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#! /usr/bin/env python |
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# |
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# Copyright (C) 2016 Rich Lewis <[email protected]> |
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# License: 3-clause BSD |
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""" |
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## skchem.descriptors.atom |
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Module specifying atom based descriptor generators. |
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""" |
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import logging |
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import subprocess |
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import tempfile |
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import pandas as pd |
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import numpy as np |
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LOGGER = logging.getLogger(__file__) |
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from ..io import write_sdf, read_sdf |
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from .. import core |
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atom_feats = ['acceptormultiplicity', 'aliphaticatom', 'aromaticatom', 'aromaticelectrophilicityorder', |
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'asymmetricatom', 'atomicpolarizability', 'chainatom', 'chargedensity', 'chiralcenter', 'distancedegree', |
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'donormultiplicity', 'eccentricity', 'electrondensity', 'electrophiliclocalizationenergy', 'hindrance', |
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'hmochargedensity', 'hmoelectrondensity', 'hmoelectrophilicityorder', 'hmoelectrophiliclocalizationenergy', |
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'hmonucleophilicityorder', 'hmonucleophiliclocalizationenergy', 'ioncharge', 'largestatomringsize', 'nucleophilicityorder', |
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'nucleophiliclocalizationenergy', 'oen', 'pichargedensity', 'ringatom', 'ringcountofatom', 'stericeffectindex', |
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'totalchargedensity'] |
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# TODO: fix averagemicrospeciescharge |
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# TODO: fix logd logp logs |
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# TODO: oen (orbital electronegativity) - sigma + pi |
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# TODO: water accessible surface area |
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class ChemAxonFeatureCalculator(object): |
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_optimal_feats = ['acceptorcount', 'accsitecount', 'aliphaticatomcount', 'aliphaticbondcount', 'aliphaticringcount', |
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'aromaticatomcount', 'aromaticbondcount', 'aromaticringcount', 'asymmetricatomcount', |
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'averagemolecularpolarizability', 'axxpol', 'ayypol', 'azzpol', 'balabanindex', 'bondcount', |
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'carboaliphaticringcount', 'carboaromaticringcount', 'carboringcount', 'chainatomcount', |
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'chainbondcount', 'charge', 'chiralcentercount', 'connectedgraph', 'cyclomaticnumber', 'dipole', |
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'donorcount', 'donorsitecount', 'doublebondstereoisomercount', 'dreidingenergy', 'formalcharge', |
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'fragmentcount', 'fsp3', 'fusedaliphaticringcount', 'fusedaromaticringcount', 'fusedringcount', |
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'hararyindex', 'heteroaliphaticringcount', 'heteroaromaticringcount', 'heteroringcount', 'hlb', |
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'hmopienergy', 'hyperwienerindex', 'largestringsize', 'largestringsystemsize', |
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'markushenumerationcount', 'maximalprojectionarea', 'maximalprojectionradius', |
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'maximalprojectionsize', 'minimalprojectionarea', 'minimalprojectionradius', |
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'minimalprojectionsize', 'mmff94energy', 'molpol', 'pienergy', 'plattindex', 'psa', 'randicindex', |
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'refractivity', 'resonantcount', 'ringatomcount', 'ringbondcount', 'ringcount', 'ringsystemcount', |
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'rotatablebondcount', 'smallestatomringsize', 'smallestringsize', 'smallestringsystemsize', |
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'stereodoublebondcount', 'stereoisomercount', 'szegedindex', 'tetrahedralstereoisomercount', |
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'vdwsa', 'volume', 'wateraccessiblesurfacearea', 'wienerindex', 'wienerpolarity'] |
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_all_feats = ['acc', 'acceptor', 'acceptorcount', 'acceptormultiplicity', 'acceptorsitecount', 'acceptortable', |
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'accsitecount', 'aliphaticatom', 'aliphaticatomcount', 'aliphaticbondcount', 'aliphaticringcount', |
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'aliphaticringcountofsize', 'aromaticatom', 'aromaticatomcount', 'aromaticbondcount', |
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'aromaticelectrophilicityorder', 'aromaticnucleophilicityorder', 'aromaticringcount', |
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'aromaticringcountofsize', 'asa', 'asymmetricatom', 'asymmetricatomcount', 'asymmetricatoms', |
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'atomicpolarizability', 'atompol', 'averagemicrospeciescharge', 'averagemolecularpolarizability', |
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'averagepol', 'avgpol', 'axxpol', 'ayypol', 'azzpol', 'balabanindex', 'bondcount', |
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'canonicalresonant', 'canonicaltautomer', 'carboaliphaticringcount', 'carboaromaticringcount', |
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'carboringcount', 'chainatom', 'chainatomcount', 'chainbondcount', 'charge', 'chargedensity', |
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'chargedistribution', 'chiralcenter', 'chiralcentercount', 'chiralcenters', 'connectedgraph', |
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'cyclomaticnumber', 'dipole', 'distancedegree', 'don', 'donor', 'donorcount', 'donormultiplicity', |
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'donorsitecount', 'donortable', 'donsitecount', 'doublebondstereoisomercount', 'dreidingenergy', |
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'eccentricity', 'electrondensity', 'electrophilicityorder', 'electrophiliclocalizationenergy', |
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'enumerationcount', 'enumerations', 'formalcharge', 'fragmentcount', 'fsp3', |
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'fusedaliphaticringcount', 'fusedaromaticringcount', 'fusedringcount', 'generictautomer', |
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'hararyindex', 'hasvalidconformer', 'hbda', 'hbonddonoracceptor', 'heteroaliphaticringcount', |
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'heteroaromaticringcount', 'heteroringcount', 'hindrance', 'hlb', 'hmochargedensity', |
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'hmoelectrondensity', 'hmoelectrophilicityorder', 'hmoelectrophiliclocalizationenergy', 'hmohuckel', |
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'hmohuckeleigenvalue', 'hmohuckeleigenvector', 'hmohuckelorbitals', 'hmohuckeltable', |
