Package rdkit :: Package Chem :: Package Pharm3D :: Module EmbedLib

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# Module EmbedLib

source code

Functions | [hide private]

GetAtomHeavyNeighbors(atom) returns a list of the heavy-atom neighbors of the atom passed in: | source code

ReplaceGroup(match, bounds, slop=0.01, useDirs=False, dirLength=defaultFeatLength) Adds an entry at the end of the bounds matrix for a point at the center of a multi-point feature | source code

EmbedMol(mol, bm, atomMatch=None, weight=2.0, randomSeed=-1, excludedVolumes=None) Generates an embedding for a molecule based on a bounds matrix and adds a conformer (id 0) to the molecule | source code

AddExcludedVolumes(bm, excludedVolumes, smoothIt=True) Adds a set of excluded volumes to the bounds matrix and returns the new matrix | source code

UpdatePharmacophoreBounds(bm, atomMatch, pcophore, useDirs=False, dirLength=defaultFeatLength, mol=None) loops over a distance bounds matrix and replaces the elements that are altered by a pharmacophore | source code

EmbedPharmacophore(mol, atomMatch, pcophore, randomSeed=-1, count=10, smoothFirst=True, silent=False, bounds=None, excludedVolumes=None, targetNumber=-1, useDirs=False) Generates one or more embeddings for a molecule that satisfy a pharmacophore | source code

isNaN(v) provides an OS independent way of detecting NaNs This is intended to be used with values returned from the C++ side of things. | source code

OptimizeMol(mol, bm, atomMatches=None, excludedVolumes=None, forceConstant=1200.0, maxPasses=5, verbose=False) carries out a UFF optimization for a molecule optionally subject to the constraints in a bounds matrix | source code

EmbedOne(mol, name, match, pcophore, count=1, silent=0, **kwargs) generates statistics for a molecule's embeddings | source code

MatchPharmacophoreToMol(mol, featFactory, pcophore) generates a list of all possible mappings of a pharmacophore to a molecule | source code

_getFeatDict(mol, featFactory, features) **INTERNAL USE ONLY** | source code

MatchFeatsToMol(mol, featFactory, features) generates a list of all possible mappings of each feature to a molecule | source code

CombiEnum(sequence) This generator takes a sequence of sequences as an argument and provides all combinations of the elements of the subsequences: | source code

DownsampleBoundsMatrix(bm, indices, maxThresh=4.0) removes rows from a bounds matrix that are that are greater than a threshold value away from a set of other points | source code

CoarseScreenPharmacophore(atomMatch, bounds, pcophore, verbose=False) >>> feats = [ChemicalFeatures.FreeChemicalFeature('HBondAcceptor', 'HAcceptor1', Geometry.Point3D(0.0, 0.0, 0.0)), ... | source code

Check2DBounds(atomMatch, mol, pcophore) checks to see if a particular mapping of features onto a molecule satisfies a pharmacophore's 2D restrictions | source code

_checkMatch(match, mol, bounds, pcophore, use2DLimits) **INTERNAL USE ONLY** | source code

ConstrainedEnum(matches, mol, pcophore, bounds, use2DLimits=False, index=0, soFar=[]) Enumerates the list of atom mappings a molecule has to a particular pharmacophore. | source code

MatchPharmacophore(matches, bounds, pcophore, useDownsampling=False, use2DLimits=False, mol=None, excludedVolumes=None, useDirs=False) | source code

GetAllPharmacophoreMatches(matches, bounds, pcophore, useDownsampling=0, progressCallback=None, use2DLimits=False, mol=None, verbose=False) | source code

ComputeChiralVolume(mol, centerIdx, confId=-1) Computes the chiral volume of an atom | source code

_test() | source code

Variables | [hide private]

| _times = `{}`
| logger = `logging.logger()`
| defaultFeatLength = `2.0`

Imports: RDConfig, sys, time, math, Stats, DG, Chem, numpy, MolDG, ChemicalFeatures, ChemicalForceFields, Pharmacophore, ExcludedVolume, Geometry, logging

Function Details | [hide private]

### GetAtomHeavyNeighbors(atom)

source code

    returns a list of the heavy-atom neighbors of the
    atom passed in:

    >>> m = Chem.MolFromSmiles('CCO')
    >>> l = GetAtomHeavyNeighbors(m.GetAtomWithIdx(0))
    >>> len(l)
    1
    >>> isinstance(l[0],Chem.Atom)
    True
    >>> l[0].GetIdx()
    1

