/* $Revision$ $Author$ $Date$ * * Copyright (C) 1997-2007 The Chemistry Development Kit (CDK) project * 2008 Gilleain Torrance <gilleain@users.sf.net> * * 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.layout; import java.util.List; import java.util.Vector; import javax.vecmath.Point2d; import javax.vecmath.Vector2d; import org.openscience.cdk.CDKConstants; import org.openscience.cdk.geometry.GeometryTools; import org.openscience.cdk.interfaces.IAtom; import org.openscience.cdk.interfaces.IAtomContainer; import org.openscience.cdk.interfaces.IBond; import org.openscience.cdk.interfaces.IMolecule; import org.openscience.cdk.interfaces.IRing; import org.openscience.cdk.interfaces.IRingSet; import org.openscience.cdk.tools.ILoggingTool; import org.openscience.cdk.tools.LoggingToolFactory; import org.openscience.cdk.tools.manipulator.AtomContainerManipulator; /** * Class providing methods for generating coordinates for ring atoms. * Various situations are supported, like condensation, spiro-attachment, etc. * They can be used for Automated Structure Diagram Generation or in the interactive * buildup of ringsystems by the user. * * @cdk.module sdg * @cdk.githash **/ public class RingPlacer { final static boolean debug = false; private static ILoggingTool logger = LoggingToolFactory.createLoggingTool(RingPlacer.class); private IMolecule molecule; private AtomPlacer atomPlacer = new AtomPlacer(); static int FUSED = 0; static int BRIDGED = 1; static int SPIRO = 2; /** * The empty constructor. */ public RingPlacer() { } /** * Generated coordinates for a given ring. Multiplexes to special handlers * for the different possible situations (spiro-, fusion-, bridged attachement) * * @param ring The ring to be placed * @param sharedAtoms The atoms of this ring, also members of another ring, which are already placed * @param sharedAtomsCenter The geometric center of these atoms * @param ringCenterVector A vector pointing the the center of the new ring * @param bondLength The standard bondlength */ public void placeRing(IRing ring, IAtomContainer sharedAtoms, Point2d sharedAtomsCenter, Vector2d ringCenterVector, double bondLength) { int sharedAtomCount = sharedAtoms.getAtomCount(); logger.debug("placeRing -> sharedAtomCount: " + sharedAtomCount); if (sharedAtomCount > 2) { placeBridgedRing(ring, sharedAtoms, sharedAtomsCenter, ringCenterVector, bondLength); } else if (sharedAtomCount == 2) { placeFusedRing(ring, sharedAtoms, sharedAtomsCenter, ringCenterVector, bondLength); } else if (sharedAtomCount == 1) { placeSpiroRing(ring, sharedAtoms, sharedAtomsCenter, ringCenterVector, bondLength); } } public void placeRing(IRing ring, Point2d ringCenter, double bondLength) { double radius = this.getNativeRingRadius(ring, bondLength); double addAngle = 2 * Math.PI / ring.getRingSize(); IAtom startAtom = ring.getFirstAtom(); Point2d p = new Point2d(ringCenter.x + radius, ringCenter.y); startAtom.setPoint2d(p); double startAngle = Math.PI*0.5; /* Different ring sizes get different start angles to have * visually correct placement */ int ringSize=ring.getRingSize(); switch (ringSize) { case 3: startAngle=Math.PI*(0.1666667); break; case 4: startAngle=Math.PI*0.25; break; case 5: startAngle=Math.PI*0.3; break; case 7: startAngle=Math.PI*0.07; break; case 8: startAngle=Math.PI*0.125; break; } List<IBond> bonds = ring.getConnectedBondsList(startAtom); /* * Store all atoms to draw in consecutive order relative to the * chosen bond. */ Vector<IAtom> atomsToDraw = new Vector<IAtom>(); IAtom currentAtom = startAtom; IBond currentBond = (IBond)bonds.get(0); for (int i = 0; i < ring.getBondCount(); i++) { currentBond = ring.getNextBond(currentBond, currentAtom); currentAtom = currentBond.getConnectedAtom(currentAtom); atomsToDraw.addElement(currentAtom); } atomPlacer.populatePolygonCorners(atomsToDraw, ringCenter, startAngle, addAngle, radius); } /** * Positions the aliphatic substituents of a ring system * * @param rs The RingSystem for which the substituents are to be laid out * @return A list of atoms that where laid out */ public IAtomContainer placeRingSubstituents(IRingSet rs, double bondLength) { logger.debug("RingPlacer.placeRingSubstituents() start"); IRing ring = null; IAtom atom = null; IRingSet rings = null; IAtomContainer unplacedPartners = rs.getBuilder().newAtomContainer(); IAtomContainer sharedAtoms = rs.getBuilder().newAtomContainer(); IAtomContainer primaryAtoms = rs.getBuilder().newAtomContainer(); IAtomContainer treatedAtoms = rs.getBuilder().newAtomContainer(); Point2d centerOfRingGravity = null; for (int j = 0; j < rs.getAtomContainerCount(); j++) { ring = (IRing)rs.getAtomContainer(j); /* Get the j-th Ring in RingSet rs */ for (int k = 0; k < ring.getAtomCount(); k++) { unplacedPartners.removeAllElements(); sharedAtoms.removeAllElements(); primaryAtoms.removeAllElements(); atom = ring.getAtom(k); rings = rs.getRings(atom); centerOfRingGravity = GeometryTools.get2DCenter(rings); atomPlacer.partitionPartners(atom, unplacedPartners, sharedAtoms); atomPlacer.markNotPlaced(unplacedPartners); try { for (int f = 0; f < unplacedPartners.getAtomCount(); f++) { logger.debug("placeRingSubstituents->unplacedPartners: " + (molecule.getAtomNumber(unplacedPartners.getAtom(f)) + 1)); } } catch(Exception exc) { } treatedAtoms.add(unplacedPartners); if (unplacedPartners.getAtomCount() > 0) { atomPlacer.distributePartners(atom, sharedAtoms, centerOfRingGravity, unplacedPartners, bondLength); } } } logger.debug("RingPlacer.placeRingSubstituents() end"); return treatedAtoms; } /** * Generated coordinates for a given ring, which is connected to another ring a bridged ring, * i.e. it shares more than two atoms with another ring. * * @param ring The ring to be placed * @param sharedAtoms The atoms of this ring, also members of another ring, which are already placed * @param sharedAtomsCenter The geometric center of these atoms * @param ringCenterVector A vector pointing the the center of the new ring * @param bondLength The standard bondlength */ private void placeBridgedRing(IRing ring, IAtomContainer sharedAtoms, Point2d sharedAtomsCenter, Vector2d ringCenterVector, double bondLength ) { double radius = getNativeRingRadius(ring, bondLength); Point2d ringCenter = new Point2d(sharedAtomsCenter); ringCenterVector.normalize(); logger.debug("placeBridgedRing->: ringCenterVector.length()" + ringCenterVector.length()); ringCenterVector.scale(radius); ringCenter.add(ringCenterVector); IAtom[] bridgeAtoms = getBridgeAtoms(sharedAtoms); IAtom bondAtom1 = bridgeAtoms[0]; IAtom bondAtom2 = bridgeAtoms[1]; Vector2d bondAtom1Vector = new Vector2d(bondAtom1.getPoint2d()); Vector2d bondAtom2Vector = new Vector2d(bondAtom2.getPoint2d()); Vector2d originRingCenterVector = new Vector2d(ringCenter); bondAtom1Vector.sub(originRingCenterVector); bondAtom2Vector.sub(originRingCenterVector); double occupiedAngle = bondAtom1Vector.angle(bondAtom2Vector); double remainingAngle = (2 * Math.PI) - occupiedAngle; double addAngle = remainingAngle / (ring.getRingSize() - sharedAtoms.getAtomCount() + 1); logger.debug("placeBridgedRing->occupiedAngle: " + Math.toDegrees(occupiedAngle)); logger.debug("placeBridgedRing->remainingAngle: " + Math.toDegrees(remainingAngle)); logger.debug("placeBridgedRing->addAngle: " + Math.toDegrees(addAngle)); IAtom startAtom; double centerX = ringCenter.x; double centerY = ringCenter.y; double xDiff = bondAtom1.getPoint2d().x - bondAtom2.getPoint2d().x; double yDiff = bondAtom1.getPoint2d().y - bondAtom2.getPoint2d().y; double startAngle; int direction = 1; // if bond is vertical if (xDiff == 0) { logger.debug("placeBridgedRing->Bond is vertical"); //starts with the lower Atom if (bondAtom1.getPoint2d().y > bondAtom2.getPoint2d().y) { startAtom = bondAtom1; } else { startAtom = bondAtom2; } //changes the drawing direction if (centerX < bondAtom1.getPoint2d().x) { direction = 1; } else { direction = -1; } } // if bond is not vertical else { //starts with the left Atom if (bondAtom1.getPoint2d().x > bondAtom2.getPoint2d().x) { startAtom = bondAtom1; } else { startAtom = bondAtom2; } //changes the drawing direction if (centerY - bondAtom1.getPoint2d().y > (centerX - bondAtom1.getPoint2d().x) * yDiff / xDiff) { direction = 1; } else { direction = -1; } } startAngle = GeometryTools.getAngle(startAtom.getPoint2d().x - ringCenter.x, startAtom.getPoint2d().y - ringCenter.y); IAtom currentAtom = startAtom; // determine first bond in Ring int k = 0; // for (k = 0; k < ring.getElectronContainerCount(); k++) { // if (ring.getElectronContainer(k) instanceof IBond) break; // } IBond currentBond = sharedAtoms.getBond(0); Vector atomsToDraw = new Vector(); for (int i = 0; i < ring.getBondCount(); i++) { currentBond = ring.getNextBond(currentBond, currentAtom); currentAtom = currentBond.getConnectedAtom(currentAtom); if (!sharedAtoms.contains(currentAtom)) { atomsToDraw.addElement(currentAtom); } } try { logger.debug("placeBridgedRing->atomsToPlace: " + atomPlacer.listNumbers(molecule, atomsToDraw)); logger.debug("placeBridgedRing->startAtom is: " + (molecule.getAtomNumber(startAtom) + 1)); logger.debug("placeBridgedRing->startAngle: " + Math.toDegrees(startAngle)); logger.debug("placeBridgedRing->addAngle: " + Math.toDegrees(addAngle)); } catch(Exception exc) { logger.debug("Caught an exception while logging in RingPlacer"); } addAngle = addAngle * direction; atomPlacer.populatePolygonCorners(atomsToDraw, ringCenter, startAngle, addAngle, radius); } /** * Generated coordinates for a given ring, which is connected to a spiro ring. * The rings share exactly one atom. * * @param ring The ring to be placed * @param sharedAtoms The atoms of this ring, also members of another ring, which are already placed * @param sharedAtomsCenter The geometric center of these atoms * @param ringCenterVector A vector pointing the the center of the new ring * @param bondLength The standard bondlength */ public void placeSpiroRing(IRing ring, IAtomContainer sharedAtoms, Point2d sharedAtomsCenter, Vector2d ringCenterVector, double bondLength) { logger.debug("placeSpiroRing"); double radius = getNativeRingRadius(ring, bondLength); Point2d ringCenter = new Point2d(sharedAtomsCenter); ringCenterVector.normalize(); ringCenterVector.scale(radius); ringCenter.add(ringCenterVector); double addAngle = 2 * Math.PI / ring.getRingSize(); IAtom startAtom = sharedAtoms.getAtom(0); //double centerX = ringCenter.x; //double centerY = ringCenter.y; //int direction = 1; IAtom currentAtom = startAtom; double startAngle = GeometryTools.getAngle(startAtom.getPoint2d().x - ringCenter.x, startAtom.getPoint2d().y - ringCenter.y); /* * Get one bond connected to the spiro bridge atom. * It