def test2():
smiles, id = "OC1=C(Cl)C=CC=C1[N+]", 1
mol = Smiles.smilin(smiles)
print mol.cansmiles()
for atom in mol.atoms:
print atom.index
def cansmiles(self) :
"""
affiche en canonical smiles une brique
"""
# sys.stderr.write("Brique.cansmiles: will call molecule.cansmiles() ...\n")
a = self.molecule.cansmiles()
m = Smiles.smilin("".join(re.split("[\[\]+-]","".join(re.split("H[0-9]*",a)))))
return m.cansmiles()
def checkSmiles(fname):
from frowns import Smiles
try:
fSmiles = open(fname, "r")
lines = fSmiles.readlines()
fSmiles.close()
asmiles = Smiles.smilin(lines[0].split()[0])
return True
except:
return False
def test():
from frowns import Smiles
import time
smiles, id = "OC1=C(Cl)C=CC=C1[N+]C2CCC3CC3CCC2", 1
mol = Smiles.smilin(smiles, transforms=[])
t1 = time.time()
for i in range(100):
atoms, bonds = getAtomsBondsInRings(mol)
print (time.time() - t1)/100
def test():
from frowns import Smiles
import time
smiles, id = "OC1=C(Cl)C=CC=C1[N+]C2CCC3CC3CCC2", 1
mol = Smiles.smilin(smiles, transforms=[])
assert frerejaqueNumber(mol) == 3
t1 = time.time()
for i in range(100):
frerejaqueNumber(mol)
print (time.time() - t1)/100
def next(self):
if not self.smiles:
return None
smile = self.smiles.pop()
m = Smiles.smilin(smile)
#addCoords(m)
#toplevel = Toplevel(self.tk)
if self.drawer:
self.drawer.frame.pack_forget()
drawer = self.drawer=TkMoleculeDrawer.MoleculeDrawer(self.tk, m, name=smile)
drawer.pack(expand=1, fill=BOTH)
def test():
from frowns import Smiles
strings = ["Cl/C(F)=C(Br)/I",
#"Cl\C)(F)=C(Br)\I", <- fix parsing bug
#"Cl\C(\F)=C(/Br)\I",
"Cl\C(F)=C(Br)\I",
"Cl\C(F)=C(Br)/I",
"Cl/C(F)=C(Br)\I"
]
for s in strings:
print s
m = Smiles.smilin(s)
assignStereo(m)
def testPath():
from frowns import Smiles
mol = Smiles.smilin("C1CCCC1CCCC2CCCC3CCC3CCC2")
rings = {}
spans = [Path(mol.atoms[0], rings)]
while spans:
new = []
for span in spans:
new += span.next()
if len(rings) == 1:
break
if len(rings) == 1:
break
spans = new
print rings
def test():
from frowns import Smiles
import time
h = BuildMatcher()
for smi in ["C",
"CC",
"c",
"C(N)O",
"[O]",
"c1ccccc1",
]:
matcher = compile(smi)
print matcher.dump()
smiles = Smiles.smilin(smi)
pathset = matcher.match(smiles)
atom.hybrid = SP2
continue
symbol = atom.symbol
hcount = atom.valences[0] - atom.sumBondOrders()
connections = len(atom.bonds) + hcount
charge = atom.charge
if atom.symbol in ["C", "N"] and connections == 2:
charge = ANY
atom.hybrid = _hybrid.get((symbol, connections, charge), "")
#print atom, `atom`, hcount, atom.hybrid
if __name__ == "__main__":
from frowns import Smiles
from frowns.perception import TrustedSmiles, sssr
smiles = "CC(=O)OC1C(N(c2c(CC1c1ccc(OC)cc1)cc(cc2)Oc1ccccc1)CCN(C)C)=O"
smiles = "O=C1NC(N)=NC2=C1N=CNC2"
#smiles = "O=C1C=CC(=O)C=C1"
print smiles
