Integration of CDK ExhaustiveFragmenter #133
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| /* | ||
| * MORTAR - MOlecule fRagmenTAtion fRamework | ||
| * Copyright (C) 2024 Felix Baensch, Jonas Schaub ([email protected], [email protected]) | ||
| * | ||
| * Source code is available at <https://github.com/FelixBaensch/MORTAR> | ||
| * | ||
| * Permission is hereby granted, free of charge, to any person obtaining a copy | ||
| * of this software and associated documentation files (the "Software"), to deal | ||
| * in the Software without restriction, including without limitation the rights | ||
| * to use, copy, modify, merge, publish, distribute, sublicense, and/or sell | ||
| * copies of the Software, and to permit persons to whom the Software is | ||
| * furnished to do so, subject to the following conditions: | ||
| * | ||
| * The above copyright notice and this permission notice shall be included in all | ||
| * copies or substantial portions of the Software. | ||
| * | ||
| * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR | ||
| * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, | ||
| * FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE | ||
| * AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER | ||
| * LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, | ||
| * OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE | ||
| * SOFTWARE. | ||
| */ | ||
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| package de.unijena.cheminf.mortar.model.fragmentation.algorithm; | ||
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| import de.unijena.cheminf.mortar.gui.util.GuiUtil; | ||
| import de.unijena.cheminf.mortar.message.Message; | ||
| import de.unijena.cheminf.mortar.model.io.Importer; | ||
| import de.unijena.cheminf.mortar.model.util.BasicDefinitions; | ||
| import de.unijena.cheminf.mortar.model.util.CollectionUtil; | ||
| import de.unijena.cheminf.mortar.model.util.SimpleIDisplayEnumConstantProperty; | ||
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| import javafx.beans.property.Property; | ||
| import javafx.beans.property.SimpleIntegerProperty; | ||
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| import org.openscience.cdk.fragment.ExhaustiveFragmenter; | ||
| import org.openscience.cdk.interfaces.IAtomContainer; | ||
| import org.openscience.cdk.silent.SilentChemObjectBuilder; | ||
| import org.openscience.cdk.smiles.SmilesParser; | ||
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| import java.util.ArrayList; | ||
| import java.util.HashMap; | ||
| import java.util.List; | ||
| import java.util.Map; | ||
| import java.util.Objects; | ||
| import java.util.logging.Level; | ||
| import java.util.logging.Logger; | ||
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| /** | ||
| * Wrapper class that makes the | ||
| * <a href="https://cdk.github.io/cdk/latest/docs/api/org/openscience/cdk/fragment/ExhaustiveFragmenter.html"> | ||
| * exhaustive fragmentation | ||
| * </a> | ||
| * from the CDK available for MORTAR. It has a performance of O(n!) where n is the number of splittable bonds. Splittable | ||
| * bonds are defined as non-ring, single bonds that are connected to at least one other atom, that is <b>not</b> an | ||
| * implicit hydrogen. | ||
| * | ||
| * @author Tom Weiß | ||
| * @version 1.0.0.0 | ||
| */ | ||
| public class CDKExhaustiveFragmenter implements IMoleculeFragmenter { | ||
| //<editor-fold desc="Public static final variables"> | ||
| /** | ||
| * The default value for the minimum fragment size used for the fragmentation. | ||
| */ | ||
| public static final int DEFAULT_MINIMUM_FRAGMENT_SIZE = 6; | ||
| // | ||
| /** | ||
| * The name of the algorithm used for fragmentation. | ||
| */ | ||
| public static final String ALGORITHM_NAME = "Exhaustive Fragmenter"; | ||
| //</editor-fold> | ||
| // | ||
| //<editor-fold desc="Private final variables"> | ||
| /** | ||
| * The minimum size of the returned fragments. This size consists of all atoms, that are connected by more than | ||