    >>> l = GetAtomHeavyNeighbors(m.GetAtomWithIdx(1))
    >>> len(l)
    2
    >>> l[0].GetIdx()
    0
    >>> l[1].GetIdx()
    2

### ReplaceGroup(match, bounds, slop=0.01, useDirs=False, dirLength=defaultFeatLength)

source code

    Adds an entry at the end of the bounds matrix for a point at
    the center of a multi-point feature

    returns a 2-tuple:
      new bounds mat
      index of point added

    >>> boundsMat = numpy.array([[0.0,2.0,2.0],[1.0,0.0,2.0],[1.0,1.0,0.0]])
    >>> match = [0,1,2]
    >>> bm,idx = ReplaceGroup(match,boundsMat,slop=0.0)

    the index is at the end:
    >>> idx == 3
    True

    and the matrix is one bigger:
    >>> bm.shape == (4, 4)
    True

    but the original bounds mat is not altered:
    >>> boundsMat.shape == (3, 3)
    True

    We make the assumption that the points of the
    feature form a regular polygon, are listed in order
    (i.e. pt 0 is a neighbor to pt 1 and pt N-1)
    and that the replacement point goes at the center:
    >>> print(', '.join(['%.3f'%x for x in bm[-1]]))
    0.577, 0.577, 0.577, 0.000
    >>> print(', '.join(['%.3f'%x for x in bm[:,-1]]))
    1.155, 1.155, 1.155, 0.000

    The slop argument (default = 0.01) is fractional:
    >>> bm,idx = ReplaceGroup(match,boundsMat)
    >>> print(', '.join(['%.3f'%x for x in bm[-1]]))
    0.572, 0.572, 0.572, 0.000
    >>> print(', '.join(['%.3f'%x for x in bm[:,-1]]))
    1.166, 1.166, 1.166, 0.000

### EmbedMol(mol, bm, atomMatch=None, weight=2.0, randomSeed=-1, excludedVolumes=None)

source code

    Generates an embedding for a molecule based on a bounds matrix and adds
    a conformer (id 0) to the molecule

    if the optional argument atomMatch is provided, it will be used to provide
    supplemental weights for the embedding routine (used in the optimization
    phase to ensure that the resulting geometry really does satisfy the
    pharmacophore).

    if the excludedVolumes is provided, it should be a sequence of
    ExcludedVolume objects

    >>> m = Chem.MolFromSmiles('c1ccccc1C')
    >>> bounds = MolDG.GetMoleculeBoundsMatrix(m)
    >>> bounds.shape == (7, 7)
    True
    >>> m.GetNumConformers()
    0
    >>> EmbedMol(m,bounds,randomSeed=23)
    >>> m.GetNumConformers()
    1

### AddExcludedVolumes(bm, excludedVolumes, smoothIt=True)

source code

    Adds a set of excluded volumes to the bounds matrix
    and returns the new matrix

    excludedVolumes is a list of ExcludedVolume objects

     >>> boundsMat = numpy.array([[0.0,2.0,2.0],[1.0,0.0,2.0],[1.0,1.0,0.0]])
     >>> ev1 = ExcludedVolume.ExcludedVolume(([(0,),0.5,1.0],),exclusionDist=1.5)
     >>> bm = AddExcludedVolumes(boundsMat,(ev1,))

     the results matrix is one bigger:
     >>> bm.shape == (4, 4)
     True

     and the original bounds mat is not altered:
     >>> boundsMat.shape == (3, 3)
     True

     >>> print(', '.join(['%.3f'%x for x in bm[-1]]))
     0.500, 1.500, 1.500, 0.000
     >>> print(', '.join(['%.3f'%x for x in bm[:,-1]]))
     1.000, 3.000, 3.000, 0.000

### UpdatePharmacophoreBounds(bm, atomMatch, pcophore, useDirs=False, dirLength=defaultFeatLength, mol=None)

source code

    loops over a distance bounds matrix and replaces the elements
    that are altered by a pharmacophore

    **NOTE** this returns the resulting bounds matrix, but it may also
    alter the input matrix

    atomMatch is a sequence of sequences containing atom indices
    for each of the pharmacophore's features.

