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2020 | OriginalPaper | Buchkapitel

BESTox: A Convolutional Neural Network Regression Model Based on Binary-Encoded SMILES for Acute Oral Toxicity Prediction of Chemical Compounds

verfasst von : Jiarui Chen, Hong-Hin Cheong, Shirley Weng In Siu

Erschienen in: Algorithms for Computational Biology

Verlag: Springer International Publishing

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Abstract

Compound toxicity prediction is a very challenging and critical task in the drug discovery and design field. Traditionally, cell or animal-based experiments are required to confirm the acute oral toxicity of chemical compounds. However, these methods are often restricted by availability of experimental facilities, long experimentation time, and high cost. In this paper, we propose a novel convolutional neural network regression model, named BESTox, to predict the acute oral toxicity (\(LD_{50}\)) of chemical compounds. This model learns the compositional and chemical properties of compounds from their two-dimensional binary matrices. Each matrix encodes the occurrences of certain atom types, number of bonded hydrogens, atom charge, valence, ring, degree, aromaticity, chirality, and hybridization along the SMILES string of a given compound. In a benchmark experiment using a dataset of 7413 observations (train/test 5931/1482), BESTox achieved a squared correlation coefficient (\(R^2\)) of 0.619, root-mean-squared error (RMSE) of 0.603, and mean absolute error (MAE) of 0.433. Despite of the use of a shallow model architecture and simple molecular descriptors, our method performs comparably against two recently published models.

