Patent Retrieval in Chemistry based on semantically tagged Named Entities

Gurulingappa H, Müller B, Klinger R, et al. Patent Retrieval in Chemistry based on semantically tagged Named Entities. In: Voorhees EM, Buckland LP, eds. The Eighteenth Text RETrieval Conference (TREC 2009) Proceedings. Gaithersburg, Maryland, USA; 2009.This paper reports on the work that has been conducted by Fraunhofer SCAI for Trec Chemistry (Trec-Chem) track 2009. The team of Fraunhofer SCAI participated in two tasks, namely Technology Survey and Prior Art Search. The core of the framework is an index of 1.2 million chemical patents provided as a data set by Trec. For the technology survey, three runs were submitted based on semantic dictionaries and noun phrases. For the prior art search task, several elds were introduced into the index that contained normalized noun phrases, biomedical as well as chemical entities. Altogether, 36 runs were submitted for this task that were based on automatic querying with tokens, noun phrases and entities along with dierent search strategies

Information retrieval and text mining technologies for chemistry

Efficient access to chemical information contained in scientific literature, patents, technical reports, or the web is a pressing need shared by researchers and patent attorneys from different chemical disciplines. Retrieval of important chemical information in most cases starts with finding relevant documents for a particular chemical compound or family. Targeted retrieval of chemical documents is closely connected to the automatic recognition of chemical entities in the text, which commonly involves the extraction of the entire list of chemicals mentioned in a document, including any associated information. In this Review, we provide a comprehensive and in-depth description of fundamental concepts, technical implementations, and current technologies for meeting these information demands. A strong focus is placed on community challenges addressing systems performance, more particularly CHEMDNER and CHEMDNER patents tasks of BioCreative IV and V, respectively. Considering the growing interest in the construction of automatically annotated chemical knowledge bases that integrate chemical information and biological data, cheminformatics approaches for mapping the extracted chemical names into chemical structures and their subsequent annotation together with text mining applications for linking chemistry with biological information are also presented. Finally, future trends and current challenges are highlighted as a roadmap proposal for research in this emerging field.A.V. and M.K. acknowledge funding from the European Community’s Horizon 2020 Program (project reference: 654021 - OpenMinted). M.K. additionally acknowledges the Encomienda MINETAD-CNIO as part of the Plan for the Advancement of Language Technology. O.R. and J.O. thank the Foundation for Applied Medical Research (FIMA), University of Navarra (Pamplona, Spain). This work was partially funded by Consellería de Cultura, Educación e Ordenación Universitaria (Xunta de Galicia), and FEDER (European Union), and the Portuguese Foundation for Science and Technology (FCT) under the scope of the strategic funding of UID/BIO/04469/2013 unit and COMPETE 2020 (POCI-01-0145-FEDER-006684). We thank Iñigo Garciá -Yoldi for useful feedback and discussions during the preparation of the manuscript.info:eu-repo/semantics/publishedVersio

Information extraction from chemical patents

The automated extraction of semantic chemical data from the existing literature is demonstrated. For reasons of copyright, the work is focused on the patent literature, though the methods are expected to apply equally to other areas of the chemical literature. Hearst Patterns are applied to the patent literature in order to discover hyponymic relations describing chemical species. The acquired relations are manually validated to determine the precision of the determined hypernyms (85.0%) and of the asserted hyponymic relations (94.3%). It is demonstrated that the system acquires relations that are not present in the ChEBI ontology, suggesting that it could function as a valuable aid to the ChEBI curators. The relations discovered by this process are formalised using the Web Ontology Language (OWL) to enable re-use. PatentEye – an automated system for the extraction of reactions from chemical patents and their conversion to Chemical Markup Language (CML) – is presented. Chemical patents published by the European Patent Office over a ten-week period are used to demonstrate the capability of PatentEye – 4444 reactions are extracted with a precision of 78% and recall of 64% with regards to determining the identity and amount of reactants employed and an accuracy of 92% with regards to product identification. NMR spectra are extracted from the text using OSCAR3, which is developed to greatly increase recall. The resulting system is presented as a significant advancement towards the large-scale and automated extraction of high-quality reaction information. Extended Polymer Markup Language (EPML), a CML dialect for the description of Markush structures as they are presented in the literature, is developed. Software to exemplify and to enable substructure searching of EPML documents is presented. Further work is recommended to refine the language and code to publication-quality before they are presented to the community.Unileve

Mining the Medical and Patent Literature to Support Healthcare and Pharmacovigilance

