The molecular structure of sorgoleone was retrieved from PubChem, 47 checking the geometry to determine the correct conformer. Structurally, sorgoleone has a polar head group and lipophilic tail similar to the lipids in bilayer. The sorgoleone tail is highly analogous to lipid acyl tails, and thus could be treated by analogy. However, the quninone head and the various electron donating and withdrawing groups mandated careful parameterization. To reduce the computational cost of parameterization, only the quinone headgroup was further optimized, with structure split at the second carbon of the tail as shown in Figure . The sorgoleone head group was mutated into dihydroxysorgoleone (Figure ), 5-Pentadecatrienyl resorcinol-3-methyl ether and 5-Pentadecatrienyl resorcinol precursor head group according to the structure given in Figure through the structure editing tools built into UCSF-Chimera. Parameters for the four quinone head groups were generated using the standard CHARMM parameterization procedures, implemented within the FFparam tool kit. Quantum mechanical (QM) potential energies for multiple conformations were calculated using Gaussian 16 C.01, which was considered a target for the fitting of MM parameters. Consistent with typical parameterization recommendations from other groups, QM geometry optimization for the head group was performed using the MP2/6-31G * basis set. Partial charge optimization was carried out using the quantum energies for water interaction at the HF/6-31G * level of theory. Optimizations of the bonding parameters were done at MP2/6-31G * level of theory. The QM scans for restrained dihedrals in the head group were restricted to 120 • with 60 • in each direction of the equilibrium angle with 10 • steps.