      >>> feats = [ChemicalFeatures.FreeChemicalFeature('HBondAcceptor', 'HAcceptor1', Geometry.Point3D(0.0, 0.0, 0.0)),
      ...                ChemicalFeatures.FreeChemicalFeature('HBondDonor', 'HDonor1', Geometry.Point3D(2.65, 0.0, 0.0)),
      ...   ]
      >>> pcophore=Pharmacophore.Pharmacophore(feats)
      >>> pcophore.setLowerBound(0,1, 1.0)
      >>> pcophore.setUpperBound(0,1, 2.0)

      >>> boundsMat = numpy.array([[0.0,3.0,3.0],[2.0,0.0,3.0],[2.0,2.0,0.0]])
      >>> atomMatch = ((0,),(1,))
      >>> bm = UpdatePharmacophoreBounds(boundsMat,atomMatch,pcophore)

       In this case, there are no multi-atom features, so the result matrix
       is the same as the input:
       >>> bm is boundsMat
       True

       this means, of course, that the input boundsMat is altered:
       >>> print(', '.join(['%.3f'%x for x in boundsMat[0]]))
       0.000, 2.000, 3.000
       >>> print(', '.join(['%.3f'%x for x in boundsMat[1]]))
       1.000, 0.000, 3.000
       >>> print(', '.join(['%.3f'%x for x in boundsMat[2]]))
       2.000, 2.000, 0.000

### EmbedPharmacophore(mol, atomMatch, pcophore, randomSeed=-1, count=10, smoothFirst=True, silent=False, bounds=None, excludedVolumes=None, targetNumber=-1, useDirs=False)

source code

    Generates one or more embeddings for a molecule that satisfy a pharmacophore

    atomMatch is a sequence of sequences containing atom indices
    for each of the pharmacophore's features.

      - count: is the maximum number of attempts to make a generating an embedding
      - smoothFirst: toggles triangle smoothing of the molecular bounds matix
      - bounds: if provided, should be the molecular bounds matrix. If this isn't
         provided, the matrix will be generated.
      - targetNumber: if this number is positive, it provides a maximum number
         of embeddings to generate (i.e. we'll have count attempts to generate
         targetNumber embeddings).

    returns: a 3 tuple:
      1) the molecular bounds matrix adjusted for the pharmacophore
      2) a list of embeddings (molecules with a single conformer)
      3) the number of failed attempts at embedding

      >>> m = Chem.MolFromSmiles('OCCN')
      >>> feats = [ChemicalFeatures.FreeChemicalFeature('HBondAcceptor', 'HAcceptor1', Geometry.Point3D(0.0, 0.0, 0.0)),
      ...                ChemicalFeatures.FreeChemicalFeature('HBondDonor', 'HDonor1', Geometry.Point3D(2.65, 0.0, 0.0)),
      ...   ]
      >>> pcophore=Pharmacophore.Pharmacophore(feats)
      >>> pcophore.setLowerBound(0,1, 2.5)
      >>> pcophore.setUpperBound(0,1, 3.5)
      >>> atomMatch = ((0,),(3,))

      >>> bm,embeds,nFail = EmbedPharmacophore(m,atomMatch,pcophore,randomSeed=23,silent=1)
      >>> len(embeds)
      10
      >>> nFail
      0

      Set up a case that can't succeed:
      >>> pcophore=Pharmacophore.Pharmacophore(feats)
      >>> pcophore.setLowerBound(0,1, 2.0)
      >>> pcophore.setUpperBound(0,1, 2.1)
      >>> atomMatch = ((0,),(3,))

      >>> bm,embeds,nFail = EmbedPharmacophore(m,atomMatch,pcophore,randomSeed=23,silent=1)
      >>> len(embeds)
      0
      >>> nFail
      10

### isNaN(v)

source code

    provides an OS independent way of detecting NaNs
    This is intended to be used with values returned from the C++
    side of things.