Recent advancements in healthcare practices and the increasing use of information technology in the medical domain has lead to the rapid generation of free-text data in forms of scientific articles, e-health records, patents, and document inventories. This has urged the development of sophisticated information retrieval and information extraction technologies. A fundamental requirement for the automatic processing of biomedical text is the identification of information carrying units such as the concepts or named entities. In this context, this work focuses on the identification of medical disorders (such as diseases and adverse effects) which denote an important category of concepts in the medical text. Two methodologies were investigated in this regard and they are dictionary-based and machine learning-based approaches. Futhermore, the capabilities of the concept recognition techniques were systematically exploited to build a semantic search platform for the retrieval of e-health records and patents. The system facilitates conventional text search as well as semantic and ontological searches. Performance of the adapted retrieval platform for e-health records and patents was evaluated within open assessment challenges (i.e. TRECMED and TRECCHEM respectively) wherein the system was best rated in comparison to several other competing information retrieval platforms. Finally, from the medico-pharma perspective, a strategy for the identification of adverse drug events from medical case reports was developed. Qualitative evaluation as well as an expert validation of the developed system's performance showed robust results. In conclusion, this thesis presents approaches for efficient information retrieval and information extraction from various biomedical literature sources in the support of healthcare and pharmacovigilance. The applied strategies have potential to enhance the literature-searches performed by biomedical, healthcare, and patent professionals. The applied strategies have potential to enhance the literature-searches performed by biomedical, healthcare, and patent professionals. This can promote the literature-based knowledge discovery, improve the safety and effectiveness of medical practices, and drive the research and development in medical and healthcare arena

Extraction of Keyphrases from Text: Evaluation of Four Algorithms

This report presents an empirical evaluation of four algorithms for automatically extracting keywords and keyphrases from documents. The four algorithms are compared using five different collections of documents. For each document, we have a target set of keyphrases, which were generated by hand. The target keyphrases were generated for human readers; they were not tailored for any of the four keyphrase extraction algorithms. Each of the algorithms was evaluated by the degree to which the algorithm’s keyphrases matched the manually generated keyphrases. The four algorithms were (1) the AutoSummarize feature in Microsoft’s Word 97, (2) an algorithm based on Eric Brill’s part-of-speech tagger, (3) the Summarize feature in Verity’s Search 97, and (4) NRC’s Extractor algorithm. For all five document collections, NRC’s Extractor yields the best match with the manually generated keyphrases

The CHEMDNER corpus of chemicals and drugs and its annotation principles

The automatic extraction of chemical information from text requires the recognition of chemical entity mentions as one of its key steps. When developing supervised named entity recognition (NER) systems, the availability of a large, manually annotated text corpus is desirable. Furthermore, large corpora permit the robust evaluation and comparison of different approaches that detect chemicals in documents. We present the CHEMDNER corpus, a collection of 10,000 PubMed abstracts that contain a total of 84,355 chemical entity mentions labeled manually by expert chemistry literature curators, following annotation guidelines specifically defined for this task. The abstracts of the CHEMDNER corpus were selected to be representative for all major chemical disciplines. Each of the chemical entity mentions was manually labeled according to its structure-associated chemical entity mention (SACEM) class: abbreviation, family, formula, identifier, multiple, systematic and trivial. The difficulty and consistency of tagging chemicals in text was measured using an agreement study between annotators, obtaining a percentage agreement of 91. For a subset of the CHEMDNER corpus (the test set of 3,000 abstracts) we provide not only the Gold Standard manual annotations, but also mentions automatically detected by the 26 teams that participated in the BioCreative IV CHEMDNER chemical mention recognition task. In addition, we release the CHEMDNER silver standard corpus of automatically extracted mentions from 17,000 randomly selected PubMed abstracts. A version of the CHEMDNER corpus in the BioC format has been generated as well. We propose a standard for required minimum information about entity annotations for the construction of domain specific corpora on chemical and drug entities. The CHEMDNER corpus and annotation guidelines are available at: http://www.biocreative.org/resources/biocreative-iv/chemdner-corpus

Information Extraction from Text for Improving Research on Small Molecules and Histone Modifications