| * a single bond or have more than one single bond. | ||
| */ | ||
| private final SimpleIntegerProperty minimumFragmentSizeSetting; | ||
| // | ||
| /** | ||
| * All settings of this fragmenter, encapsulated in JavaFX properties for binding in GUI. | ||
| */ | ||
| private final List<Property<?>> settings; | ||
| // | ||
| /** | ||
| * Map to store pairs of {@literal <setting name, tooltip text>}. | ||
| */ | ||
| private final HashMap<String, String> settingNameTooltipTextMap; | ||
| // | ||
| /** | ||
| * Map to store pairs of {@literal <setting name, display name>}. | ||
| */ | ||
| private final HashMap<String, String> settingNameDisplayNameMap; | ||
| // | ||
| /** | ||
| * Instance of ExhaustiveFragmenter class to fragment a molecule. | ||
| */ | ||
| private final ExhaustiveFragmenter cdkEFInstance; | ||
| // | ||
| /** | ||
| * Logger of this class. | ||
| */ | ||
| private static final Logger LOGGER = Logger.getLogger(CDKExhaustiveFragmenter.class.getName()); | ||
| //</editor-fold> | ||
| // | ||
| //<editor-fold desc="Constructor"> | ||
| /** | ||
| * Constructor, all settings are initialised with their default values as declared in the respective public constants. | ||
| */ | ||
| public CDKExhaustiveFragmenter() { | ||
| int tmpNumberOfSettingsForTooltipMapSize = 1; | ||
| int tmpInitialCapacityForSettingNameTooltipTextMap = CollectionUtil.calculateInitialHashCollectionCapacity( | ||
| tmpNumberOfSettingsForTooltipMapSize, | ||
| BasicDefinitions.DEFAULT_HASH_COLLECTION_LOAD_FACTOR); | ||
| this.settingNameTooltipTextMap = new HashMap<>(tmpInitialCapacityForSettingNameTooltipTextMap, | ||
| BasicDefinitions.DEFAULT_HASH_COLLECTION_LOAD_FACTOR); | ||
| this.settingNameDisplayNameMap = new HashMap<>(tmpInitialCapacityForSettingNameTooltipTextMap, | ||
| BasicDefinitions.DEFAULT_HASH_COLLECTION_LOAD_FACTOR); | ||
| this.cdkEFInstance = new ExhaustiveFragmenter(); | ||
| this.minimumFragmentSizeSetting = new SimpleIntegerProperty(this, | ||
| "Minimum Size for the returned fragments", | ||
| CDKExhaustiveFragmenter.DEFAULT_MINIMUM_FRAGMENT_SIZE) { | ||
| @Override | ||
| public void set(int newValue) { | ||
| if (newValue > 0) { | ||
| CDKExhaustiveFragmenter.this.cdkEFInstance.setMinimumFragmentSize(newValue); | ||
| super.set(newValue); | ||
| } | ||
| else { | ||
| IllegalArgumentException anException = new IllegalArgumentException("The minimum fragment size can not be zero"); | ||
| CDKExhaustiveFragmenter.LOGGER.log(Level.WARNING, anException.toString(), anException); | ||
| GuiUtil.guiExceptionAlert(Message.get("Fragmenter.IllegalSettingValue.Title"), | ||
| Message.get("Fragmenter.IllegalSettingValue.Header"), | ||
| anException.toString(), | ||
| anException); | ||
| //re-throws the exception to properly reset the binding | ||
| throw anException; | ||
| } | ||
| } | ||
| }; | ||
| this.settingNameTooltipTextMap.put(this.minimumFragmentSizeSetting.getName(), | ||
| Message.get("CDKExhaustiveFragmenter.minFragmentSize.tooltip")); | ||
| this.settingNameDisplayNameMap.put(this.minimumFragmentSizeSetting.getName(), | ||
| Message.get("CDKExhaustiveFragmenter.minFragmentSize.displayName")); | ||
| this.settings = new ArrayList<>(tmpNumberOfSettingsForTooltipMapSize); | ||
| this.settings.add(this.minimumFragmentSizeSetting); | ||
| } | ||
| //</editor-fold> | ||
| // | ||
| //<editor-fold desc="Public properties get"> | ||
| /** | ||
| * Returns the setting for the minimum fragment size. | ||
| * | ||
| * @return the setting for the minimum fragment size. | ||
| */ | ||
| public SimpleIntegerProperty getMinimumFragmentSizeSetting() { | ||
| return this.minimumFragmentSizeSetting; | ||
| } | ||
| /** | ||
| * Returns the minimum fragment size currently set. | ||
| * | ||
| * @return the currently set minimum fragment size. | ||
| */ | ||
| public int getMinimumFragmentSize() { | ||
| return this.minimumFragmentSizeSetting.get(); | ||
| } | ||
| //</editor-fold> | ||
| // | ||
| //<editor-fold desc="Public properties set"> | ||
