public void TestAutomatic_Set_Active_Bond()
{
/* ionize all possible double bonds */
IAtomContainer reactant = builder.NewAtomContainer();//Miles("C=CC")
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.AddBond(reactant.Atoms[0], reactant.Atoms[1], BondOrder.Double);
reactant.AddBond(reactant.Atoms[1], reactant.Atoms[2], BondOrder.Single);
AddExplicitHydrogens(reactant);
var setOfReactants = ChemObjectBuilder.Instance.NewAtomContainerSet();
setOfReactants.Add(reactant);
/* initiate */
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(reactant);
MakeSureAtomTypesAreRecognized(reactant);
IReactionProcess type = new ElectronImpactPDBReaction();
var setOfReactions = type.Initiate(setOfReactants, null);
Assert.AreEqual(2, setOfReactions.Count);
IAtomContainer molecule = setOfReactions[0].Products[0];
Assert.AreEqual(1, molecule.Atoms[0].FormalCharge.Value);
Assert.AreEqual(1, molecule.GetConnectedSingleElectrons(molecule.Atoms[1]).Count());
molecule = setOfReactions[1].Products[0];
Assert.AreEqual(1, molecule.Atoms[1].FormalCharge.Value);
Assert.AreEqual(1, molecule.GetConnectedSingleElectrons(molecule.Atoms[0]).Count());
}
/// <summary>
/// set the active center for this molecule.
/// The active center will be those which correspond with X=Y.
/// </summary>
/// <param name="reactant">The molecule to set the activity</param>
private static void SetActiveCenters(IAtomContainer reactant)
{
if (AtomContainerManipulator.GetTotalCharge(reactant) != 0)
{
return;
}
foreach (var bondi in reactant.Bonds)
{
if (((bondi.Order == BondOrder.Double) || (bondi.Order == BondOrder.Triple)))
{
int chargeAtom0 = bondi.Begin.FormalCharge ?? 0;
int chargeAtom1 = bondi.End.FormalCharge ?? 0;
if (chargeAtom0 >= 0 && chargeAtom1 >= 0 &&
!reactant.GetConnectedSingleElectrons(bondi.Begin).Any() &&
!reactant.GetConnectedSingleElectrons(bondi.End).Any() &&
!reactant.GetConnectedLonePairs(bondi.Begin).Any() &&
!reactant.GetConnectedLonePairs(bondi.End).Any())
{
bondi.IsReactiveCenter = true;
bondi.Begin.IsReactiveCenter = true;
bondi.End.IsReactiveCenter = true;
}
}
}
}
internal IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents, BondCheck bondChecker)
{
CheckInitiateParams(reactants, agents);
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
// if the parameter hasActiveCenter is not fixed yet, set the active centers
IParameterReaction ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant, bondChecker);
}
foreach (var bondi in reactant.Bonds)
{
IAtom atom1 = bondi.Begin;
IAtom atom2 = bondi.End;
if (bondi.IsReactiveCenter &&
bondChecker(bondi) &&
atom1.IsReactiveCenter && atom2.IsReactiveCenter &&
(atom1.FormalCharge ?? 0) == 0 &&
(atom2.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atom1).Any() &&
!reactant.GetConnectedSingleElectrons(atom2).Any())
{
for (int j = 0; j < 2; j++)
{
var atomList = new List <IAtom>();
if (j == 0)
{
atomList.Add(atom1);
atomList.Add(atom2);
}
else
{
atomList.Add(atom2);
atomList.Add(atom1);
}
var bondList = new List <IBond>
{
bondi
};
IChemObjectSet <IAtomContainer> moleculeSet = reactant.Builder.NewAtomContainerSet();
moleculeSet.Add(reactant);
IReaction reaction = Mechanism.Initiate(moleculeSet, atomList, bondList);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
}
return(setOfReactions);
}
/// <summary>
/// set the active center for this molecule.
/// The active center will be those which correspond with X=Y-Z-H.
