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dimorphite_dl
Commit 5b6129b0 authored by jdurrant's avatar jdurrant
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Updates to readme and help.

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CONTRIBUTORS.md
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CONTRIBUTORS
============
Patrick Ropp
Jacob Durrant
Jacob Spiegel
Jesse Kaminsky
Patrick Ropp
Jacob Spiegel
Sara Yablonski
README.md
View file @ 5b6129b0
Protonation 1.0
===============
Dimorphite-DL 1.0
=================
What is it?
-----------
Protonation 1.0 adds hydrogen atoms to molecular representations, as
Dimorphite-DL 1.0 adds hydrogen atoms to molecular representations, as
appropriate for a user-specified pH range.
Users can provide SMILES strings from the command line or via an .smi file.
......@@ -12,31 +12,32 @@ Users can provide SMILES strings from the command line or via an .smi file.
Licensing
---------
Protonation is released under the Apache 2.0 license. See LICENCE.txt for
Protonation is released under the Apache 2.0 license. See LICENCE.txt for
details.
Usage
-----
```
usage: protonate.py [-h] [--min_ph MIN] [--max_ph MAX] [--st_dev STD]
[--smiles SMILES] [--smiles_file SMILES_FILE]
[--output_file OUTPUT_FILE] [--label_states]
usage: dimorphite-dl.py [-h] [--min_ph MIN] [--max_ph MAX]
[--pka_precision PRE] [--smiles SMI]
[--smiles_file FILE] [--output_file FILE]
[--label_states] [--test]
Protonates small molecules.
Protonates small moleucles.
optional arguments:
-h, --help show this help message and exit
--min_ph MIN Minimum pH to consider.
--max_ph MAX Maximum pH to consider.
--st_dev STD Standard devation range (number of standard devs).
--smiles SMILES SMILE string to protonate.
--smiles_file SMILES_FILE
File which contains SMILES strings to protonate.
--output_file OUTPUT_FILE
File to write protonated SMILES. (Optional)
--label_states Label protonated SMILES with target state
("DEPROTONATED", "PROTONATED", or "BOTH").
-h, --help show this help message and exit
--min_ph MIN minimum pH to consider (default: 6.4)
--max_ph MAX maximum pH to consider (default: 8.4)
--pka_precision PRE pKa precision factor (number of standard devations,
default: 1.0)
--smiles SMI SMILES string to protonate
--smiles_file FILE file that contains SMILES strings to protonate
--output_file FILE output file to write protonated SMILES (optional)
--label_states label protonated SMILES with target state (i.e.,
"DEPROTONATED", "PROTONATED", or "BOTH").
--test run unit tests (for debugging)
```
The default pH range is 6.4 to 8.4, considered biologically relevant pH.
......@@ -45,23 +46,15 @@ Examples
--------
```
python protonate.py --smiles_file sample_molecules.smi
```
```
python protonate.py --smiles "CCC(=O)O" --min_ph -3 --max_ph -2
```
```
python protonate.py --smiles "CCCN" --min_ph -3 --max_ph -2 --output_file output.smi
```
```
python protonate.py --smiles_file sample_molecules.smi --st_dev 2.0 --label_states
python dimorphite-dl.py --smiles_file sample_molecules.smi
python dimorphite-dl.py --smiles "CCC(=O)O" --min_ph -3.0 --max_ph -2.0
python dimorphite-dl.py --smiles "CCCN" --min_ph -3.0 --max_ph -2.0 --output_file output.smi
python dimorphite-dl.py --smiles_file sample_molecules.smi --pka_precision 2.0 --label_states
python dimorphite-dl.py --test
```
Authors and Contacts
--------------------
See the `CONTRIBUTORS.md` file for a full list of contributors. Please contact
Jacob Durrant (durrantj@pitt.edu) with any questions.
\ No newline at end of file
Jacob Durrant (durrantj@pitt.edu) with any questions.
protonate.py → dimorphite-dl.py
View file @ 5b6129b0
......@@ -19,10 +19,17 @@ strings.
import copy
import os
import rdkit
from rdkit import Chem
from rdkit.Chem import AllChem
import argparse
import sys
try:
import rdkit
from rdkit import Chem
from rdkit.Chem import AllChem
except:
msg = "Dimorphite-DL requires RDKit. See https://www.rdkit.org/"
print(msg)
raise Exception(msg)
def main():
"""The main definition run when you call the script from the commandline."""
......@@ -30,6 +37,12 @@ def main():
parser = get_args()
args = vars(parser.parse_args())
# If being run from the command line, print out all parameters.
if __name__ == "__main__":
print("\nPARAMETERS:\n")
for k in sorted(args.keys()):
print(k.rjust(13) + ": " + str(args[k]))
if args["test"]:
# Run tests.
test()
......@@ -44,28 +57,64 @@ def main():
for out in output:
print(out)
class MyParser(argparse.ArgumentParser):
"""Overwrite default parse so it displays help file on error. See
https://stackoverflow.com/questions/4042452/display-help-message-with-python-argparse-when-script-is-called-without-any-argu"""
def error(self, message):
"""Overwrites the default error message.
