/* $Revision$ $Author$ $Date$ * * Copyright (C) 2001-2007 Nina Jeliazkova * * Contact: cdk-devel@lists.sourceforge.net * * This program is free software; you can redistribute it and/or * modify it under the terms of the GNU Lesser General Public License * as published by the Free Software Foundation; either version 2.1 * of the License, or (at your option) any later version. * All we ask is that proper credit is given for our work, which includes * - but is not limited to - adding the above copyright notice to the beginning * of your source code files, and to any copyright notice that you may distribute * with programs based on this work. * * This program is distributed in the hope that it will be useful, * but WITHOUT ANY WARRANTY; without even the implied warranty of * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the * GNU Lesser General Public License for more details. * * You should have received a copy of the GNU Lesser General Public License * along with this program; if not, write to the Free Software * Foundation, Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA. */ package org.openscience.cdk.graph; import org.openscience.cdk.CDKConstants; import org.openscience.cdk.annotations.TestClass; import org.openscience.cdk.annotations.TestMethod; import org.openscience.cdk.exception.NoSuchAtomException; import org.openscience.cdk.interfaces.IAtom; import org.openscience.cdk.interfaces.IAtomContainer; import org.openscience.cdk.interfaces.IBond; import org.openscience.cdk.interfaces.IRing; import org.openscience.cdk.interfaces.IRingSet; /** * Spanning tree of a molecule. * Used to discover the number of cyclic bonds in order to prevent the * inefficient AllRingsFinder to run for too long. * * @author Nina Jeliazkova * @cdk.module core * @cdk.githash * @cdk.dictref blue-obelisk:graphSpanningTree * @cdk.keyword spanning tree * @cdk.keyword ring finding * @cdk.bug 1817487 */ @TestClass("org.openscience.cdk.graph.SpanningTreeTest") public class SpanningTree { private final static String ATOM_NUMBER = "ST_ATOMNO"; private int[] parent = null; private int[][] cb = null; // what is cb??? cyclic bonds? protected boolean[] bondsInTree; private int sptSize = 0; private int edrSize = 0; private int bondsAcyclicCount = 0,bondsCyclicCount = 0; private IAtomContainer molecule = null; private int totalEdgeCount=0, totalVertexCount=0; private boolean disconnected; private boolean identifiedBonds; @TestMethod("testIsDisconnected") public boolean isDisconnected() { return disconnected; } @TestMethod("testSpanningTree_IAtomContainer") public SpanningTree(IAtomContainer atomContainer) { identifiedBonds = false; buildSpanningTree(atomContainer); } private boolean fastfind(int v1,int v2, boolean union) { int i = v1; while (parent[i] > 0) i = parent[i]; int j = v2; while (parent[j] > 0) j = parent[j]; int t ; while (parent[v1] > 0) { t = v1; v1 = parent[v1]; parent[t] = i; } while (parent[v2] > 0) { t = v2; v2 = parent[v2]; parent[t] = j; } if (union && (i!