def testFromOldAdjacencyList1(self):
"""
adjlist: Test the Group.fromAdjacencyList() method on an old style adjacency list.
"""
adjlist = """
1 *2 {Cs,Cd} 0 {2,{S,D}} {3,S}
2 *1 {Os,Od} 0 {1,{S,D}}
3 R!H {0,1} {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
atom1, atom2, atom3 = group.atoms
self.assertTrue(group.hasBond(atom1, atom2))
self.assertTrue(group.hasBond(atom1, atom3))
self.assertFalse(group.hasBond(atom2, atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == '*2')
self.assertTrue(atom1.atomType[0].label in ['Cs', 'Cd'])
self.assertTrue(atom1.atomType[1].label in ['Cs', 'Cd'])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == '*1')
self.assertTrue(atom2.atomType[0].label in ['Os', 'Od'])
self.assertTrue(atom2.atomType[1].label in ['Os', 'Od'])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == '')
self.assertTrue(atom3.atomType[0].label == 'R!H')
self.assertTrue(atom3.radicalElectrons == [0, 1])
self.assertTrue(bond12.order == [1, 2])
self.assertTrue(bond13.isSingle())
def testFromAdjacencyList(self):
"""
adjlist: Test the Group.fromAdjacencyList() method.
"""
adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
atom1, atom2, atom3 = group.atoms
self.assertTrue(group.hasBond(atom1, atom2))
self.assertTrue(group.hasBond(atom1, atom3))
self.assertFalse(group.hasBond(atom2, atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == "*2")
self.assertTrue(atom1.atomType[0].label in ["Cs", "Cd"])
self.assertTrue(atom1.atomType[1].label in ["Cs", "Cd"])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == "*1")
self.assertTrue(atom2.atomType[0].label in ["Os", "Od"])
self.assertTrue(atom2.atomType[1].label in ["Os", "Od"])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == "")
self.assertTrue(atom3.atomType[0].label == "R!H")
self.assertTrue(atom3.radicalElectrons == [0])
self.assertTrue(bond12.order == ["S", "D"])
self.assertTrue(bond13.order == ["S"])
def testFromOldAdjacencyList1(self):
"""
adjlist: Test the Group.fromAdjacencyList() method on an old style adjacency list.
"""
adjlist = """
1 *2 {Cs,Cd} 0 {2,{S,D}} {3,S}
2 *1 {Os,Od} 0 {1,{S,D}}
3 R!H {0,1} {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
atom1, atom2, atom3 = group.atoms
self.assertTrue(group.hasBond(atom1, atom2))
self.assertTrue(group.hasBond(atom1, atom3))
self.assertFalse(group.hasBond(atom2, atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == '*2')
self.assertTrue(atom1.atomType[0].label in ['Cs', 'Cd'])
self.assertTrue(atom1.atomType[1].label in ['Cs', 'Cd'])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == '*1')
self.assertTrue(atom2.atomType[0].label in ['Os', 'Od'])
self.assertTrue(atom2.atomType[1].label in ['Os', 'Od'])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == '')
self.assertTrue(atom3.atomType[0].label == 'R!H')
self.assertTrue(atom3.radicalElectrons == [0, 1])
self.assertTrue(bond12.order == ['S', 'D'])
self.assertTrue(bond13.order == ['S'])
def testFromAdjacencyList(self):
"""
adjlist: Test the Group.fromAdjacencyList() method.
"""
adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
atom1, atom2, atom3 = group.atoms
self.assertTrue(group.hasBond(atom1, atom2))
self.assertTrue(group.hasBond(atom1, atom3))
self.assertFalse(group.hasBond(atom2, atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == '*2')
self.assertTrue(atom1.atomType[0].label in ['Cs', 'Cd'])
self.assertTrue(atom1.atomType[1].label in ['Cs', 'Cd'])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == '*1')
self.assertTrue(atom2.atomType[0].label in ['Os', 'Od'])
self.assertTrue(atom2.atomType[1].label in ['Os', 'Od'])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == '')
self.assertTrue(atom3.atomType[0].label == 'R!H')
self.assertTrue(atom3.radicalElectrons == [0])
self.assertTrue(bond12.order == ['S', 'D'])
self.assertTrue(bond13.order == ['S'])
def setUp(self):
self.adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
self.group = Group().fromAdjacencyList(self.adjlist)
def drawGroup(request, adjlist, format='png'):
"""
Returns an image of the provided adjacency list `adjlist` for a molecular
group. urllib is used to quote/unquote the adjacency list.
"""
from rmgpy.molecule.group import Group
from rmgpy.molecule.adjlist import InvalidAdjacencyListError
adjlist = str(urllib.unquote(adjlist))
try:
group = Group().fromAdjacencyList(adjlist)
except (InvalidAdjacencyListError, ValueError):
response = HttpResponseRedirect(static('img/invalid_icon.png'))
else:
if format == 'png':
response = HttpResponse(content_type="image/png")
response.write(group.draw('png'))
elif format == 'svg':
response = HttpResponse(content_type="image/svg+xml")
svgdata = group.draw('svg')
# Remove the scale and rotate transformations applied by pydot
svgdata = re.sub(r'scale\(0\.722222 0\.722222\) rotate\(0\) ', '', svgdata)
response.write(svgdata)
else:
response = HttpResponse('Image format not implemented.', status=501)
return response
def testSubgraphIsomorphismManyLabels(self):
molecule = Molecule() # specific case (species)
molecule.fromAdjacencyList("""
1 *1 C 1 {2,S} {3,S} {4,S}
2 C 0 {1,S} {3,S} {5,S} {6,S}
3 C 0 {1,S} {2,S} {7,S} {8,S}
4 H 0 {1,S}
5 H 0 {2,S}
6 H 0 {2,S}
7 H 0 {3,S}
8 H 0 {3,S}
""")
print molecule.toAdjacencyList()
group = Group() # general case (functional group)
group.fromAdjacencyList("""
1 *1 C 1 {2,S}, {3,S}
2 R!H 0 {1,S}
3 R!H 0 {1,S}
""")
labeled1 = molecule.getLabeledAtoms()
labeled2 = group.getLabeledAtoms()
initialMap = {}
for label,atom1 in labeled1.iteritems():
initialMap[atom1] = labeled2[label]
self.assertTrue(molecule.isSubgraphIsomorphic(group, initialMap))
mapping = molecule.findSubgraphIsomorphisms(group, initialMap)
self.assertEqual(len(mapping), 2)
for map in mapping:
self.assertTrue(len(map) == min(len(molecule.atoms), len(group.atoms)))
for key, value in map.iteritems():
self.assertTrue(key in molecule.atoms)
self.assertTrue(value in group.atoms)
def test_isomorphism_sulfurGroup_sulfurMolecule():
"""
Test isormophism check of a CS group vs. a sulfur containing molecule
"""
gp1 = Group().fromAdjacencyList("""
1 S u0 {2,S} {3,S}
2 H u0 {1,S}
3 C u0 {1,S} {4,D}
4 S u0 {3,D}
""")
gp2 = Group().fromAdjacencyList("""
1 S u0 {2,S} {3,S}
2 H u0 {1,S}
3 CS u0 {1,S} {4,D}
4 S u0 {3,D}
""")
mol = Molecule().fromAdjacencyList("""
1 S 0 {2,S} {3,S}
2 H 0 {1,S}
3 C 0 {1,S} {4,D} {5,S}
4 S 0 {3,D}
5 H 0 {3,S}
""")
assert_true(mol.isSubgraphIsomorphic(gp1))
assert_true(mol.isSubgraphIsomorphic(gp2))
def testFromAdjacencyList(self):
"""
adjlist: Test the Group.fromAdjacencyList() method.
"""
adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
atom1, atom2, atom3 = group.atoms
self.assertTrue(group.hasBond(atom1, atom2))
self.assertTrue(group.hasBond(atom1, atom3))
self.assertFalse(group.hasBond(atom2, atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == '*2')
self.assertTrue(atom1.atomType[0].label in ['Cs', 'Cd'])
self.assertTrue(atom1.atomType[1].label in ['Cs', 'Cd'])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == '*1')
self.assertTrue(atom2.atomType[0].label in ['Os', 'Od'])
self.assertTrue(atom2.atomType[1].label in ['Os', 'Od'])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == '')
self.assertTrue(atom3.atomType[0].label == 'R!H')
self.assertTrue(atom3.radicalElectrons == [0])
self.assertTrue(bond12.order == [1, 2])
self.assertTrue(bond13.isSingle())
def testSubgraphIsomorphismManyLabels(self):
molecule = Molecule() # specific case (species)
molecule.fromAdjacencyList("""
1 *1 C u1 {2,S} {3,S} {4,S}
2 C u0 {1,S} {3,S} {5,S} {6,S}
3 C u0 {1,S} {2,S} {7,S} {8,S}
4 H u0 {1,S}
5 H u0 {2,S}
6 H u0 {2,S}
7 H u0 {3,S}
8 H u0 {3,S}
""")
group = Group() # general case (functional group)
group.fromAdjacencyList("""
1 *1 C u1 {2,S}, {3,S}
2 R!H u0 {1,S}
3 R!H u0 {1,S}
""")
labeled1 = molecule.getLabeledAtoms()
labeled2 = group.getLabeledAtoms()
initialMap = {}
for label,atom1 in labeled1.iteritems():
initialMap[atom1] = labeled2[label]
self.assertTrue(molecule.isSubgraphIsomorphic(group, initialMap))
mapping = molecule.findSubgraphIsomorphisms(group, initialMap)
self.assertEqual(len(mapping), 2)
for map in mapping:
self.assertTrue(len(map) == min(len(molecule.atoms), len(group.atoms)))
for key, value in map.iteritems():
self.assertTrue(key in molecule.atoms)
self.assertTrue(value in group.atoms)
def testSortByConnectivity(self):
"""
Tests sortByConnectivity method
"""
#Basic test, we should get *1, *3 *2
adjlist1 = """
1 *1 C u0 {3,B}
2 *2 C u0 {3,B}
3 *3 C u0 {1,B} {2,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
orderedAtoms = group1.sortByConnectivity(group1.atoms)
self.assertEquals([x.label for x in orderedAtoms], ["*1", "*3", "*2"])
#Check a detached case, we should get *1, *3, *4, *2, *5
adjlist2 = """
1 *1 C u0 {3,B}
2 *2 C u0 {4,S} {5,B}
3 *3 C u0 {1,B} {4,B}
4 *4 C u0 {3,B} {2,S}
5 *5 C u0 {2,B}
"""
group2 = Group().fromAdjacencyList(adjlist2)
orderedAtoms = group2.sortByConnectivity(group2.atoms)
self.assertEquals([x.label for x in orderedAtoms], ["*1", "*3", "*4", "*2", "*5"])
def testFromOldAdjacencyList1(self):
"""
adjlist: Test the Group.fromAdjacencyList() method on an old style adjacency list.