doesn't matter in which direction we draw. */ java.util.List bonds = ring.getConnectedBondsList(startAtom); IBond currentBond = (IBond)bonds.get(0); Vector atomsToDraw = new Vector(); /* * Store all atoms to draw in consequtive order relative to the * chosen bond. */ for (int i = 0; i < ring.getBondCount(); i++) { currentBond = ring.getNextBond(currentBond, currentAtom); currentAtom = currentBond.getConnectedAtom(currentAtom); atomsToDraw.addElement(currentAtom); } logger.debug("currentAtom "+currentAtom); logger.debug("startAtom "+startAtom); atomPlacer.populatePolygonCorners(atomsToDraw, ringCenter, startAngle, addAngle, radius); } /** * Generated coordinates for a given ring, which is fused to another ring. * The rings share exactly one bond. * * @param ring The ring to be placed * @param sharedAtoms The atoms of this ring, also members of another ring, which are already placed * @param sharedAtomsCenter The geometric center of these atoms * @param ringCenterVector A vector pointing the the center of the new ring * @param bondLength The standard bondlength */ public void placeFusedRing(IRing ring, IAtomContainer sharedAtoms, Point2d sharedAtomsCenter, Vector2d ringCenterVector, double bondLength ) { logger.debug("RingPlacer.placeFusedRing() start"); Point2d ringCenter = new Point2d(sharedAtomsCenter); double radius = getNativeRingRadius(ring, bondLength); double newRingPerpendicular = Math.sqrt(Math.pow(radius, 2) - Math.pow(bondLength/2, 2)); ringCenterVector.normalize(); logger.debug("placeFusedRing->: ringCenterVector.length()" + ringCenterVector.length()); ringCenterVector.scale(newRingPerpendicular); ringCenter.add(ringCenterVector); IAtom bondAtom1 = sharedAtoms.getAtom(0); IAtom bondAtom2 = sharedAtoms.getAtom(1); Vector2d bondAtom1Vector = new Vector2d(bondAtom1.getPoint2d()); Vector2d bondAtom2Vector = new Vector2d(bondAtom2.getPoint2d()); Vector2d originRingCenterVector = new Vector2d(ringCenter); bondAtom1Vector.sub(originRingCenterVector); bondAtom2Vector.sub(originRingCenterVector); double occupiedAngle = bondAtom1Vector.angle(bondAtom2Vector); double remainingAngle = (2 * Math.PI) - occupiedAngle; double addAngle = remainingAngle / (ring.getRingSize()-1); logger.debug("placeFusedRing->occupiedAngle: " + Math.toDegrees(occupiedAngle)); logger.debug("placeFusedRing->remainingAngle: " + Math.toDegrees(remainingAngle)); logger.debug("placeFusedRing->addAngle: " + Math.toDegrees(addAngle)); IAtom startAtom; double centerX = ringCenter.x; double centerY = ringCenter.y; double xDiff = bondAtom1.getPoint2d().x - bondAtom2.getPoint2d().x; double yDiff = bondAtom1.getPoint2d().y - bondAtom2.getPoint2d().y; double startAngle;; int direction = 1; // if bond is vertical if (xDiff == 0) { logger.debug("placeFusedRing->Bond is vertical"); //starts with the lower Atom if (bondAtom1.getPoint2d().y > bondAtom2.getPoint2d().y) { startAtom = bondAtom1; } else { startAtom = bondAtom2; } //changes the drawing direction if (centerX < bondAtom1.getPoint2d().x) { direction = 1; } else { direction = -1; } } // if bond is not vertical else { //starts with the left Atom if (bondAtom1.getPoint2d().x > bondAtom2.getPoint2d().x) { startAtom = bondAtom1; } else { startAtom = bondAtom2; } //changes the drawing direction if (centerY - bondAtom1.getPoint2d().y > (centerX - bondAtom1.getPoint2d().x) * yDiff / xDiff) { direction = 1; } else { direction = -1; } } startAngle = GeometryTools.getAngle(startAtom.getPoint2d().x - ringCenter.x, startAtom.getPoint2d().y - ringCenter.y); IAtom currentAtom = startAtom; // determine