def testRandomSampleAllBBs(self):
log("testRandomSampleAllBBs")
rxn = rdChemReactions.ChemicalReaction()
rgroups = [[Chem.MolFromSmiles("C")] * 10,
[Chem.MolFromSmiles("N")] * 5,
[Chem.MolFromSmiles("O")] * 6]
randProd = rdChemReactions.RandomSampleAllBBsStrategy()
randProd.Initialize(rxn, rgroups)
self.assertEquals(randProd.GetNumPermutations(), 10 * 5 * 6)
groups = []
for i in range(10 * 5 * 6):
groups.append(tuple(randProd.next()))
print(len(set(groups)), "out of", 10 * 5 * 6)
randProd = rdChemReactions.RandomSampleAllBBsStrategy()
randProd.Initialize(rxn, rgroups)
self.assertEquals(randProd.GetNumPermutations(), 10 * 5 * 6)
groups = []
for i in range(10):
groups.append(tuple(randProd.next()))
for i in range(3):
print(i, len(set([g[i] for g in groups])), "out of", [10, 5, 6][i])
self.assertEquals(len(set([g[i] for g in groups])), [10, 5, 6][i])
copy.copy(randProd)
def testTimings(self):
log("testTimings")
rxn = rdChemReactions.ChemicalReaction()
rgroups = [[Chem.MolFromSmiles("C")] * 17000,
[Chem.MolFromSmiles("N")] * 50000,
[Chem.MolFromSmiles("O")] * 4000]
cartProd = rdChemReactions.CartesianProductStrategy()
randProd = rdChemReactions.RandomSampleStrategy()
randAllBBs = rdChemReactions.RandomSampleAllBBsStrategy()
for r in [cartProd, randProd, randAllBBs]:
r.Initialize(rxn, rgroups)
num = 10000000
t1 = time.time()
r.Skip(num)
t2 = time.time()
print("%s Skipped %s in %s seconds" % (r, num, t2 - t1))
def testRGroupState(self):
if not rdChemReactions.EnumerateLibraryCanSerialize():
print(
"-- Skipping testRGroupState, serialization of EnumerateLibrary not enabled",
file=sys.stderr)
return
log("testRGroupState")
smirks_thiourea = "[N;$(N-[#6]):3]=[C;$(C=S):1].[N;$(N[#6]);!$(N=*);!$([N-]);!$(N#*);!$([ND3]);!$([ND4]);!$(N[O,N]);!$(N[C,S]=[S,O,N]):2]>>[N:3]-[C:1]-[N+0:2]"
rxn = rdChemReactions.ReactionFromSmarts(smirks_thiourea)
reagents = [[
Chem.MolFromSmiles('C=CCN=C=S'),
Chem.MolFromSmiles('CC=CCN=C=S')
],
[
Chem.MolFromSmiles('NCc1ncc(Cl)cc1Br'),
Chem.MolFromSmiles('NCCc1ncc(Cl)cc1Br'),
Chem.MolFromSmiles('NCCCc1ncc(Cl)cc1Br'),
]]
def tostr(l):
return [[str(x) for x in v] for v in l]
enumerator = rdChemReactions.EnumerateLibrary(rxn, reagents)
state = enumerator.GetState()
p = enumerator.nextSmiles()
p2 = enumerator.nextSmiles()
enumerator.SetState(state)
self.assertEquals(tostr(enumerator.nextSmiles()), tostr(p))
self.assertEquals(tostr(enumerator.nextSmiles()), tostr(p2))
enumerator = rdChemReactions.EnumerateLibrary(
rxn, reagents, rdChemReactions.RandomSampleStrategy())
state = enumerator.GetState()
p = enumerator.nextSmiles()
p2 = enumerator.nextSmiles()
enumerator.SetState(state)
self.assertEquals(tostr(enumerator.nextSmiles()), tostr(p))
self.assertEquals(tostr(enumerator.nextSmiles()), tostr(p2))
enumerator = rdChemReactions.EnumerateLibrary(
rxn, reagents, rdChemReactions.RandomSampleAllBBsStrategy())
state = enumerator.GetState()
p = enumerator.nextSmiles()
p2 = enumerator.nextSmiles()
enumerator.SetState(state)
self.assertEquals(tostr(enumerator.nextSmiles()), tostr(p))
self.assertEquals(tostr(enumerator.nextSmiles()), tostr(p2))
enumerator = rdChemReactions.EnumerateLibrary(rxn, reagents)
smiresults = [
'C=CCNC(=S)NCc1ncc(Cl)cc1Br', 'CC=CCNC(=S)NCc1ncc(Cl)cc1Br',
'C=CCNC(=S)NCCc1ncc(Cl)cc1Br', 'CC=CCNC(=S)NCCc1ncc(Cl)cc1Br',
