Reliable gas-phase tautomer equilibria of drug-like molecule scaffolds and the issue of continuum solvation
Accurate calculation of relative tautomer energies in different environments is a prerequisite to many parameters of relevance in drug discovery. This work provides a thorough benchmark of the semiempirical methods AM1, PM3 and GFN2-xTB, the force-field OPLS4, Hartree–Fock and HF-3c, the density fun...
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| Veröffentlicht in: | Journal of computer-aided molecular design 2022-11, Vol.36 (11), p.805-824 |
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| container_title | Journal of computer-aided molecular design |
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| creator | Göller, Andreas H. |
| description | Accurate calculation of relative tautomer energies in different environments is a prerequisite to many parameters of relevance in drug discovery. This work provides a thorough benchmark of the semiempirical methods AM1, PM3 and GFN2-xTB, the force-field OPLS4, Hartree–Fock and HF-3c, the density functionals PBEh-3c, B97-3c, r2SCAN-3c, PBE, PBE0, TPSS, r2SCAN, ω-B97X-V, M06-2X, B3LYP, B2PLYP, and second-order perturbation theory MP2 versus the gold-standard coupled-cluster DLPNO-CCSD(T) using the def2-QZVPP basis set. The outperforming method identified is M06-2X, whereas r2SCAN-3c is the best-perfoming one in the set of cost-optimized methods. Application of the two methods on a challenging subset from the SAMPL2 challenge provides evidence that deviations from experiment are caused by deficiencies of current continuum solvation methods. |
| doi_str_mv | 10.1007/s10822-022-00480-3 |
| format | Article |
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| subjects | Animal Anatomy Chemistry Chemistry and Materials Science Computer Applications in Chemistry Datasets Energy Equilibrium Histology Methods Morphology Perturbation theory Physical Chemistry Solvation Tautomers |
| title | Reliable gas-phase tautomer equilibria of drug-like molecule scaffolds and the issue of continuum solvation |
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