Reliable and accurate prediction of basic pKa values in nitrogen compounds: the pKa shift in supramolecular systems as a case study

Alcázar, Jackson; Misad, Alessandra; Campodónico,  Paola

Publication:
Reliable and accurate prediction of basic pKa values in nitrogen compounds: the pKa shift in supramolecular systems as a case study

dc.contributor.author	Alcázar, Jackson
dc.contributor.author	Misad, Alessandra
dc.contributor.author	Campodónico, Paola
dc.date.accessioned	2024-03-14T13:16:21Z
dc.date.available	2024-03-14T13:16:21Z
dc.date.issued	2023
dc.description.abstract	This article presents a quantitative structure–activity relationship (QSAR) approach for predicting the acid dissociation constant (pKa ) of nitrogenous compounds, including those within supramolecular complexes based on cucurbiturils. The model combines low-cost quantum mechanical calculations with QSAR methodology and linear regressions to achieve accurate predictions for a broad range of nitrogen-containing compounds. The model was developed using a diverse dataset of 130 nitrogenous compounds and exhibits excellent predictive performance, with a high coefficient of determination (R2 ) of 0.9905, low standard error (s) of 0.3066, and high Fisher statistic (F) of 2142. The model outperforms existing methods, such as Chemaxon software and previous studies, in terms of accuracy and its ability to handle heterogeneous datasets. External validation on pharmaceutical ingredients, dyes, and supramolecular complexes based on cucurbiturils confirms the reliability of the model. To enhance usability, a script-like tool has been developed, providing a streamlined process for users to access the model. This study represents a significantadvancement in pKa prediction, offering valuable insights for drug design and supramolecular system optimization.
dc.description.version	Publicada
dc.identifier.citation	Alcázar J, Misad Saide AC, Campodónico PR. Reliable and accurate prediction of basic pK[Formula: see text] values in nitrogen compounds: the pK[Formula: see text] shift in supramolecular systems as a case study. J Cheminform. 2023 Sep 28;15(1):90. doi: 10.1186/s13321-023-00763-3
dc.identifier.doi	https://doi.org/10.1186/s13321-023-00763-3
dc.identifier.uri	https://hdl.handle.net/11447/8534
dc.language.iso	en
dc.subject	Acidity
dc.subject	QSAR
dc.subject	Quantum descriptors
dc.subject	DFT
dc.subject	Cucurbiturils
dc.title	Reliable and accurate prediction of basic pKa values in nitrogen compounds: the pKa shift in supramolecular systems as a case study
dc.type	Article
dcterms.accessRights	Acceso Abierto
dcterms.source	Journal of cheminformatics
dspace.entity.type	Publication