scholarly journals RegioML: Predicting the regioselectivity of electrophilic aromatic substitution reactions using machine learning

2021 ◽  
Author(s):  
Nicolai Ree ◽  
Andreas H. Göller ◽  
Jan H. Jensen
Keyword(s):  
Machine Learning ◽  
Tight Binding ◽  
Reaction Centers ◽  
Gradient Boosting ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Test Set ◽  
Light Gradient ◽  
Out Of Sample

We present RegioML, an atom-based machine learning model for predicting the regioselectivities of electrophilic aromatic substitution reactions. The model relies on CM5 atomic charges computed using semiempirical tight binding (GFN1-xTB) combined with the ensemble decision tree variant light gradient boosting machine (LightGBM). The model is trained and tested on 21,201 bromination reactions with 101K reaction centers, which is split into a training, test, and out-of-sample datasets with 58K, 15K, and 27K reaction centers, respectively. The accuracy is 93% for the test set and 90% for the out-of-sample set, while the precision (the percentage of positive predictions that are correct) is 88% and 80%, respectively. The test-set performance is very similar to the graph-based WLN method developed by Struble et al. (React. Chem. Eng. 2020, 5, 896) though the comparison is complicated by the possibility that some of the test and out-of-sample molecules are used to train WLN. RegioML out-performs our physics-based RegioSQM20 method (J. Cheminform. 2021, 13:10) where the precision is only 75%. Even for the out-of-sample dataset, RegioML slightly outperforms RegioSQM20. The good performance of RegioML and WLN is in large part due to the large datasets available for this type of reaction. However, for reactions where there is little experimental data, physics-based approaches like RegioSQM20 can be used to generate synthetic data for model training. We demonstrate this by showing that the performance of RegioSQM20 can be reproduced by a ML-model trained on RegioSQM20-generated data.

scholarly journals Development and validation of a difficult laryngoscopy prediction model using machine learning of neck circumference and thyromental height

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Jong Ho Kim ◽  
Haewon Kim ◽  
Ji Su Jang ◽  
Sung Mi Hwang ◽  
So Young Lim ◽  
...  
Keyword(s):  
Machine Learning ◽  
Random Forest ◽  
Confidence Interval ◽  
Neck Circumference ◽  
Difficult Laryngoscopy ◽  
Gradient Boosting ◽  
Test Set ◽  
Equal Distribution ◽  
Light Gradient ◽  
Extreme Gradient Boosting

Abstract Background Predicting difficult airway is challengeable in patients with limited airway evaluation. The aim of this study is to develop and validate a model that predicts difficult laryngoscopy by machine learning of neck circumference and thyromental height as predictors that can be used even for patients with limited airway evaluation. Methods Variables for prediction of difficulty laryngoscopy included age, sex, height, weight, body mass index, neck circumference, and thyromental distance. Difficult laryngoscopy was defined as Grade 3 and 4 by the Cormack-Lehane classification. The preanesthesia and anesthesia data of 1677 patients who had undergone general anesthesia at a single center were collected. The data set was randomly stratified into a training set (80%) and a test set (20%), with equal distribution of difficulty laryngoscopy. The training data sets were trained with five algorithms (logistic regression, multilayer perceptron, random forest, extreme gradient boosting, and light gradient boosting machine). The prediction models were validated through a test set. Results The model’s performance using random forest was best (area under receiver operating characteristic curve = 0.79 [95% confidence interval: 0.72–0.86], area under precision-recall curve = 0.32 [95% confidence interval: 0.27–0.37]). Conclusions Machine learning can predict difficult laryngoscopy through a combination of several predictors including neck circumference and thyromental height. The performance of the model can be improved with more data, a new variable and combination of models.

Radiomics with Ensemble Machine Learning Predicts Dopamine Agonist Response in Patients with Prolactinoma

2021 ◽  
Author(s):  
Yae Won Park ◽  
Jihwan Eom ◽  
Sooyon Kim ◽  
Hwiyoung Kim ◽  
Sung Soo Ahn ◽  
...  
Keyword(s):  
Machine Learning ◽  
Area Under The Curve ◽  
Ensemble Classifier ◽  
Magnetic Resonance Images ◽  
Gradient Boosting ◽  
Test Set ◽  
Discrimination Analysis ◽  
Severance Hospital ◽  
Light Gradient ◽  
Ensemble Machine Learning

