', 'BR3', 'FU', 'BIP'],
'singles': ['\u03A6', '\u03C3', '\u03B5\u00B2\u1d30', '\U0001D45E\u00B3\u1d30', '\U0001D464', '\U0001D45A'],
}, # phi-flexibility, sigma-symmetry, epsilon(3D)-eccentricity, q(3D)-asphericity, w-Wiener index, m-mass
'fp_type': 'upper',
'fp_path': '/path/to/fingerprint/example.csv',
'd_path': '/path/to/darray/example.pkl',
}Set train and predict to True.
procedure_params = {'construct_fp': False,
'multiprocessing': False, # cv for multiple models
'model': 'xgb',
'train': True,
'predict': True,
'hyperparametrize': False, # and trains
'feature_reduction': False,
}Set path to featurization (fp_path), path to target property (target_path), and target column name (target_name).
data_params = {'fp_path': '/path/to/fingerprint/example.csv',
'target_path': '/path/to/dataset/example.csv',
'target_name': 'Target Name',
}Set train/test split.
split_params = {'split': {'train': 0.9, 'test': 0.1},
'random_state': 123,
'train_indices': np.array([]),
'test_indices': np.array([]),
}For this example, set parameters of XGBoost (see XGBoost's documentation).
xgb_train_params = {'learning_rate': 0.3,
'n_estimators': 100,
'objective': 'reg:squarederror',
}Set paths where to save trained model and results.
save_load_params = {'save_model': True,
'save_model_path': '/path/to/model/example.pkl,
'train_fp_path': '/path/to/fingerprint/of/trained/model/example.csv',
'npz_train_path': '/path/to/training/results/example.npz',
'npz_test_path': '/path/to/testing/results/example.npz',
}This example executes a hyperparameter search, trains and tests.
procedure_params = {'construct_fp': False,
'multiprocessing': False, # cv for multiple models
'model': 'xgb',
'train': True,
'predict': True,
'hyperparametrize': True, # and trains
'feature_reduction': False,
}In addition to training/testing parameters, set ranges to search parameters.
xgb_hyper_params = [
{'max_depth': np.arange(1, 11), # (0, inf), default = 3
'min_child_weight': [0, 1, 10, 100, 1000], # [0, inf), default = 1
},
{'gamma': [0, 1, 10, 100, 1000], # [0, inf), default = 0
},
{'subsample': np.linspace(0.1, 1, 10), # (0, 1], default = 1
'colsample_bytree': np.linspace(0.1, 1, 10), # (0, 1], default = 1
},
{'alpha': [0, 0.001, 0.01, 0.1, 1], # [0,inf), default = 0
},
]To load and use a trained model, set predict to True in procedure_params, edit data_params and save_load_params.
save_load_params = {'load_model': True,
'load_model_path': '/path/to/model/example.pkl',
'train_fp_path': '/path/to/fingerprint/of/trained/model/example.csv',
'npz_train_path': '/path/to/training/results/example.npz',
'npz_test_path': '/path/to/testing/results/example.npz',
}Here, load_model is True. Paths to model (load_model_path) and training featurization (train_fp_path) are specified.
python input.pyNote that params.py and input.py should be in the same directory.
During featurization, the code fragments the molecules, assigns them to environmental groups, and indicates whether the number of fragments and assignments are equal.
2019-10-28 11:29:00,711 - root - INFO - indices of molecules with inconsistent number of frags:
[]
2019-10-28 11:29:00,712 - root - INFO - and their smiles:
[]Molecules with fragments that do not belong to the current groups will be identified. For such cases, new groups must be added to the code. Groups are attributes of the Descriptors class in src/upper/descripts.py. ReduceMultiCount in scr/upper/utils.py must also be edited to ensure each fragment belongs to one environmental group.
Generally speaking, a trained model is applicable if groups of the test set are a subset of those in the training set.
For details of UPPER's descriptors, see J. Pharm. 103:2710-2723, 2014.
Contributors:
Andrew E. Sifain
Brian C. Barnes
This project is licensed under the Apache 2.0 license.