"""
adjlist = """
1 *2 {Cs,Cd} 0 {2,{S,D}} {3,S}
2 *1 {Os,Od} 0 {1,{S,D}}
3 R!H {0,1} {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
atom1, atom2, atom3 = group.atoms
self.assertTrue(group.hasBond(atom1, atom2))
self.assertTrue(group.hasBond(atom1, atom3))
self.assertFalse(group.hasBond(atom2, atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == "*2")
self.assertTrue(atom1.atomType[0].label in ["Cs", "Cd"])
self.assertTrue(atom1.atomType[1].label in ["Cs", "Cd"])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == "*1")
self.assertTrue(atom2.atomType[0].label in ["Os", "Od"])
self.assertTrue(atom2.atomType[1].label in ["Os", "Od"])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == "")
self.assertTrue(atom3.atomType[0].label == "R!H")
self.assertTrue(atom3.radicalElectrons == [0, 1])
self.assertTrue(bond12.order == ["S", "D"])
self.assertTrue(bond13.order == ["S"])
def drawGroup(request, adjlist, format='png'):
"""
Returns an image of the provided adjacency list `adjlist` for a molecular
group. urllib is used to quote/unquote the adjacency list.
"""
from rmgpy.molecule.group import Group
from rmgpy.molecule.adjlist import InvalidAdjacencyListError
adjlist = urllib.parse.unquote(adjlist)
try:
group = Group().from_adjacency_list(adjlist)
except (InvalidAdjacencyListError, ValueError):
response = HttpResponseRedirect(static('img/invalid_icon.png'))
else:
if format == 'png':
response = HttpResponse(content_type="image/png")
response.write(group.draw('png'))
elif format == 'svg':
response = HttpResponse(content_type="image/svg+xml")
svg_data = group.draw('svg')
# Remove the scale and rotate transformations applied by pydot
svg_data = re.sub(r'scale\(0\.722222 0\.722222\) rotate\(0\) ', '',
svg_data)
response.write(svg_data)
else:
response = HttpResponse('Image format not implemented.',
status=501)
return response
def performSampMoleComparison(adjlist, answer_smiles):
"""
Creates a sample molecule from the adjlist and returns if it is isomorphic to a molecule created from
the inputted smiles
"""
group = Group().fromAdjacencyList(adjlist)
result = group.makeSampleMolecule()
return (result.isIsomorphic(Molecule().fromSMILES(answer_smiles)))
def testMakeSampleMolecule(self):
"""
Test the Group.makeSampleMolecule method
"""
def performSampMoleComparison(adjlist, answer_smiles):
"""
Creates a sample molecule from the adjlist and returns if it is isomorphic to a molecule created from
the inputted smiles
"""
group = Group().fromAdjacencyList(adjlist)
result = group.makeSampleMolecule()
return (result.isIsomorphic(Molecule().fromSMILES(answer_smiles)))
########################################################################################################################
#tests adding implicit atoms
adjlist = """
1 *1 Cd u0
"""
answer_smiles = 'C=C'
self.assertTrue(performSampMoleComparison(adjlist, answer_smiles))
#test creating implicit benzene atoms
adjlist2 = """
1 *1 Cbf u0 {2,B}
2 Cbf u0 {1,B}
"""
group2 = Group().fromAdjacencyList(adjlist2)
result2 = group2.makeSampleMolecule()
naphthaleneMolecule = Molecule().fromSMILES('C1=CC=C2C=CC=CC2=C1')
resonanceList2=naphthaleneMolecule.generateResonanceIsomers()
self.assertTrue(any([result2.isIsomorphic(x) for x in resonanceList2]))
#test the creation of a positively charged species
adjlist = """
1 *1 N5s u0
"""
answer_smiles = '[NH4+]'
self.assertTrue(performSampMoleComparison(adjlist, answer_smiles))
#test the creation of a negatively charged species
#commented out until new nitrogen atom types added in
# adjlist = """
# 1 *1 N2s u0
# """
# answer_smiles = '[NH2-]'
# self.assertTrue(performSampMoleComparison(adjlist, answer_smiles))
#test creation of charged species when some single bonds present
adjlist = """
1 *2 [N5s,N5d] u0 {2,S} {3,S}
2 *3 R!H u1 {1,S}
3 *4 H u0 {1,S}
"""
answer_smiles = '[NH3+][CH2]'
self.assertTrue(performSampMoleComparison(adjlist, answer_smiles))
def testIsSubgraphIsomorphic(self):
"""
Test the Group.isSubgraphIsomorphic() method.
"""
adjlist = """
1 *1 [Cs,Cd] u0
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isSubgraphIsomorphic(group))
self.assertFalse(group.isIsomorphic(self.group))
def testIsSubgraphIsomorphic(self):
"""
Test the Group.isSubgraphIsomorphic() method.
"""
adjlist = """
1 *1 [Cs,Cd] u0
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isSubgraphIsomorphic(group))
self.assertFalse(group.isIsomorphic(self.group))
def test_repr_png(self):
"""Test that a png representation can be created."""
adjlist = """
1 *1 [C,Cd,Ct,CO,CS,Cb] u1 {2,[S,D,T,B]}
2 *2 [C,Cd,Ct,CO,CS,Cb] u0 {1,[S,D,T,B]} {3,[S,D,T,B]}
3 *3 [C,Cd,Ct,CO,CS,Cb] u0 {2,[S,D,T,B]} {4,[S,D,T,B]}
4 *4 [C,Cd,Ct,CO,CS,Cb] u0 {3,[S,D,T,B]}
"""
group = Group().fromAdjacencyList(adjlist)
result = group._repr_png_()
self.assertIsNotNone(result)
def test_repr_png(self):
"""Test that a png representation can be created."""
adjlist = """
1 *1 [C,Cd,Ct,CO,CS,Cb] u1 {2,[S,D,T,B]}
2 *2 [C,Cd,Ct,CO,CS,Cb] u0 {1,[S,D,T,B]} {3,[S,D,T,B]}
3 *3 [C,Cd,Ct,CO,CS,Cb] u0 {2,[S,D,T,B]} {4,[S,D,T,B]}
4 *4 [C,Cd,Ct,CO,CS,Cb] u0 {3,[S,D,T,B]}
"""
group = Group().fromAdjacencyList(adjlist)
result = group._repr_png_()
self.assertIsNotNone(result)
def testGroupAdjacencyList(self):
"""
adjlist: Check the adjacency list read/write functions for a full molecule.
"""
adjlist = """1 C u0 {2,D}
2 O u1 p1 c[-1,0,+1] {1,D}
"""
group = Group().fromAdjacencyList("""
1 C u0 {2,D}
2 O u1 p1 c[-1,0,+1] {1,D}
""")
self.assertEqual(adjlist, group.toAdjacencyList())
def testMergeGroups(self):
"""
Test the mergeGroups() function
"""
#basic test of merging a backbone and end group
backbone1 = Group().fromAdjacencyList("""
1 *1 R!H u1 {2,S}
2 *4 R!H u0 {1,S} {3,S}
3 *6 R!H u0 {2,S} {4,S}
4 *5 R!H u0 {3,S} {5,S}
5 *2 R!H u0 {4,S} {6,S}
6 *3 H u0 {5,S}
""")
end1 = Group().fromAdjacencyList("""
1 *2 Cs u0 {2,S} {3,S}
2 *3 H u0 {1,S}
3 S u0 {1,S}
""")
desiredMerge1 = Group().fromAdjacencyList("""
1 *1 R!H u1 {2,S}
2 *4 R!H u0 {1,S} {3,S}
3 *6 R!H u0 {2,S} {4,S}
4 *5 R!H u0 {3,S} {5,S}
5 *2 Cs u0 {4,S} {6,S} {7,S}
6 *3 H u0 {5,S}
7 S u0 {5,S}
""")
mergedGroup = backbone1.mergeGroups(end1)
self.assertTrue(mergedGroup.isIdentical(desiredMerge1))
#test it works when there is a cyclical structure to the backbone
backbone2 = Group().fromAdjacencyList("""
1 *1 R!H u1 {2,S} {4,S}
2 *4 R!H u0 {1,S} {3,S}
3 *2 R!H u0 {2,S} {4,S}
4 *3 R!H u0 {3,S} {1,S}
""")
end2 = Group().fromAdjacencyList("""
1 *2 Os u0 {2,S}
2 *3 Cs u0 {1,S}
""")
desiredMerge2 = Group().fromAdjacencyList("""
1 *1 R!H u1 {2,S} {4,S}
2 *4 R!H u0 {1,S} {3,S}
3 *2 Os u0 {2,S} {4,S}
4 *3 Cs u0 {3,S} {1,S}
""")
mergedGroup = backbone2.mergeGroups(end2)
self.assertTrue(mergedGroup.isIdentical(desiredMerge2))
def testGroupAdjacencyList(self):
"""
adjlist: Check the adjacency list read/write functions for a full molecule.
"""
adjlist = """1 C u0 {2,D}
2 O u1 p1 c[-1,0,+1] {1,D}
"""
group = Group().fromAdjacencyList("""
1 C u0 {2,D}
2 O u1 p1 c[-1,0,+1] {1,D}
""")
self.assertEqual(adjlist, group.toAdjacencyList())
def testIsIsomorphic(self):
"""
Test the Group.isIsomorphic() method.
"""
adjlist = """
1 *1 [Os,Od] u0 {3,[S,D]}
2 R!H u0 {3,S}
3 *2 [Cs,Cd] u0 {1,[S,D]} {2,S}
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isIsomorphic(group))
self.assertTrue(group.isIsomorphic(self.group))
def testIsIsomorphic(self):
"""
Test the Group.isIsomorphic() method.
"""
adjlist = """
1 *1 [Os,Od] u0 {3,[S,D]}
2 R!H u0 {3,S}
3 *2 [Cs,Cd] u0 {1,[S,D]} {2,S}
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isIsomorphic(group))
self.assertTrue(group.isIsomorphic(self.group))
def testToAdjacencyList(self):
"""
adjlist: Test the Group.toAdjacencyList() method.
"""
adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
adjlist2 = group.toAdjacencyList()
self.assertEqual(adjlist.strip(), adjlist2.strip())
def testToAdjacencyList(self):
"""
adjlist: Test the Group.toAdjacencyList() method.