    We can't actually test this from Python (which traps
    zero division errors), but it would work something like
    this if we could:
    >>> isNaN(0)
    False

    #>>> isNan(1/0)
    #True

### OptimizeMol(mol, bm, atomMatches=None, excludedVolumes=None, forceConstant=1200.0, maxPasses=5, verbose=False)

source code

    carries out a UFF optimization for a molecule optionally subject
    to the constraints in a bounds matrix

      - atomMatches, if provided, is a sequence of sequences
      - forceConstant is the force constant of the spring used to enforce
        the constraints

     returns a 2-tuple:
       1) the energy of the initial conformation
       2) the energy post-embedding
     NOTE that these energies include the energies of the constraints

      >>> m = Chem.MolFromSmiles('OCCN')
      >>> feats = [ChemicalFeatures.FreeChemicalFeature('HBondAcceptor', 'HAcceptor1', Geometry.Point3D(0.0, 0.0, 0.0)),
      ...                ChemicalFeatures.FreeChemicalFeature('HBondDonor', 'HDonor1', Geometry.Point3D(2.65, 0.0, 0.0)),
      ...   ]
      >>> pcophore=Pharmacophore.Pharmacophore(feats)
      >>> pcophore.setLowerBound(0,1, 2.5)
      >>> pcophore.setUpperBound(0,1, 2.8)
      >>> atomMatch = ((0,),(3,))
      >>> bm,embeds,nFail = EmbedPharmacophore(m,atomMatch,pcophore,randomSeed=23,silent=1)
      >>> len(embeds)
      10
      >>> testM = embeds[0]

      Do the optimization:
      >>> e1,e2 = OptimizeMol(testM,bm,atomMatches=atomMatch)

      Optimizing should have lowered the energy:
      >>> e2 < e1
      True

      Check the constrained distance:
      >>> conf = testM.GetConformer(0)
      >>> p0 = conf.GetAtomPosition(0)
      >>> p3 = conf.GetAtomPosition(3)
      >>> d03 = p0.Distance(p3)
      >>> d03 >= pcophore.getLowerBound(0,1)-.01
      True
      >>> d03 <= pcophore.getUpperBound(0,1)+.01
      True

      If we optimize without the distance constraints (provided via the atomMatches
      argument) we're not guaranteed to get the same results, particularly in a case
      like the current one where the pharmcophore brings the atoms uncomfortably
      close together:
      >>> testM = embeds[1]
      >>> e1,e2 = OptimizeMol(testM,bm)
      >>> e2 < e1
      True
      >>> conf = testM.GetConformer(0)
      >>> p0 = conf.GetAtomPosition(0)
      >>> p3 = conf.GetAtomPosition(3)
      >>> d03 = p0.Distance(p3)
      >>> d03 >= pcophore.getLowerBound(0,1)-.01
      True
      >>> d03 <= pcophore.getUpperBound(0,1)+.01
      False

### EmbedOne(mol, name, match, pcophore, count=1, silent=0, **kwargs)

source code

    generates statistics for a molecule's embeddings

    Four energies are computed for each embedding:
        1) E1: the energy (with constraints) of the initial embedding
        2) E2: the energy (with constraints) of the optimized embedding
        3) E3: the energy (no constraints) the geometry for E2
        4) E4: the energy (no constraints) of the optimized free-molecule
           (starting from the E3 geometry)

    Returns a 9-tuple:
        1) the mean value of E1
        2) the sample standard deviation of E1
        3) the mean value of E2
        4) the sample standard deviation of E2
        5) the mean value of E3
        6) the sample standard deviation of E3
        7) the mean value of E4
        8) the sample standard deviation of E4
        9) The number of embeddings that failed

### MatchPharmacophoreToMol(mol, featFactory, pcophore)

source code

    generates a list of all possible mappings of a pharmacophore to a molecule

    Returns a 2-tuple:
      1) a boolean indicating whether or not all features were found
      2) a list, numFeatures long, of sequences of features

      >>> import os.path
      >>> dataDir = os.path.join(RDConfig.RDCodeDir,'Chem/Pharm3D/test_data')
      >>> featFactory = ChemicalFeatures.BuildFeatureFactory(os.path.join(dataDir,'BaseFeatures.fdef'))
      >>> activeFeats = [ChemicalFeatures.FreeChemicalFeature('Acceptor', Geometry.Point3D(0.0, 0.0, 0.0)),
      ...  ChemicalFeatures.FreeChemicalFeature('Donor',Geometry.Point3D(0.0, 0.0, 0.0))]
      >>> pcophore= Pharmacophore.Pharmacophore(activeFeats)
      >>> m = Chem.MolFromSmiles('FCCN')
      >>> match,mList = MatchPharmacophoreToMol(m,featFactory,pcophore)
      >>> match
      True

