def plot_tsne(func):
n_mols = 250
mols = get_chembl(max_size=n_mols, as_mols=True)
smile_strings = [m.smiles for m in mols]
title = f"{func} ot-dist"
distance_computer = OTChemDistanceComputer(
mass_assignment_method='molecular_mass',
normalisation_method='total_mass',
struct_pen_method='bond_frac')
distances_mat = distance_computer(smile_strings, smile_strings)[0]
# title = f"{func} similarity kernel"
# kernel = mol_kern_factory('similarity_kernel')
# kern_mat = kernel(mols, mols)
# distances_mat = 1/kern_mat
# title = f"{func} fingerprint dist"
# distances_mat = np.zeros((len(smile_strings), len(smile_strings)))
# for i in tqdm(range(len(smile_strings))):
# for j in range(len(smile_strings)):
# distances_mat[i, j] = np.sum((mols[i].to_fingerprint(ftype='numeric') -
# mols[j].to_fingerprint(ftype='numeric')) ** 2 )
tsne = TSNE(metric='precomputed')
points_to_plot = tsne.fit_transform(distances_mat)
mols = get_chembl(max_size=n_mols)
smile_strings = [mol.to_smiles() for mol in mols]
func_ = get_objective_by_name(func)
prop_list = [func_(mol) for mol in mols]
plt.title(title, fontsize=22)
plt.scatter(points_to_plot[:, 0],
points_to_plot[:, 1],
c=prop_list,
cmap=plt.cm.Spectral,
s=15,
alpha=0.8)
plt.xticks([])
plt.yticks([])
# extent = ax.get_window_extent().transformed(fig.dpi_scale_trans.inverted())
plt.savefig(os.path.join(VIS_DIR,
title.replace(" ", "_") + '.eps'),
format='eps',
dpi=1000) # bbox_inches=extent, pad_inches=0
def compute_sa_score_datasets():
sas = get_objective_by_name("sascore")
chembl = get_chembl(max_size=50)
res = [sas(m) for m in chembl]
print("ChEMBL: {:.3f} +- std {:.3f}".format(np.mean(res), np.std(res)))
zinc = get_zinc250(max_size=50)
res = [sas(m) for m in zinc]
print("ZINC: {:.3f} +- std {:.3f}".format(np.mean(res), np.std(res)))
def compute_novel_percentage(mol_list):
chembl = get_chembl(max_size=-1) # smiles list
chembl = [m.smiles for m in chembl]
zinc = get_zinc250(max_size=-1) # smiles list
zinc = [m.smiles for m in zinc]
# n_total = len(chembl) + len(zinc)
n_mols = len(mol_list)
n_in_data = 0.
for mol in tqdm(mol_list):
if (mol in chembl) or (mol in zinc):
n_in_data += 1
return 1 - n_in_data / n_mols
def make_pairwise(func, n_mols, to_randomize=True):
if func == 'prop':
smile_strings, smiles_to_prop = get_chembl_prop(n_mols=n_mols)
prop_list = [smiles_to_prop[sm] for sm in smile_strings]
else:
n_mols_to_get = 5 * n_mols if to_randomize else n_mols
mols = get_chembl(n_mols=n_mols_to_get)
np.random.shuffle(mols)
mols = mols[:n_mols]
smile_strings = [mol.to_smiles() for mol in mols]
func_ = get_objective_by_name(func)
prop_list = [func_(mol) for mol in mols]
dist_computer = OTChemDistanceComputer() # <-- default computer
dists = dist_computer(smile_strings, smile_strings)
num_rows = max(2, int(np.ceil(dist_computer.get_num_distances() / 4.0)))
print(num_rows)
f, ll_ax = plt.subplots(num_rows, 4, figsize=(15, 15))
axes = itertools.chain.from_iterable(ll_ax)
for ind, (ax, distmat) in enumerate(zip(axes, dists)):
xs, ys = [], []
pairs = []
for i in range(n_mols):
for j in range(i, n_mols):
dist_in_dist = distmat[i, j]
dist_in_val = np.abs(prop_list[i] - prop_list[j])
xs.append(dist_in_dist)