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| /** | ||
| * Returns the minimum fragment size currently set. | ||
| * | ||
| * @param minimumFragmentSize the new minimum fragment size. | ||
| */ | ||
| public void setMinimumFragmentSize(int minimumFragmentSize) { | ||
| this.minimumFragmentSizeSetting.set(minimumFragmentSize); | ||
| } | ||
| //</editor-fold> | ||
| // | ||
| //<editor-fold desc="IMoleculeFragmenter methods"> | ||
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| @Override | ||
|
There was a problem hiding this comment. Please add an empty line, the code fold is not working properly, otherwise (because of the @OverRide below it) |
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| public List<Property<?>> settingsProperties() { | ||
| return this.settings; | ||
| } | ||
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| @Override | ||
| public Map<String, String> getSettingNameToTooltipTextMap() { | ||
| return this.settingNameTooltipTextMap; | ||
| } | ||
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| @Override | ||
| public Map<String, String> getSettingNameToDisplayNameMap() { | ||
| return this.settingNameDisplayNameMap; | ||
| } | ||
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| @Override | ||
| public String getFragmentationAlgorithmName() { | ||
| return CDKExhaustiveFragmenter.ALGORITHM_NAME; | ||
| } | ||
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| @Override | ||
| public String getFragmentationAlgorithmDisplayName() { | ||
| return Message.get("CDKExhaustiveFragmenter.displayName"); | ||
| } | ||
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| @Override | ||
| public FragmentSaturationOption getFragmentSaturationSetting() throws UnsupportedOperationException { | ||
| //TODO: there is currently no possibility to implement saturation settings for the exhaustive fragmenter. | ||
|
There was a problem hiding this comment. Can you describe this in more detail here like you did below? |
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| // Because the exhaustive fragmenter in the CDK saturates the fragments by default and is not configurable. | ||
| throw new UnsupportedOperationException("The saturation is currently not configurable for the " + CDKExhaustiveFragmenter.ALGORITHM_NAME); | ||
| } | ||
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| @Override | ||
| public SimpleIDisplayEnumConstantProperty fragmentSaturationSettingProperty() throws UnsupportedOperationException { | ||
| //TODO: there is currently no possibility to implement saturation settings for the exhaustive fragmenter. | ||
| // Because the exhaustive fragmenter in the CDK saturates the fragments by default and is not configurable. | ||
| throw new UnsupportedOperationException("The saturation is currently not configurable for the " + CDKExhaustiveFragmenter.ALGORITHM_NAME); | ||
| } | ||
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| @Override | ||
| public void setFragmentSaturationSetting(FragmentSaturationOption anOption) throws UnsupportedOperationException { | ||
| //TODO: there is currently no possibility to implement saturation settings for the exhaustive fragmenter. | ||
| // Because the exhaustive fragmenter in the CDK saturates the fragments by default and is not configurable. | ||
| throw new UnsupportedOperationException("The saturation is currently not configurable for the " + CDKExhaustiveFragmenter.ALGORITHM_NAME); | ||
| } | ||
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| @Override | ||
| public IMoleculeFragmenter copy() { | ||
| CDKExhaustiveFragmenter tmpCopy = new CDKExhaustiveFragmenter(); | ||
| tmpCopy.minimumFragmentSizeSetting.set(this.minimumFragmentSizeSetting.get()); | ||
| return tmpCopy; | ||
| } | ||
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| @Override | ||
| public void restoreDefaultSettings() { | ||
| this.minimumFragmentSizeSetting.set(CDKExhaustiveFragmenter.DEFAULT_MINIMUM_FRAGMENT_SIZE); | ||
| } | ||
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| @Override | ||