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'hmolocalizationenergy', 'hmonucleophilicityorder', 'hmonucleophiliclocalizationenergy', |
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'hmopienergy', 'huckel', 'huckeleigenvalue', 'huckeleigenvector', 'huckelorbitals', 'huckeltable', |
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'hyperwienerindex', 'ioncharge', 'isoelectricpoint', 'largestatomringsize', 'largestringsize', |
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'largestringsystemsize', 'localizationenergy', 'logd', 'logdcalculator', 'logp', 'logpcalculator', |
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'logs', 'majormicrospecies', 'majorms', 'majorms2', 'majortautomer', 'markushenumerationcount', |
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'markushenumerations', 'maximalprojectionarea', 'maximalprojectionradius', 'maximalprojectionsize', |
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'minimalprojectionarea', 'minimalprojectionradius', 'minimalprojectionsize', 'mmff94energy', |
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'molecularpolarizability', 'molecularsurfacearea', 'molpol', 'moststabletautomer', 'msa', 'msacc', |
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'msdon', 'name', 'nucleophilicityorder', 'nucleophiliclocalizationenergy', 'oen', |
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'orbitalelectronegativity', 'pi', 'pichargedensity', 'pienergy', 'pka', 'pkacalculator', 'pkat', |
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'plattindex', 'pol', 'polarizability', 'polarsurfacearea', 'psa', 'randicindex', |
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'randommarkushenumerations', 'refractivity', 'resonantcount', 'resonants', 'ringatom', |
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'ringatomcount', 'ringbondcount', 'ringcount', 'ringcountofatom', 'ringcountofsize', |
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'ringsystemcount', 'ringsystemcountofsize', 'rotatablebondcount', 'smallestatomringsize', |
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'smallestringsize', 'smallestringsystemsize', 'stereodoublebondcount', 'stereoisomercount', |
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'stericeffectindex', 'sterichindrance', 'szegedindex', 'tautomercount', 'tautomers', |
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'tetrahedralstereoisomercount', 'tholepolarizability', 'topanal', 'topologyanalysistable', |
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'totalchargedensity', 'tpol', 'tpolarizability', 'vdwsa', 'volume', 'wateraccessiblesurfacearea', |
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'wienerindex', 'wienerpolarity'] |
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View Code Duplication |
def __init__(self, feat_set='all'): |
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if feat_set == 'all': |
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self.index = self._all_feats |
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elif feat_set == 'optimal': |
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self.index = self._optimal_feats |
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elif feat_set in self._all_feats: |
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self.index = [feat_set] |
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elif isinstance(feat_set, (list, tuple)): |
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valid = np.array([feat in self._all_feats for feat in feat_set]) |
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if all(valid): |
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self.index = feat_set |
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else: |
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self.index = feat_set |
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raise NotImplementedError('Descriptor \'{}\' not available.'.format(np.array(feat_set)[~valid])) |
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else: |
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raise NotImplementedError('Feature set {} not available.'.format(feat_set)) |
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def transform(self, obj): |
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if isinstance(obj, core.Mol): |
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return self._transform_series(pd.Series(obj)).iloc[0] |
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elif isinstance(obj, pd.Series): |
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return self._transform_series(obj) |
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elif isinstance(obj, pd.DataFrame): |
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return self._transform_series(obj.structure) |
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elif isinstance(obj, (tuple, list)): |
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return self._transform_series(obj) |
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else: |
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raise NotImplementedError |
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def _transform_series(self, series): |
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with tempfile.NamedTemporaryFile(suffix='.sdf') as in_file, tempfile.NamedTemporaryFile() as out_file: |
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# write mols to file |
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write_sdf(series, in_file.name) |
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args = ['cxcalc', in_file.name, '-o', out_file.name] + self.index |
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LOGGER.info('Running: ' + ' '.join(args)) |
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# call command line |
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subprocess.call(args) |
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try: |
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finished = pd.read_table(out_file.name).set_index('id') |
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except Exception: |
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finished = None |
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finished.index = series.index |
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return finished |
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class ChemAxonAtomFeatureCalculator(object): |
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_all_feats = ['acceptormultiplicity', 'aliphaticatom', 'aromaticatom', 'aromaticelectrophilicityorder', |
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'asymmetricatom', 'atomicpolarizability', 'chainatom', 'chargedensity', 'chiralcenter', |
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'distancedegree', 'donormultiplicity', 'eccentricity', 'electrondensity', |
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'electrophiliclocalizationenergy', 'hindrance', 'hmochargedensity', 'hmoelectrondensity', 'hmoelectrophilicityorder', |
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'hmoelectrophiliclocalizationenergy', 'hmonucleophilicityorder', 'hmonucleophiliclocalizationenergy', 'ioncharge', 'largestatomringsize', |
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'nucleophilicityorder', 'nucleophiliclocalizationenergy', 'oen', 'pichargedensity', 'ringatom', 'ringcountofatom', |
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'stericeffectindex', 'totalchargedensity'] |
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_h_inc_feats = ['acc', 'atomicpolarizability', 'charge', 'distancedegree', 'don', |
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'eccentricity', 'hindrance', 'largestatomringsize', 'oen', |
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'ringcountofatom', 'smallestatomringsize', 'stericeffectindex'] |
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View Code Duplication |