first bond in Ring // int k = 0; // for (k = 0; k < ring.getElectronContainerCount(); k++) { // if (ring.getElectronContainer(k) instanceof IBond) break; // } IBond currentBond = sharedAtoms.getBond(0); Vector atomsToDraw = new Vector(); for (int i = 0; i < ring.getBondCount() - 2; i++) { currentBond = ring.getNextBond(currentBond, currentAtom); currentAtom = currentBond.getConnectedAtom(currentAtom); atomsToDraw.addElement(currentAtom); } addAngle = addAngle * direction; try { logger.debug("placeFusedRing->startAngle: " + Math.toDegrees(startAngle)); logger.debug("placeFusedRing->addAngle: " + Math.toDegrees(addAngle)); logger.debug("placeFusedRing->startAtom is: " + (molecule.getAtomNumber(startAtom) + 1)); logger.debug("AtomsToDraw: " + atomPlacer.listNumbers(molecule, atomsToDraw)); } catch(Exception exc) { logger.debug("Caught an exception while logging in RingPlacer"); } atomPlacer.populatePolygonCorners(atomsToDraw, ringCenter, startAngle, addAngle, radius); } /** * True if coordinates have been assigned to all atoms in all rings. * * @param rs The ringset to be checked * @return True if coordinates have been assigned to all atoms in all rings. */ public boolean allPlaced(IRingSet rs) { for (int i = 0; i < rs.getAtomContainerCount(); i++) { if (!((IRing)rs.getAtomContainer(i)).getFlag(CDKConstants.ISPLACED)) { return false; } } return true; } /** * Walks throught the atoms of each ring in a ring set and marks * a ring as PLACED if all of its atoms have been placed. * * @param rs The ringset to be checked */ public void checkAndMarkPlaced(IRingSet rs) { IRing ring = null; boolean allPlaced = true; for (int i = 0; i < rs.getAtomContainerCount(); i++) { ring = (IRing)rs.getAtomContainer(i); allPlaced = true; for (int j = 0; j < ring.getAtomCount(); j++) { if (!((IAtom)ring.getAtom(j)).getFlag(CDKConstants.ISPLACED)) { allPlaced = false; break; } } ring.setFlag(CDKConstants.ISPLACED, allPlaced); } } /** * Returns the bridge atoms, that is the outermost atoms in * the chain of more than two atoms which are shared by two rings * * @param sharedAtoms The atoms (n > 2) which are shared by two rings * @return The bridge atoms, i.e. the outermost atoms in the chain of more than two atoms which are shared by two rings */ private IAtom[] getBridgeAtoms(IAtomContainer sharedAtoms) { IAtom[] bridgeAtoms = new IAtom[2]; IAtom atom; int counter = 0; for (int f = 0; f < sharedAtoms.getAtomCount(); f++) { atom = sharedAtoms.getAtom(f); if (sharedAtoms.getConnectedAtomsList(atom).size() == 1) { bridgeAtoms[counter] = atom; counter ++; } } return bridgeAtoms; } /** * Partition the bonding partners of a given atom into ring atoms and non-ring atoms * * @param atom The atom whose bonding partners are to be partitioned * @param ring The ring against which the bonding partners are checked * @param ringAtoms An AtomContainer to store the ring bonding partners * @param nonRingAtoms An AtomContainer to store the non-ring bonding partners */ public void partitionNonRingPartners(IAtom atom, IRing ring, IAtomContainer ringAtoms, IAtomContainer nonRingAtoms) { java.util.List atoms = molecule.getConnectedAtomsList(atom); for (int i = 0; i < atoms.size(); i++) { IAtom curAtom = (IAtom)atoms.get(i); if (!ring.contains(curAtom)) { nonRingAtoms.addAtom(curAtom); } else { ringAtoms.addAtom(curAtom); } } } /** * Returns the ring radius of a perfect polygons of size ring.getAtomCount() * The ring radius is the distance of each atom to the ringcenter. * * @param ring The ring for which the radius is to calculated * @param bondLength