import numpy as np
import pandas as pd
from rdkit.Chem import MolFromSmiles
from rdkit.Chem.rdmolfiles import MolToPDBFile
from sklearn.decomposition import PCA
from sklearn.manifold import MDS, TSNE, Isomap, SpectralEmbedding
from sklearn.preprocessing import StandardScaler
from AIMSim.chemical_datastructures import Molecule, MoleculeSet
from AIMSim.ops import Descriptor, SimilarityMeasure
from AIMSim.exceptions import NotInitializedError, InvalidConfigurationError
SUPPORTED_SIMILARITIES = SimilarityMeasure.get_supported_metrics()
SUPPORTED_FPRINTS = Descriptor.get_supported_fprints()
class TestMoleculeSet(unittest.TestCase):
test_smarts = [
"[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([B:7]([OH:8])[OH:9])[cH:10][cH:11]1",
"[NH:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1.[O:7]=[S:8]=[O:9]",
]
test_smiles = [
"CCCCCCC",
"CCCC",
"CCC",
"CO",
"CN",
"C1=CC=CC=C1",
def __call__(
self,
molecule_set_configs,
fingerprint_type=None,
fingerprint_params=None,
similarity_measure=None,
subsample_subset_size=0.01,
optim_algo='max_min',
show_top=0,
only_metric=True,
):
"""
Calculate the correlation in the properties of molecules in set
and their nearest and furthest neighbors using different
fingerprints / similarity measure choices. Choose the best fingerprint
and similarity measure pair (called measure choice for brevity)
based on an optimization strategy.
Args:
molecule_set_configs (dict): All configurations (except
fingerprint_type, fingerprint_params and similarity_measure)
needed to form the moleculeSet.
fingerprint_type (str): Label to indicate which fingerprint to
use. If supplied, fingerprint is fixed and optimization
carried out over similarity measures. Use None to indicate
that optimization needs to be carried out over fingerprints.
Default is None.
fingerprint_params (dict): Hyper-parameters for fingerprints.
Passed to the MoleculeSet constructor. If None is passed,
set to empty dictionary before passing to MoleculeSet.
similarity_measure (str): Label to indicate which similarity
measure to use. If supplied, similarity measure is fixed
and optimization carried out over similarity measures.
Use None to indicate that optimization needs to be carried
out over fingerprints. Default is None.
subsample_subset_size (float): Fraction of molecule_set to
subsample. This is separate from the sample_ratio parameter
used when creating a moleculeSet since it is recommended
to have an more aggressive subsampling strategy for this task
due to the combinatorial explosion of looking at multiple
fingerprints and similarity measures. Default is 0.01.
optim_algo (str): Label to indicate the optimization algorithm
chosen. Options are:
'max': The measure choice which maximizes correlation
of properties between nearest neighbors (most similar).
This is the default.
'min': The measure choice which minimizes the absolute value
of property correlation
between furthest neighbors (most dissimilar).
'max_min': The measure choice which maximizes correlation
of properties between nearest neighbors (most similar)
and minimizes he absolute value of property correlation
between furthest neighbors (most dissimilar).
This is the default.
show_top (int): Number of top performing measures to show in plot.
If 0, no plots are generated and the top performer is returned.
only_metric (bool): If True only similarity measures satisfying
the metricity property
(i.e. can be converted to distance metrics) are selected.
Returns:
(NamedTuple): Top performer with fields:
fingerprint_type (str): Label for fingerprint type
similarity_measure (str): Label for similarity measure
nearest_neighbor_correlation (float): Correlation of property
of molecule and its nearest neighbor.
furthest_neighbor_correlation (float): Correlation of property
of molecule and its furthest neighbor.
score_ (float): Overall score based on optimization strategy.
More is better.