mol = Smiles.smilin(smiles, [sssr.sssr])
getHybridAtoms(mol)
for cycle in mol.cycles:
print [(atom, atom.symbol, atom.hybrid) for atom in cycle.atoms]
atoms, bonds = toposort(atoms)
rings.append((atoms, bonds))
cycles.append(Cycle(atoms, bonds))
molecule.rings = rings
molecule.cycles = cycles
return molecule
if __name__ == "__main__":
from frowns import Smiles
import time
data = open("../Working/frowns/test/data/NCI_small").read()
count = 0
i = 0
for line in data.split("\n"):
i += 1
smiles = line.split()[0]
m = Smiles.smilin(smiles)
t1 = time.time()
m = sssr(m)
t2 = time.time()
count += (t2-t1)
assert len(m.cycles) == len(m.rings), "failed %s in %f average"%(float(count)/i)
print "average sssr", float(count)/i
print len(molecule.atoms)
print connections
raise
rings = potentialCycles #checkRings(potentialCycles)
molecule.rings = rings
molecule.cycles = [Cycle(atoms, bonds) for atoms, bonds in rings]
return molecule
if __name__ == "__main__":
from frowns import Smiles
import time
data = open("../Working/frowns/test/data/NCI_small").read()
count = 0
i = 0
for line in data.split("\n"):
i += 1
smiles = line.split()[0]
m = Smiles.smilin(smiles)
t1 = time.time()
m = sssr(m)
t2 = time.time()
count += (t2 - t1)
assert len(m.cycles) == len(
m.rings), "failed %s in %f average" % (float(count) / i)
print "average sssr", float(count) / i
from frowns import Smiles
print "*"*33
print "benzene with default transforms"
mol = Smiles.smilin("c1ccccc1")
print mol.cansmiles()
print "atoms"
for atom in mol.atoms:
print "\tsymbol %s hcount %s aromatic %s"%(
atom.symbol, atom.hcount, atom.aromatic)
print "bonds"
for bond in mol.bonds:
print "\tbondorder %s, bondtype %s fixed %s"%(
bond.bondorder, bond.bondtype, bond.fixed)
print "*"*33
print "benzene with no transforms"
mol = Smiles.smilin("c1ccccc1", transforms=[])
print mol.cansmiles()
print "atoms"
for atom in mol.atoms:
print "\tsymbol %s hcount %s aromatic %s"%(
atom.symbol, atom.hcount, atom.aromatic)
print "bonds"
for bond in mol.bonds:
print "\tbondorder %s, bondtype %s fixed %s"%(
bond.bondorder, bond.bondtype, bond.fixed)
from frowns import Smiles
m = Smiles.smilin("N[C@](C)(F)C(=O)O")
print "initial smiles:", m.arbsmiles(isomeric=1)
print "canonical smiles:", m.cansmiles(isomeric=1)
print
m = Smiles.smilin("[C@H](C)(F)(O)")
print "initial smiles:", m.arbsmiles(isomeric=1)
print "canonical smiles:", m.cansmiles(isomeric=1)
from frowns import Smiles
mol = Smiles.smilin("c1ccccc1")
print mol.cansmiles()
print "atoms"
for atom in mol.atoms:
print atom.symbol, atom.hcount, atom.aromatic
print "bonds"
for bond in mol.bonds:
print bond.bondorder, bond.bondtype
#is the coordinates of hydrogen stored somewhere in the
#atom the hydrogen is attached to?
## hatom.x =
## hatom.y =
## hatom.z =
#does the hcount need to be changed?