      Two feature types:
      >>> len(mList)
      2

      The first feature type, Acceptor, has two matches:
      >>> len(mList[0])
      2
      >>> mList[0][0].GetAtomIds()
      (0,)
      >>> mList[0][1].GetAtomIds()
      (3,)

      The first feature type, Donor, has a single match:
      >>> len(mList[1])
      1
      >>> mList[1][0].GetAtomIds()
      (3,)

### _getFeatDict(mol, featFactory, features)

source code

    **INTERNAL USE ONLY**

    >>> import os.path
    >>> dataDir = os.path.join(RDConfig.RDCodeDir,'Chem/Pharm3D/test_data')
    >>> featFactory = ChemicalFeatures.BuildFeatureFactory(os.path.join(dataDir,'BaseFeatures.fdef'))
    >>> activeFeats = [ChemicalFeatures.FreeChemicalFeature('Acceptor', Geometry.Point3D(0.0, 0.0, 0.0)),
    ...  ChemicalFeatures.FreeChemicalFeature('Donor',Geometry.Point3D(0.0, 0.0, 0.0))]
    >>> m = Chem.MolFromSmiles('FCCN')
    >>> d =_getFeatDict(m,featFactory,activeFeats)
    >>> sorted(list(d.keys()))
    ['Acceptor', 'Donor']
    >>> donors = d['Donor']
    >>> len(donors)
    1
    >>> donors[0].GetAtomIds()
    (3,)
    >>> acceptors = d['Acceptor']
    >>> len(acceptors)
    2
    >>> acceptors[0].GetAtomIds()
    (0,)
    >>> acceptors[1].GetAtomIds()
    (3,)

### MatchFeatsToMol(mol, featFactory, features)

source code

    generates a list of all possible mappings of each feature to a molecule

    Returns a 2-tuple:
      1) a boolean indicating whether or not all features were found
      2) a list, numFeatures long, of sequences of features

      >>> import os.path
      >>> dataDir = os.path.join(RDConfig.RDCodeDir,'Chem/Pharm3D/test_data')
      >>> featFactory = ChemicalFeatures.BuildFeatureFactory(os.path.join(dataDir,'BaseFeatures.fdef'))
      >>> activeFeats = [ChemicalFeatures.FreeChemicalFeature('Acceptor', Geometry.Point3D(0.0, 0.0, 0.0)),
      ...  ChemicalFeatures.FreeChemicalFeature('Donor',Geometry.Point3D(0.0, 0.0, 0.0))]
      >>> m = Chem.MolFromSmiles('FCCN')
      >>> match,mList = MatchFeatsToMol(m,featFactory,activeFeats)
      >>> match
      True

      Two feature types:
      >>> len(mList)
      2

      The first feature type, Acceptor, has two matches:
      >>> len(mList[0])
      2
      >>> mList[0][0].GetAtomIds()
      (0,)
      >>> mList[0][1].GetAtomIds()
      (3,)

      The first feature type, Donor, has a single match:
      >>> len(mList[1])
      1
      >>> mList[1][0].GetAtomIds()
      (3,)

### CombiEnum(sequence)

source code

    This generator takes a sequence of sequences as an argument and
    provides all combinations of the elements of the subsequences:

    >>> gen = CombiEnum(((1,2),(10,20)))
    >>> next(gen)
    [1, 10]
    >>> next(gen)
    [1, 20]

    >>> [x for x in CombiEnum(((1,2),(10,20)))]
    [[1, 10], [1, 20], [2, 10], [2, 20]]

    >>> [x for x in CombiEnum(((1,2),(10,20),(100,200)))]
    [[1, 10, 100], [1, 10, 200], [1, 20, 100], [1, 20, 200], [2, 10, 100], [2, 10, 200], [2, 20, 100], [2, 20, 200]]

### DownsampleBoundsMatrix(bm, indices, maxThresh=4.0)

source code

    removes rows from a bounds matrix that are
    that are greater than a threshold value away from a set of
    other points

    returns the modfied bounds matrix

    The goal of this function is to remove rows from the bounds matrix
    that correspond to atoms that are likely to be quite far from
    the pharmacophore we're interested in. Because the bounds smoothing
    we eventually have to do is N^3, this can be a big win

