Molecular descriptors from SMILES — SmilesMolecularWeight • rmorie

SmilesMolecularWeight: average molecular weight with implicit hydrogens. SmilesHba, SmilesHbd: Lipinski N+O acceptors and NH+OH donors. SmilesRotatableBonds: Veber rotatable bonds (amide C-N excluded). SmilesTpsa: Ertl topological polar surface area. LipinskiDescriptors: all of them. SMILES are read by the Avalon parser. Identical to the Python arm morie.fn.moldesc.

Usage

SmilesMolecularWeight(smiles)

SmilesHba(smiles)

SmilesHbd(smiles)

SmilesRotatableBonds(smiles, exclude_amide = TRUE)

SmilesTpsa(smiles)

LipinskiDescriptors(smiles)

Arguments

smiles: SMILES string.
exclude_amide: Exclude amide C-N bonds.

Value

Number or list.

References

Ertl, P., Rohde, B. and Selzer, P. (2000). Fast calculation of molecular polar surface area as a sum of fragment-based contributions. Journal of Medicinal Chemistry 43, 3714-3717.

Lipinski, C. A., Lombardo, F., Dominy, B. W. and Feeney, P. J. (1997). Experimental and computational approaches to estimate solubility and permeability. Advanced Drug Delivery Reviews 23, 3-25.

Veber, D. F. et al. (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry 45, 2615-2623.

Examples

SmilesMolecularWeight("CC(=O)Oc1ccccc1C(=O)O")
#> [1] 180.159
SmilesTpsa("CC(=O)Oc1ccccc1C(=O)O")$tpsa
#> [1] 63.6