Volume 5 Supplement 1

8th German Conference on Chemoinformatics: 26 CIC-Workshop

Open Access

The influence of hashed fingerprints density on the machine learning methods performance

Journal of Cheminformatics20135(Suppl 1):P25

https://doi.org/10.1186/1758-2946-5-S1-P25

Published: 22 March 2013

Computational techniques have become a vital part of today's drug discovery campaigns. Among a wide range of tools applied in this process, machine learning methods can be distinguished. They are used for instance in virtual screening (VS), where its role is to identify potentially active compounds out of large libraries of structures [1].

In order to enable the application of various learning algorithms in VS tasks, an appropriate representation of molecules is needed. One of the solutions comes from the hashed fingerprints, encoding the information about the structure in a form of a bit string [2].

Both length and density (the percentage of 1's) can be modified during hashed fingerprint generation, which (as it was already proved) influence the similarity searching process [3]. The aim of our study was to examine the impact of such fingerprint density on the performance of machine learning methods. A series of bit strings with different density values and of various lengths was generated by means of the RDKit software [4]. They were tested in classification tests of 5-HT1A ligands, with the use of a set of algorithms (Naïve Bayes, SMO, Ibk, Decorate, Hyperpipes, J48 and Random Forest), in order to determine an optimal values of the variables for machine learning experiments.

Declarations

Acknowledgements

The study was supported by a grant PRELUDIUM 2011/03/N/NZ2/02478 financed by the National Science Centre.

Authors’ Affiliations

(1)
Department of Medicinal Chemistry, Institute of Pharmacology Polish Academy of Sciences
(2)
Faculty of Chemistry, Jagiellonian University

References

  1. Geppert H, Vogt M, Bajorath J: Current Trends in Ligand-Based Virtual Screening: Molecular Representations, Data Mining Methods, New Application Areas, and Performance Evaluation. J Chem Inf Model. 2010, 50: 205-216. 10.1021/ci900419k.View ArticleGoogle Scholar
  2. Rijnbeek M, Steinbeck C: OrChem - An open source chemistry search engine for Oracle®. J Cheminf. 2009, 1: 17-10.1186/1758-2946-1-17.View ArticleGoogle Scholar
  3. Wang Y, Bajorath J: Balancing the Influence of Molecular Complexity on Fingerprint Similarity Searching. J Chem Inf Model. 2008, 48: 75-84. 10.1021/ci700314x.View ArticleGoogle Scholar
  4. RDKit: Open-source cheminformatics. [http://www.rdkit.org]

Copyright

© Smusz et al.; licensee BioMed Central Ltd. 2013

This article is published under license to BioMed Central Ltd. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.