ys.append(dist_in_val)
pairs.append((i,j))
# pairs.append('(%d,%d)'%(i,j))
ax.set_title(f'Distance {ind}') # TODO: parameters of distance
if n_mols > 12:
ax.scatter(xs, ys, s=1, alpha=0.6)
else:
for xval, yval, pval in zip(xs, ys, pairs):
print(xval, yval, pval)
if pval[0] == pval[1]:
# ax.scatter([xval], [yval], s=1, alpha=0.8)
ax.text(xval, yval, '*', fontsize=14)
else:
ax.text(xval, yval, '(%d, %d)'%(pval[0], pval[1]))
ax.set_xlim((0.0, max(xs) * 1.25))
# ax.set_xticks([])
# ax.set_yticks([])
plt.savefig(os.path.join(VIS_DIR, "dist_vs_value_%d_%s_%s"%(n_mols, func,
datetime.now().strftime('%m%d%H%M%S'))))
print(smile_strings, len(smile_strings))
def test(N=100):
dist_computer = OTChemDistanceComputer()
mols = get_chembl(max_size=N, as_mols=True)
natoms = [mol.to_rdkit().GetNumAtoms() for mol in mols]
times = defaultdict(list)
for i in range(N):
for j in range(i):
t0 = time()
dist_computer([mols[i].to_smiles()], [mols[j].to_smiles()])
time_elapsed = time() - t0
times[natoms[i] + natoms[j]].append(time_elapsed)
for k, res_lst in times.items():
times[k] = np.mean(res_lst)
return times
def make_pairwise_kernel(kernel_name, func, **kwargs):
n_mols = 100
mols = get_chembl(max_size=n_mols)
# smile_strings = [mol.to_smiles() for mol in mols]
func_ = get_objective_by_name(func)
kernel = mol_kern_factory(kernel_name, **kwargs)
kern_mat = kernel(mols, mols)
prop_list = [func_(mol) for mol in mols]
xs, ys = [], []
for i in range(n_mols):
for j in range(n_mols):
if mode == "inverse_sim":
dist_in_dist = 1 / kern_mat[i, j]
elif mode == "scaled_kernel":
dist_in_dist = 1 / kern_mat[i, j]
dist_in_dist /= np.sqrt(kern_mat[i, i] * kern_mat[j, j])
elif mode == "fps_distance":
dist_in_dist = np.sum(
(mols[i].to_fingerprint(ftype='numeric') -
mols[j].to_fingerprint(ftype='numeric'))**2)
else:
raise ValueError
dist_in_val = np.abs(prop_list[i] - prop_list[j])
xs.append(dist_in_dist)
ys.append(dist_in_val)
fig = plt.figure() # figsize=fsize
ax = fig.add_subplot(1, 1, 1)
plt.scatter(xs, ys, s=2, alpha=0.6)
# plt.yscale('log')
plt.xscale('log')
plt.xlim([11, 80])
plt.xticks([])
plt.yticks([])
# extent = ax.get_window_extent().transformed(fig.dpi_scale_trans.inverted())
plt.savefig(os.path.join(VIS_DIR, f"{kernel_name}_{func}.eps"),
format='eps',
dpi=1000) # bbox_inches=extent, pad_inches=0
plt.clf()
def gen_gp_test_data():
""" Xs are molecules, Ys are some numeric value """
n_all = 100
mols = get_chembl(n_all * 3)
ys = np.array([func(m) for m in mols])
mols1, mols2, mols3 = mols[:n_all], mols[n_all:2 *
n_all], mols[2 * n_all:3 * n_all]
ys1, ys2, ys3 = ys[:n_all], ys[n_all:2 * n_all], ys[2 * n_all:3 * n_all]
n_train = int(n_all * 0.8)
ys = np.array([SAScore(m) for m in mols])
X1_tr, X1_te = mols1[:n_train], mols1[n_train:]
Y1_tr, Y1_te = ys1[:n_train], ys1[n_train:]
X2_tr, X2_te = mols2[:n_train], mols2[n_train:]
Y2_tr, Y2_te = ys2[:n_train], ys2[n_train:]
X3_tr, X3_te = mols3[:n_train], mols3[n_train:]
Y3_tr, Y3_te = ys3[:n_train], ys3[n_train:]
return [(X1_tr, Y1_tr, X1_te, Y1_te), (X2_tr, Y2_tr, X2_te, Y2_te),
(X3_tr, Y3_tr, X3_te, Y3_te)]
def make_tsne(func, as_subplots=False):
"""
Plot TSNE embeddings colored with property
for several distance computers.
