Datasets:
## Script to sanitize and split AggregatorAdvisor dataset | |
# 1. Load modules | |
pip install rdkit | |
pip install molvs | |
import pandas as pd | |
import numpy as np | |
import urllib.request | |
import tqdm | |
import rdkit | |
from rdkit import Chem | |
import molvs | |
standardizer = molvs.Standardizer() | |
fragment_remover = molvs.fragment.FragmentRemover() | |
#3. Resolve SMILES parse error | |
# Smiles is 'None', found the compound on ChemSpider | |
# Smiles displayed 'Explicit valence for atom # 2 O, 3, is greater than permitted' | |
# https://www.chemspider.com/Chemical-Structure.17588253.html?rid=026abd00-5d7b-4c7a-b279-3ba43ab46203 | |
AA.loc[AA['smiles'] == '[O-][N+](=[O-])C1=CC=CC(=C1)C2=NC(CO2)C3=CC=CC=C3' , 'smiles'] = 'c1ccc(cc1)C2COC(=N2)c3cccc(c3)[N+](=O)[O-]' | |
# Smiles is 'None', found the compound on ChemSpider | |
# Smiles displayed 'Explicit valence for atom # 2 O, 3, is greater than permitted' | |
# https://www.chemspider.com/Chemical-Structure.17588254.html?rid=0f94ced5-dee6-4274-b0c5-796500b40be7 | |
AA.loc[AA['smiles'] == '[O-][N+](=[O-])C1=CC=CC(=C1)C2=NCCC(O2)C3=CC=CC=C3', 'smiles'] = 'c1ccc(cc1)C2CCN=C(O2)c3cccc(c3)[N+](=O)[O-]' | |
#4. Sanitize with MolVS and print problems | |
AA['X'] = [ \ | |
rdkit.Chem.MolToSmiles( | |
fragment_remover.remove( | |
standardizer.standardize( | |
rdkit.Chem.MolFromSmiles( | |
smiles)))) | |
for smiles in AA['smiles']] | |
problems = [] | |
for index, row in tqdm.tqdm(AA.iterrows()): | |
result = molvs.validate_smiles(row['X']) | |
if len(result) == 0: | |
continue | |
problems.append( (row['substance_id'], result) ) | |
# most are because it includes the salt form and/or it is not neutralized | |
for substance_id, alert in problems: | |
print(f"substance_id: {substance_id}, problem: {alert[0]}") | |
#5. Select columns and rename the dataset | |
AA.rename(columns={'X': 'new SMILES'}, inplace=True) | |
AA[['new SMILES', 'substance_id', 'aggref_index', 'logP']].to_csv('AggregatorAdvisor.csv', index=False) |