Quantum mechanical polar surface area

Abstract

A correlation has been established between the absorbed fraction of training-set molecules after oral administration in humans and the Quantum Mechanical Polar Surface Area (QMPSA). This correlation holds for the QMPSA calculated with structures where carboxyl groups are deprotonated. The correlation of the absorbed fraction and the QMPSA calculated on the neutral gas phase optimized structures is much less pronounced. This suggests that the absorption process is mainly determined by polar interactions of the drug molecules in water solution. Rules are given to derive the optimal polar/apolar ranges of the electrostatic potential.

3,4‐Dithiaphosphole and 3,3′,4,4′‐Tetrathia‐1,1′‐Biphosphole π‐Conjugated Systems: S Makes the Impact

“…The solvent effect of THF was modeled with the PCM 33. For the visualization of the structures, the Molden program34 was used.…”

Synthesis of Thiol Esters Using PhSZnBr as Sulfenylating Agent: A DFT‐Guided Optimization of Reaction Conditions

“…Frequency calculations were exploited to derive the thermodynamic data summarized in Table S2. The results of the calculations were examined with Gauss-View 5.0.9 [44] and Molden 5.2 [45] programs.…”

Leveraging chromatography based physicochemical properties for efficient drug design

“…In addition to dynamic, molecular and topological polar surface areas, quantum mechanical polar surface area (QMPSA) was recently introduced and showed a good correlation with the fraction absorbed (FA) after oral administration for a set of 18 drugs when carboxyl groups were deprotonated, suggesting adsorption to be strongly related to polar interactions of molecules in water solution [73]. It should be noted that significant increases in computing resources are needed to generate QMPSA, compared to the table-entry recalling TPSA.…”