"""
n_mols = 200
dist_computers = [
OTChemDistanceComputer(mass_assignment_method='equal',
normalisation_method='none',
struct_pen_method='bond_frac'),
OTChemDistanceComputer(mass_assignment_method='equal',
normalisation_method='total_mass',
struct_pen_method='bond_frac'),
OTChemDistanceComputer(mass_assignment_method='molecular_mass',
normalisation_method='none',
struct_pen_method='bond_frac'),
OTChemDistanceComputer(mass_assignment_method='molecular_mass',
normalisation_method='total_mass',
struct_pen_method='bond_frac')
]
titles = [
'Equal mass assign, no norm', 'Equal mass assign, total mass norm',
'Mol mass assign, no norm', 'Mol mass assign, total mass norm'
]
smile_strings, smiles_to_prop = get_chembl_prop(n_mols=n_mols)
if func == 'prop':
smile_strings, smiles_to_prop = get_chembl_prop(n_mols=n_mols)
prop_list = [smiles_to_prop[sm] for sm in smile_strings]
else:
mols = get_chembl(max_size=n_mols)
smile_strings = [mol.to_smiles() for mol in mols]
func_ = get_objective_by_name(func)
prop_list = [func_(mol) for mol in mols]
f, ll_ax = plt.subplots(2, 2, figsize=(15, 15))
axes = itertools.chain.from_iterable(ll_ax)
for ind, (ax, dist_computer,
title) in enumerate(zip(axes, dist_computers, titles)):
distances_mat = dist_computer(smile_strings, smile_strings)[0]
# plot them
tsne = TSNE(metric='precomputed')
points_to_plot = tsne.fit_transform(distances_mat)
if as_subplots:
ax.set_title(title)
ax.scatter(points_to_plot[:, 0],
points_to_plot[:, 1],
c=prop_list,
cmap=plt.cm.Spectral,
s=9,
alpha=0.8)
ax.set_xticks([])
ax.set_yticks([])
else:
# save separately:
plt.clf()
fig = plt.figure() # figsize=fsize
ax = fig.add_subplot(1, 1, 1)
plt.title(title)
plt.scatter(points_to_plot[:, 0],
points_to_plot[:, 1],
c=prop_list,
cmap=plt.cm.Spectral,
s=9,
alpha=0.8)
plt.xticks([])
plt.yticks([])
# extent = ax.get_window_extent().transformed(fig.dpi_scale_trans.inverted())
plt.savefig(os.path.join(VIS_DIR,
f'tsne_vis_{func}_{dist_computer}.eps'),
format='eps',
dpi=1000) # bbox_inches=extent, pad_inches=0
plt.clf()
if as_subplots:
plt.savefig(os.path.join(VIS_DIR, f'tsne_vis_{func}.eps'),
format='eps',
dpi=1000)
plt.clf()
def make_pairwise(func, as_subplots=False):
n_mols = 100
if func == 'prop':
smile_strings, smiles_to_prop = get_chembl_prop(n_mols=n_mols)
prop_list = [smiles_to_prop[sm] for sm in smile_strings]
else:
mols = get_chembl(max_size=n_mols)
smile_strings = [mol.to_smiles() for mol in mols]
func_ = get_objective_by_name(func)
prop_list = [func_(mol) for mol in mols]
dist_computers = [
OTChemDistanceComputer(mass_assignment_method='equal',
normalisation_method='none',
struct_pen_method='bond_frac'),
OTChemDistanceComputer(mass_assignment_method='equal',
normalisation_method='total_mass',
struct_pen_method='bond_frac'),
OTChemDistanceComputer(mass_assignment_method='molecular_mass',
normalisation_method='none',
struct_pen_method='bond_frac'),
OTChemDistanceComputer(mass_assignment_method='molecular_mass',
normalisation_method='total_mass',
struct_pen_method='bond_frac')
]
titles = [
'Unit weight, Unnormalized', 'Unit weight, Normalized',
'Molecular mass weight, Unnormalized',
'Molecular mass weight, Normalized'
]
f, ll_ax = plt.subplots(2, 2, figsize=(15, 15))
axes = itertools.chain.from_iterable(ll_ax)
for ind, (ax, dist_computer,
title) in enumerate(zip(axes, dist_computers, titles)):
distmat = dist_computer(smile_strings, smile_strings)[0]
xs, ys = [], []
for i in range(n_mols):
for j in range(n_mols):
dist_in_dist = distmat[i, j]
dist_in_val = np.abs(prop_list[i] - prop_list[j])
xs.append(dist_in_dist)
ys.append(dist_in_val)
if as_subplots:
ax.set_title(title)
ax.scatter(xs, ys, s=2, alpha=0.6)
ax.set_xticks([])
ax.set_yticks([])
else:
# save separately:
plt.clf()
fig = plt.figure() # figsize=fsize
ax = fig.add_subplot(1, 1, 1)
plt.title(title, fontsize=22)
plt.scatter(xs, ys, s=2, alpha=0.6)
plt.xscale('log')
plt.xticks([])
plt.yticks([])
plt.xlim([None, 1.03 * max(xs)])
plt.xlabel("OT-distance, log scale", fontsize=20)
if ind == 0:
plt.ylabel(f"Difference in SA score", fontsize=20)
extent = ax.get_window_extent().transformed(
fig.dpi_scale_trans.inverted())
extent.x0 -= 0.5
extent.x1 += 0.1
extent.y0 -= 0.6
extent.y1 += 0.7
else:
extent = ax.get_window_extent().transformed(
fig.dpi_scale_trans.inverted())
extent.x0 -= 0.5
extent.x1 += 0.1
extent.y0 -= 0.6
extent.y1 += 0.7
plt.savefig(
os.path.join(VIS_DIR, f"dist_vs_value_{func}_{ind+1}.pdf"),
bbox_inches=extent,
pad_inches=0
) #bbox_inches=extent, pad_inches=0, format='eps', dpi=1000,
plt.clf()
if as_subplots:
plt.savefig(os.path.join(VIS_DIR, f"dist_vs_value_{func}.eps"),
format='eps',
dpi=1000)
plt.clf()