| public List<IAtomContainer> fragmentMolecule(IAtomContainer aMolecule) throws NullPointerException, IllegalArgumentException, CloneNotSupportedException { | ||
| //<editor-fold desc="Parameter tests"> | ||
| Objects.requireNonNull(aMolecule, "Given molecule is null."); | ||
| boolean tmpCanBeFragmented = this.canBeFragmented(aMolecule); | ||
| if (!tmpCanBeFragmented) { | ||
| throw new IllegalArgumentException("Given molecule cannot be fragmented but should be filtered or preprocessed first."); | ||
| } | ||
| //</editor-fold> | ||
| IAtomContainer tmpMoleculeClone = aMolecule.clone(); | ||
| // a rough estimation of the number of unique fragments produced by this fragmenter. | ||
| int fragmentListSizeEstimation = tmpMoleculeClone.getAtomCount() / 2; | ||
| List<IAtomContainer> tmpFragments = new ArrayList<>(fragmentListSizeEstimation); | ||
| try { | ||
| SmilesParser tmpSmilesParser = new SmilesParser(SilentChemObjectBuilder.getInstance()); | ||
| this.cdkEFInstance.generateFragments(tmpMoleculeClone); | ||
| // TODO: there is also an option to extract atom containers directly with getFragmentsAsContainers but this | ||
| // oversaturates fragments described in this issue https://github.com/cdk/cdk/issues/1119. | ||
| List<String> tmpSmiles = new ArrayList<>(List.of(this.cdkEFInstance.getFragments())); | ||
| for (String smile : tmpSmiles) { | ||
| tmpFragments.add(tmpSmilesParser.parseSmiles(smile)); | ||
| } | ||
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| } catch (Exception anException) { | ||
| throw new IllegalArgumentException("An error occurred during fragmentation: " + anException.toString() + " Molecule Name: " + aMolecule.getProperty(Importer.MOLECULE_NAME_PROPERTY_KEY)); | ||
| } | ||
| return tmpFragments; | ||
| } | ||
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| @Override | ||
| public boolean shouldBeFiltered(IAtomContainer aMolecule) { | ||
| return (Objects.isNull(aMolecule) || aMolecule.isEmpty()); | ||
| } | ||
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| @Override | ||
| public boolean shouldBePreprocessed(IAtomContainer aMolecule) throws NullPointerException { | ||
| Objects.requireNonNull(aMolecule, "Given molecule is null."); | ||
| return false; | ||
| } | ||
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| @Override | ||
| public boolean canBeFragmented(IAtomContainer aMolecule) throws NullPointerException { | ||
| Objects.requireNonNull(aMolecule, "Given molecule is null."); | ||
| boolean tmpShouldBeFiltered = this.shouldBeFiltered(aMolecule); | ||
| boolean tmpShouldBePreprocessed = this.shouldBePreprocessed(aMolecule); | ||
| return !(tmpShouldBeFiltered || tmpShouldBePreprocessed); | ||
| } | ||
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| @Override | ||
| public IAtomContainer applyPreprocessing(IAtomContainer aMolecule) throws NullPointerException, IllegalArgumentException, CloneNotSupportedException { | ||
| Objects.requireNonNull(aMolecule, "Given molecule is null."); | ||
| boolean tmpShouldBeFiltered = this.shouldBeFiltered(aMolecule); | ||
| if (tmpShouldBeFiltered) { | ||
| throw new IllegalArgumentException("The given molecule cannot be preprocessed but should be filtered."); | ||
| } | ||
| return aMolecule.clone(); | ||
|
There was a problem hiding this comment. The if statement is unnecessary. I guess you wanted to leave room between the if statement and the return statement for actual preprocessing should you need to add it later? If yes, please add a comment, at least. Or simply remove the if. |
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| } | ||
| //</editor-fold> | ||
| } | ||
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Please use CollectionUtil.calculateInitialHashCollectionCapacity() or HashMap.newHashMap().
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I see now that you only have one setting but are initialising the maps with a capacity of 2, ok. But for the future, please use the ways I indicated.