The cumulative number of publications, in particular in the life sciences, requires efficient methods for the automated extraction of information and semantic information retrieval. The recognition and identification of information-carrying units in text – concept denominations and named entities – relevant to a certain domain is a fundamental step. The focus of this thesis lies on the recognition of chemical entities and the new biological named entity type histone modifications, which are both important in the field of drug discovery. As the emergence of new research fields as well as the discovery and generation of novel entities goes along with the coinage of new terms, the perpetual adaptation of respective named entity recognition approaches to new domains is an important step for information extraction. Two methodologies have been investigated in this concern: the state-of-the-art machine learning method, Conditional Random Fields (CRF), and an approximate string search method based on dictionaries. Recognition methods that rely on dictionaries are strongly dependent on the availability of entity terminology collections as well as on its quality. In the case of chemical entities the terminology is distributed over more than 7 publicly available data sources. The join of entries and accompanied terminology from selected resources enables the generation of a new dictionary comprising chemical named entities. Combined with the automatic processing of respective terminology – the dictionary curation – the recognition performance reached an F1 measure of 0.54. That is an improvement by 29 % in comparison to the raw dictionary. The highest recall was achieved for the class of TRIVIAL-names with 0.79. The recognition and identification of chemical named entities provides a prerequisite for the extraction of related pharmacological relevant information from literature data. Therefore, lexico-syntactic patterns were defined that support the automated extraction of hypernymic phrases comprising pharmacological function terminology related to chemical compounds. It was shown that 29-50 % of the automatically extracted terms can be proposed for novel functional annotation of chemical entities provided by the reference database DrugBank. Furthermore, they are a basis for building up concept hierarchies and ontologies or for extending existing ones. Successively, the pharmacological function and biological activity concepts obtained from text were included into a novel descriptor for chemical compounds. Its successful application for the prediction of pharmacological function of molecules and the extension of chemical classification schemes, such as the the Anatomical Therapeutic Chemical (ATC), is demonstrated. In contrast to chemical entities, no comprehensive terminology resource has been available for histone modifications. Thus, histone modification concept terminology was primary recognized in text via CRFs with a F1 measure of 0.86. Subsequent, linguistic variants of extracted histone modification terms were mapped to standard representations that were organized into a newly assembled histone modification hierarchy. The mapping was accomplished by a novel developed term mapping approach described in the thesis. The combination of term recognition and term variant resolution builds up a new procedure for the assembly of novel terminology collections. It supports the generation of a term list that is applicable in dictionary-based methods. For the recognition of histone modification in text it could be shown that the named entity recognition method based on dictionaries is superior to the used machine learning approach. In conclusion, the present thesis provides techniques which enable an enhanced utilization of textual data, hence, supporting research in epigenomics and drug discovery

Identifying chemical entities on literature:a machine learning approach using dictionaries as domain knowledge

Tese de doutoramento, Informática (Bioinformática), Universidade de Lisboa, Faculdade de Ciências, 2013The volume of life science publications, and therefore the underlying biomedical knowledge, are growing at a fast pace. However the manual literature analysis is a slow and painful task. Hence, text mining systems have been developed to automatically locate the relevant information contained in the literature. An essential step in text mining is named entitiy recognition, but the inherent complexity of biomedical entities, such as chemical compounds, makes it difficult to obtain good performances in this task. This thesis proposes methods capable to improve the current performance of chemical entity recognition from text. Hereby a case based method for recognizing chemical entities is proposed and the obtained evaluation results outperform the most widely used methods, based in dictionaries. A lexical similarity based chemical entity resolution method was also developed and allows an efficient mapping of the recognized entities to the ChEBI database. To improve the chemical entity identification results we developed a validation method that exploits the semantic relationships in ChEBI to measure the similarity between the entities found in the text, in order to discriminate between the correctly identified entities that can be validated and identification errors that should be discarded. A machine learning method for entity recognition error is also proposed, which can efectively find recognition errors in rule based systems. The methods were integrated in a system capable of recognizing chemical entities in texts, map them to the ChEBI database, and provide evidence of validation or recognition error for the recognized entities.O volume de publicações científicas nas ciências da vida está a aumentar a um ritmo crescente. Contudo a análise manual da literatura é um processo árduo e moroso, pelo que têm sido desenvolvidos sistemas de prospecção de texto para identificar automaticamente a informação relevante contida na literatura. Um passo essencial em prospecção de texto é a identificação de entidades nomeadas, mas a complexidade inerente às entidades biomédicas, como é o caso dos compostos químicos, torna difícil obter bons desempenhos nesta tarefa. Esta tese propõe métodos para melhorar o desempenho actual do processo de reconhecimento de entidades químicas em texto. Para tal propõe-se um método para reconhecimento de entidades químicas baseado em aprendizagem automática, que obteve resultados superiores aos métodos baseados em dicionários utilizados actualmente. Desenvolveu-se ainda um método baseado em semelhança lexical que realiza o mapeamento de entidades para a ontologia ChEBI. Para melhorar os resultados de identificação de entidades químicas desenvolveu-se um método de validação que explora as relações semânticas do ChEBI para medir a semelhança entre as entidades encontradas no texto, de forma a discriminar as entidades correctamente identificadas dos erros de identificação. Um método de filtragem de erros baseado em aprendizagem automática é também proposto, e foi testado num sistema baseado em regras. Estes métodos foram integrados num sistema capaz de reconhecer as entidades químicas em texto, mapear para o ChEBI, e fornecer evidência para validação ou detecção de erros das entidades reconhecidas.Fundação para a Ciência e a Tecnologia (FCT, SFRH/BD/36015/2007