"""
adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
group = Group().fromAdjacencyList(adjlist)
adjlist2 = group.toAdjacencyList()
self.assertEqual(adjlist.strip(), adjlist2.strip())
def testCreateAndConnectAtom(self):
"""
Tests createAndConnectAtom method
"""
adjlist1 = """
1 *1 C u0 {2,S}
2 *2 C u0 {1,S}
"""
answer1 = """
1 *1 C u0 {2,S} {3,B}
2 *2 C u0 {1,S}
3 Cb u0 {1,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
answer1 = Group().fromAdjacencyList(answer1)
atom1 = group1.getLabeledAtom("*1")
newAtom = group1.createAndConnectAtom(atomtypes = ["Cb"], connectingAtom = atom1, bondOrders = ["B"])
self.assertTrue(group1.isIsomorphic(answer1))
answer2 = """
1 *1 C u0 {2,S} {3,[S,D]}
2 *2 C u0 {1,S}
3 [Cs,Cd] u0 {1,[S,D]}
"""
#Test that wildcards work alright
group2 = Group().fromAdjacencyList(adjlist1)
answer2 = Group().fromAdjacencyList(answer2)
atom1 = group2.getLabeledAtom("*1")
newAtom = group2.createAndConnectAtom(atomtypes = ["Cs", "Cd"], connectingAtom = atom1, bondOrders = ["S","D"])
self.assertTrue(group2.isIsomorphic(answer2))
def setUp(self):
self.adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
self.group = Group().fromAdjacencyList(self.adjlist)
def test_isSubgraphIsomorphic4(self):
from rmgpy.molecule.group import Group
smiles_like = '[CH2]CR'
fragment = afm.fragment.Fragment().from_SMILES_like_string(smiles_like)
fragment.assign_representative_molecule()
adj = """
1 * Cs u1 {2,S}
2 N u0 {1,S}
"""
other = Group().fromAdjacencyList(adj)
# create initial map
frag_atom_star = None
for frag_atom in fragment.vertices:
if isinstance(frag_atom, Atom) and frag_atom.radicalElectrons == 1:
frag_atom_star = frag_atom
break
group_atom_star = other.vertices[0]
initialMap = {frag_atom_star: group_atom_star}
self.assertFalse(
fragment.isSubgraphIsomorphic(other, initialMap=initialMap))
def drawGroup(request, adjlist):
"""
Returns an image of the provided adjacency list `adjlist` for a molecular
pattern. Note that the newline character cannot be represented in a URL;
semicolons should be used instead.
"""
from rmgpy.molecule.group import Group
import pydot
response = HttpResponse(mimetype="image/png")
adjlist = str(adjlist.replace(';', '\n'))
pattern = Group().fromAdjacencyList(adjlist)
graph = pydot.Dot(graph_type='graph', dpi="52")
for index, atom in enumerate(pattern.atoms):
atomType = '%s ' % atom.label if atom.label != '' else ''
atomType += ','.join([atomType.label for atomType in atom.atomType])
graph.add_node(pydot.Node(name='%i' % (index+1), label=atomType, fontname='Helvetica', fontsize="16"))
for atom1 in pattern.atoms:
for atom2, bond in atom1.bonds.iteritems():
index1 = pattern.atoms.index(atom1)
index2 = pattern.atoms.index(atom2)
if index1 < index2:
bondType = ','.join([order for order in bond.order])
graph.add_edge(pydot.Edge(
src = '%i' % (index1+1),
dst = '%i' % (index2+1),
label = bondType,
fontname='Helvetica', fontsize = "16",
))
response.write(graph.create(prog='neato', format='png'))
return response
def groupFromURL(adjlist):
"""
Convert a given adjacency list `adjlist` from a URL to the corresponding
:class:`Group` object.
"""
group = Group().fromAdjacencyList(str(adjlist.replace(';', '\n')))
return group
def testFromAdjacencyList_multiplicity(self):
gp = Group().fromAdjacencyList("""
multiplicity [1]
1 C u0 p0 c0
""")
self.assertEqual(len(gp.multiplicity), 1)
self.assertEqual(gp.multiplicity[0], 1)
def test_isotope_subgraph_isomorphism_molecule_and_group():
"""
Checks that subgraph isomorphism works with enriched molecules and groups
"""
methanei = Molecule().fromAdjacencyList("""
1 C u0 p0 c0 i13 {2,S} {3,S} {4,S} {5,S}
2 H u0 p0 c0 {1,S}
3 H u0 p0 c0 {1,S}
4 H u0 p0 c0 {1,S}
5 H u0 p0 c0 {1,S}
""")
methane = Molecule().fromAdjacencyList("""
1 C u0 p0 c0 {2,S} {3,S} {4,S} {5,S}
2 H u0 p0 c0 {1,S}
3 H u0 p0 c0 {1,S}
4 H u0 p0 c0 {1,S}
5 H u0 p0 c0 {1,S}
""")
group_methane = Group().fromAdjacencyList("""
1 C u0 {2,S} {3,S} {4,S} {5,S}
2 H u0 {1,S}
3 H u0 {1,S}
4 H u0 {1,S}
5 H u0 {1,S}
""")
assert_true(methanei.isSubgraphIsomorphic(group_methane))
assert_true(methane.isSubgraphIsomorphic(group_methane))
assert_false(methanei.isIsomorphic(methane))
def testSubgraphIsomorphismAgain(self):
molecule = Molecule()
molecule.fromAdjacencyList(
"""
1 * C 0 {2,D} {7,S} {8,S}
2 C 0 {1,D} {3,S} {9,S}
3 C 0 {2,S} {4,D} {10,S}
4 C 0 {3,D} {5,S} {11,S}
5 C 0 {4,S} {6,S} {12,S} {13,S}
6 C 0 {5,S} {14,S} {15,S} {16,S}
7 H 0 {1,S}
8 H 0 {1,S}
9 H 0 {2,S}
10 H 0 {3,S}
11 H 0 {4,S}
12 H 0 {5,S}
13 H 0 {5,S}
14 H 0 {6,S}
15 H 0 {6,S}
16 H 0 {6,S}
"""
)
group = Group()
group.fromAdjacencyList(
"""
1 * C 0 {2,D} {3,S} {4,S}
2 C 0 {1,D}
3 H 0 {1,S}
4 H 0 {1,S}
"""
)
labeled1 = molecule.getLabeledAtoms().values()[0]
labeled2 = group.getLabeledAtoms().values()[0]
initialMap = {labeled1: labeled2}
self.assertTrue(molecule.isSubgraphIsomorphic(group, initialMap))
initialMap = {labeled1: labeled2}
mapping = molecule.findSubgraphIsomorphisms(group, initialMap)
self.assertTrue(len(mapping) == 2, "len(mapping) = %d, should be = 2" % (len(mapping)))
for map in mapping:
self.assertTrue(len(map) == min(len(molecule.atoms), len(group.atoms)))
for key, value in map.iteritems():
self.assertTrue(key in molecule.atoms)
self.assertTrue(value in group.atoms)
def groupFromURL(adjlist):
"""
Convert a given adjacency list `adjlist` from a URL to the corresponding
:class:`Group` object.
"""
adjlist = str(urllib.unquote(adjlist))
group = Group().fromAdjacencyList(adjlist)
return group
def testSubgraphIsomorphismAgain(self):
molecule = Molecule()
molecule.fromAdjacencyList("""
1 * C 0 {2,D} {7,S} {8,S}
2 C 0 {1,D} {3,S} {9,S}
3 C 0 {2,S} {4,D} {10,S}
4 C 0 {3,D} {5,S} {11,S}
5 C 0 {4,S} {6,S} {12,S} {13,S}
6 C 0 {5,S} {14,S} {15,S} {16,S}
7 H 0 {1,S}
8 H 0 {1,S}
9 H 0 {2,S}
10 H 0 {3,S}
11 H 0 {4,S}
12 H 0 {5,S}
13 H 0 {5,S}
14 H 0 {6,S}
15 H 0 {6,S}
16 H 0 {6,S}
""")
group = Group()
group.fromAdjacencyList("""
1 * C 0 {2,D} {3,S} {4,S}
2 C 0 {1,D}
3 H 0 {1,S}
4 H 0 {1,S}
""")
labeled1 = molecule.getLabeledAtoms().values()[0]
labeled2 = group.getLabeledAtoms().values()[0]
initialMap = {labeled1: labeled2}
self.assertTrue(molecule.isSubgraphIsomorphic(group, initialMap))
initialMap = {labeled1: labeled2}
mapping = molecule.findSubgraphIsomorphisms(group, initialMap)
self.assertTrue(
len(mapping) == 2,
"len(mapping) = %d, should be = 2" % (len(mapping)))
for map in mapping:
self.assertTrue(
len(map) == min(len(molecule.atoms), len(group.atoms)))
for key, value in map.iteritems():
self.assertTrue(key in molecule.atoms)
self.assertTrue(value in group.atoms)
def test_atom_props(self):
"""Test that the atom props attribute can be properly read and written."""
adjlist = """
1 *1 R!H u1 r0 {2,S}
2 *4 R!H u0 r0 {1,S} {3,S}
3 *2 Cb u0 r1 {2,S} {4,B}
4 *3 Cb u0 r1 {3,B}
"""
group = Group().from_adjacency_list(adjlist)
for atom in group.atoms:
if atom.atomtype[0].label == 'R!H':
self.assertFalse(atom.props['inRing'])
elif atom.atomtype[0].label == 'Cb':
self.assertTrue(atom.props['inRing'])
adjlist2 = group.to_adjacency_list()
self.assertEqual(adjlist.strip(), adjlist2.strip())
def test_from_adjacency_list_multiplicity_list(self):
gp = Group().from_adjacency_list("""
multiplicity [ 1, 3, 5 ]
1 C u0 p0 c0
""")
self.assertEqual(len(gp.multiplicity), 3)
self.assertEqual(gp.multiplicity[0], 1)
self.assertEqual(gp.multiplicity[1], 3)
self.assertEqual(gp.multiplicity[2], 5)
def test_isomorphism__r():
mol = Molecule().from_adjacency_list("""
1 C u0 p0 c0
""", saturate_h=True)
gp = Group().from_adjacency_list("""
1 R u0 p0 c0
""")
assert_true(len(mol.find_subgraph_isomorphisms(gp)) > 0)
def test_isomorphism_R():
mol = Molecule().fromAdjacencyList("""
1 C u0 p0 c0
""", saturateH=True)
gp = Group().fromAdjacencyList("""
1 R u0 p0 c0
""")
assert_true(len(mol.findSubgraphIsomorphisms(gp)) > 0)
def benzylradical_in_naphthalene():
adjlist_mol = """
1 C u0 p0 c0 {2,D} {10,S} {11,S}
2 C u0 p0 c0 {1,D} {3,S} {12,S}
3 C u0 p0 c0 {2,S} {4,D} {13,S}
4 C u0 p0 c0 {3,D} {5,S} {9,S}
5 C u0 p0 c0 {4,S} {6,D} {14,S}
6 C u0 p0 c0 {5,D} {7,S} {15,S}
7 C u0 p0 c0 {6,S} {8,D} {16,S}
8 C u0 p0 c0 {7,D} {9,S} {17,S}
9 C u0 p0 c0 {4,S} {8,S} {10,D}
10 C u0 p0 c0 {1,S} {9,D} {18,S}
11 H u0 p0 c0 {1,S}
12 H u0 p0 c0 {2,S}
13 H u0 p0 c0 {3,S}
14 H u0 p0 c0 {5,S}
15 H u0 p0 c0 {6,S}
16 H u0 p0 c0 {7,S}
17 H u0 p0 c0 {8,S}
18 H u0 p0 c0 {10,S}
"""
mol = Group().fromAdjacencyList(adjlist_mol)
adjlist_group = """
1 C u1 p0 c0 {2,S} {3,S} {4,S}
2 H u0 p0 c0 {1,S}
3 H u0 p0 c0 {1,S}
4 C u0 p0 c0 {1,S} {5,T}
5 C u0 p0 c0 {4,T} {6,S}
6 H u0 p0 c0 {5,S}
"""
"""
replaced with propargyl radical... doesn't work..
