Quacpac TK 2.0.0

New features

  • A new OEGetReasonableTautomers function has been added that generates an ensemble of biologically relevant tautomers.

  • A new OEGetUniqueProtomer function has been added that generates a canonical representation of a molecule.

  • A new OEGetReasonableProtomers function has been added that generates an ensemble of reasonable protomers.

  • The handling of keto-enol tautomerization by default has been improved. The improvement extends to include imine-enamine tautomerization and related analogs. The keto and imine forms are favored except in the case of 1,3 diketones, where the internal hydrogen bond can be formed.

  • Controlling the interaction between tautomerization and tetrahedral stereochemistry has been improved. The method OETautomerOptions::SetSaveStereo can still be set to true in order to prevent any stereo atom from ever becoming an sp2 center. However, the behavior when the vale is set to false can now be controlled by passing a constant from the new OERacemicType namespace to the method OETautomerOptions::SetRacemicType. This functionality allows users to control which stereochemistry will be cleared on each generated tautomer.

  • Reasonable tautomers for many simple and complex pyridone analogs, pyrrole analogs, and pyridine analogs have been improved.

  • A new OEHypervalentNormalization function has been added to prepare molecules for tautomer enumeration (OEEnumerateTautomers).

  • The user control of the algorithms memory and CPU usage by separately exposing the number of tautomers generated and the number of tautomers returned by the methods OETautomerOptions::SetMaxTautomersGenerated and OETautomerOptions::SetMaxTautomersToReturn, respectively, has been improved.

  • The default parameters of the OETautomerOptions class have been updated to reflect the underlying improved tautomer generation algorithm.

Major bug fixes

  • Several issues that caused double bonds and hydrogens to be allowed to move too far through a series of sp3 centers have been fixed.

  • The default behavior of peptide tautomers and peptide stereochemistry has been improved.

  • Keto-enol tautomerization by default has been added to improve the canonical grouping of unique molecules by their representative tautomers.

Minor bug fixes

  • Aromatic bond count has been added to scoring to improve the handling of fused pyrrole and pyrazine chemistries when estimating low-energy tautomers.

Documentation changes

  • The tautomers theory chapter has been rewritten to reflect common usages of the tautomer library.