## atom.hcount -= 1
mol.add_atom(hatom)
bond = Bond()
mol.add_bond(bond, atom, hatom)
#reset atom indices
index = 0
for atom in mol.atoms:
atom.index = index
index += 1
mol.explicitHydrogens = 1 #change flag to let know that hydrogens are explicit in this mol
return mol
from frowns import Smiles
m = Smiles.smilin("CCCCc1ccccc1")
m.explicitHydrogens = 0
addHydrogens(m)
print m.cansmiles()
def nanotube(width, height):
N = width * 2
first, middle, last = make_lines(width * 2)
lines = [first]
for i in range(height - 1):
lines.append(middle)
lines.append(last)
return ".".join(lines)
tube = nanotube(4, 100)
print tube
from frowns import Smiles
import time
#try:
# import psyco
# psyco.full()
#except:
# print "nope"
# pass
Smiles.smilin("c1cccc1")
t1 = time.time()
mol = Smiles.smilin(tube)
t2 = time.time()
print mol.cansmiles()
print t2 - t1
from frowns import Smiles
mol = Smiles.smilin("C(\C)(C)=C(/C)(C)")
print mol.cansmiles()
mol = Smiles.smilin("F/C=C/F")
print mol.cansmiles()
for bond in mol.bonds:
print bond.symbol
print bond.equiv_class
from Tkinter import *
from frowns.Depict.MoleculeDock import MoleculeDock
from frowns import Smiles
# read in a molecule
smiles = [
"c1ccccc1C=O",
"c1ccc2cc1cccc2",
"CCN",
"CCCC(=O)NNCC",
"CCC(CC)([CH](OC(N)=O)C1=CC=CC=C1)C2=CC=CC=C2",
"ON=C(CC1=CC=CC=C1)[CH](C#N)C2=CC=CC=C2",
"C1=CC=C(C=C1)C(N=C(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4",
]
# create the moleculedock widget and place it
# into a tk window
tk = top = Tk()
m = MoleculeDock(top, cols=4)
m.pack(fill=BOTH, expand=1)
for smile in smiles:
mol = Smiles.smilin(smile)
mol.name = smile
m.addMolecule(mol)
mainloop()
from frowns.perception import sssr, TrustedSmiles
from frowns import Smiles
s = 'c12[nH]c(c3ccc(CC)cc3)[nH0]c2[nH0]ccc1'
m = Smiles.smilin(s, transforms=[sssr.sssr, TrustedSmiles.trusted_smiles])
print m.arbsmarts()
for atom in m.atoms:
print atom.symbol, atom.hcount, atom.explicit_hcount
_recurse(next, visited)
def components(molecule):
atoms = {}
for atom in molecule.atoms:
atoms[atom] = 1
components = []
while atoms:
start = atoms.keys()[0]
visited = {start:1}
_recurse(start, visited)
bonds = {}
for atom in visited.keys():
del atoms[atom]
for bond in atom.bonds:
bonds[bond] = 1
components.append((visited.keys(), bonds.keys()))
return components
if __name__ == "__main__":
from frowns import Smiles
mol = Smiles.smilin("CCC.NNN")
print components(mol)
print mol.cansmiles()
from frowns import Smiles from frowns.perception import figueras badsmi = "C1=CC(=C2C=CC=C(N=CC34C5=C6C7=C3[Fe]456789%10%11C%12C8=C9C%10=C%11%12)C2=C1)N=CC%13%14C%15=C%16C%17=C%13[Fe]%14%15%16%17%18%19%20%21C%22C%18=C%19C%20=C%21%22" m1 = Smiles.smilin(badsmi, transforms=[figueras.sssr]) m2 = Smiles.smilin(badsmi) print len(m1.cycles) print len(m2.cycles)
from Tkinter import *
from frowns.Depict.MoleculeDock import MoleculeDock
from frowns import Smiles
# read in a molecule
smiles = ["c1ccccc1C=O", "c1ccc2cc1cccc2",
"CCN", "CCCC(=O)NNCC"]
# create the moleculedock widget and place it
# into a tk window
tk = top = Tk()
m = MoleculeDock(top)
m.pack(fill=BOTH, expand=1)
for smile in smiles:
mol = Smiles.smilin(smile)
m.addMolecule(mol)
mainloop()
import Components
def computeMW(mol):
"""mol -> mw of largest fragment, mw of total molecule"""
fragments = []
total = 0.0
if not mol.atoms: return 0.0, 0.0
for atoms, bonds in Components.components(mol):
mw = 0.0
for atom in atoms:
mw += atom.mass + atom.hcount
fragments.append(mw)
total += mw
largest = max(fragments)
return largest, total
if __name__ == "__main__":
from frowns import Smiles
mol = Smiles.smilin("CCC.NNN.Br")
print computeMW(mol)
def createFP(self, molecule):
p = SplitFingerprint(self.maxdepth, self.integersPerAtoms)
paths = generatePaths(molecule, maxdepth=self.maxdepth)
paths.sort()
for length, s in paths:
p.addPath(length, s)
return p
if __name__ == "__main__":
from frowns import Smiles
mol = Smiles.smilin("CCCc1cc[nH]c1")
mol2 = Smiles.smilin("c1cc[nH]c1")
paths = generatePaths(mol)
pathLengths = {}
for p in paths:
l, s = p
pathLengths[l] = pathLengths.get(l, []) + [s]
generator = SplitFingerprintGenerator()
sp = generator.createFP(mol)
sp2 = generator.createFP(mol2)
assert sp in sp
assert sp2 in sp
from frowns import Smiles
mol = Smiles.smilin("c1ccccc1CCC1CC1")
index = 0
for cycle in mol.cycles:
print "cycle", index
print "\t", cycle.atoms
print "\t", cycle.bonds
index = index + 1
from frowns.perception import sssr, TrustedSmiles
from frowns import Smiles
s = "c12[nH]c(c3ccc(CC)cc3)[nH0]c2[nH0]ccc1"
m = Smiles.smilin(s, transforms=[sssr.sssr, TrustedSmiles.trusted_smiles])
print m.arbsmarts()
for atom in m.atoms:
print atom.symbol, atom.hcount, atom.explicit_hcount
def generatePaths(molecule, maxdepth=5,
name_atom=name_atom, name_bond=name_bond,
name_ring_atom=name_ring_atom, name_ring_bond=name_ring_bond,
make_rpath=0):
"""(molecule, maxdepth, *name_atom, *name_bond) -> linear paths
Generate all linear paths through a molecule up to maxdepth
change name_atom and name_bond to name the atoms and bonds
in the molecule
name_atom and name_bond must return a stringable value"""
paths = {}
for atom in molecule.atoms:
_bfswalk(atom, {atom:1}, [name_atom(atom)], [name_ring_atom(atom)], paths, 1, maxdepth,
name_atom, name_bond, name_ring_atom, name_ring_bond, make_rpath)
return paths.keys()
if __name__ == "__main__":
from frowns import Smiles
mol = Smiles.smilin("CCNc1cccc1")
paths = generatePaths(mol)
print len(paths)
print paths
ONE_STRING_PER_PATH = 1
paths = generatePaths(mol)
print len(paths)
print paths
from frowns import Smiles
print "*" * 33
print "benzene with default transforms"
mol = Smiles.smilin("c1ccccc1")
print mol.cansmiles()
print "atoms"
for atom in mol.atoms:
print "\tsymbol %s hcount %s aromatic %s" % (atom.symbol, atom.hcount,
atom.aromatic)
print "bonds"
for bond in mol.bonds:
print "\tbondorder %s, bondtype %s fixed %s" % (bond.bondorder,
bond.bondtype, bond.fixed)
print "*" * 33
print "benzene with no transforms"
mol = Smiles.smilin("c1ccccc1", transforms=[])
print mol.cansmiles()
print "atoms"
for atom in mol.atoms:
print "\tsymbol %s hcount %s aromatic %s" % (atom.symbol, atom.hcount,
atom.aromatic)
print "bonds"
for bond in mol.bonds:
print "\tbondorder %s, bondtype %s fixed %s" % (bond.bondorder,
bond.bondtype, bond.fixed)
import time
from frowns import Smiles
from frowns import Smarts
mol = Smiles.smilin("CCCCC(C)CCCC(C)CCCCCC(C)C(C)CCCCCC(C)CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCN")
pat = Smarts.compile("C*")
print len(pat.match(mol))
pat2 = Smarts.compile("[#6]")
t1 = time.time()
print len(pat2.match(mol))
t2 = time.time()
print t2-t1
t1 = time.time()
print len(pat2.match(mol))
t2 = time.time()
print t2-t1
print mol.vfgraph
_dfswalk(oatom, visitedAtoms, visitedBonds, nonPathBonds, path, paths, depth+1, mindepth, maxdepth)