'C=CCNC(=S)NCCCc1ncc(Cl)cc1Br', 'CC=CCNC(=S)NCCCc1ncc(Cl)cc1Br'
]
smiresults = [
Chem.MolToSmiles(Chem.MolFromSmiles(smi)) for smi in smiresults
]
enumerator.GetEnumerator().Skip(10)
enumerator.ResetState()
results = []
for result in enumerator:
for prodSet in result:
for mol in prodSet:
results.append(Chem.MolToSmiles(mol))
self.assertEquals(results, smiresults)
def testRandomEnumerateAllBBsLibrary(self):
log("testRandomEnumerateAllBBsLibrary")
smirks_thiourea = "[N;$(N-[#6]):3]=[C;$(C=S):1].[N;$(N[#6]);!$(N=*);!$([N-]);!$(N#*);!$([ND3]);!$([ND4]);!$(N[O,N]);!$(N[C,S]=[S,O,N]):2]>>[N:3]-[C:1]-[N+0:2]"
rxn = rdChemReactions.ReactionFromSmarts(smirks_thiourea)
reagents = [[
Chem.MolFromSmiles('C=CCN=C=S'),
Chem.MolFromSmiles('CC=CCN=C=S')
],
[
Chem.MolFromSmiles('NCc1ncc(Cl)cc1Br'),
Chem.MolFromSmiles('NCCc1ncc(Cl)cc1Br'),
Chem.MolFromSmiles('NCCCc1ncc(Cl)cc1Br'),
]]
enumerator = rdChemReactions.EnumerateLibrary(
rxn, reagents, rdChemReactions.RandomSampleAllBBsStrategy())
self.assertTrue(enumerator)
# test the BB sampling here
strategy = iter(enumerator)
r1 = set()
r2 = set()
strategy.next()
groups = strategy.GetPosition()
print("**", list(groups), file=sys.stderr)
r1.add(groups[0])
r2.add(groups[1])
strategy.next()
groups = strategy.GetPosition()
print("**", list(groups), file=sys.stderr)
r1.add(groups[0])
r2.add(groups[1])
self.assertEquals(r1, set(
[0, 1])) # two bbs at reagent one all sampled at one iteration
strategy.next()
groups = strategy.GetPosition()
print("**", list(groups), file=sys.stderr)
r1.add(groups[0])
r2.add(groups[1])
self.assertEquals(r2, set(
[0, 1,
2])) # three bbs at reagent one all sampled in three iterations
smiresults = [
'C=CCNC(=S)NCc1ncc(Cl)cc1Br', 'CC=CCNC(=S)NCc1ncc(Cl)cc1Br',
'C=CCNC(=S)NCCc1ncc(Cl)cc1Br', 'CC=CCNC(=S)NCCc1ncc(Cl)cc1Br',
'C=CCNC(=S)NCCCc1ncc(Cl)cc1Br', 'CC=CCNC(=S)NCCCc1ncc(Cl)cc1Br'
]
results = [
Chem.MolToSmiles(Chem.MolFromSmiles(smi)) for smi in smiresults
]
if rdChemReactions.EnumerateLibraryCanSerialize():
enumerator = rdChemReactions.EnumerateLibrary(
rxn, reagents, rdChemReactions.RandomSampleAllBBsStrategy())
self.assertTrue(enumerator)
pickle = enumerator.Serialize()
enumerator2 = rdChemReactions.EnumerateLibrary()
enumerator2.InitFromString(pickle)
self.assertEquals(enumerator.GetEnumerator().Type(),
enumerator2.GetEnumerator().Type())
iteren = iter(enumerator)
iteren2 = iter(enumerator2)
outsmiles = []
for i in range(10):
prods1 = iteren.next()
prods2 = iteren2.next()
self.assertEquals(len(prods1), len(prods2))
for mols1, mols2 in zip(prods1, prods2):
self.assertEquals(len(mols1), 1)
smi1 = Chem.MolToSmiles(mols1[0])
self.assertEquals(smi1, Chem.MolToSmiles(mols2[0]))
outsmiles.append(smi1)
if i == 1:
pickle_at_2 = enumerator.Serialize()
# make sure we can pickle the state as well
enumerator3 = rdChemReactions.EnumerateLibrary()
enumerator3.InitFromString(pickle_at_2)
self.assertEquals(enumerator.GetEnumerator().Type(),
enumerator3.GetEnumerator().Type())
iteren3 = iter(enumerator3)
outsmiles2 = []
for i in range(8):
prods3 = iteren3.next()
for mols3 in prods3:
self.assertEquals(len(mols3), 1)
smi1 = Chem.MolToSmiles(mols3[0])
self.assertEquals(smi1, Chem.MolToSmiles(mols3[0]))
outsmiles2.append(smi1)
self.assertEquals(outsmiles2, outsmiles[2:])