Experimentally, the free energies of binding are typically determined from phase-solubility studies or from isothermal caliometric titration. The ability to form host-guest inclusion complexes brings a wealth of applications in areas such as health technology where CDs are either drugs, carriers of drug-like molecules or part of a drug formulation. Native CDs themselves are, however, poorly soluble which makes them less than ideal to bring other molecules into solution. CDs have also been found to be toxic to some extent when used in certain drug formulations. To overcome the limitations of the native CDs, derivative or functionalized CDs have long been an active area of research where the hydroxy groups on glycopyranose (Figure ) are substituted with various side chains to alter the chemical properties. Prominent examples of such functionalized CDs specifically designed to increase solubility of both CDs and drug-like molecules are methylated cyclodextrin, 8 sulfobutylether cyclodextrin (SBE-CD) and 2-hydroxypropyl cyclodextrin (HP-CD). Only SBE-β-CD and HP-β-CD are commercially available and both already play a significant role in drug formulation. HP-β-CD, has furthermore been used in clinical trials to treat Niemann Pick Type C disease, suggested as a way to treat cholesterol accumulation and as part of a general formulation of lipofilic drugs. Theoretical studies of native CD inclusion complexes used to support experimental findings by means of classical molecular dynamics (MD) simulations are commonly used. CDs are typically treated with general carbohydrate force fields such as GLYCAM06, GROMOS 22 or CHARMM or modified carbohydrate force fields with additions or changes to address any shortcomings like Q4MD-CD 24 based on GLYCAM04. The performance of different force fields in combination with computational methods for both structural properties and free energies of binding for especially β-CD with various ligands have been reported. Theoretical studies of HP-CDs are inherently more difficult to carry out due to the fact that there are 8 7 -1 = 2, 097, 151 isomers of HP-β-CD to consider. To support experimental findings in the context of substituted cyclodextrins, simulations involving one or a few substituted side chains (Figure ) are typically carried out. There have been attempts to generalize force fields to overcome these short comings. For example, Wang et al. applied the general amber force field 36 (GAFF) to both CD and HP-CD with recent efforts to expand this approach by Arsiccio et al. who created HP-CD parameters for the ADD force field. In this work, we derive general GLYCAM06 compatible parameters of the 2-hydroxypropyl side chains for glucopyranose to treat all possible isomers of HP-CD. We do this by considering substitutions on the 2nd (R 1 ), 3rd (R 2 ) and 6th (R 3 ) hydroxy group (Figure ) which in total gives 8 unique permutations of the glucopyranose unit: 7 different single, double and triple substitutions and a single non-substituted glucopyranose. In Table we show which substitutions are included along with a three-letter residue name that is compatible with GLYCAM06. The 4GA residue name from GLYCAM06, for example, is non-substituted (α-1,4)-linked D-glucopyranose. We have extended these residue names to accommodate single substituted (4GX, 4GY and 4GZ), double substituted (4GR, 4GS and 4GT) and fully substituted (4GW) glucopyranose.