     >>> boundsMat = numpy.array([[0.0,3.0,4.0],[2.0,0.0,3.0],[2.0,2.0,0.0]])
     >>> bm = DownsampleBoundsMatrix(boundsMat,(0,),3.5)
     >>> bm.shape == (2, 2)
     True

     we don't touch the input matrix:
     >>> boundsMat.shape == (3, 3)
     True

     >>> print(', '.join(['%.3f'%x for x in bm[0]]))
     0.000, 3.000
     >>> print(', '.join(['%.3f'%x for x in bm[1]]))
     2.000, 0.000

     if the threshold is high enough, we don't do anything:
     >>> boundsMat = numpy.array([[0.0,4.0,3.0],[2.0,0.0,3.0],[2.0,2.0,0.0]])
     >>> bm = DownsampleBoundsMatrix(boundsMat,(0,),5.0)
     >>> bm.shape == (3, 3)
     True

     If there's a max value that's close enough to *any* of the indices
     we pass in, we'll keep it:
     >>> boundsMat = numpy.array([[0.0,4.0,3.0],[2.0,0.0,3.0],[2.0,2.0,0.0]])
     >>> bm = DownsampleBoundsMatrix(boundsMat,(0,1),3.5)
     >>> bm.shape == (3, 3)
     True

### CoarseScreenPharmacophore(atomMatch, bounds, pcophore, verbose=False)

source code

    >>> feats = [ChemicalFeatures.FreeChemicalFeature('HBondAcceptor', 'HAcceptor1', Geometry.Point3D(0.0, 0.0, 0.0)),
    ...                ChemicalFeatures.FreeChemicalFeature('HBondDonor', 'HDonor1', Geometry.Point3D(2.65, 0.0, 0.0)),
    ...                ChemicalFeatures.FreeChemicalFeature('Aromatic', 'Aromatic1', Geometry.Point3D(5.12, 0.908, 0.0)),
    ...                ]
    >>> pcophore=Pharmacophore.Pharmacophore(feats)
    >>> pcophore.setLowerBound(0,1, 1.1)
    >>> pcophore.setUpperBound(0,1, 1.9)
    >>> pcophore.setLowerBound(0,2, 2.1)
    >>> pcophore.setUpperBound(0,2, 2.9)
    >>> pcophore.setLowerBound(1,2, 2.1)
    >>> pcophore.setUpperBound(1,2, 3.9)

    >>> bounds = numpy.array([[0,2,3],[1,0,4],[2,3,0]],numpy.float)
    >>> CoarseScreenPharmacophore(((0,),(1,)),bounds,pcophore)
    True

    >>> CoarseScreenPharmacophore(((0,),(2,)),bounds,pcophore)
    False

    >>> CoarseScreenPharmacophore(((1,),(2,)),bounds,pcophore)
    False

    >>> CoarseScreenPharmacophore(((0,),(1,),(2,)),bounds,pcophore)
    True

    >>> CoarseScreenPharmacophore(((1,),(0,),(2,)),bounds,pcophore)
    False

    >>> CoarseScreenPharmacophore(((2,),(1,),(0,)),bounds,pcophore)
    False

    # we ignore the point locations here and just use their definitions:
    >>> feats = [ChemicalFeatures.FreeChemicalFeature('HBondAcceptor', 'HAcceptor1', Geometry.Point3D(0.0, 0.0, 0.0)),
    ...                ChemicalFeatures.FreeChemicalFeature('HBondDonor', 'HDonor1', Geometry.Point3D(2.65, 0.0, 0.0)),
    ...                ChemicalFeatures.FreeChemicalFeature('Aromatic', 'Aromatic1', Geometry.Point3D(5.12, 0.908, 0.0)),
    ...                ChemicalFeatures.FreeChemicalFeature('HBondDonor', 'HDonor1', Geometry.Point3D(2.65, 0.0, 0.0)),
    ...                ]
    >>> pcophore=Pharmacophore.Pharmacophore(feats)
    >>> pcophore.setLowerBound(0,1, 2.1)
    >>> pcophore.setUpperBound(0,1, 2.9)
    >>> pcophore.setLowerBound(0,2, 2.1)
    >>> pcophore.setUpperBound(0,2, 2.9)
    >>> pcophore.setLowerBound(0,3, 2.1)
    >>> pcophore.setUpperBound(0,3, 2.9)
    >>> pcophore.setLowerBound(1,2, 1.1)
    >>> pcophore.setUpperBound(1,2, 1.9)
    >>> pcophore.setLowerBound(1,3, 1.1)
    >>> pcophore.setUpperBound(1,3, 1.9)
    >>> pcophore.setLowerBound(2,3, 1.1)
    >>> pcophore.setUpperBound(2,3, 1.9)
    >>> bounds = numpy.array([[0,3,3,3],[2,0,2,2],[2,1,0,2],[2,1,1,0]],numpy.float)