"""
print(f'Using subsample size {subsample_subset_size} for '
f'measure search')
trial_ = namedtuple('trial_', [
'fingerprint_type', 'similarity_measure',
'nearest_neighbor_correlation', 'furthest_neighbor_correlation',
'score_'
])
if fingerprint_type is None:
all_fingerprint_types = Descriptor.get_supported_fprints()
fingerprint_params = None
else:
all_fingerprint_types = [fingerprint_type]
if similarity_measure is None:
if only_metric:
print('Only trying measures with valid distance metrics')
all_similarity_measures = SimilarityMeasure.get_uniq_metrics()
else:
all_similarity_measures = [similarity_measure]
is_verbose = molecule_set_configs.get("is_verbose", False)
all_scores = []
if fingerprint_params is None:
fingerprint_params = {}
for similarity_measure in all_similarity_measures:
if only_metric and not SimilarityMeasure(
metric=similarity_measure).is_distance_metric():
continue
if is_verbose:
print(f'Trying {similarity_measure} similarity')
for fingerprint_type in all_fingerprint_types:
if is_verbose:
print(f'Trying {fingerprint_type} fingerprint')
try:
molecule_set = MoleculeSet(
molecule_database_src=molecule_set_configs[
'molecule_database_src'],
molecule_database_src_type=molecule_set_configs[
'molecule_database_src_type'],
similarity_measure=similarity_measure,
fingerprint_type=fingerprint_type,
fingerprint_params=fingerprint_params,
is_verbose=is_verbose,
n_threads=molecule_set_configs.get('n_threads', 1),
sampling_ratio=subsample_subset_size)
except (InvalidConfigurationError, ValueError) as e:
if is_verbose:
print(
f'Could not try {fingerprint_type} with '
f'similarity measure {similarity_measure} due to '
f'{e}')
continue
nearest_corr, nearest_p_val = self.prop_var_w_similarity. \
get_property_correlations_in_most_similar(
molecule_set)
furthest_corr, furthest_p_val = self.prop_var_w_similarity. \
get_property_correlations_in_most_dissimilar(
molecule_set)
if optim_algo == 'max_min':
score_ = nearest_corr - abs(furthest_corr)
elif optim_algo == 'max':
score_ = nearest_corr
elif optim_algo == 'min':
score_ = -abs(furthest_corr)
else:
raise InvalidConfigurationError(f'{optim_algo} '
f'not implemented')
all_scores.append(
trial_(fingerprint_type=fingerprint_type,
similarity_measure=similarity_measure,
nearest_neighbor_correlation=nearest_corr,
furthest_neighbor_correlation=furthest_corr,
score_=score_))
all_scores.sort(key=lambda x: x[-1], reverse=True)
if self.log_fpath is not None:
print('Writing to ', self.log_fpath)
log_data = [trial._asdict() for trial in all_scores]
with open(self.log_fpath, "w") as fp:
json.dump(log_data, fp)
if show_top > 0:
top_performers = all_scores[:show_top]
all_nearest_neighbor_correlations = []
all_furthest_neighbor_correlations = []
top_scores = []
all_measures = []
for trial in top_performers:
all_nearest_neighbor_correlations.append(
trial.nearest_neighbor_correlation)
all_furthest_neighbor_correlations.append(
trial.furthest_neighbor_correlation)
top_scores.append(trial.score_)
all_measures.append(
Descriptor.shorten_label(trial.fingerprint_type) + '\n' +
trial.similarity_measure)
bar_heights = np.array([
top_scores, all_nearest_neighbor_correlations,
all_furthest_neighbor_correlations
])
colors = self.plot_settings.pop('colors')
plot_multiple_barchart(x=[_ for _ in range(len(top_performers))],
heights=bar_heights,
legend_labels=[
'Overall scores',
'Nearest neighbor property '
'correlation',
'Furthest neighbor property '
'correlations'
],
colors=colors,
xtick_labels=all_measures,
ylabel='Value',
xlabel='Measure',
**self.plot_settings)
return all_scores[0]