Obtain transformation products (TPs) from a library with formula data

Automatically obtains transformation products from a library with formula data.

generateTPsLibraryFormula(
  parents = NULL,
  TPLibrary,
  generations = 1,
  skipInvalid = TRUE,
  prefCalcChemProps = TRUE,
  neutralChemProps = FALSE,
  matchParentsBy = "name",
  matchGenerationsBy = "name"
)

Arguments

parents: The parents for which transformation products should be obtained. This should be either a suspect list (see suspect screening for more information) or the resulting output of screenSuspects. The suspect (hits) are used as parents. If NULL then TPs for all parents in the library are obtained.
TPLibrary: A data.frame. See the details below.
generations: An integer that specifies the number of transformation generations. TPs for subsequent iterations obtained by repeating the library search where the TPs from the previous generation are considered parents.
skipInvalid: If set to TRUE then the parents will be skipped (with a warning) for which insufficient information (e.g. SMILES) is available.
prefCalcChemProps: If TRUE then calculated chemical properties such as the formula and InChIKey are preferred over what is already present in the parent suspect list. For efficiency reasons it is recommended to set this to TRUE. See the Validating and calculating chemical properties section for more details.
neutralChemProps: If TRUE then the neutral form of the molecule is considered to calculate SMILES, formulae etc. Enabling this may improve feature matching when considering common adducts (e.g. [M+H]+, [M-H]-). See the Validating and calculating chemical properties section for more details.
matchParentsBy: A character that specifies how the input parents are matched with the data from the TP library. Valid options are: "InChIKey", "InChIKey1", "InChI", "SMILES", "formula", "name". If the parent from the TP library is matched with multiple input parents then only the first is considered.
matchGenerationsBy: Similar to matchParentsBy, but specifies how parents/TPs are matched when generations>1.

Value

The TPs are stored in an object derived from the transformationProductsFormula class.

Details

This function uses a library to obtain transformation products. This function is called when calling generateTPs with algorithm="library_formula".

This function is similar to generateTPsLibrary, however, it only require formula information of the parent and TPs.

Note

Unlike generateTPsLibrary, this function defaults the matchParentsBy and matchGenerationsBy arguments to "name". While matching by formula is also possible, it is likely that duplicate parent formulae (i.e. isomers) are present in parents and/or TPLibrary, making matching by formula unsuitable. However, if you are sure that no duplicate formulae are present, it may be better to set the matching method to "formula".

TP libraries

The TPLibrary argument is used to specify a custom TP library. This should be a data.frame where each row specifies a TP for a parent, with the following columns:

parent_name and TP_name: The name of the parent/TP.
parent_formula and TP_formula The formula of the parent/TP structure.
retDir The retention direction of the TP compared to its parent: -1 (elutes before), 1 (elutes after) or 0 (elutes similarly or unknown). If not specified then the log P values below may be used to calculate retention time directions. (optional)
parent_LogP and TP_LogP The log P values for the parent/TP. (optional)
LogPDiff The difference between parent and TP Log P values. Ignored if both parent_LogP and TP_LogP are specified. (optional)

Other columns are allowed, and will be included in the final object. Multiple TPs for a single parent are specified by repeating the value within parent_ columns.

Validating and calculating chemical properties

Chemical properties such as SMILES, InChIKey and formula in the parent suspect list are automatically validated and calculated if missing/invalid.

The internal validation/calculation process performs the following steps:

Validation of SMILES, InChI, InChIKey and formula data (if present). Invalid entries will be set to NA.
If neutralChemProps=TRUE then chemical data (SMILES, formulae etc.) is neutralized by (de-)protonation (using the --neutralized option of OpenBabel). An additional column molNeutralized is added to mark those molecules that were neutralized. Note that neutralization requires either SMILES or InChI data to be available.
The SMILES and InChI data are used to calculate missing or invalid SMILES, InChI, InChIKey and formula data. If prefCalcChemProps=TRUE then existing InChIKey and formula data is overwritten by calculated values whenever possible.
The chemical formulae which were not calculated are verified and normalized. This process may be time consuming, and is potentially largely avoided by setting prefCalcChemProps=TRUE.
Neutral masses are calculated for missing values (prefCalcChemProps=FALSE) or whenever possible (prefCalcChemProps=TRUE).

Note that calculation of formulae for molecules that are isotopically labelled is currently only supported for deuterium (2H) elements.

This functionality relies heavily on OpenBabel, please make sure it is installed.

References

OBoyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR (2011). “Open Babel: An open chemical toolbox.” Journal of Cheminformatics, 3(1). doi:10.1186/1758-2946-3-33 .