/// <pre>
/// X: Atom
/// =: bond
/// Y: Atom
/// -: bond
/// Z: Atom
/// -: bond
/// H: Atom
/// </pre>
/// </summary>
/// <param name="reactant">The molecule to set the activity</param>
private static void SetActiveCenters(IAtomContainer reactant)
{
foreach (var atomi in reactant.Atoms)
{
if ((atomi.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atomi).Any())
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.Order == BondOrder.Double)
{
IAtom atomj = bondi.GetOther(atomi);
if ((atomj.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atomj).Any())
{
foreach (var bondj in reactant.GetConnectedBonds(atomj))
{
if (bondj.Equals(bondi))
{
continue;
}
if (bondj.Order == BondOrder.Single)
{
IAtom atomk = bondj.GetOther(atomj);
if ((atomk.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atomk).Any()
)
{
foreach (var bondk in reactant.GetConnectedBonds(atomk))
{
if (bondk.Equals(bondj))
{
continue;
}
if (bondk.Order == BondOrder.Single)
{
IAtom atoml = bondk.GetOther(atomk); // Atom pos 4
if (atoml.AtomicNumber.Equals(AtomicNumbers.H))
{
atomi.IsReactiveCenter = true;
atomj.IsReactiveCenter = true;
atomk.IsReactiveCenter = true;
atoml.IsReactiveCenter = true;
bondi.IsReactiveCenter = true;
bondj.IsReactiveCenter = true;
bondk.IsReactiveCenter = true;
}
}
}
}
}
}
}
}
}
}
}
}
public void TestAutomatic_Set_Active_Bond2()
{
/* ionize >C=C< , set the reactive center */
IAtomContainer reactant = builder.NewAtomContainer();//CreateFromSmiles("C=CCC(=O)CC")
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("O"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.AddBond(reactant.Atoms[0], reactant.Atoms[1], BondOrder.Double);
reactant.AddBond(reactant.Atoms[1], reactant.Atoms[2], BondOrder.Single);
reactant.AddBond(reactant.Atoms[2], reactant.Atoms[3], BondOrder.Single);
reactant.AddBond(reactant.Atoms[3], reactant.Atoms[4], BondOrder.Double);
reactant.AddBond(reactant.Atoms[3], reactant.Atoms[5], BondOrder.Single);
reactant.AddBond(reactant.Atoms[5], reactant.Atoms[6], BondOrder.Single);
AddExplicitHydrogens(reactant);
var setOfReactants = ChemObjectBuilder.Instance.NewAtomContainerSet();
setOfReactants.Add(reactant);
/* initiate */
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(reactant);
MakeSureAtomTypesAreRecognized(reactant);
var type = new ElectronImpactPDBReaction();
var paramList = new List <IParameterReaction>();
var param = new SetReactionCenter
{
IsSetParameter = false
};
paramList.Add(param);
type.ParameterList = paramList;
var setOfReactions = type.Initiate(setOfReactants, null);
Assert.AreEqual(3, setOfReactions.Count);
IAtomContainer molecule = setOfReactions[0].Products[0];
Assert.AreEqual(1, molecule.Atoms[0].FormalCharge.Value);
Assert.AreEqual(1, molecule.GetConnectedSingleElectrons(molecule.Atoms[1]).Count());
molecule = setOfReactions[1].Products[0];
Assert.AreEqual(1, molecule.Atoms[1].FormalCharge.Value);
Assert.AreEqual(1, molecule.GetConnectedSingleElectrons(molecule.Atoms[0]).Count());
Assert.AreEqual(17, setOfReactions[0].Mappings.Count);
}
public override void TestInitiate_IAtomContainerSet_IAtomContainerSet()
{
/* Ionize(>C=O): C=CCC(=O)CC -> C=CCC(=O*)CC , set the reactive center */
IAtomContainer reactant = builder.NewAtomContainer();//CreateFromSmiles("C=CCC(=O)CC")
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("O"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.AddBond(reactant.Atoms[0], reactant.Atoms[1], BondOrder.Double);
reactant.AddBond(reactant.Atoms[1], reactant.Atoms[2], BondOrder.Single);
reactant.AddBond(reactant.Atoms[2], reactant.Atoms[3], BondOrder.Single);
reactant.AddBond(reactant.Atoms[3], reactant.Atoms[4], BondOrder.Double);
reactant.AddBond(reactant.Atoms[3], reactant.Atoms[5], BondOrder.Single);
reactant.AddBond(reactant.Atoms[5], reactant.Atoms[6], BondOrder.Single);
AddExplicitHydrogens(reactant);
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(reactant);
CDK.LonePairElectronChecker.Saturate(reactant);
foreach (var atom in reactant.Atoms)
{
if (reactant.GetConnectedLonePairs(atom).Count() > 0)
{
atom.IsReactiveCenter = true;
}
}
var setOfReactants = ChemObjectBuilder.Instance.NewAtomContainerSet();
setOfReactants.Add(reactant);
/* initiate */
MakeSureAtomTypesAreRecognized(reactant);
IReactionProcess type = new ElectronImpactNBEReaction();
var paramList = new List <IParameterReaction>();
IParameterReaction param = new SetReactionCenter
{
IsSetParameter = true
};
paramList.Add(param);
type.ParameterList = paramList;
var setOfReactions = type.Initiate(setOfReactants, null);
Assert.AreEqual(1, setOfReactions.Count);
Assert.AreEqual(1, setOfReactions[0].Products.Count);
IAtomContainer molecule = setOfReactions[0].Products[0];
Assert.AreEqual(1, molecule.Atoms[4].FormalCharge.Value);
Assert.AreEqual(1, molecule.GetConnectedSingleElectrons(molecule.Atoms[4]).Count());
Assert.IsTrue(setOfReactions[0].Mappings.Any());
}
/// <summary>
/// set the active center for this molecule.