:param message: The default error message.
"""
self.print_help()
sys.stderr.write('error: %s\n\n' % message)
sys.exit(2)
def print_help(self, file=None):
"""Overwrite the default print_help function
:param file: Output file, defaults to None
"""
print("")
if file is None:
file = sys.stdout
self._print_message(self.format_help(), file)
print """
examples:
python dimorphite-dl.py --smiles_file sample_molecules.smi
python dimorphite-dl.py --smiles "CCC(=O)O" --min_ph -3.0 --max_ph -2.0
python dimorphite-dl.py --smiles "CCCN" --min_ph -3.0 --max_ph -2.0 --output_file output.smi
python dimorphite-dl.py --smiles_file sample_molecules.smi --pka_precision 2.0 --label_states
python dimorphite-dl.py --test"""
print("")
def get_args():
"""Gets the arguments from the command line.
:return: A parser object.
"""
parser = argparse.ArgumentParser(description="Protonates small moleucles.")
parser = MyParser(description="Creates models of appropriately protonated " +
"small moleucles. Apache 2.0 License. " +
"Copyright 2018 Jacob D. Durrant")
parser.add_argument('--min_ph', metavar='MIN', type=float, default=6.4,
help='minimum pH to consider')
help='minimum pH to consider (default: 6.4)')
parser.add_argument('--max_ph', metavar='MAX', type=float, default=8.4,
help='maximum pH to consider')
help='maximum pH to consider (default: 8.4)')
parser.add_argument('--pka_precision', metavar='PRE', type=float, default=1.0,
help='pKa precision factor (number of standard devations)')
parser.add_argument('--smiles', type=str,
help='pKa precision factor (number of standard devations, default: 1.0)')
parser.add_argument('--smiles', metavar='SMI', type=str,
help='SMILES string to protonate')
parser.add_argument('--smiles_file', type=str,
parser.add_argument('--smiles_file', metavar="FILE", type=str,
help='file that contains SMILES strings to protonate')
parser.add_argument('--output_file', type=str,
parser.add_argument('--output_file', metavar="FILE", type=str,
help='output file to write protonated SMILES (optional)')
parser.add_argument('--label_states', action="store_true",
help='label protonated SMILES with target state ' + \
'("DEPROTONATED", "PROTONATED", or "BOTH").')
'(i.e., "DEPROTONATED", "PROTONATED", or "BOTH").')
parser.add_argument('--test', action="store_true",
help='run unit tests (for debugging)')
......@@ -167,7 +216,9 @@ def clean_args(args):
elif "smiles_file" in args:
args["smiles"], args["data"] = load_files(args["smiles_file"])
else:
raise Exception("Error: No SMILES in params.")
msg = "Error: No SMILES in params. Use the -h parameter for help."
print(msg)
raise Exception(msg)
mol_str_list = []
for i, smiles_str in enumerate(args["smiles"]):
......@@ -358,7 +409,9 @@ def define_protonation_state(mean, std, min_ph, max_ph):
# We are error handling here
if protonation_state == 'ERROR':
raise Exception("HORRIBLE NONSENSE HAS OCCURED.")
msg = "HORRIBLE NONSENSE HAS OCCURED."
print(msg)
raise Exception(msg)
return protonation_state
......@@ -745,20 +798,23 @@ def _test_check(args, expected_output, labels):
num_states = len(expected_output)
if (len(output) != num_states):
raise Exception(
args["smiles"][0] + " should have " + str(num_states) + " states at at pH " + str(args["min_ph"]) + ": " + \
str(output)
)
msg = args["smiles"][0] + " should have " + str(num_states) + \
" states at at pH " + str(args["min_ph"]) + ": " + str(output)
print(msg)
raise Exception(msg)
if (len(set([l[0] for l in output]) - set(expected_output)) != 0):
raise Exception(
args["smiles"][0] + " is not " + " AND ".join(expected_output) + " at pH " + str(args["min_ph"]) + " - " + str(args["max_ph"]) + "; it is " + " AND ".join([l[0] for l in output])
)
msg = args["smiles"][0] + " is not " + " AND ".join(expected_output) + \
" at pH " + str(args["min_ph"]) + " - " + str(args["max_ph"]) + \
"; it is " + " AND ".join([l[0] for l in output])
print(msg)
raise Exception(msg)
if (len(set([l[1] for l in output]) - set(labels)) != 0):
raise Exception(
args["smiles"][0] + " not labeled as " + " AND ".join(labels) + "; it is " + " AND ".join([l[1] for l in output])
)
msg = args["smiles"][0] + " not labeled as " + " AND ".join(labels) + \
"; it is " + " AND ".join([l[1] for l in output])
print(msg)
raise Exception(msg)
ph_range = sorted(list(set([args["min_ph"], args["max_ph"]])))
ph_range_str = "(" + " - ".join("{0:.2f}".format(n) for n in ph_range) + ")"
......
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