"""
group = Group().fromAdjacencyList(adjlist_group)
result = mol.findSubgraphIsomorphisms(group)
return result
def methyl_in_ethane_no_H():
"""
"""
adjlist_mol_no_H = """
1 C u0 p0 c0 {2,S}
2 C u0 p0 c0 {1,S}
"""
mol = Group().fromAdjacencyList(adjlist_mol_no_H)
adjlist_group_no_H = """
1 C ux p0 c0
"""
group = Group().fromAdjacencyList(adjlist_group_no_H)
result = mol.findSubgraphIsomorphisms(group)
return result
def drawGroup(request, adjlist):
"""
Returns an image of the provided adjacency list `adjlist` for a molecular
pattern. urllib is used to quote/unquote the adjacency list.
"""
from rmgpy.molecule.group import Group
response = HttpResponse(content_type="image/svg+xml")
adjlist = str(urllib.unquote(adjlist))
pattern = Group().fromAdjacencyList(adjlist)
# Create an svg drawing of the group
svgdata = pattern.draw('svg')
# Remove the scale and rotate transformations applied by pydot
svgdata = re.sub(r'scale\(0\.722222 0\.722222\) rotate\(0\) ', '', svgdata)
response.write(svgdata)
return response
def testIsBenzeneExplicit(self):
"""
Test the Group.isBenzeneExplicit method
"""
adjlist1 = """
1 *1 Cb u0 {2,B}
2 *2 Cb u0 {1,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
self.assertFalse(group1.isBenzeneExplicit())
benzene ="""
1 C u0 {2,B} {6,B}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {1,B}
"""
benzene = Group().fromAdjacencyList(benzene)
self.assertTrue(benzene.isBenzeneExplicit())
def convertCycleToGroup(cycle):
"""
This function converts a list of atoms in a cycle to a functional Group object
"""
from rmgpy.molecule.group import GroupAtom, GroupBond, Group
# Create GroupAtom object for each atom in the cycle, label the first one in the cycle with a *
groupAtoms = {}
bonds = []
for atom in cycle:
groupAtoms[atom] = GroupAtom(atomType=[atom.atomType],
radicalElectrons=[0],
label='*' if cycle.index(atom)==0 else '')
group = Group(atoms=groupAtoms.values())
# Create GroupBond for each bond between atoms in the cycle, but not outside of the cycle
for atom in cycle:
for bondedAtom, bond in atom.edges.iteritems():
if bondedAtom in cycle:
# create a group bond with the same bond order as in the original molecule,
# if it hasn't already been created
if not group.hasBond(groupAtoms[atom],groupAtoms[bondedAtom]):
group.addBond(GroupBond(groupAtoms[atom],groupAtoms[bondedAtom],order=[bond.order]))
else:
pass
group.update()
return group
def testSortByConnectivity(self):
"""
Tests sortByConnectivity method
"""
#Basic test, we should get *1, *3 *2
adjlist1 = """
1 *1 C u0 {3,B}
2 *2 C u0 {3,B}
3 *3 C u0 {1,B} {2,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
orderedAtoms = group1.sortByConnectivity(group1.atoms)
self.assertEquals([x.label for x in orderedAtoms], ["*1", "*3", "*2"])
#Check a detached case, we should get *1, *3, *4, *2, *5
adjlist2 = """
1 *1 C u0 {3,B}
2 *2 C u0 {4,S} {5,B}
3 *3 C u0 {1,B} {4,B}
4 *4 C u0 {3,B} {2,S}
5 *5 C u0 {2,B}
"""
group2 = Group().fromAdjacencyList(adjlist2)
orderedAtoms = group2.sortByConnectivity(group2.atoms)
self.assertEquals([x.label for x in orderedAtoms],
["*1", "*3", "*4", "*2", "*5"])
def testPickWildcards(self):
"""
Test the Group.pickWildCards function
"""
#The following tests are for picking optimal bond orders when there are bond wilcards
#test that Cb/Cbf atoms with [D,B] chooses [B] instead of [D] bonds
adjlist1 = """
1 *1 R!H u1 {2,[D,B]}
2 *2 [Cbf,Cdd] u0 {1,[D,B]} {3,[D,B]}
3 *3 [Cb,Cd] u0 {2,[D,B]} {4,S}
4 *4 R!H u0 {3,S} {5,S}
5 *5 H u0 {4,S}
"""
group1 = Group().fromAdjacencyList(adjlist1)
group1.pickWildcards()
atoms = group1.atoms
self.assertTrue(atoms[0].bonds[atoms[1]].isBenzene())
self.assertTrue(atoms[1].bonds[atoms[2]].isBenzene())
adjlist2 = """
1 *1 R!H u1 {2,[S,D]} {4,[S,D]}
2 *2 [CO,Cdd] u0 {1,[S,D]} {3,[S,D]}
3 *3 [Od,Cd] u0 {2,[S,D]}
4 *4 [Cdd,Cd] u0 {1,[S,D]}
"""
group2 = Group().fromAdjacencyList(adjlist2)
group2.pickWildcards()
atoms = group2.atoms
self.assertTrue(atoms[1].bonds[atoms[2]].isDouble)
self.assertTrue(atoms[0].bonds[atoms[3]].isDouble)
def test_isSubgraphIsomorphic1(self):
from rmgpy.molecule.group import Group
smiles_like = '[CH2]CR'
fragment = afm.fragment.Fragment().from_SMILES_like_string(smiles_like)
adj = """
1 * R u1
"""
other = Group().fromAdjacencyList(adj)
self.assertTrue(fragment.isSubgraphIsomorphic(other))
def testDrawGroup(self):
"""Test that the draw method returns the expected pydot graph."""
adjlist = """
1 *1 [C,Cd,Ct,CO,CS,Cb] u1 {2,[S,D,T,B]}
2 *2 [C,Cd,Ct,CO,CS,Cb] u0 {1,[S,D,T,B]} {3,[S,D,T,B]}
3 *3 [C,Cd,Ct,CO,CS,Cb] u0 {2,[S,D,T,B]} {4,[S,D,T,B]}
4 *4 [C,Cd,Ct,CO,CS,Cb] u0 {3,[S,D,T,B]}
"""
# Use of tabs in the expected string is intentional
expected = """
graph G {
graph [dpi=52];
node [label="\N"];
1 [fontname=Helvetica,
fontsize=16,
label="*1 C,Cd,Ct,CO,CS,Cb"];
2 [fontname=Helvetica,
fontsize=16,
label="*2 C,Cd,Ct,CO,CS,Cb"];
1 -- 2 [fontname=Helvetica,
fontsize=16,
label="S,D,T,B"];
3 [fontname=Helvetica,
fontsize=16,
label="*3 C,Cd,Ct,CO,CS,Cb"];
2 -- 3 [fontname=Helvetica,
fontsize=16,
label="S,D,T,B"];
4 [fontname=Helvetica,
fontsize=16,
label="*4 C,Cd,Ct,CO,CS,Cb"];
3 -- 4 [fontname=Helvetica,
fontsize=16,
label="S,D,T,B"];
}
"""
group = Group().fromAdjacencyList(adjlist)
result = group.draw('canon')
self.assertEqual(''.join(result.split()), ''.join(expected.split()))
def testDrawGroup(self):
"""Test that the draw method returns the expected pydot graph."""
adjlist = """
1 *1 [C,Cd,Ct,CO,CS,Cb] u1 {2,[S,D,T,B]}
2 *2 [C,Cd,Ct,CO,CS,Cb] u0 {1,[S,D,T,B]} {3,[S,D,T,B]}
3 *3 [C,Cd,Ct,CO,CS,Cb] u0 {2,[S,D,T,B]} {4,[S,D,T,B]}
4 *4 [C,Cd,Ct,CO,CS,Cb] u0 {3,[S,D,T,B]}
"""
# Use of tabs in the expected string is intentional
expected = """
graph G {
graph [dpi=52];
node [label="\N"];
1 [fontname=Helvetica,
fontsize=16,
label="*1 C,Cd,Ct,CO,CS,Cb"];
2 [fontname=Helvetica,
fontsize=16,
label="*2 C,Cd,Ct,CO,CS,Cb"];
1 -- 2 [fontname=Helvetica,
fontsize=16,
label="S,D,T,B"];
3 [fontname=Helvetica,
fontsize=16,
label="*3 C,Cd,Ct,CO,CS,Cb"];
2 -- 3 [fontname=Helvetica,
fontsize=16,
label="S,D,T,B"];
4 [fontname=Helvetica,
fontsize=16,
label="*4 C,Cd,Ct,CO,CS,Cb"];
3 -- 4 [fontname=Helvetica,
fontsize=16,
label="S,D,T,B"];
}
"""
group = Group().fromAdjacencyList(adjlist)
result = group.draw('canon')
self.assertEqual(''.join(result.split()), ''.join(expected.split()))
def testMakeSampleMolecule(self):
"""
Test the Group.makeSampleMolecule method
"""
# result = self.group.makeSampleMolecule()
# print result.multiplicity
# self.assertTrue(result.isIsomorphic(Molecule().fromSMILES('OCC')))
#tests adding implicit atoms
adjlist1 = """
1 *1 Cd u0
"""
group1 = Group().fromAdjacencyList(adjlist1)
result1 = group1.makeSampleMolecule()
self.assertTrue(result1.isIsomorphic(Molecule().fromSMILES('C=C')))
#test creating implicit benzene atoms
adjlist2 = """
1 *1 Cbf u0 {2,B}
2 Cbf u0 {1,B}
"""
group2 = Group().fromAdjacencyList(adjlist2)
result2 = group2.makeSampleMolecule()
naphthaleneMolecule = Molecule().fromSMILES('C1=CC=C2C=CC=CC2=C1')
resonanceList2=naphthaleneMolecule.generateResonanceIsomers()
self.assertTrue(any([result2.isIsomorphic(x) for x in resonanceList2]))
#test the creation of a charged species
adjlist3 = """
1 *1 N5s u0
"""
group3 = Group().fromAdjacencyList(adjlist3)
result3 = group3.makeSampleMolecule()
self.assertTrue(result3.isIsomorphic(Molecule().fromSMILES('[NH4+]')))
#test creation of charged species when some single bonds present
adjlist4 = """
1 *2 [N5s,N5d] u0 {2,S} {3,S}
2 *3 R!H u1 {1,S}
3 *4 H u0 {1,S}
"""
group4 = Group().fromAdjacencyList(adjlist4)
result4 = group4.makeSampleMolecule()
self.assertTrue(result4.isIsomorphic(Molecule().fromSMILES('[NH3+][CH2]')))
def testFindSubgraphIsomorphisms(self):
"""
Test the Group.findSubgraphIsomorphisms() method.
