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MolTaut: A Tool for the Rapid Generation of Favorable Tautomer in Aqueous Solution.
Pan, Xiaolin; Zhao, Fanyu; Zhang, Yueqing; Wang, Xingyu; Xiao, Xudong; Zhang, John Z H; Ji, Changge.
Afiliación
  • Pan X; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
  • Zhao F; NYU-ECNU Center for Computational Chemistry at NYU Shanghai, Shanghai 200062, China.
  • Zhang Y; NYU-ECNU Center for Computational Chemistry at NYU Shanghai, Shanghai 200062, China.
  • Wang X; Department of Chemistry, New York University, New York 10003, United States.
  • Xiao X; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
  • Zhang JZH; NYU-ECNU Center for Computational Chemistry at NYU Shanghai, Shanghai 200062, China.
  • Ji C; NYU-ECNU Center for Computational Chemistry at NYU Shanghai, Shanghai 200062, China.
J Chem Inf Model ; 63(7): 1833-1840, 2023 04 10.
Article en En | MEDLINE | ID: mdl-36939644
Fast and proper treatment of the tautomeric states for drug-like molecules is critical in computer-aided drug discovery since the major tautomer of a molecule determines its pharmacophore features and physical properties. We present MolTaut, a tool for the rapid generation of favorable states of drug-like molecules in water. MolTaut works by enumerating possible tautomeric states with tautomeric transformation rules, ranking tautomers with their relative internal energies and solvation energies calculated by AI-based models, and generating preferred ionization states according to predicted microscopic pKa. Our test shows that the ranking ability of the AI-based tautomer scoring approach is comparable to the DFT method (wB97X/6-31G*//M062X/6-31G*/SMD) from which the AI models try to learn. We find that the substitution effect on tautomeric equilibrium is well predicted by MolTaut, which is helpful in computer-aided ligand design. The source code of MolTaut is freely available to researchers and can be accessed at https://github.com/xundrug/moltaut. To facilitate the usage of MolTaut by medicinal chemists, we made a free web server, which is available at http://moltaut.xundrug.cn. MolTaut is a handy tool for investigating the tautomerization issue in drug discovery.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Agua Tipo de estudio: Prognostic_studies Idioma: En Revista: J Chem Inf Model Asunto de la revista: INFORMATICA MEDICA / QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Agua Tipo de estudio: Prognostic_studies Idioma: En Revista: J Chem Inf Model Asunto de la revista: INFORMATICA MEDICA / QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos