Pharmacophore models play an essential role in drug discovery. Generating pharmacophore models which encode accurate molecular recognition features are highly dependent on properly defined annotations. Simplistic or ill-defined pharmacophore annotations which do not capture subtle electronic or geometric effects lead to many inaccuracies. SMARTS patterns which are often used to specify annotation "rules" are subject to such inaccuracies.
The application of Extended Huckel Theory (EHT) to pharmacophore annotations compensates for deficiencies observed in "rule" based methods by taking into account electron withdrawal and resonance effects and treating these effects in a consistent manner independent of structural depiction. The application of the EHT approach will be further described and discussed through a number of case studies.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made.
The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder.
To view a copy of this licence, visit https://creativecommons.org/licenses/by/4.0/.
About this article
Cite this article
Labute, P., Kossner, M., Ajamian, A. et al. Pharmacophore annotation using extended Hückel theory. J Cheminform 6 (Suppl 1), P54 (2014). https://doi.org/10.1186/1758-2946-6-S1-P54
Published:
DOI: https://doi.org/10.1186/1758-2946-6-S1-P54