    >>> CoarseScreenPharmacophore(((0,),(1,),(2,),(3,)),bounds,pcophore)
    True

    >>> CoarseScreenPharmacophore(((0,),(1,),(3,),(2,)),bounds,pcophore)
    True

    >>> CoarseScreenPharmacophore(((1,),(0,),(3,),(2,)),bounds,pcophore)
    False

### Check2DBounds(atomMatch, mol, pcophore)

source code

    checks to see if a particular mapping of features onto
    a molecule satisfies a pharmacophore's 2D restrictions

      >>> activeFeats = [ChemicalFeatures.FreeChemicalFeature('Acceptor', Geometry.Point3D(0.0, 0.0, 0.0)),
      ...  ChemicalFeatures.FreeChemicalFeature('Donor',Geometry.Point3D(0.0, 0.0, 0.0))]
      >>> pcophore= Pharmacophore.Pharmacophore(activeFeats)
      >>> pcophore.setUpperBound2D(0,1,3)
      >>> m = Chem.MolFromSmiles('FCC(N)CN')
      >>> Check2DBounds(((0,),(3,)),m,pcophore)
      True
      >>> Check2DBounds(((0,),(5,)),m,pcophore)
      False

### _checkMatch(match, mol, bounds, pcophore, use2DLimits)

source code

    **INTERNAL USE ONLY**

    checks whether a particular atom match can be satisfied by
    a molecule

### ConstrainedEnum(matches, mol, pcophore, bounds, use2DLimits=False, index=0, soFar=[])

source code

    Enumerates the list of atom mappings a molecule
    has to a particular pharmacophore.
    We do check distance bounds here.

### MatchPharmacophore(matches, bounds, pcophore, useDownsampling=False, use2DLimits=False, mol=None, excludedVolumes=None, useDirs=False)

source code

    if use2DLimits is set, the molecule must also be provided and topological
    distances will also be used to filter out matches

### ComputeChiralVolume(mol, centerIdx, confId=-1)

source code

    Computes the chiral volume of an atom

    We're using the chiral volume formula from Figure 7 of
    Blaney and Dixon, Rev. Comp. Chem. V, 299-335 (1994)

      >>> import os.path
      >>> dataDir = os.path.join(RDConfig.RDCodeDir,'Chem/Pharm3D/test_data')

      R configuration atoms give negative volumes:
      >>> mol = Chem.MolFromMolFile(os.path.join(dataDir,'mol-r.mol'))
      >>> Chem.AssignStereochemistry(mol)
      >>> mol.GetAtomWithIdx(1).GetProp('_CIPCode')
      'R'
      >>> ComputeChiralVolume(mol,1) < 0
      True

      S configuration atoms give positive volumes:
      >>> mol = Chem.MolFromMolFile(os.path.join(dataDir,'mol-s.mol'))
      >>> Chem.AssignStereochemistry(mol)
      >>> mol.GetAtomWithIdx(1).GetProp('_CIPCode')
      'S'
      >>> ComputeChiralVolume(mol,1) > 0
      True

      Non-chiral (or non-specified) atoms give zero volume:
      >>> ComputeChiralVolume(mol,0) == 0.0
      True

      We also work on 3-coordinate atoms (with implicit Hs):
      >>> mol = Chem.MolFromMolFile(os.path.join(dataDir,'mol-r-3.mol'))
      >>> Chem.AssignStereochemistry(mol)
      >>> mol.GetAtomWithIdx(1).GetProp('_CIPCode')
      'R'
      >>> ComputeChiralVolume(mol,1)<0
      True

      >>> mol = Chem.MolFromMolFile(os.path.join(dataDir,'mol-s-3.mol'))
      >>> Chem.AssignStereochemistry(mol)
      >>> mol.GetAtomWithIdx(1).GetProp('_CIPCode')
      'S'
      >>> ComputeChiralVolume(mol,1)>0
      True