=j)) { if (parent[j] < parent[i]) { parent[j] = parent[j] + parent[i]-1; parent[i] = j; } else { parent[i] = parent[i] + parent[j]-1; parent[j] = i; } } return (i != j); } private void fastFindInit(int V) { parent = new int[V+1]; for (int i = 1; i <= V; i++) { parent[i] = 0; } } /* * Kruskal algorithm */ private void buildSpanningTree(IAtomContainer atomContainer){ disconnected = false; molecule = atomContainer; totalVertexCount = atomContainer.getAtomCount(); totalEdgeCount = atomContainer.getBondCount(); sptSize = 0;edrSize = 0; fastFindInit(totalVertexCount); for (int i = 0; i < totalVertexCount; i++) { (atomContainer.getAtom(i)).setProperty(ATOM_NUMBER, Integer.toString(i+1)); } IBond bond; int v1,v2; bondsInTree = new boolean[totalEdgeCount]; for (int b=0; b < totalEdgeCount; b++ ) { bondsInTree[b] = false; bond = atomContainer.getBond(b); v1 = Integer.parseInt((bond.getAtom(0)).getProperty(ATOM_NUMBER).toString()); v2 = Integer.parseInt((bond.getAtom(1)).getProperty(ATOM_NUMBER).toString()); //this below is a little bit slower //v1 = atomContainer.getAtomNumber(bond.getAtomAt(0))+1; //v2 = atomContainer.getAtomNumber(bond.getAtomAt(1))+1; if (fastfind(v1,v2,true)) { bondsInTree[b] = true; sptSize++; //logger.debug("ST : includes bond between atoms "+v1+","+v2); } if (sptSize>=(totalVertexCount-1)) break; } // if atomcontainer is connected then the number of bonds in the spanning tree = (No atoms-1) //i.e. edgesRings = new Bond[E-V+1]; //but to hold all bonds if atomContainer was disconnected then edgesRings = new Bond[E-sptSize]; if (sptSize != (totalVertexCount-1)) disconnected = true; for (int b=0; b < totalEdgeCount; b++ ) if (!bondsInTree[b]){ // edgesRings[edrSize] = atomContainer.getBondAt(b); edrSize++; } cb = new int[edrSize][totalEdgeCount]; for (int i = 0; i < edrSize; i++) for (int a = 0; a < totalEdgeCount; a++) cb[i][a] = 0; // remove ATOM_NUMBER props again for (IAtom atom : atomContainer.atoms()) atom.removeProperty(ATOM_NUMBER); } @TestMethod("testGetSpanningTree") public IAtomContainer getSpanningTree() { IAtomContainer ac = molecule.getBuilder().newAtomContainer(); for (int a=0 ; a < totalVertexCount; a++) ac.addAtom(molecule.getAtom(a)); for (int b=0; b < totalEdgeCount; b++ ) if (bondsInTree[b]) ac.addBond(molecule.getBond(b)); return ac; } @TestMethod("testGetPath_IAtomContainer_IAtom_IAtom") public IAtomContainer getPath(IAtomContainer spt,IAtom a1, IAtom a2) throws NoSuchAtomException { IAtomContainer path = spt.getBuilder().newAtomContainer(); PathTools.resetFlags(spt); path.addAtom(a1); PathTools.depthFirstTargetSearch(spt,a1,a2,path); if (path.getAtomCount() == 1) path.removeAtom(a1); // no path found: remove initial atom return path; } private IRing getRing(IAtomContainer spt, IBond bond) { IRing ring = spt.getBuilder().newRing(); PathTools.resetFlags(spt); ring.addAtom(bond.getAtom(0)); PathTools.depthFirstTargetSearch(spt,bond.getAtom(0),bond.getAtom(1),ring); ring.addBond(bond); return ring; } private void getBondsInRing(IAtomContainer mol, IRing ring, int[] bonds) { for (int i=0; i < ring.getBondCount(); i++ ) { int m = mol.getBondNumber(ring.getBond(i)); bonds[m] = 1; } } @TestMethod("testGetBasicRings") public IRingSet getBasicRings() throws NoSuchAtomException { IRingSet ringset = molecule.getBuilder().newRingSet(); IAtomContainer spt = getSpanningTree(); for (int i = 0; i < totalEdgeCount; i++) if (!bondsInTree[i]) ringset.addAtomContainer(getRing(spt,molecule.getBond(i))); return ringset; } /** * Returns an IAtomContainer which contains all the atoms and bonds which * are involved in ring systems. * * @see #getAllRings() * @see #getBasicRings() * @return the IAtomContainer as