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      Consensus versus Individual QSARs in Classification: Comparison on a Large-Scale Case Study

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          Abstract

          Consensus strategies have been widely applied in many different scientific fields, based on the assumption that the fusion of several sources of information increases the outcome reliability. Despite the widespread application of consensus approaches, their advantages in quantitative structure–activity relationship (QSAR) modeling have not been thoroughly evaluated, mainly due to the lack of appropriate large-scale data sets. In this study, we evaluated the advantages and drawbacks of consensus approaches compared to single classification QSAR models. To this end, we used a data set of three properties (androgen receptor binding, agonism, and antagonism) for approximately 4000 molecules with predictions performed by more than 20 QSAR models, made available in a large-scale collaborative project. The individual QSAR models were compared with two consensus approaches, majority voting and the Bayes consensus with discrete probability distributions, in both protective and nonprotective forms. Consensus strategies proved to be more accurate and to better cover the analyzed chemical space than individual QSARs on average, thus motivating their widespread application for property prediction. Scripts and data to reproduce the results of this study are available for download.

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          Most cited references42

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          Extended-connectivity fingerprints.

          Extended-connectivity fingerprints (ECFPs) are a novel class of topological fingerprints for molecular characterization. Historically, topological fingerprints were developed for substructure and similarity searching. ECFPs were developed specifically for structure-activity modeling. ECFPs are circular fingerprints with a number of useful qualities: they can be very rapidly calculated; they are not predefined and can represent an essentially infinite number of different molecular features (including stereochemical information); their features represent the presence of particular substructures, allowing easier interpretation of analysis results; and the ECFP algorithm can be tailored to generate different types of circular fingerprints, optimized for different uses. While the use of ECFPs has been widely adopted and validated, a description of their implementation has not previously been presented in the literature.
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            PubChem 2019 update: improved access to chemical data

            Abstract PubChem (https://pubchem.ncbi.nlm.nih.gov) is a key chemical information resource for the biomedical research community. Substantial improvements were made in the past few years. New data content was added, including spectral information, scientific articles mentioning chemicals, and information for food and agricultural chemicals. PubChem released new web interfaces, such as PubChem Target View page, Sources page, Bioactivity dyad pages and Patent View page. PubChem also released a major update to PubChem Widgets and introduced a new programmatic access interface, called PUG-View. This paper describes these new developments in PubChem.
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              Why is Tanimoto index an appropriate choice for fingerprint-based similarity calculations?

              Background Cheminformaticians are equipped with a very rich toolbox when carrying out molecular similarity calculations. A large number of molecular representations exist, and there are several methods (similarity and distance metrics) to quantify the similarity of molecular representations. In this work, eight well-known similarity/distance metrics are compared on a large dataset of molecular fingerprints with sum of ranking differences (SRD) and ANOVA analysis. The effects of molecular size, selection methods and data pretreatment methods on the outcome of the comparison are also assessed. Results A supplier database (https://mcule.com/) was used as the source of compounds for the similarity calculations in this study. A large number of datasets, each consisting of one hundred compounds, were compiled, molecular fingerprints were generated and similarity values between a randomly chosen reference compound and the rest were calculated for each dataset. Similarity metrics were compared based on their ranking of the compounds within one experiment (one dataset) using sum of ranking differences (SRD), while the results of the entire set of experiments were summarized on box and whisker plots. Finally, the effects of various factors (data pretreatment, molecule size, selection method) were evaluated with analysis of variance (ANOVA). Conclusions This study complements previous efforts to examine and rank various metrics for molecular similarity calculations. Here, however, an entirely general approach was taken to neglect any a priori knowledge on the compounds involved, as well as any bias introduced by examining only one or a few specific scenarios. The Tanimoto index, Dice index, Cosine coefficient and Soergel distance were identified to be the best (and in some sense equivalent) metrics for similarity calculations, i.e. these metrics could produce the rankings closest to the composite (average) ranking of the eight metrics. The similarity metrics derived from Euclidean and Manhattan distances are not recommended on their own, although their variability and diversity from other similarity metrics might be advantageous in certain cases (e.g. for data fusion). Conclusions are also drawn regarding the effects of molecule size, selection method and data pretreatment on the ranking behavior of the studied metrics. Graphical Abstract A visual summary of the comparison of similarity metrics with sum of ranking differences (SRD). Electronic supplementary material The online version of this article (doi:10.1186/s13321-015-0069-3) contains supplementary material, which is available to authorized users.
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                Author and article information

                Journal
                J Chem Inf Model
                J Chem Inf Model
                ci
                jcisd8
                Journal of Chemical Information and Modeling
                American Chemical Society
                1549-9596
                1549-960X
                19 February 2020
                23 March 2020
                : 60
                : 3
                : 1215-1223
                Affiliations
                []Milano Chemometrics and QSAR Research Group, University of Milano Bicocca , P.za della Scienza 1, 20126 Milano, Italy
                []Department of Chemistry and Applied Biosciences, ETH Zurich , Vladimir-Prelog-Weg 4, 8049 Zurich, Switzerland
                Author notes
                Article
                10.1021/acs.jcim.9b01057
                7997107
                32073844
                f8b99a31-48da-4419-9cb6-a2f96495de4d

                Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained ( https://creativecommons.org/licenses/by/4.0/).

                History
                : 13 November 2019
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                ci9b01057
                ci9b01057

                Computational chemistry & Modeling
                Computational chemistry & Modeling

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