"""
adjlist = """
1 *1 [Cs,Cd] u0
"""
group = Group().fromAdjacencyList(adjlist)
result = self.group.findSubgraphIsomorphisms(group)
self.assertEqual(len(result), 1)
for atom1, atom2 in result[0].iteritems():
self.assertTrue(atom1 in self.group.atoms)
self.assertTrue(atom2 in group.atoms)
self.assertTrue(atom1.equivalent(atom2))
def test_isomorphism_mol_group_not_identical():
"""
Testing multiplicities in mol and group that don't match
"""
mol = Molecule().from_adjacency_list("""
1 C u0 p0 c0
""", saturate_h=True)
gp = Group().from_adjacency_list("""
multiplicity [2]
1 R u0 p0 c0
""")
assert_false(mol.is_subgraph_isomorphic(gp))
assert_false(len(mol.find_subgraph_isomorphisms(gp)) > 0)
def drawGroup(request, adjlist, format='png'):
"""
Returns an image of the provided adjacency list `adjlist` for a molecular
group. urllib is used to quote/unquote the adjacency list.
"""
from rmgpy.molecule.group import Group
adjlist = str(urllib.unquote(adjlist))
group = Group().fromAdjacencyList(adjlist)
if format == 'png':
response = HttpResponse(content_type="image/png")
response.write(group.draw('png'))
elif format == 'svg':
response = HttpResponse(content_type="image/svg+xml")
svgdata = group.draw('svg')
# Remove the scale and rotate transformations applied by pydot
svgdata = re.sub(r'scale\(0\.722222 0\.722222\) rotate\(0\) ', '',
svgdata)
response.write(svgdata)
else:
response = HttpResponse('Image format not implemented.', status=501)
return response
def loadEntry(self, label, molecule=None, group=None, data=None):
"""
Load an entry from the forbidden structures database. This method is
automatically called during loading of the forbidden structures
database.
"""
assert molecule is not None or group is not None
assert not (molecule is not None and group is not None)
if molecule is not None:
item = Molecule().fromAdjacencyList(molecule)
elif group is not None:
item = Group().fromAdjacencyList(group)
self.entries[label] = Entry(
label=label,
item=item,
data=data,
)
class TestGroup(unittest.TestCase):
"""
Contains unit tests of the Graph class.
"""
def setUp(self):
self.adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
self.group = Group().fromAdjacencyList(self.adjlist)
def testClearLabeledAtoms(self):
"""
Test the Group.clearLabeledAtoms() method.
"""
self.group.clearLabeledAtoms()
for atom in self.group.atoms:
self.assertEqual(atom.label, '')
def testContainsLabeledAtom(self):
"""
Test the Group.containsLabeledAtom() method.
"""
for atom in self.group.atoms:
if atom.label != '':
self.assertTrue(self.group.containsLabeledAtom(atom.label))
self.assertFalse(self.group.containsLabeledAtom('*3'))
self.assertFalse(self.group.containsLabeledAtom('*4'))
self.assertFalse(self.group.containsLabeledAtom('*5'))
self.assertFalse(self.group.containsLabeledAtom('*6'))
def testGetLabeledAtom(self):
"""
Test the Group.getLabeledAtom() method.
"""
for atom in self.group.atoms:
if atom.label != '':
self.assertEqual(atom, self.group.getLabeledAtom(atom.label))
try:
self.group.getLabeledAtom('*3')
self.fail('Unexpected successful return from Group.getLabeledAtom() with invalid atom label.')
except ValueError:
pass
def testGetLabeledAtoms(self):
"""
Test the Group.getLabeledAtoms() method.
"""
labeled = self.group.getLabeledAtoms()
for atom in self.group.atoms:
if atom.label != '':
self.assertTrue(atom.label in labeled)
self.assertTrue(atom in labeled.values())
else:
self.assertFalse(atom.label in labeled)
self.assertFalse(atom in labeled.values())
def testFromAdjacencyList(self):
"""
Test the Group.fromAdjacencyList() method.
"""
atom1, atom2, atom3 = self.group.atoms
self.assertTrue(self.group.hasBond(atom1,atom2))
self.assertTrue(self.group.hasBond(atom1,atom3))
self.assertFalse(self.group.hasBond(atom2,atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == '*2')
self.assertTrue(atom1.atomType[0].label in ['Cs','Cd'])
self.assertTrue(atom1.atomType[1].label in ['Cs','Cd'])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == '*1')
self.assertTrue(atom2.atomType[0].label in ['Os','Od'])
self.assertTrue(atom2.atomType[1].label in ['Os','Od'])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == '')
self.assertTrue(atom3.atomType[0].label == 'R!H')
self.assertTrue(atom3.radicalElectrons == [0])
self.assertTrue(bond12.order == [1,2])
self.assertTrue(bond13.isSingle())
def testToAdjacencyList(self):
"""
Test the Group.toAdjacencyList() method.
"""
adjlist = self.group.toAdjacencyList()
self.assertEqual(adjlist.strip(), self.adjlist.strip(),adjlist)
def testIsIsomorphic(self):
"""
Test the Group.isIsomorphic() method.
"""
adjlist = """
1 *1 [Os,Od] u0 {3,[S,D]}
2 R!H u0 {3,S}
3 *2 [Cs,Cd] u0 {1,[S,D]} {2,S}
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isIsomorphic(group))
self.assertTrue(group.isIsomorphic(self.group))
def testFindIsomorphism(self):
"""
Test the Group.findIsomorphism() method.
"""
adjlist = """
1 *1 [Os,Od] u0 {3,[S,D]}
2 R!H u0 {3,S}
3 *2 [Cs,Cd] u0 {1,[S,D]} {2,S}
"""
group = Group().fromAdjacencyList(adjlist)
result = self.group.findIsomorphism(group)
self.assertEqual(len(result), 1)
for atom1, atom2 in result[0].items():
self.assertTrue(atom1 in self.group.atoms)
self.assertTrue(atom2 in group.atoms)
self.assertTrue(atom1.equivalent(atom2))
for atom3 in atom1.bonds:
atom4 = result[0][atom3]
self.assertTrue(atom4 in atom2.bonds)
self.assertTrue(atom3.equivalent(atom4))
bond1 = atom1.bonds[atom3]
bond2 = atom2.bonds[atom4]
self.assertTrue(bond1.equivalent(bond2))
def testIsSubgraphIsomorphic(self):
"""
Test the Group.isSubgraphIsomorphic() method.
"""
adjlist = """
1 *1 [Cs,Cd] u0
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isSubgraphIsomorphic(group))
self.assertFalse(group.isIsomorphic(self.group))
def testFindSubgraphIsomorphisms(self):
"""
Test the Group.findSubgraphIsomorphisms() method.
"""
adjlist = """
1 *1 [Cs,Cd] u0
"""
group = Group().fromAdjacencyList(adjlist)
result = self.group.findSubgraphIsomorphisms(group)
self.assertEqual(len(result), 1)
for atom1, atom2 in result[0].iteritems():
self.assertTrue(atom1 in self.group.atoms)
self.assertTrue(atom2 in group.atoms)
self.assertTrue(atom1.equivalent(atom2))
def testPickle(self):
"""
Test that a Group object can be successfully pickled and
unpickled with no loss of information.