/// The active center will be those which correspond with [A+]=B.
/// <pre>
/// A: Atom with positive charge
/// =: Double bond
/// B: Atom
/// </pre>
/// </summary>
/// <param name="reactant">The molecule to set the activity</param>
private static void SetActiveCenters(IAtomContainer reactant)
{
foreach (var atomi in reactant.Atoms)
{
if (atomi.FormalCharge == 1)
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.Order != BondOrder.Single)
{
IAtom atomj = bondi.GetOther(atomi);
if (atomj.FormalCharge == 0)
{
if (!reactant.GetConnectedSingleElectrons(atomj).Any())
{
atomi.IsReactiveCenter = true;
bondi.IsReactiveCenter = true;
atomj.IsReactiveCenter = true;
}
}
}
}
}
}
}
/// <summary>
/// Generate the displayed atom symbol for an atom in given structure with the specified hydrogen
/// position.
/// </summary>
/// <param name="container">structure to which the atom belongs</param>
/// <param name="atom">the atom to generate the symbol for</param>
/// <param name="position">the hydrogen position</param>
/// <param name="model">additional rendering options</param>
/// <returns>atom symbol</returns>
public AtomSymbol GenerateSymbol(IAtomContainer container, IAtom atom, HydrogenPosition position, RendererModel model)
{
if (atom is IPseudoAtom pAtom)
{
if (pAtom.AttachPointNum <= 0)
{
if ("*".Equals(pAtom.Label, StringComparison.Ordinal))
{
var mass = pAtom.MassNumber ?? 0;
var charge = pAtom.FormalCharge ?? 0;
var hcnt = pAtom.ImplicitHydrogenCount ?? 0;
var nrad = container.GetConnectedSingleElectrons(atom).Count();
if (mass != 0 || charge != 0 || hcnt != 0)
{
return(GeneratePeriodicSymbol(0, hcnt, mass, charge, nrad, position));
}
}
return(GeneratePseudoSymbol(AccessPseudoLabel(pAtom, "?"), position));
}
else
{
return(null); // attach point drawn in bond generator
}
}
else
{
var number = atom.AtomicNumber;
// unset the mass if it's the major isotope (could be an option)
var mass = atom.MassNumber;
if (number != 0 &&
mass != null &&
model != null &&
model.GetOmitMajorIsotopes() &&
IsMajorIsotope(number, mass.Value))
{
mass = null;
}
return(GeneratePeriodicSymbol(
number,
atom.ImplicitHydrogenCount ?? 0,
mass ?? -1,
atom.FormalCharge ?? 0,
container.GetConnectedSingleElectrons(atom).Count(), position));
}
}
private static void SetActiveCenters(IAtomContainer reactant, CheckReactant checkReatant, CheckReactantAtom checkReatantAtom, CheckAtom checkAtom)
{
if (checkReatant != null && !checkReatant(reactant))
{
return;
}
foreach (var atomi in reactant.Atoms)
{
if (checkReatantAtom(reactant, atomi))
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.Order == BondOrder.Single)
{
IAtom atomj = bondi.GetOther(atomi);
if ((atomj.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atomj).Any())
{
foreach (var bondj in reactant.GetConnectedBonds(atomj))
{
if (bondj.Equals(bondi))
{
continue;
}
if (bondj.Order == BondOrder.Double)
{
IAtom atomk = bondj.GetOther(atomj);
if (checkAtom(atomk) &&
!reactant.GetConnectedSingleElectrons(atomk).Any())
{
atomi.IsReactiveCenter = true;
atomj.IsReactiveCenter = true;
atomk.IsReactiveCenter = true;
bondi.IsReactiveCenter = true;