def __init__(self, feat_set='all', include_hs=False, max_atoms=75): |
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""" |
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Args: |
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feat_set (str or list<str>): |
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The feature sets to calculate. |
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- a single identifier as a `str` |
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- a list of identifiers |
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- 'h_inc' or those that also calculate for Hs. |
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- 'all' for all |
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max_atoms: |
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- The maximum number of atoms available. |
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""" |
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self.max_atoms = max_atoms |
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if feat_set in self._all_feats: |
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self.index = [feat_set] |
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elif feat_set == 'h_inclusive': |
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self.index = self._h_inc_feats |
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elif feat_set == 'all': |
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self.index = self._all_feats |
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elif isinstance(feat_set, (list, tuple)): |
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valid = np.array([feat in self._all_feats for feat in feat_set]) |
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if all(valid): |
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self.index = feat_set |
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else: |
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raise NotImplementedError('Descriptor \'{}\' not available.'.format(np.array(feat_set)[~valid])) |
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self.feature_names = feat_set |
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else: |
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raise NotImplementedError('{} feature set is not available'.format(feat_set)) |
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@property |
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def feature_names(self): |
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return self.index |
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def transform(self, obj): |
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if isinstance(obj, core.Atom): |
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return self._transform_atom(obj) |
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elif isinstance(obj, core.Mol): |
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return self._transform_mol(obj) |
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elif isinstance(obj, pd.Series): |
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return self._transform_series(obj) |
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elif isinstance(obj, pd.DataFrame): |
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return self._transform_series(obj.structure) |
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elif isinstance(obj, (tuple, list)): |
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return self._transform_series(obj) |
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else: |
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raise NotImplementedError |
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def _transform_atom(self, atom): |
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raise NotImplementedError('Cannot calculate atom wise with Chemaxon') |
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def _transform_mol(self, mol): |
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ser = pd.Series([mol], name=mol.name) |
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res = self._transform_series(ser) |
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return res.iloc[0] |
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# make into series then use self._transform_mol |
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def _transform_series(self, series): |
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with tempfile.NamedTemporaryFile(suffix='.sdf') as in_file, tempfile.NamedTemporaryFile() as out_file: |
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# write mols to file |
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write_sdf(series, in_file.name) |
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218
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args = ['cxcalc', in_file.name, '-o', out_file.name] + self.index |
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219
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220
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LOGGER.info('Running: ' + ' '.join(args)) |
|
221
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|
222
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# call command line |
|
223
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subprocess.call(args) |
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224
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finished = pd.read_table(out_file.name).set_index('id') |
|
225
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226
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def to_padded(s): |
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|
227
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res = np.repeat(np.nan, self.max_atoms) |
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228
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229
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def parse_string(s): |
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|
230
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|
|
if s == '': |
|
231
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return np.nan |
|
232
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|
elif s == 'false': |
|
233
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return 0 |
|
234
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elif s == 'true': |
|
235
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|
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return 1 |
|
236
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else: |
|
237
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return float(s) |
|
238
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|
239
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ans = np.array([parse_string(i) for i in s.split(';')]) |
|
240
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res[:len(ans)] = ans |
|
241
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|
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return res |
|
242
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res = np.array([[to_padded(i) for k, i in val.items()] for idx, val in finished.T.items()]) |
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|
243
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res = pd.Panel(res, items=series.index, major_axis=pd.Index(finished.columns, name='cx_atom_desc'), |
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|
244
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minor_axis=pd.Index(range(self.max_atoms), name='atom_idx')) |
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|
245
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return res.swapaxes(1, 2) # to be consistent with AtomFeatureCalculator |
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246
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richlewis42 /
scikit-chem
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