while len(path) != mark:
path.pop()
while len(nonPathBonds) != markNonPathBonds:
nonPathBonds.pop()
del visitedAtoms[oatom]
del visitedBonds[bond]
def generatePaths(molecule, mindepth=6, maxdepth=7):
"""(molecule, mindepth maxdepth) -> linear paths
Generate all linear paths through a molecule from mindepth atoms
to maxdepth atoms
"""
paths = {}
for atom in molecule.atoms:
_dfswalk(atom, {atom:1}, {}, [], [atom], paths, 1, mindepth, maxdepth)
return paths.keys()
if __name__ == "__main__":
from frowns import Smiles
m = Smiles.smilin("CCCNc1ccccc1")
for paths in generatePaths(m):
print paths
from frowns import Smiles
mol = Smiles.smilin("C1CC=1")
print mol.arbsmiles()
# Just some simple postive testing for smarts
# negative testing is a little harder to come by
from frowns import Smiles
from frowns import Smarts
mol = Smiles.smilin("C1CCCCC1CCN(=O)OCCN=C")
# search for ring atoms
matcher = Smarts.compile("[R1]")
print matcher.dump()
pathset = matcher.match(mol)
assert pathset
print pathset.atoms
print pathset.bonds
# search for CCN=O or CCN=C
matcher = Smarts.compile("CCN=[O,C]")
print matcher.dump()
pathset = matcher.match(mol)
assert pathset
for path in pathset:
print path.atoms, path.bonds
# search for a wildcard
matcher = Smarts.compile("*=O")
print matcher.dump()
pathset = matcher.match(mol)
assert pathset
for path in pathset:
molecule = fixBonds(molecule, pyroleLike)
# add implicit hydrogens
return addHydrogens(molecule, usedPyroles)
if __name__ == "__main__":
smiles = 'C1=CC(NC=C2)=C2C=C1'
smiles = 'C1=CC(NC=C2)=C2C=C1'
smiles = 'C1C=C[NH]2C=1C=CC=C2'
smiles = 'C1[NH]C=CC=1CCC2C=CC=CC=2'
#smiles = 'C1NC=CC=1'
smiles = 'c1ccccc1'
smiles = 'CC1=CC=CC2=NC=C(C)C(=C12)Cl'
smiles = 'O=n1ccccc1'
#smiles = 'O=N1=CC=CC=C1'
from frowns import Smiles
import RingDetection
print smiles,
mol = Smiles.smilin(smiles, transforms=[RingDetection.sssr,
aromatize])
print '->', mol.cansmiles()
print "atoms"
for atom in mol.atoms:
print "\t", atom.symbol, atom.valences, atom.hcount, atom.sumBondOrders(), atom.charge, atom.aromatic
print "bonds"
for bond in mol.bonds:
print "\t", bond.bondtype, bond.bondorder, bond.aromatic
def test():
from frowns import Smiles
import RingDetection
import sssr as sssr2
import time
from frowns.Canonicalization import Disambiguate, Traverse
##mol = Smiles.smilin("C12C3C4C1C5C4C3C25CCCCCC12C3C4C1C5C4C3C25")
##mol1 = Smiles.smilin("C1O[CH]1C2=CC=CC=C2",
## transforms = [])
##print mol1.cansmiles()
smiles = "COC(=O)[CH]1C2CCC(CC2)[CH]1C(=O)OCC"
smiles = "CC1(C)[CH]2CC[CH](CC(O)=O)[CH]1C2"
smiles = "C[CH]1C(=O)O[CH]2CCN3CC=C(COC(=O)[C](C)(O)[C]1(C)O)[CH]23"
#smiles = "CC1=CC(=O)C=CC1=O"
smiles = "NC1=CC2=C(C=C1)C(=O)C3=C(C=CC=C3)C2=O"
smiles = "COC1=CC2=C(C=C1OC)[C]34CCN5CC6=CCO[CH]7CC(=O)N2[CH]3[CH]7[CH]6C[CH]45.OS(O)(=O)=O"
mol1 = Smiles.smilin(smiles,
transforms = [])
print mol1.cansmiles()
NUM = 1
t1 = time.time()
for i in range(NUM):
sssr(mol1)
t2 = time.time()
print (t2-t1)/NUM
symbols = []
for atom in mol1.atoms:
symbols.append(atom.symbol)
for atom in mol1.atoms:
atom.symbol += ".%s."%atom.index
atom.symorder = mol1.atoms.index(atom)
index = 0
for cycle in mol1.cycles:
print cycle.atoms
print cycle.bonds
for atom in cycle.atoms:
atom.symbol += "<%s>"%index
index += 1
print Traverse.draw(mol1)[0]
for atom, symbol in zip(mol1.atoms, symbols):
atom.symbol = symbol
for atom in mol1.atoms:
atom.symbol += ".%s."%atom.index