"""
import cPickle
group = cPickle.loads(cPickle.dumps(self.group))
self.assertEqual(len(self.group.atoms), len(group.atoms))
for atom0, atom in zip(group.atoms, self.group.atoms):
self.assertTrue(atom0.equivalent(atom))
self.assertTrue(self.group.isIsomorphic(group))
self.assertTrue(group.isIsomorphic(self.group))
def testCreateAndConnectAtom(self):
"""
Tests createAndConnectAtom method
"""
adjlist1 = """
1 *1 C u0 {2,S}
2 *2 C u0 {1,S}
"""
answer1 = """
1 *1 C u0 {2,S} {3,B}
2 *2 C u0 {1,S}
3 Cb u0 {1,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
answer1 = Group().fromAdjacencyList(answer1)
atom1 = group1.getLabeledAtom("*1")
newAtom = group1.createAndConnectAtom(atomtypes = ["Cb"], connectingAtom = atom1, bondOrders = ["B"])
self.assertTrue(group1.isIsomorphic(answer1))
answer2 = """
1 *1 C u0 {2,S} {3,[S,D]}
2 *2 C u0 {1,S}
3 [Cs,Cd] u0 {1,[S,D]}
"""
#Test that wildcards work alright
group2 = Group().fromAdjacencyList(adjlist1)
answer2 = Group().fromAdjacencyList(answer2)
atom1 = group2.getLabeledAtom("*1")
newAtom = group2.createAndConnectAtom(atomtypes = ["Cs", "Cd"], connectingAtom = atom1, bondOrders = ["S","D"])
self.assertTrue(group2.isIsomorphic(answer2))
def testAddImplicitAtomsFromAtomType(self):
"""
test Group.addImplicitAtomsFromAtomType() method
"""
#basic test adding oDouble
adjlist1 = """
1 *1 CO u0
"""
adjlist2 = """
1 *1 CO u0 {2,D}
2 O u0 {1,D}
"""
group1 = Group().fromAdjacencyList(adjlist1)
group2 = Group().fromAdjacencyList(adjlist2)
newGroup = group1.addImplicitAtomsFromAtomType()
self.assertTrue(group2.isIsomorphic(newGroup))
#testing the allDouble match (more complicated
adjlist3 = """
1 *1 Cdd u0
"""
adjlist4 = """
1 *1 Cdd u0 {2,D} {3,D}
2 C u0 {1,D}
3 C u0 {1,D}
"""
group3 = Group().fromAdjacencyList(adjlist3)
group4 = Group().fromAdjacencyList(adjlist4)
newGroup =group3.addImplicitAtomsFromAtomType()
self.assertTrue(group4.isIsomorphic(newGroup))
#test adding a triple bond
adjlist5 = """
1 *1 Ct u0
"""
adjlist6 = """
1 *1 Ct u0 {2,T}
2 C u0 {1,T}
"""
group5 = Group().fromAdjacencyList(adjlist5)
group6 = Group().fromAdjacencyList(adjlist6)
newGroup =group5.addImplicitAtomsFromAtomType()
self.assertTrue(group6.isIsomorphic(newGroup))
#test addition of lone pairs
adjlist7 = """
1 *1 N1d u0
"""
adjlist8 = """
1 *1 N1d u0 p2 {2,D}
2 C u0 {1,D}
"""
group7 = Group().fromAdjacencyList(adjlist7)
group8 = Group().fromAdjacencyList(adjlist8)
newGroup = group7.addImplicitAtomsFromAtomType()
self.assertTrue(group8.isIsomorphic(newGroup))
#test multiple implicit atoms at a time
adjlist9 = """
1 *1 Cd u0 {2,S}
2 Ct u0 {1,S}
"""
adjlist10 = """
1 *1 C u0 {2,S} {3,D}
2 Ct u0 {1,S} {4,T}
3 C u0 {1,D}
4 C u0 {2,T}
"""
group9 = Group().fromAdjacencyList(adjlist9)
group10 = Group().fromAdjacencyList(adjlist10)
newGroup =group9.addImplicitAtomsFromAtomType()
self.assertTrue(group10.isIsomorphic(newGroup))
def testClassifyBenzeneCarbons(self):
"""
Tests the method classifyingBenzeneCarbons
"""
#This tests that we classify Cb atom types correctly
adjlist1 = """
1 *1 Cb u0 {2,B}
2 *2 Cb u0 {1,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group1.classifyBenzeneCarbons()
self.assertEquals(len(cbfAtomList), 0)
for atom in group1.atoms:
self.assertIn(atom, cbAtomList)
#This tests that we classify Cbf atomtypes correctly
adjlist2 = """
1 *1 Cbf u0
"""
group2 = Group().fromAdjacencyList(adjlist2)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group2.classifyBenzeneCarbons()
self.assertIn(group2.atoms[0], cbfAtomList)
self.assertIn(group2.atoms[0], cbfAtomList1)
#This tests that we can classify Cb atoms based on bonding and not just atomtype
adjlist3 = """
1 *1 C u0 {2,B}
2 *2 C u0 {1,B} {3,B}
3 *3 C u0 {2,B}
"""
group3 = Group().fromAdjacencyList(adjlist3)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group3.classifyBenzeneCarbons()
for atom in group3.atoms:
self.assertIn(atom, cbAtomList)
#This tests that we can classify Cbf1 atoms based on bonding and not just atomtype
adjlist4 = """
1 *1 C u0 {2,B} {3,B} {4,B}
2 *2 C u0 {1,B}
3 *3 C u0 {1,B}
4 *4 C u0 {1,B}
"""
group4 = Group().fromAdjacencyList(adjlist4)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group4.classifyBenzeneCarbons()
self.assertEquals(len(cbfAtomList), 1)
self.assertEquals(len(cbfAtomList1), 1)
#This tests that we can classify Cbf2 atoms. In the following partial group, we should have:
#one Cbf2 atom, two Cbf1 atoms, and 5 Cb atoms
adjlist5 = """
1 *1 C u0 {2,B} {3,B} {4,B}
2 *2 C u0 {1,B} {5,B} {6,B}
3 *3 C u0 {1,B} {7,B} {8,B}
4 *4 C u0 {1,B}
5 *5 C u0 {2,B}
6 *6 C u0 {2,B}
7 *7 C u0 {3,B}
8 *8 C u0 {3,B}
"""
group5 = Group().fromAdjacencyList(adjlist5)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group5.classifyBenzeneCarbons()
self.assertEquals(len(cbfAtomList1), 2)
self.assertEquals(len(cbfAtomList2), 1)
self.assertEquals(len(cbAtomList), 5)
#Tests that we can classify connected Cbfs correctly. *1 should be connected to both *2 and *3
atom1 = group5.getLabeledAtom("*1")
atom2 = group5.getLabeledAtom("*2")
atom3 = group5.getLabeledAtom("*3")
self.assertIn(atom2, connectedCbfs[atom1])
self.assertIn(atom3, connectedCbfs[atom1])
self.assertIn(atom1, connectedCbfs[atom2])
self.assertIn(atom1, connectedCbfs[atom3])
def testSortByConnectivity(self):
"""
Tests sortByConnectivity method
"""
#Basic test, we should get *1, *3 *2
adjlist1 = """
1 *1 C u0 {3,B}
2 *2 C u0 {3,B}
3 *3 C u0 {1,B} {2,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
orderedAtoms = group1.sortByConnectivity(group1.atoms)
self.assertEquals([x.label for x in orderedAtoms], ["*1", "*3", "*2"])
#Check a detached case, we should get *1, *3, *4, *2, *5
adjlist2 = """
1 *1 C u0 {3,B}
2 *2 C u0 {4,S} {5,B}
3 *3 C u0 {1,B} {4,B}
4 *4 C u0 {3,B} {2,S}
5 *5 C u0 {2,B}
"""
group2 = Group().fromAdjacencyList(adjlist2)
orderedAtoms = group2.sortByConnectivity(group2.atoms)
self.assertEquals([x.label for x in orderedAtoms], ["*1", "*3", "*4", "*2", "*5"])
def testAddImplicitBenzene(self):
"""
Test the Group.addImplicitBenzene method
"""
#tests it can make a benzene molecule
adjlist1 = """
1 *1 Cb u0 {2,B}
2 *2 Cb u0 {1,B}
"""
#tests it can make a bi-phenyl
adjlist2 = """
1 *1 Cb u0 {2,S}
2 *2 Cb u0 {1,S}
"""
#tests it can make a napthalene
adjlist3 = """
1 *1 Cbf u0
"""
#Test handling of Cbf2 atoms
adjlist4 = """
1 *1 Cbf u0 p2 c0 {2,B}
2 *2 Cbf u0 p0 c0 {1,B} {3,B}
3 *3 Cbf u0 p0 c0 {2,B}
"""
#test handling of heteroatoms and wildcards
adjlist5 = """
1 *1 Cbf u0 {2,B} {3,B} {4,B}
2 R!H u0 {1,B}
3 R!H u0 {1,B}
4 R!H u0 {1,B}
"""
adjlist6 = """
1 *1 Cbf u0 p2 c0 {2,B}
2 *2 Cb u0 p0 c0 {1,B} {3,B}
3 *3 Cb u0 p0 c0 {2,B} {4,S}
4 *4 O u0 p0 c0 {3,S}
"""
adjlist7="""
1 *1 Cb u0 {4,B}
2 *2 Cb u0 {3,B}
3 *3 Cb u0 {4,B} {2,B}
4 *4 Cb u0 {1,B} {3,B}
"""
benzene ="""
1 C u0 {2,B} {6,B}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {1,B}
"""
biphenyl ="""
1 C u0 {2,B} {6,B} {7,S}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {1,B}
7 C u0 {8,B} {12,B} {1,S}
8 C u0 {7,B} {9,B}
9 C u0 {8,B} {10,B}
10 C u0 {9,B} {11,B}
11 C u0 {10,B} {12,B}
12 C u0 {11,B} {7,B}
"""
naphthalene ="""
1 C u0 {2,B} {10,B}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B} {9,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {7,B}
7 C u0 {6,B} {8,B}
8 C u0 {7,B} {9,B}
9 C u0 {4,B} {8,B} {10,B}
10 C u0 {1,B} {9,B}
"""
phenanthrene = """
1 Cbf u0 p2 c0 {2,B} {7,B} {11,B}
2 Cbf u0 p0 c0 {1,B} {3,B} {5,B}
3 Cbf u0 p0 c0 {2,B} {4,B} {6,B}
4 C u0 {3,B} {8,B} {14,B}
5 C u0 {2,B} {9,B}
6 C u0 {3,B} {12,B}
7 C u0 {1,B} {8,B}
8 C u0 {4,B} {7,B}
9 C u0 {5,B} {10,B}
10 C u0 {9,B} {11,B}
11 C u0 {1,B} {10,B}
12 C u0 {6,B} {13,B}
13 C u0 {12,B} {14,B}
14 C u0 {4,B} {13,B}
"""
answer5 = """
1 *1 Cbf u0 {2,B} {3,B} {4,B}
2 R!H u0 {1,B} {5,B}
3 R!H u0 {1,B} {7,B} {10,B}
4 R!H u0 {1,B} {8,B}
5 Cb u0 {2,B} {6,B}
6 Cb u0 {5,B} {7,B}
7 Cb u0 {3,B} {6,B}
8 Cb u0 {4,B} {9,B}
9 Cb u0 {8,B} {10,B}
10 Cb u0 {3,B} {9,B}
"""
answer6="""
1 *1 Cbf u0 p2 c0 {2,B} {5,B} {8,B}
2 *2 Cb u0 p0 c0 {1,B} {3,B} {11,B}
3 *3 Cb u0 p0 c0 {2,B} {4,S} {7,B}
4 *4 O u0 p0 c0 {3,S}
5 Cb u0 {1,B} {6,B}
6 Cb u0 {5,B} {7,B}
7 Cb u0 {3,B} {6,B}
8 Cb u0 {1,B} {9,B}
9 Cb u0 {8,B} {10,B}
10 Cb u0 {9,B} {11,B}
11 Cb u0 {2,B} {10,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
group2 = Group().fromAdjacencyList(adjlist2)
group3 = Group().fromAdjacencyList(adjlist3)
group4 = Group().fromAdjacencyList(adjlist4)
group5 = Group().fromAdjacencyList(adjlist5)
group6 = Group().fromAdjacencyList(adjlist6)