described above */ @TestMethod("testGetCyclicFragmentsContainer") public IAtomContainer getCyclicFragmentsContainer() { IAtomContainer fragContainer = this.molecule.getBuilder().newAtomContainer(); IAtomContainer spt = getSpanningTree(); for (int i = 0; i < totalEdgeCount; i++) if (!bondsInTree[i]) { IRing ring = getRing(spt, molecule.getBond(i)); for (int b = 0; b < ring.getBondCount(); b++) { IBond ringBond = ring.getBond(b); if (!fragContainer.contains(ringBond)) { fragContainer.addBond(ringBond); for (int atomCount = 0; atomCount < ringBond.getAtomCount(); atomCount++) { IAtom atom = ringBond.getAtom(atomCount); if (!fragContainer.contains(atom)) { atom.setFlag(CDKConstants.ISINRING, true); fragContainer.addAtom(atom); } } } } } return fragContainer; } /** * Identifies whether bonds are cyclic or not. It is used by several other methods. */ private void identifyBonds() { IAtomContainer spt = getSpanningTree(); IRing ring; int nBasicRings = 0; for (int i = 0; i < totalEdgeCount; i++) { if (!bondsInTree[i]) { ring = getRing(spt,molecule.getBond(i)); for (int b=0; b < ring.getBondCount(); b++ ) { int m = molecule.getBondNumber(ring.getBond(b)); cb[nBasicRings][m] = 1; } nBasicRings++; } } bondsAcyclicCount = 0; bondsCyclicCount = 0; for (int i = 0; i < totalEdgeCount; i++) { int s = 0; for (int j = 0; j < nBasicRings; j++) { s+= cb[j][i]; } switch(s) { case(0): { bondsAcyclicCount++; break; } case(1): { bondsCyclicCount ++; break; } default: { bondsCyclicCount ++; } } } identifiedBonds = true; } @TestMethod("testGetAllRings") public IRingSet getAllRings() throws NoSuchAtomException { IRingSet ringset = getBasicRings(); IRing newring; int nBasicRings = ringset.getAtomContainerCount(); for (int i = 0; i < nBasicRings; i++) getBondsInRing(molecule,(IRing) ringset.getAtomContainer(i), cb[i]); for (int i= 0; i < nBasicRings; i++) { for (int j= i+1; j < nBasicRings; j++) { //logger.debug("combining rings "+(i+1)+","+(j+1)); newring = combineRings(ringset, i, j); //newring = combineRings((Ring)ringset.get(i),(Ring)ringset.get(j)); if (newring != null) ringset.addAtomContainer(newring); } } return ringset; } @TestMethod("testGetSpanningTreeSize") public int getSpanningTreeSize() { return sptSize; } private IRing combineRings(IRingSet ringset, int i, int j) { int c = 0; for (int b= 0; b < cb[i].length; b++) { c = cb[i][b] + cb[j][b]; if (c > 1) break; //at least one common bond } if (c < 2) return null; IRing ring = molecule.getBuilder().newRing(); IRing ring1 = (IRing) ringset.getAtomContainer(i); IRing ring2 = (IRing) ringset.getAtomContainer(j); for (int b= 0; b < cb[i].length; b++) { c = cb[i][b] + cb[j][b]; if ((c == 1) && (cb[i][b] == 1)) ring.addBond(molecule.getBond(b)); else if ((c == 1) && (cb[j][b] == 1)) ring.addBond(molecule.getBond(b)); } for (int a = 0; a < ring1.getAtomCount(); a++) ring.addAtom(ring1.getAtom(a)); for (int a = 0; a < ring2.getAtomCount(); a++) ring.addAtom(ring2.getAtom(a)); return ring; } /** * @return Returns the bondsAcyclicCount. */ @TestMethod("testGetBondsAcyclicCount") public int getBondsAcyclicCount() { if (!identifiedBonds) identifyBonds(); return bondsAcyclicCount; } /** * @return Returns the bondsCyclicCount. */ @TestMethod("testGetBondsCyclicCount") public int getBondsCyclicCount() { if (!identifiedBonds) identifyBonds(); return bondsCyclicCount; } }