atom.symorder = mol1.atoms.index(atom)
t1 = time.time()
for i in range(NUM):
RingDetection.sssr(mol1)
t2 = time.time()
print (t2-t1)/NUM
index = 0
for cycle in mol1.cycles:
print cycle.atoms
print cycle.bonds
for atom in cycle.atoms:
atom.symbol += "<%s>"%index
index += 1
print Traverse.draw(mol1)[0]
from frowns import Smiles
m = Smiles.smilin("[CH0]")
assert m.cansmiles() == "[C]"
m = Smiles.smilin("C")
assert m.cansmiles() == "C"
from frowns import Smiles
from frowns import Smarts
from frowns.perception import sssr
from frowns.perception import RingDetection
## '*' is ok
mol=Smiles.smilin("SCCCCSCCCC",transforms=[RingDetection.sssr])
#pattern=Smarts.compile("S*CC")
##!! '~' has problem
pattern=Smarts.compile("S~C~C")
##!! pattern can't match itself
mol=Smiles.smilin("C[CH](C1=CC=CC=C1)[C](C)(C#N)C2=CC=CC=C2")
pattern = Smarts.compile(mol.arbsmarts())
print mol.arbsmarts()
pattern=Smarts.compile("CC(C1=CC=CC=C1)C(C)(C#N)C2=CC=CC=C2")
match=pattern.match(mol)
assert match
index=1
for path in match:
print "match",index
print "\tatoms",path.atoms
print "\tbond",path.bonds
index=index+1
from frowns import Smiles, Smarts
for smiles in ['OC1C=CC(=O)C=C1', 'c1ccccc1']:
mol = Smiles.smilin(smiles)
print mol.cansmiles()
print "with square brackets"
pattern = Smarts.compile('OC(C)[A]')
match = pattern.match(mol)
if match:
for path in match:
print path.atoms
print
print "without square brackets"
pattern2 = Smarts.compile('O=C(C)A')
match2 = pattern2.match(mol)
if match2:
for path2 in match2:
print path2.atoms
m = Smiles.smilin("c1ccccc1")
p = Smarts.compile("c1ccccc1")
assert p.match(m)
import sys
sys.path.append("/Users/stockwel/Working")
from frowns import Smiles
import time
from frowns.perception import RingDetection, BasicAromaticity, figueras, pysssr
transforms = [figueras.sssr,
BasicAromaticity.aromatize]
tests = [x.split()[0] for x in open("data/NCI_small")][0:100]
t1 = time.time()
for smiles in tests:
m = Smiles.smilin(smiles, transforms)
t2 = time.time()
time1 = (t2-t1)/len(tests)
print "start", t1
print "end", t2
print "elapsed", t2-t1
print "number of smiles", len(tests)
print "average molecule generation", time1
transforms = [pysssr.sssr,
BasicAromaticity.aromatize]
t1 = time.time()
for smiles in tests:
import frowns.Fingerprint
from frowns import Smiles
patterns_and_targets = (
("CCN",
("CCN", "CCNCC", "c1cccc1CCN")),
)
for pattern, targets in patterns_and_targets:
pattern_molecule = Smiles.smilin(pattern)
pfp = frowns.Fingerprint.generateFingerprint(pattern_molecule)
for target in targets:
mol = Smiles.smilin(target)
molfp = \
frowns.Fingerprint.generateFingerprint(mol)
# pfp must be "in" molfp for test to pass
assert pfp in molfp, "match %s is not in target %s!"%(pattern, target)
from frowns import Smiles
from frowns import Smarts
from frowns.perception import sssr
from frowns.perception import RingDetection
## '*' is ok
mol = Smiles.smilin("SCCCCSCCCC", transforms=[RingDetection.sssr])
#pattern=Smarts.compile("S*CC")
##!! '~' has problem
pattern = Smarts.compile("S~C~C")
##!! pattern can't match itself
mol = Smiles.smilin("C[CH](C1=CC=CC=C1)[C](C)(C#N)C2=CC=CC=C2")
pattern = Smarts.compile(mol.arbsmarts())
print mol.arbsmarts()
pattern = Smarts.compile("CC(C1=CC=CC=C1)C(C)(C#N)C2=CC=CC=C2")
match = pattern.match(mol)
assert match
index = 1
for path in match:
print "match", index
print "\tatoms", path.atoms
print "\tbond", path.bonds
index = index + 1
