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Abstract Motivation Application of chemical named entity recognition (CNER) algorithms allows retrieval of information from texts about chemical compound identifiers and creates associations with physical–chemical properties and biological activities. Scientific texts represent low-formalized sources of information. Most methods aimed at CNER are based on machine learning approaches, including conditional random fields and deep neural networks. In general, most machine learning approaches require either vector or sparse word representation of texts. Chemical named entities (CNEs) constitute only a small fraction of the whole text, and the datasets used for training are highly imbalanced. Methods and results We propose a new method for extracting CNEs from texts based on the naïve Bayes classifier combined with specially developed filters. In contrast to the earlier developed CNER methods, our approach uses the representation of the data as a set of fragments of text (FoTs) with the subsequent preparati`on of a set of multi-n-grams (sequences from one to n symbols) for each FoT. Our approach may provide the recognition of novel CNEs. For CHEMDNER corpus, the values of the sensitivity (recall) was 0.95, precision was 0.74, specificity was 0.88, and balanced accuracy was 0.92 based on five-fold cross validation. We applied the developed algorithm to the extracted CNEs of potential Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease (Mpro) inhibitors. A set of CNEs corresponding to the chemical substances evaluated in the biochemical assays used for the discovery of Mpro inhibitors was retrieved. Manual analysis of the appropriate texts showed that CNEs of potential SARS-CoV-2 Mpro inhibitors were successfully identified by our method. Conclusion The obtained results show that the proposed method can be used for filtering out words that are not related to CNEs; therefore, it can be successfully applied to the extraction of CNEs for the purposes of cheminformatics and medicinal chemistry.

Motivation: Application of chemical named entity recognition (CNER) algorithms allows retrieval of information from texts about chemical compound identifiers and creates associations with physical–chemical properties and biological activities. Scientific texts represent low-formalized sources of information. Most methods aimed at CNER are based on machine learning approaches, including conditional random fields and deep neural networks. In general, most machine learning approaches require either vector or sparse word representation of texts. Chemical named entities (CNEs) constitute only a small fraction of the whole text, and the datasets used for training are highly imbalanced. Methods and results: We propose a new method for extracting CNEs from texts based on the naïve Bayes classifier combined with specially developed filters. In contrast to the earlier developed CNER methods, our approach uses the representation of the data as a set of fragments of text (FoTs) with the subsequent preparati'on of a set of multi-n-grams (sequences from one to n symbols) for each FoT. Our approach may provide the recognition of novel CNEs. For CHEMDNER corpus, the values of the sensitivity (recall) was 0.95, precision was 0.74, specificity was 0.88, and balanced accuracy was 0.92 based on five-fold cross validation. We applied the developed algorithm to the extracted CNEs of potential Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease (Mpro) inhibitors. A set of CNEs corresponding to the chemical substances evaluated in the biochemical assays used for the discovery of Mpro inhibitors was retrieved. Manual analysis of the appropriate texts showed that CNEs of potential SARS-CoV-2 Mpro inhibitors were successfully identified by our method. Conclusion: The obtained results show that the proposed method can be used for filtering out words that are not related to CNEs; therefore, it can be successfully applied to the extraction of CNEs for the purposes of cheminformatics and medicinal chemistry. [ABSTRACT FROM AUTHOR]

Chemical Named Entity Recognition (NER) is the basic step for consequent information extraction tasks such as named entity resolution, drug-drug interaction discovery, extraction of the names of the molecules and their properties. Improvement in the performance of such systems may affects the quality of the subsequent tasks. Chemical text from which data for named entity recognition is extracted is naturally imbalanced since chemical entities are fewer compared to other segments in text. In this paper, the class imbalance problem in the context of chemical named entity recognition has been studied and adopted version of random undersampling for NER data, has been leveraged to generate a pool of classifiers. In order to keep the classes’ distribution balanced within each sentence, the well-known random undersampling method is modified to a sentence based version where the random removal of samples takes place within each sentence instead of considering the dataset as a whole. Furthermore, to take the advantages of combination of a set of diverse predictors, an ensemble of classifiers trained with the set of different training data resulted by sentence-based undersampling, is created. The proposed approach is developed and tested using the ChemDNER corpus released by BioCreative IV. Results show that the proposed method improves the classification performance of the baseline classifiers mainly as a result of an increase in recall. Furthermore, the combination of high performing classifiers trained using undersampled train data surpasses the performance of all single best classifiers and the combination of classifiers using full data.

The huge space of experimental data on biological and chemical objects and their interactions contributes to the rapid growth of scientific publications containing their analysis. Such data may include characteristics of low-molecular-weight compounds, results of their biological activity evaluation, and their interaction with human and animal proteins, methods of synthesis of organic compounds, and their classification. The past decades saw the development of methods for automated extraction of data from texts of scientific publications, including those for retrieval of names of organic compounds. These data can be used for the automatic identification of the names of organic compounds, including all possible synonyms. Since the topics of scientific publications are diverse, the extracted data can be applied to obtain information about (1) classification of organic compounds (2) methods of synthesis of a given organic compound; (3) physicochemical properties of this compound; (4) its interaction with high-molecular-weight compounds (including proteins, mRNA of animals and humans); and (5) the therapeutic properties of organic compounds, the active substance of the drug, and data on clinical trials. This review considers the methods aimed at searching and extracting data on names of low-molecular-weight compounds and interactions between them and animal and human proteins (biological objects), as well as data on experimentally confirmed biological activity and the effects of organic compounds (including drugs) on pathological processes. Here, we discuss the methods developed and the results of their application published over the past 10 years. [ABSTRACT FROM AUTHOR]

Recently, methods for Chemical Named Entity Recognition (NER) have gained substantial interest, driven by the need for automatically analyzing todays ever growing collections of biomedical text. Chemical NER for patents is particularly essential due to the high economic importance of pharmaceutical findings. However, NER on patents has essentially been neglected by the research community for long, mostly because of the lack of enough annotated corpora. A recent international competition specifically targeted this task, but evaluated tools only on gold standard patent abstracts instead of full patents; furthermore, results from such competitions are often difficult to extrapolate to real-life settings due to the relatively high homogeneity of training and test data. Here, we evaluate the two state-of-the-art chemical NER tools, tmChem and ChemSpot, on four different annotated patent corpora, two of which consist of full texts. We study the overall performance of the tools, compare their results at the instance level, report on high-recall and high-precision ensembles, and perform cross-corpus and intra-corpus evaluations. Our findings indicate that full patents are considerably harder to analyze than patent abstracts and clearly confirm the common wisdom that using the same text genre (patent vs. scientific) and text type (abstract vs. full text) for training and testing is a pre-requisite for achieving high quality text mining results. [ABSTRACT FROM AUTHOR]

In a case study current methodologies for chemical compound searching in patents were assessed. The dyestuff Disperse Orange 25 was used to compare search results obtained from different database categories. Namely, search results from three databases with automated chemical compound recognition (SciWalker, SureChEMBL, Patentscope), a full-text database (FullPat), and a value added database (CAPLUS) were compared. Most databases retrieved unique hit documents. The working thesis that databases with automated chemical compound recognition might substitute traditional databases could not be confirmed. For patent searches aiming completeness with regard to specific chemical compounds, the combined use of databases from all categories is needed. [ABSTRACT FROM AUTHOR]