Abstract Context Early identification of the response of prolactinoma patients to dopamine agonists (DA) is crucial in treatment planning. Objective To develop a radiomics model using an ensemble machine learning classifier with conventional magnetic resonance images (MRIs) to predict the DA response in prolactinoma patients. Design Retrospective study Setting Severance Hospital Patients A total of 177 prolactinoma patients who underwent baseline MRI (109 DA responders and 68 DA non-responders) were allocated to the training (n = 141) and test (n = 36) sets. Radiomic features (n = 107) were extracted from coronal T2-weighed MRIs. After feature selection, single models (random forest, light gradient boosting machine, extra-trees, quadratic discrimination analysis, and linear discrimination analysis) with oversampling methods were trained to predict the DA response. A soft voting ensemble classifier was used to achieve the final performance. The performance of the classifier was validated in the test set. Results The ensemble classifier showed an area under the curve (AUC) of 0.81 (95 % confidence interval [CI], 0.74–0.87) in the training set. In the test set, the ensemble classifier showed an AUC, accuracy, sensitivity, and specificity of 0.81 (95 % CI, 0.67–0.96), 77.8 %, 78.6 %, and 77.3 %, respectively. The ensemble classifier achieved the highest performance among all the individual models in the test set. Conclusions Radiomic features may be useful biomarkers to predict the DA response in prolactinoma patients.

Unveiling the Regioselectivity in Electrophilic Aromatic Substitution Reactions of Deactivated Benzenes through Molecular Electron Density Theory

2021 ◽  
Author(s):  
Luis R. Domingo ◽  
Mar Ríos-Gutiérrez ◽  
María José Aurell
Keyword(s):  
Electron Density ◽  
Electrophilic Aromatic Substitution ◽  
Benzene Derivatives ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Molecular Electron ◽  
Molecular Electron Density Theory

The origin of the meta regioselectivity in electrophilic aromatic substitution (EAS) reactions of deactivated benzene derivatives is herein analysed through Molecular Electron Density Theory (MEDT). To this end, the EAS...

Boosting Algorithm Choice in Predictive Machine Learning Models for Fracturing Applications

2021 ◽  
Author(s):  
Abdul Muqtadir Khan
Keyword(s):  
Machine Learning ◽  
Data Science ◽  
Oil And Gas ◽  
Oil And Gas Industry ◽  
Injection Rate ◽  
Model Construction ◽  
Gradient Boosting ◽  
Light Gradient ◽  
Fracture Damage ◽  
Boosting Technique

Abstract With the advancement in machine learning (ML) applications, some recent research has been conducted to optimize fracturing treatments. There are a variety of models available using various objective functions for optimization and different mathematical techniques. There is a need to extend the ML techniques to optimize the choice of algorithm. For fracturing treatment design, the literature for comparative algorithm performance is sparse. The research predominantly shows that compared to the most commonly used regressors and classifiers, some sort of boosting technique consistently outperforms on model testing and prediction accuracy. A database was constructed for a heterogeneous reservoir. Four widely used boosting algorithms were used on the database to predict the design only from the output of a short injection/falloff test. Feature importance analysis was done on eight output parameters from the falloff analysis, and six were finalized for the model construction. The outputs selected for prediction were fracturing fluid efficiency, proppant mass, maximum proppant concentration, and injection rate. Extreme gradient boost (XGBoost), categorical boost (CatBoost), adaptive boost (AdaBoost), and light gradient boosting machine (LGBM) were the algorithms finalized for the comparative study. The sensitivity was done for a different number of classes (four, five, and six) to establish a balance between accuracy and prediction granularity. The results showed that the best algorithm choice was between XGBoost and CatBoost for the predicted parameters under certain model construction conditions. The accuracy for all outputs for the holdout sets varied between 80 and 92%, showing robust significance for a wider utilization of these models. Data science has contributed to various oil and gas industry domains and has tremendous applications in the stimulation domain. The research and review conducted in this paper add a valuable resource for the user to build digital databases and use the appropriate algorithm without much trial and error. Implementing this model reduced the complexity of the proppant fracturing treatment redesign process, enhanced operational efficiency, and reduced fracture damage by eliminating minifrac steps with crosslinked gel.

scholarly journals Interpretable Machine Learning for Early Neurological Deterioration Prediction in Atrial Fibrillation-Related Stroke

2021 ◽  
Author(s):  
Seong Hwan Kim ◽  
Eun-Tae Jeon ◽  
Sungwook Yu ◽  
Kyungmi O ◽  
Chi Kyung Kim ◽  
...  
Keyword(s):  
Machine Learning ◽  
Atrial Fibrillation ◽  
Neurological Deterioration ◽  
Gradient Boosting ◽  
Support Vector ◽  
Light Gradient ◽  
Interpretable Machine Learning ◽  
Extreme Gradient Boosting ◽  
Early Neurological Deterioration ◽  
Feature Importance