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Literatur
1.
Zurück zum Zitat Bailey, J., Balls, M.: Recent efforts to elucidate the scientific validity of animal-based drug tests by the pharmaceutical industry, pro-testing lobby groups, and animal welfare organisations. BMC Med. Ethics 20, 16 (2019)CrossRef Bailey, J., Balls, M.: Recent efforts to elucidate the scientific validity of animal-based drug tests by the pharmaceutical industry, pro-testing lobby groups, and animal welfare organisations. BMC Med. Ethics 20, 16 (2019)CrossRef
3.
Zurück zum Zitat Hirohara, M., Saito, Y., Koda, Y., Sato, K., Sakakibara, Y.: Convolutional neural network based on SMILES representation of compounds for detecting chemical motif. BMC Bioinform. 19, 526 (2018)CrossRef Hirohara, M., Saito, Y., Koda, Y., Sato, K., Sakakibara, Y.: Convolutional neural network based on SMILES representation of compounds for detecting chemical motif. BMC Bioinform. 19, 526 (2018)CrossRef
4.
Zurück zum Zitat Idakwo, G., et al.: A review on machine learning methods for in silico toxicity prediction. J. Environ. Sci. Health Part C 36(4), 169–191 (2018)CrossRef Idakwo, G., et al.: A review on machine learning methods for in silico toxicity prediction. J. Environ. Sci. Health Part C 36(4), 169–191 (2018)CrossRef
5.
Zurück zum Zitat Karim, A., Mishra, A., Newton, M.H., Sattar, A.: Efficient toxicity prediction via simple features using shallow neural networks and decision trees. ACS Omega 4(1), 1874–1888 (2019)CrossRef Karim, A., Mishra, A., Newton, M.H., Sattar, A.: Efficient toxicity prediction via simple features using shallow neural networks and decision trees. ACS Omega 4(1), 1874–1888 (2019)CrossRef
7.
Zurück zum Zitat Kubinyi, H., Mannhold, R., Timmerman, H.: Virtual Screening for Bioactive Molecules, vol. 10. Wiley, Hoboken (2008) Kubinyi, H., Mannhold, R., Timmerman, H.: Virtual Screening for Bioactive Molecules, vol. 10. Wiley, Hoboken (2008)
8.
Zurück zum Zitat Landrum, G., et al.: RDkit: open-source cheminformatics (2006) Landrum, G., et al.: RDkit: open-source cheminformatics (2006)
9.
Zurück zum Zitat Llanos, E.J., Leal, W., Luu, D.H., Jost, J., Stadler, P.F., Restrepo, G.: Exploration of the chemical space and its three historical regimes. Proc. Natl. Acad. Sci. 116(26), 12660–12665 (2019)CrossRef Llanos, E.J., Leal, W., Luu, D.H., Jost, J., Stadler, P.F., Restrepo, G.: Exploration of the chemical space and its three historical regimes. Proc. Natl. Acad. Sci. 116(26), 12660–12665 (2019)CrossRef
10.
Zurück zum Zitat Mayr, A., Klambauer, G., Unterthiner, T., Hochreiter, S.: DeepTox: toxicity prediction using deep learning. Front. Environ. Sci. 3, 80 (2016)CrossRef Mayr, A., Klambauer, G., Unterthiner, T., Hochreiter, S.: DeepTox: toxicity prediction using deep learning. Front. Environ. Sci. 3, 80 (2016)CrossRef
11.
Zurück zum Zitat McInnes, C.: Virtual screening strategies in drug discovery. Curr. Opin. Chem. Biol. 11(5), 494–502 (2007)CrossRef McInnes, C.: Virtual screening strategies in drug discovery. Curr. Opin. Chem. Biol. 11(5), 494–502 (2007)CrossRef
12.
Zurück zum Zitat Nguyen, L.A., He, H., Pham-Huy, C.: Chiral drugs: an overview. Int. J. Biomed. Sci. IJBS 2(2), 85 (2006) Nguyen, L.A., He, H., Pham-Huy, C.: Chiral drugs: an overview. Int. J. Biomed. Sci. IJBS 2(2), 85 (2006)
13.
Zurück zum Zitat O’Boyle, N.M., Banck, M., James, C.A., Morley, C., Vandermeersch, T., Hutchison, G.R.: Open Babel: an open chemical toolbox. J. Cheminform. 3(1), 33 (2011)CrossRef O’Boyle, N.M., Banck, M., James, C.A., Morley, C., Vandermeersch, T., Hutchison, G.R.: Open Babel: an open chemical toolbox. J. Cheminform. 3(1), 33 (2011)CrossRef
14.
Zurück zum Zitat Oprea, T.I., Matter, H.: Integrating virtual screening in lead discovery. Curr. Opin. Chem. Biol. 8(4), 349–358 (2004) CrossRef Oprea, T.I., Matter, H.: Integrating virtual screening in lead discovery. Curr. Opin. Chem. Biol. 8(4), 349–358 (2004) CrossRef
15.
Zurück zum Zitat Quintanilha, J.C.F., Berlofa, M.: New promising approaches to treatment of chemotherapy-induced toxicities. AvidScience Chemother. 2–52 (2017) Quintanilha, J.C.F., Berlofa, M.: New promising approaches to treatment of chemotherapy-induced toxicities. AvidScience Chemother. 2–52 (2017)
16.
Zurück zum Zitat Raies, A.B., Bajic, V.B.: In silico toxicology: computational methods for the prediction of chemical toxicity. Wiley Interdiscip. Rev. Comput. Mol. Sci. 6(2), 147–172 (2016)CrossRef Raies, A.B., Bajic, V.B.: In silico toxicology: computational methods for the prediction of chemical toxicity. Wiley Interdiscip. Rev. Comput. Mol. Sci. 6(2), 147–172 (2016)CrossRef
17.
Zurück zum Zitat Roy, K., Kar, S., Das, R.: Chapter 7–validation of QSAR models. Understanding the basics of QSAR for applications in pharmaceutical sciences and risk assessment, pp. 231–289 (2015) Roy, K., Kar, S., Das, R.: Chapter 7–validation of QSAR models. Understanding the basics of QSAR for applications in pharmaceutical sciences and risk assessment, pp. 231–289 (2015)
18.
Zurück zum Zitat Tice, R.R., Austin, C.P., Kavlock, R.J., Bucher, J.R.: Improving the human hazard characterization of chemicals: a TOX21 update. Environ. Health Perspect. 121(7), 756–765 (2013)CrossRef Tice, R.R., Austin, C.P., Kavlock, R.J., Bucher, J.R.: Improving the human hazard characterization of chemicals: a TOX21 update. Environ. Health Perspect. 121(7), 756–765 (2013)CrossRef
20.
Zurück zum Zitat Weininger, D.: SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules. J. Chem. Inf. Comput. Sci. 28(1), 31–36 (1988)CrossRef Weininger, D.: SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules. J. Chem. Inf. Comput. Sci. 28(1), 31–36 (1988)CrossRef
21.
Zurück zum Zitat Weininger, D., Weininger, A., Weininger, J.L.: SMILES. 2. Algorithm for generation of unique SMILES notation. J. Chem. Inf. Comput. Sci. 29(2), 97–101 (1989)CrossRef Weininger, D., Weininger, A., Weininger, J.L.: SMILES. 2. Algorithm for generation of unique SMILES notation. J. Chem. Inf. Comput. Sci. 29(2), 97–101 (1989)CrossRef
22.
Zurück zum Zitat Wexler, P., Gad, S.C., et al.: Encyclopedia of Toxicology. Academic Press, Cambridge (1998) Wexler, P., Gad, S.C., et al.: Encyclopedia of Toxicology. Academic Press, Cambridge (1998)
23.
Zurück zum Zitat Wu, K., Wei, G.W.: Quantitative toxicity prediction using topology based multitask deep neural networks. J. Chem. Inf. Model. 58(2), 520–531 (2018)CrossRef Wu, K., Wei, G.W.: Quantitative toxicity prediction using topology based multitask deep neural networks. J. Chem. Inf. Model. 58(2), 520–531 (2018)CrossRef
24.
Zurück zum Zitat Wu, Y., Wang, G.: Machine learning based toxicity prediction: from chemical structural description to transcriptome analysis. Int. J. Mol. Sci. 19(8), 2358 (2018)CrossRef Wu, Y., Wang, G.: Machine learning based toxicity prediction: from chemical structural description to transcriptome analysis. Int. J. Mol. Sci. 19(8), 2358 (2018)CrossRef
25.
Zurück zum Zitat Yap, C.W.: Padel-descriptor: an open source software to calculate molecular descriptors and fingerprints. J. Comput. Chem. 32(7), 1466–1474 (2011)MathSciNetCrossRef Yap, C.W.: Padel-descriptor: an open source software to calculate molecular descriptors and fingerprints. J. Comput. Chem. 32(7), 1466–1474 (2011)MathSciNetCrossRef
26.
Zurück zum Zitat Zhang, X., Zhao, J., LeCun, Y.: Character-level convolutional networks for text classification. In: Advances in Neural Information Processing Systems, pp. 649–657 (2015) Zhang, X., Zhao, J., LeCun, Y.: Character-level convolutional networks for text classification. In: Advances in Neural Information Processing Systems, pp. 649–657 (2015)
Metadaten
Titel
BESTox: A Convolutional Neural Network Regression Model Based on Binary-Encoded SMILES for Acute Oral Toxicity Prediction of Chemical Compounds
verfasst von
Jiarui Chen
Hong-Hin Cheong
Shirley Weng In Siu
Copyright-Jahr
2020
DOI
https://doi.org/10.1007/978-3-030-42266-0_12