group7 = Group().fromAdjacencyList(adjlist7)
benzeneGroup = Group().fromAdjacencyList(benzene)
biphenylGroup = Group().fromAdjacencyList(biphenyl)
naphthaleneGroup = Group().fromAdjacencyList(naphthalene)
phenanthreneGroup = Group().fromAdjacencyList(phenanthrene)
answer5 = Group().fromAdjacencyList(answer5)
answer6 = Group().fromAdjacencyList(answer6)
group1 = group1.addImplicitBenzene()
self.assertTrue(benzeneGroup.isIsomorphic(group1))
group2 = group2.addImplicitBenzene()
self.assertTrue(biphenylGroup.isIsomorphic(group2))
group3 = group3.addImplicitBenzene()
self.assertTrue(naphthaleneGroup.isIsomorphic(group3))
group4 = group4.addImplicitBenzene()
self.assertTrue(phenanthreneGroup.isIsomorphic(group4))
group5 = group5.addImplicitBenzene()
self.assertTrue(answer5.isIsomorphic(group5))
group6 = group6.addImplicitBenzene()
self.assertTrue(answer6.isIsomorphic(group6))
group7 = group7.addImplicitBenzene()
self.assertTrue(benzeneGroup.isIsomorphic(group7))
def testMakeSampleMolecule(self):
"""
Test the Group.makeSampleMolecule method
"""
# result = self.group.makeSampleMolecule()
# print result.multiplicity
# self.assertTrue(result.isIsomorphic(Molecule().fromSMILES('OCC')))
#tests adding implicit atoms
adjlist1 = """
1 *1 Cd u0
"""
group1 = Group().fromAdjacencyList(adjlist1)
result1 = group1.makeSampleMolecule()
self.assertTrue(result1.isIsomorphic(Molecule().fromSMILES('C=C')))
#test creating implicit benzene atoms
adjlist2 = """
1 *1 Cbf u0 {2,B}
2 Cbf u0 {1,B}
"""
group2 = Group().fromAdjacencyList(adjlist2)
result2 = group2.makeSampleMolecule()
naphthaleneMolecule = Molecule().fromSMILES('C1=CC=C2C=CC=CC2=C1')
resonanceList2=naphthaleneMolecule.generateResonanceIsomers()
self.assertTrue(any([result2.isIsomorphic(x) for x in resonanceList2]))
#test the creation of a charged species
adjlist3 = """
1 *1 N5s u0
"""
group3 = Group().fromAdjacencyList(adjlist3)
result3 = group3.makeSampleMolecule()
self.assertTrue(result3.isIsomorphic(Molecule().fromSMILES('[NH4+]')))
#test creation of charged species when some single bonds present
adjlist4 = """
1 *2 [N5s,N5d] u0 {2,S} {3,S}
2 *3 R!H u1 {1,S}
3 *4 H u0 {1,S}
"""
group4 = Group().fromAdjacencyList(adjlist4)
result4 = group4.makeSampleMolecule()
self.assertTrue(result4.isIsomorphic(Molecule().fromSMILES('[NH3+][CH2]')))
def testIsBenzeneExplicit(self):
"""
Test the Group.isBenzeneExplicit method
"""
adjlist1 = """
1 *1 Cb u0 {2,B}
2 *2 Cb u0 {1,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
self.assertFalse(group1.isBenzeneExplicit())
benzene ="""
1 C u0 {2,B} {6,B}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {1,B}
"""
benzene = Group().fromAdjacencyList(benzene)
self.assertTrue(benzene.isBenzeneExplicit())
def test_repr_png(self):
"""Test that a png representation can be created."""
adjlist = """
1 *1 [C,Cd,Ct,CO,CS,Cb] u1 {2,[S,D,T,B]}
2 *2 [C,Cd,Ct,CO,CS,Cb] u0 {1,[S,D,T,B]} {3,[S,D,T,B]}
3 *3 [C,Cd,Ct,CO,CS,Cb] u0 {2,[S,D,T,B]} {4,[S,D,T,B]}
4 *4 [C,Cd,Ct,CO,CS,Cb] u0 {3,[S,D,T,B]}
"""
group = Group().fromAdjacencyList(adjlist)
result = group._repr_png_()
self.assertIsNotNone(result)
def testAddImplicitAtomsFromAtomType(self):
"""
test Group.addImplicitAtomsFromAtomType() method
"""
#basic test adding oDouble
adjlist1 = """
1 *1 CO u0
"""
adjlist2 = """
1 *1 CO u0 {2,D}
2 O u0 {1,D}
"""
group1 = Group().fromAdjacencyList(adjlist1)
group2 = Group().fromAdjacencyList(adjlist2)
newGroup = group1.addImplicitAtomsFromAtomType()
self.assertTrue(group2.isIsomorphic(newGroup))
#testing the allDouble match (more complicated
adjlist3 = """
1 *1 Cdd u0
"""
adjlist4 = """
1 *1 Cdd u0 {2,D} {3,D}
2 C u0 {1,D}
3 C u0 {1,D}
"""
group3 = Group().fromAdjacencyList(adjlist3)
group4 = Group().fromAdjacencyList(adjlist4)
newGroup =group3.addImplicitAtomsFromAtomType()
self.assertTrue(group4.isIsomorphic(newGroup))
#test adding a triple bond
adjlist5 = """
1 *1 Ct u0
"""
adjlist6 = """
1 *1 Ct u0 {2,T}
2 C u0 {1,T}
"""
group5 = Group().fromAdjacencyList(adjlist5)
group6 = Group().fromAdjacencyList(adjlist6)
newGroup =group5.addImplicitAtomsFromAtomType()
self.assertTrue(group6.isIsomorphic(newGroup))
#test addition of lone pairs
adjlist7 = """
1 *1 N1d u0
"""
adjlist8 = """
1 *1 N1d u0 p2 {2,D}
2 C u0 {1,D}
"""
group7 = Group().fromAdjacencyList(adjlist7)
group8 = Group().fromAdjacencyList(adjlist8)
newGroup = group7.addImplicitAtomsFromAtomType()
self.assertTrue(group8.isIsomorphic(newGroup))
#test multiple implicit atoms at a time
adjlist9 = """
1 *1 Cd u0 {2,S}
2 Ct u0 {1,S}
"""
adjlist10 = """
1 *1 C u0 {2,S} {3,D}
2 Ct u0 {1,S} {4,T}
3 C u0 {1,D}
4 C u0 {2,T}
"""
group9 = Group().fromAdjacencyList(adjlist9)
group10 = Group().fromAdjacencyList(adjlist10)
newGroup =group9.addImplicitAtomsFromAtomType()
self.assertTrue(group10.isIsomorphic(newGroup))
class TestGroup(unittest.TestCase):
"""
Contains unit tests of the Graph class.
"""
def setUp(self):
self.adjlist = """
1 *2 [Cs,Cd] u0 {2,[S,D]} {3,S}
2 *1 [Os,Od] u0 {1,[S,D]}
3 R!H u0 {1,S}
"""
self.group = Group().fromAdjacencyList(self.adjlist)
def testClearLabeledAtoms(self):
"""
Test the Group.clearLabeledAtoms() method.
"""
self.group.clearLabeledAtoms()
for atom in self.group.atoms:
self.assertEqual(atom.label, '')
def testContainsLabeledAtom(self):
"""
Test the Group.containsLabeledAtom() method.
"""
for atom in self.group.atoms:
if atom.label != '':
self.assertTrue(self.group.containsLabeledAtom(atom.label))
self.assertFalse(self.group.containsLabeledAtom('*3'))
self.assertFalse(self.group.containsLabeledAtom('*4'))
self.assertFalse(self.group.containsLabeledAtom('*5'))
self.assertFalse(self.group.containsLabeledAtom('*6'))
def testGetLabeledAtom(self):
"""
Test the Group.getLabeledAtom() method.
"""
for atom in self.group.atoms:
if atom.label != '':
self.assertEqual(atom, self.group.getLabeledAtom(atom.label))
try:
self.group.getLabeledAtom('*3')
self.fail('Unexpected successful return from Group.getLabeledAtom() with invalid atom label.')
except ValueError:
pass
def testGetLabeledAtoms(self):
"""
Test the Group.getLabeledAtoms() method.
"""
labeled = self.group.getLabeledAtoms()
for atom in self.group.atoms:
if atom.label != '':
self.assertTrue(atom.label in labeled)
self.assertTrue(atom in labeled.values())
else:
self.assertFalse(atom.label in labeled)
self.assertFalse(atom in labeled.values())
def testFromAdjacencyList(self):
"""
Test the Group.fromAdjacencyList() method.
"""
atom1, atom2, atom3 = self.group.atoms
self.assertTrue(self.group.hasBond(atom1,atom2))
self.assertTrue(self.group.hasBond(atom1,atom3))
self.assertFalse(self.group.hasBond(atom2,atom3))
bond12 = atom1.bonds[atom2]
bond13 = atom1.bonds[atom3]
self.assertTrue(atom1.label == '*2')
self.assertTrue(atom1.atomType[0].label in ['Cs','Cd'])
self.assertTrue(atom1.atomType[1].label in ['Cs','Cd'])
self.assertTrue(atom1.radicalElectrons == [0])
self.assertTrue(atom2.label == '*1')
self.assertTrue(atom2.atomType[0].label in ['Os','Od'])
self.assertTrue(atom2.atomType[1].label in ['Os','Od'])
self.assertTrue(atom2.radicalElectrons == [0])
self.assertTrue(atom3.label == '')
self.assertTrue(atom3.atomType[0].label == 'R!H')
self.assertTrue(atom3.radicalElectrons == [0])
self.assertTrue(bond12.order == ['S','D'])
self.assertTrue(bond13.order == ['S'])
def testToAdjacencyList(self):
"""
Test the Group.toAdjacencyList() method.
"""
adjlist = self.group.toAdjacencyList()
self.assertEqual(adjlist.strip(), self.adjlist.strip(),adjlist)
def testIsIsomorphic(self):
"""
Test the Group.isIsomorphic() method.
"""
adjlist = """
1 *1 [Os,Od] u0 {3,[S,D]}
2 R!H u0 {3,S}
3 *2 [Cs,Cd] u0 {1,[S,D]} {2,S}
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isIsomorphic(group))
self.assertTrue(group.isIsomorphic(self.group))
def testFindIsomorphism(self):
"""
Test the Group.findIsomorphism() method.
"""
adjlist = """
1 *1 [Os,Od] u0 {3,[S,D]}
2 R!H u0 {3,S}
3 *2 [Cs,Cd] u0 {1,[S,D]} {2,S}
"""
group = Group().fromAdjacencyList(adjlist)
result = self.group.findIsomorphism(group)
self.assertEqual(len(result), 1)
for atom1, atom2 in result[0].items():
self.assertTrue(atom1 in self.group.atoms)
self.assertTrue(atom2 in group.atoms)
self.assertTrue(atom1.equivalent(atom2))
for atom3 in atom1.bonds:
atom4 = result[0][atom3]
self.assertTrue(atom4 in atom2.bonds)
self.assertTrue(atom3.equivalent(atom4))
bond1 = atom1.bonds[atom3]
bond2 = atom2.bonds[atom4]
self.assertTrue(bond1.equivalent(bond2))
def testIsSubgraphIsomorphic(self):
"""
Test the Group.isSubgraphIsomorphic() method.