bondj.IsReactiveCenter = true;
}
}
}
}
}
}
}
}
}
public override void TestInitiate_IAtomContainerSet_IAtomContainerSet()
{
/* Ionize(>C-C<): C=CCC -> C=C* + C+ , set the reactive center */
var setOfReactants = GetExampleReactants();
IAtomContainer reactant = setOfReactants[0];
foreach (var bond in reactant.Bonds)
{
IAtom atom1 = bond.Atoms[0];
IAtom atom2 = bond.Atoms[1];
if (bond.Order == BondOrder.Single && atom1.Symbol.Equals("C") && atom2.Symbol.Equals("C"))
{
bond.IsReactiveCenter = true;
atom1.IsReactiveCenter = true;
atom2.IsReactiveCenter = true;
}
}
Assert.AreEqual(0, reactant.SingleElectrons.Count);
/* initiate */
var type = new ElectronImpactSDBReaction();
var paramList = new List <IParameterReaction>();
var param = new SetReactionCenter
{
IsSetParameter = true
};
paramList.Add(param);
type.ParameterList = paramList;
var setOfReactions = type.Initiate(setOfReactants, null);
Assert.AreEqual(2, setOfReactions.Count);
Assert.AreEqual(2, setOfReactions[0].Products.Count);
IAtomContainer molecule1 = setOfReactions[0].Products[0];//[H][C+]=C([H])[H]
Assert.AreEqual(1, molecule1.Atoms[1].FormalCharge.Value);
Assert.AreEqual(0, molecule1.SingleElectrons.Count);
IAtomContainer molecule2 = setOfReactions[0].Products[1];//[H][C*]([H])[H]
Assert.AreEqual(1, molecule2.SingleElectrons.Count);
Assert.AreEqual(1, molecule2.GetConnectedSingleElectrons(molecule2.Atoms[0]).Count());
Assert.IsTrue(setOfReactions[0].Mappings.Any());
Assert.AreEqual(2, setOfReactions[1].Products.Count);
molecule1 = setOfReactions[1].Products[0];//[H]C=[C*]([H])[H]
Assert.AreEqual(1, molecule1.GetConnectedSingleElectrons(molecule1.Atoms[1]).Count());
molecule2 = setOfReactions[1].Products[1];//[H][C+]([H])[H]
Assert.AreEqual(0, molecule2.SingleElectrons.Count);
Assert.AreEqual(1, molecule2.Atoms[0].FormalCharge.Value);
}
private static void SetActiveCenters(IAtomContainer reactant, BondCheck bondCheck)
{
foreach (var bond in reactant.Bonds)
{
var atom1 = bond.Begin;
var atom2 = bond.End;
if ((bondCheck == null || bondCheck(bond)) &&
(atom1.FormalCharge ?? 0) == 0 &&
(atom2.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atom1).Any() &&
!reactant.GetConnectedSingleElectrons(atom2).Any())
{
atom1.IsReactiveCenter = true;
atom2.IsReactiveCenter = true;
bond.IsReactiveCenter = true;
}
}
}
private static void SetActiveCenters(IAtomContainer reactant, BondCheck bondChecker)
{
foreach (var bondi in reactant.Bonds)
{
IAtom atom1 = bondi.Begin;
IAtom atom2 = bondi.End;
if (bondChecker(bondi) &&
(atom1.FormalCharge ?? 0) == 0 &&
(atom2.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atom1).Any() &&
!reactant.GetConnectedSingleElectrons(atom2).Any())
{
bondi.IsReactiveCenter = true;
atom1.IsReactiveCenter = true;
atom2.IsReactiveCenter = true;
}
}
}
internal IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents, bool isReverse, CheckReactantAtom checkReactantAtom, CheckAtom checkAtom, CheckBond checkBond)
{
CheckInitiateParams(reactants, agents);
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
// if the parameter hasActiveCenter is not fixed yet, set the active centers