The bond length for each bond in the ring * @return The radius of the ring. */ public double getNativeRingRadius(IRing ring, double bondLength) { int size = ring.getAtomCount(); double radius = bondLength / (2 * Math.sin((Math.PI) / size)); return radius; } /** * Calculated the center for the first ring so that it can * layed out. Only then, all other rings can be assigned * coordinates relative to it. * * @param ring The ring for which the center is to be calculated * @return A Vector2d pointing to the new ringcenter */ Vector2d getRingCenterOfFirstRing(IRing ring, Vector2d bondVector, double bondLength) { int size = ring.getAtomCount(); double radius = bondLength / (2 * Math.sin((Math.PI) / size)); double newRingPerpendicular = Math.sqrt(Math.pow(radius, 2) - Math.pow(bondLength/2, 2)); /* get the angle between the x axis and the bond vector */ double rotangle = GeometryTools.getAngle(bondVector.x, bondVector.y); /* Add 90 Degrees to this angle, this is supposed to be the new ringcenter vector */ rotangle += Math.PI / 2; return new Vector2d(Math.cos(rotangle) * newRingPerpendicular, Math.sin(rotangle) * newRingPerpendicular); } /** * Layout all rings in the given RingSet that are connected to a given Ring * * @param rs The RingSet to be searched for rings connected to Ring * @param ring The Ring for which all connected rings in RingSet are to be layed out. */ void placeConnectedRings(IRingSet rs, IRing ring, int handleType, double bondLength) { IRingSet connectedRings = rs.getConnectedRings(ring); IRing connectedRing; IAtomContainer sharedAtoms; int sac; Point2d oldRingCenter, sharedAtomsCenter, tempPoint; Vector2d tempVector, oldRingCenterVector, newRingCenterVector; // logger.debug(rs.reportRingList(molecule)); for (IAtomContainer container : connectedRings.atomContainers()) { connectedRing = (IRing)container; if (!connectedRing.getFlag(CDKConstants.ISPLACED)) { // logger.debug(ring.toString(molecule)); // logger.debug(connectedRing.toString(molecule)); sharedAtoms = AtomContainerManipulator.getIntersection(ring, connectedRing); sac = sharedAtoms.getAtomCount(); logger.debug("placeConnectedRings-> connectedRing: " + (ring.toString())); if ((sac == 2 && handleType == FUSED) ||(sac == 1 && handleType == SPIRO)||(sac > 2 && handleType == BRIDGED)) { sharedAtomsCenter = GeometryTools.get2DCenter(sharedAtoms); oldRingCenter = GeometryTools.get2DCenter(ring); tempVector = (new Vector2d(sharedAtomsCenter)); newRingCenterVector = new Vector2d(tempVector); newRingCenterVector.sub(new Vector2d(oldRingCenter)); oldRingCenterVector = new Vector2d(newRingCenterVector); logger.debug("placeConnectedRing -> tempVector: " + tempVector + ", tempVector.length: " + tempVector.length()); logger.debug("placeConnectedRing -> bondCenter: " + sharedAtomsCenter); logger.debug("placeConnectedRing -> oldRingCenterVector.length(): " + oldRingCenterVector.length()); logger.debug("placeConnectedRing -> newRingCenterVector.length(): " + newRingCenterVector.length()); tempPoint = new Point2d(sharedAtomsCenter); tempPoint.add(newRingCenterVector); placeRing(connectedRing, sharedAtoms, sharedAtomsCenter, newRingCenterVector, bondLength); connectedRing.setFlag(CDKConstants.ISPLACED, true); placeConnectedRings(rs, connectedRing, handleType, bondLength); } } } } public IMolecule getMolecule() { return this.molecule; } public void setMolecule(IMolecule molecule) { this.molecule = molecule; } public AtomPlacer getAtomPlacer() { return this.atomPlacer; } public void setAtomPlacer(AtomPlacer atomPlacer) { this.atomPlacer = atomPlacer; } }