Future extensions of the HTA algorithm will require a robust SMILES sanitization process for complex monomers. For enhancing the accuracy of the head-and-tail assignments, we suggest including an analysis of LUMO and frontier orbitals in the quantum chemical simulation process. A refinement of the implemented chemical rules and the addition of new polymerization classes should lead to further HTA performance enhancements. To overcome the data bottleneck, we encourage researchers to contribute more data to each polymer class of the initial data set. Starting from a SMILES string Hydrogen atoms were added and conformers were created with a distance-geometry-based conformation generator. Finally, the structure was optimized using the UFF force field and the canonical molecular orbital HOMO was calculated using PySCF , using the STO-3G basis set at SCF / RHF theory level.