"""
adjlist = """
1 *1 [Cs,Cd] u0
"""
group = Group().fromAdjacencyList(adjlist)
self.assertTrue(self.group.isSubgraphIsomorphic(group))
self.assertFalse(group.isIsomorphic(self.group))
def testFindSubgraphIsomorphisms(self):
"""
Test the Group.findSubgraphIsomorphisms() method.
"""
adjlist = """
1 *1 [Cs,Cd] u0
"""
group = Group().fromAdjacencyList(adjlist)
result = self.group.findSubgraphIsomorphisms(group)
self.assertEqual(len(result), 1)
for atom1, atom2 in result[0].iteritems():
self.assertTrue(atom1 in self.group.atoms)
self.assertTrue(atom2 in group.atoms)
self.assertTrue(atom1.equivalent(atom2))
def testPickle(self):
"""
Test that a Group object can be successfully pickled and
unpickled with no loss of information.
"""
import cPickle
group = cPickle.loads(cPickle.dumps(self.group))
self.assertEqual(len(self.group.atoms), len(group.atoms))
for atom0, atom in zip(group.atoms, self.group.atoms):
self.assertTrue(atom0.equivalent(atom))
self.assertTrue(self.group.isIsomorphic(group))
self.assertTrue(group.isIsomorphic(self.group))
def testClassifyBenzeneCarbons(self):
"""
Tests the method classifyingBenzeneCarbons
"""
#This tests that we classify Cb atom types correctly
adjlist1 = """
1 *1 Cb u0 {2,B}
2 *2 Cb u0 {1,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group1.classifyBenzeneCarbons()
self.assertEquals(len(cbfAtomList), 0)
for atom in group1.atoms:
self.assertIn(atom, cbAtomList)
#This tests that we classify Cbf atomtypes correctly
adjlist2 = """
1 *1 Cbf u0
"""
group2 = Group().fromAdjacencyList(adjlist2)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group2.classifyBenzeneCarbons()
self.assertIn(group2.atoms[0], cbfAtomList)
self.assertIn(group2.atoms[0], cbfAtomList1)
#This tests that we can classify Cb atoms based on bonding and not just atomtype
adjlist3 = """
1 *1 C u0 {2,B}
2 *2 C u0 {1,B} {3,B}
3 *3 C u0 {2,B}
"""
group3 = Group().fromAdjacencyList(adjlist3)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group3.classifyBenzeneCarbons()
for atom in group3.atoms:
self.assertIn(atom, cbAtomList)
#This tests that we can classify Cbf1 atoms based on bonding and not just atomtype
adjlist4 = """
1 *1 C u0 {2,B} {3,B} {4,B}
2 *2 C u0 {1,B}
3 *3 C u0 {1,B}
4 *4 C u0 {1,B}
"""
group4 = Group().fromAdjacencyList(adjlist4)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group4.classifyBenzeneCarbons()
self.assertEquals(len(cbfAtomList), 1)
self.assertEquals(len(cbfAtomList1), 1)
#This tests that we can classify Cbf2 atoms. In the following partial group, we should have:
#one Cbf2 atom, two Cbf1 atoms, and 5 Cb atoms
adjlist5 = """
1 *1 C u0 {2,B} {3,B} {4,B}
2 *2 C u0 {1,B} {5,B} {6,B}
3 *3 C u0 {1,B} {7,B} {8,B}
4 *4 C u0 {1,B}
5 *5 C u0 {2,B}
6 *6 C u0 {2,B}
7 *7 C u0 {3,B}
8 *8 C u0 {3,B}
"""
group5 = Group().fromAdjacencyList(adjlist5)
(cbAtomList, cbfAtomList, cbfAtomList1, cbfAtomList2, connectedCbfs)=group5.classifyBenzeneCarbons()
self.assertEquals(len(cbfAtomList1), 2)
self.assertEquals(len(cbfAtomList2), 1)
self.assertEquals(len(cbAtomList), 5)
#Tests that we can classify connected Cbfs correctly. *1 should be connected to both *2 and *3
atom1 = group5.getLabeledAtom("*1")
atom2 = group5.getLabeledAtom("*2")
atom3 = group5.getLabeledAtom("*3")
self.assertIn(atom2, connectedCbfs[atom1])
self.assertIn(atom3, connectedCbfs[atom1])
self.assertIn(atom1, connectedCbfs[atom2])
self.assertIn(atom1, connectedCbfs[atom3])
def testAddImplicitBenzene(self):
"""
Test the Group.addImplicitBenzene method
"""
#tests it can make a benzene molecule
adjlist1 = """
1 *1 Cb u0 {2,B}
2 *2 Cb u0 {1,B}
"""
#tests it can make a bi-phenyl
adjlist2 = """
1 *1 Cb u0 {2,S}
2 *2 Cb u0 {1,S}
"""
#tests it can make a napthalene
adjlist3 = """
1 *1 Cbf u0
"""
#Test handling of Cbf2 atoms
adjlist4 = """
1 *1 Cbf u0 p2 c0 {2,B}
2 *2 Cbf u0 p0 c0 {1,B} {3,B}
3 *3 Cbf u0 p0 c0 {2,B}
"""
#test handling of heteroatoms and wildcards
adjlist5 = """
1 *1 Cbf u0 {2,B} {3,B} {4,B}
2 R!H u0 {1,B}
3 R!H u0 {1,B}
4 R!H u0 {1,B}
"""
adjlist6 = """
1 *1 Cbf u0 p2 c0 {2,B}
2 *2 Cb u0 p0 c0 {1,B} {3,B}
3 *3 Cb u0 p0 c0 {2,B} {4,S}
4 *4 O u0 p0 c0 {3,S}
"""
adjlist7="""
1 *1 Cb u0 {4,B}
2 *2 Cb u0 {3,B}
3 *3 Cb u0 {4,B} {2,B}
4 *4 Cb u0 {1,B} {3,B}
"""
benzene ="""
1 C u0 {2,B} {6,B}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {1,B}
"""
biphenyl ="""
1 C u0 {2,B} {6,B} {7,S}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {1,B}
7 C u0 {8,B} {12,B} {1,S}
8 C u0 {7,B} {9,B}
9 C u0 {8,B} {10,B}
10 C u0 {9,B} {11,B}
11 C u0 {10,B} {12,B}
12 C u0 {11,B} {7,B}
"""
naphthalene ="""
1 C u0 {2,B} {10,B}
2 C u0 {1,B} {3,B}
3 C u0 {2,B} {4,B}
4 C u0 {3,B} {5,B} {9,B}
5 C u0 {4,B} {6,B}
6 C u0 {5,B} {7,B}
7 C u0 {6,B} {8,B}
8 C u0 {7,B} {9,B}
9 C u0 {4,B} {8,B} {10,B}
10 C u0 {1,B} {9,B}
"""
phenanthrene = """
1 Cbf u0 p2 c0 {2,B} {7,B} {11,B}
2 Cbf u0 p0 c0 {1,B} {3,B} {5,B}
3 Cbf u0 p0 c0 {2,B} {4,B} {6,B}
4 C u0 {3,B} {8,B} {14,B}
5 C u0 {2,B} {9,B}
6 C u0 {3,B} {12,B}
7 C u0 {1,B} {8,B}
8 C u0 {4,B} {7,B}
9 C u0 {5,B} {10,B}
10 C u0 {9,B} {11,B}
11 C u0 {1,B} {10,B}
12 C u0 {6,B} {13,B}
13 C u0 {12,B} {14,B}
14 C u0 {4,B} {13,B}
"""
answer5 = """
1 *1 Cbf u0 {2,B} {3,B} {4,B}
2 R!H u0 {1,B} {5,B}
3 R!H u0 {1,B} {7,B} {10,B}
4 R!H u0 {1,B} {8,B}
5 Cb u0 {2,B} {6,B}
6 Cb u0 {5,B} {7,B}
7 Cb u0 {3,B} {6,B}
8 Cb u0 {4,B} {9,B}
9 Cb u0 {8,B} {10,B}
10 Cb u0 {3,B} {9,B}
"""
answer6="""
1 *1 Cbf u0 p2 c0 {2,B} {5,B} {8,B}
2 *2 Cb u0 p0 c0 {1,B} {3,B} {11,B}
3 *3 Cb u0 p0 c0 {2,B} {4,S} {7,B}
4 *4 O u0 p0 c0 {3,S}
5 Cb u0 {1,B} {6,B}
6 Cb u0 {5,B} {7,B}
7 Cb u0 {3,B} {6,B}
8 Cb u0 {1,B} {9,B}
9 Cb u0 {8,B} {10,B}
10 Cb u0 {9,B} {11,B}
11 Cb u0 {2,B} {10,B}
"""
group1 = Group().fromAdjacencyList(adjlist1)
group2 = Group().fromAdjacencyList(adjlist2)
group3 = Group().fromAdjacencyList(adjlist3)
group4 = Group().fromAdjacencyList(adjlist4)
group5 = Group().fromAdjacencyList(adjlist5)
group6 = Group().fromAdjacencyList(adjlist6)
group7 = Group().fromAdjacencyList(adjlist7)
benzeneGroup = Group().fromAdjacencyList(benzene)
biphenylGroup = Group().fromAdjacencyList(biphenyl)
naphthaleneGroup = Group().fromAdjacencyList(naphthalene)
phenanthreneGroup = Group().fromAdjacencyList(phenanthrene)
answer5 = Group().fromAdjacencyList(answer5)
answer6 = Group().fromAdjacencyList(answer6)
group1 = group1.addImplicitBenzene()
self.assertTrue(benzeneGroup.isIsomorphic(group1))
group2 = group2.addImplicitBenzene()
self.assertTrue(biphenylGroup.isIsomorphic(group2))
group3 = group3.addImplicitBenzene()
self.assertTrue(naphthaleneGroup.isIsomorphic(group3))
group4 = group4.addImplicitBenzene()
self.assertTrue(phenanthreneGroup.isIsomorphic(group4))
group5 = group5.addImplicitBenzene()
self.assertTrue(answer5.isIsomorphic(group5))
group6 = group6.addImplicitBenzene()
self.assertTrue(answer6.isIsomorphic(group6))
group7 = group7.addImplicitBenzene()
self.assertTrue(benzeneGroup.isIsomorphic(group7))