IParameterReaction ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant, checkReactantAtom, checkAtom, checkBond);
}
foreach (var atomi in reactant.Atoms)
{
if (atomi.IsReactiveCenter && checkReactantAtom(reactant, atomi))
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.IsReactiveCenter && checkBond(bondi))
{
IAtom atomj = bondi.GetOther(atomi);
if (atomj.IsReactiveCenter && checkAtom(atomj) && !reactant.GetConnectedSingleElectrons(atomj).Any())
{
IAtom[] atomList;
if (isReverse)
{
atomList = new[] { atomj, atomi }
}
;
else
{
atomList = new[] { atomi, atomj }
};
var bondList = new[] { bondi };
IChemObjectSet <IAtomContainer> moleculeSet = reactant.Builder.NewChemObjectSet <IAtomContainer>();
moleculeSet.Add(reactant);
IReaction reaction = Mechanism.Initiate(moleculeSet, atomList, bondList);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
}
}
}
return(setOfReactions);
}
/// <summary>
/// set the active center for this molecule. The active center
/// will be heteroatoms which contain at least one group of
/// lone pair electrons.
/// </summary>
/// <param name="reactant">The molecule to set the activity</param>
private static void SetActiveCenters(IAtomContainer reactant)
{
foreach (var atom in reactant.Atoms)
{
if (reactant.GetConnectedLonePairs(atom).Any() && !reactant.GetConnectedSingleElectrons(atom).Any())
{
atom.IsReactiveCenter = true;
}
}
}
internal IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents, string atomSymbol)
{
CheckInitiateParams(reactants, agents);
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
IParameterReaction ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant);
}
if (AtomContainerManipulator.GetTotalCharge(reactant) > 0)
{
return(setOfReactions);
}
foreach (var atomi in reactant.Atoms)
{
if (atomi.IsReactiveCenter &&
(atomi.FormalCharge ?? 0) <= 0 &&
reactant.GetConnectedLonePairs(atomi).Any() &&
!reactant.GetConnectedSingleElectrons(atomi).Any())
{
var atomList = new List <IAtom> {
atomi
};
IAtom atomH = reactant.Builder.NewAtom(atomSymbol);
atomH.FormalCharge = 1;
atomList.Add(atomH);
var moleculeSet = reactant.Builder.NewAtomContainerSet();
moleculeSet.Add(reactant);
IAtomContainer adduct = reactant.Builder.NewAtomContainer();
adduct.Atoms.Add(atomH);
moleculeSet.Add(adduct);
IReaction reaction = Mechanism.Initiate(moleculeSet, atomList, null);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
return(setOfReactions);
}
/// <summary>
/// Performs a BreadthFirstSearch in an AtomContainer starting with a
/// particular sphere, which usually consists of one start atom. While
/// searching the graph, the method marks each visited atom. It then puts all
/// the atoms connected to the atoms in the given sphere into a new vector
/// which forms the sphere to search for the next recursive method call. All
/// atoms that have been visited are put into a molecule container. This
/// BreadthFirstSearch does thus find the connected graph for a given start
/// atom.
/// <para>IMPORTANT: this method does not reset the VISITED flags, which must be
/// done if calling this method twice!
