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Quantitative structure–activity relationships to predict sweet and non-sweet tastes

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Abstract

The aim of this work was the calibration and validation of mathematical models based on a quantitative structure–activity relationship approach to discriminate sweet, tasteless and bitter molecules. The sweet-tasteless and the sweet-bitter datasets included 566 and 508 compounds, respectively. A total of 3763 conformation-independent Dragon molecular descriptors were calculated and subsequently reduced through both unsupervised reduction and supervised selection coupled with the k-nearest neighbors classification technique. A model based on nine descriptors was retained as the optimal one for sweet and tasteless molecules, while a model based on four descriptors was calibrated for the sweetness-bitterness dataset. Models were properly validated through cross-validation and external test sets. The applicability domain of models was investigated, and the interpretation of the role of the molecular descriptors in classifying sweet and non-sweet tastes was evaluated. The classification and the performance of the models presented in this paper are simple but accurate. They are based on a relatively small number of descriptors and a straightforward classification approach. The results presented here indicate that the proposed models can be used to accurately select new compounds as potential sweetener candidates.

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Acknowledgments

Cristian Rojas is grateful for his PhD Fellowship from the National Secretary of Higher Education, Science, Technology and Innovation (SENESCYT) from the Republic of Ecuador, as well as for the financial support provided by the Ministry of Foreign Affairs and International Cooperation (FARNESINA) from the Italian Government for the PhD research conducted at the University of Milano-Bicocca.

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Authors and Affiliations

  1. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas INIFTA (CCT La Plata-CONICET, UNLP), Diag. 113 y 64, C.C. 16, Sucursal 4, 1900, La Plata, Argentina

    Cristian Rojas

  2. Decanato General de Investigaciones, Universidad del Azuay, Av. 24 de Mayo 7-77 y Hernán Malo, Apartado Postal 01.01.981, Cuenca, Ecuador

    Cristian Rojas

  3. Milano Chemometrics and QSAR Research Group, Department of Earth and Environmental Sciences, University of Milano-Bicocca, P.za della Scienza 1, 20126, Milan, Italy

    Davide Ballabio, Viviana Consonni, Andrea Mauri & Roberto Todeschini

  4. Laboratorio de Química-Física de Alimentos, Facultad de Ciencia y Tecnología, Universidad del Azuay, Av. 24 de Mayo 7-77 y Hernán Malo, Apartado Postal 01.01.981, Cuenca, Ecuador

    Piercosimo Tripaldi

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  1. Cristian Rojas
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  2. Davide Ballabio
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  3. Viviana Consonni
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  4. Piercosimo Tripaldi
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  5. Andrea Mauri
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  6. Roberto Todeschini
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Correspondence to Cristian Rojas.

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Rojas, C., Ballabio, D., Consonni, V. et al. Quantitative structure–activity relationships to predict sweet and non-sweet tastes. Theor Chem Acc 135, 66 (2016). https://doi.org/10.1007/s00214-016-1812-1

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