Abstract We aimed to develop a novel prediction model for early neurological deterioration (END) based on an interpretable machine learning (ML) algorithm for atrial fibrillation (AF)-related stroke and to evaluate the prediction accuracy and feature importance of ML models. Data from multi-center prospective stroke registries in South Korea were collected. After stepwise data preprocessing, we utilized logistic regression, support vector machine, extreme gradient boosting, light gradient boosting machine (LightGBM), and multilayer perceptron models. We used the Shapley additive explanations (SHAP) method to evaluate feature importance. Of the 3,623 stroke patients, the 2,363 who had arrived at the hospital within 24 hours of symptom onset and had available information regarding END were included. Of these, 318 (13.5%) had END. The LightGBM model showed the highest area under the receiver operating characteristic curve (0.778, 95% CI, 0.726 - 0.830). The feature importance analysis revealed that fasting glucose level and the National Institute of Health Stroke Scale score were the most influential factors. Among ML algorithms, the LightGBM model was particularly useful for predicting END, as it revealed new and diverse predictors. Additionally, the SHAP method can be adjusted to individualize the features’ effects on the predictive power of the model.

Homoazulene electrophilic aromatic substitution reactions. Parallels to the chemistry of azulene

1989 ◽  
Vol 30 (3) ◽  
pp. 305-308 ◽  
Author(s):  
Lawrence T. Scott ◽  
Chris A. Sumpter ◽  
Mitsunori Oda ◽  
Ihsan Erden
Keyword(s):  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions

Development of a Diabetes Melitus Detection and Prediction Model Using Light Gradient Boosting Machine and K-Nearest Neighbour

2021 ◽  
Vol 3 (1) ◽  
Author(s):  
B. A Omodunbi
Keyword(s):  
Diabetes Mellitus ◽  
Machine Learning ◽  
Hybrid Model ◽  
Learning Model ◽  
Experimental Result ◽  
Gradient Boosting ◽  
Light Gradient ◽  
Machine Learning Model ◽  
Gradient Boosting Machine ◽  
Receiver Operating

Diabetes mellitus is a health disorder that occurs when the blood sugar level becomes extremely high due to body resistance in producing the required amount of insulin. The aliment happens to be among the major causes of death in Nigeria and the world at large. This study was carried out to detect diabetes mellitus by developing a hybrid model that comprises of two machine learning model namely Light Gradient Boosting Machine (LGBM) and K-Nearest Neighbor (KNN). This research is aimed at developing a machine learning model for detecting the occurrence of diabetes in patients. The performance metrics employed in evaluating the finding for this study are Receiver Operating Characteristics (ROC) Curve, Five-fold Cross-validation, precision, and accuracy score. The proposed system had an accuracy of 91% and the area under the Receiver Operating Characteristic Curve was 93%. The experimental result shows that the prediction accuracy of the hybrid model is better than traditional machine learning

scholarly journals Bacterial Immunogenicity Prediction by Machine Learning Methods

Vaccines ◽  
2020 ◽  
Vol 8 (4) ◽  
pp. 709
Author(s):  
Ivan Dimitrov ◽  
Nevena Zaharieva ◽  
Irini Doytchinova
Keyword(s):  
Machine Learning ◽  
Nearest Neighbor ◽  
Predictive Ability ◽  
Initial Step ◽  
Majority Voting ◽  
Gradient Boosting ◽  
Support Vector ◽  
K Nearest Neighbor ◽  
Test Set ◽  
Extreme Gradient Boosting

The identification of protective immunogens is the most important and vigorous initial step in the long-lasting and expensive process of vaccine design and development. Machine learning (ML) methods are very effective in data mining and in the analysis of big data such as microbial proteomes. They are able to significantly reduce the experimental work for discovering novel vaccine candidates. Here, we applied six supervised ML methods (partial least squares-based discriminant analysis, k nearest neighbor (kNN), random forest (RF), support vector machine (SVM), random subspace method (RSM), and extreme gradient boosting) on a set of 317 known bacterial immunogens and 317 bacterial non-immunogens and derived models for immunogenicity prediction. The models were validated by internal cross-validation in 10 groups from the training set and by the external test set. All of them showed good predictive ability, but the xgboost model displays the most prominent ability to identify immunogens by recognizing 84% of the known immunogens in the test set. The combined RSM-kNN model was the best in the recognition of non-immunogens, identifying 92% of them in the test set. The three best performing ML models (xgboost, RSM-kNN, and RF) were implemented in the new version of the server VaxiJen, and the prediction of bacterial immunogens is now based on majority voting.

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