Chapter 8. Tauthor: Generate Tautomers
Tauthor is a command-line tool for the enumeration of tautomers and the estimation of their
stability in the aqueous medium.
Tautomerism plays an important role in determining the chemical and biological
properties of numerous compounds.
However, chemical databases and literature data often represent a compound in an irrelevant tautomeric
form, which might lead to misleading results when you try to predict physical-chemical
properties such as ionization constants, lipophilicity, and solubility.
Tautomerism is a challenge in virtual screening.
Electrostatic interactions between a ligand and a protein are strongly influenced by hydrogen bonds
between nitrogen and oxygen atoms, and tautomerism changes the hydrogen bond donor or acceptor properties of an atom
Therefore, knowledge of the relative stabilities
of the possible tautomeric forms is extremely useful for a correct
understanding of the properties of a compound.
Tauthor allows you to easily process an SD or mol2 file and obtain a list of each tautomer calculated
to be in the aqueous medium above the specified abundance threshold. You can select which output options suits you better, by choosing
one of the commands shown below.
$ tauthor/tauthor
Too few parameters on the command-line
usage: tauthor/tauthor [options] <filename>
<filename> can be a SD (.sd or .sdf) or MOL2 (.mol2) file
options are:
-h, --help display this help
--version show version info
--input-type=<sd|mol2> input file type ( autodetect )
--load-model=<database> use a custom model database for predictions
-o, --output=FILE output file name ( SD only )
-t <abundance> percentage threshold value ( 0.0 ) |
Usage example
tauthor -o taut1.sdf myfile.sdf |
reads myfile.sdf and outputs an SD (taut1.sdf) with all possible tautomers (some unreasonable forms
might be automatically excluded)
tauthor -o taut1.sdf -t 10 myfile.sdf |
reads myfile.sdf and outputs an SD (taut1.sdf) with all tautomers that have abundance above 10% in the
aqueous medium.