/// </para>
/// </summary>
/// <param name="atomContainer">The AtomContainer to be searched</param>
/// <param name="sphere">A sphere of atoms to start the search with</param>
/// <param name="molecule">A molecule into which all the atoms and bonds are stored that are found during search</param>
/// <param name="max">max</param>
public static void BreadthFirstSearch(IAtomContainer atomContainer, IEnumerable <IAtom> sphere, IAtomContainer molecule, int max)
{
IAtom nextAtom;
List <IAtom> newSphere = new List <IAtom>();
foreach (var atom in sphere)
{
molecule.Atoms.Add(atom);
// first copy LonePair's and SingleElectron's of this Atom as they need
// to be copied too
var lonePairs = atomContainer.GetConnectedLonePairs(atom);
foreach (var lonePair in lonePairs)
{
molecule.LonePairs.Add(lonePair);
}
var singleElectrons = atomContainer.GetConnectedSingleElectrons(atom);
foreach (var singleElectron in singleElectrons)
{
molecule.SingleElectrons.Add(singleElectron);
}
// now look at bonds
var bonds = atomContainer.GetConnectedBonds(atom);
foreach (var bond in bonds)
{
nextAtom = bond.GetOther(atom);
if (!bond.IsVisited)
{
molecule.Atoms.Add(nextAtom);
molecule.Bonds.Add(bond);
bond.IsVisited = true;
}
if (!nextAtom.IsVisited)
{
newSphere.Add(nextAtom);
nextAtom.IsVisited = true;
}
}
if (max > -1 && molecule.Atoms.Count > max)
{
return;
}
}
if (newSphere.Count > 0)
{
BreadthFirstSearch(atomContainer, newSphere, molecule, max);
}
}
public void TestSpinMultiplicity()
{
var mol = new AtomContainer();
Atom atom = new Atom("C");
mol.Atoms.Add(atom);
mol.SingleElectrons.Add(new SingleElectron(atom));
IAtomContainer roundTrippedMol = CMLRoundTripTool.RoundTripMolecule(convertor, mol);
Assert.AreEqual(1, roundTrippedMol.Atoms.Count);
Assert.AreEqual(1, roundTrippedMol.GetElectronContainers().Count());
IAtom roundTrippedAtom = roundTrippedMol.Atoms[0];
Assert.AreEqual(1, roundTrippedMol.GetConnectedSingleElectrons(roundTrippedAtom).Count());
}
/// <summary>
/// Initiate process.
/// It is needed to call the addExplicitHydrogensToSatisfyValency
/// from the class tools.HydrogenAdder.
/// </summary>
/// <param name="reactants">Reactants of the reaction</param>
/// <param name="agents">Agents of the reaction (Must be in this case null)</param>
/// <exception cref="CDKException"> Description of the Exception</exception>
public IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents)
{
Debug.WriteLine("initiate reaction: ElectronImpactNBEReaction");
if (reactants.Count != 1)
{
throw new CDKException("ElectronImpactNBEReaction only expects one reactant");
}
if (agents != null)
{
throw new CDKException("ElectronImpactNBEReaction don't expects agents");
}
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
// if the parameter hasActiveCenter is not fixed yet, set the active centers
IParameterReaction ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant);
}
foreach (var atom in reactant.Atoms)
{
if (atom.IsReactiveCenter && reactant.GetConnectedLonePairs(atom).Any() &&
!reactant.GetConnectedSingleElectrons(atom).Any())
{
var atomList = new List <IAtom>
{
atom
};
IChemObjectSet <IAtomContainer> moleculeSet = reactant.Builder.NewAtomContainerSet();
moleculeSet.Add(reactant);
IReaction reaction = Mechanism.Initiate(moleculeSet, atomList, null);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
return(setOfReactions);
}
private static void SetActiveCenters(IAtomContainer reactant)
{
if (AtomContainerManipulator.GetTotalCharge(reactant) > 0)
{
return;
}
foreach (var atomi in reactant.Atoms)
{
if ((atomi.FormalCharge ?? 0) <= 0 &&
reactant.GetConnectedLonePairs(atomi).Any() &&
!reactant.GetConnectedSingleElectrons(atomi).Any())
{
atomi.IsReactiveCenter = true;
}
}
}
private static void SetActiveCenters(IAtomContainer reactant, int length, bool checkPrev, AtomCheck atomCheck)
{
var hcg = new HOSECodeGenerator();
foreach (var atomi in reactant.Atoms)
{
if (reactant.GetConnectedSingleElectrons(atomi).Count() == 1)
{
IEnumerable <IAtom> atom1s = null;
if (checkPrev)
{
hcg.GetSpheres(reactant, atomi, length - 1, true);
atom1s = hcg.GetNodesInSphere(length - 1);
}
hcg.GetSpheres(reactant, atomi, length, true);
foreach (var atoml in hcg.GetNodesInSphere(length))
{
if (atoml != null &&
!atoml.IsInRing &&
(atoml.FormalCharge ?? 0) == 0 &&
!atoml.AtomicNumber.Equals(AtomicNumbers.H) &&
reactant.GetMaximumBondOrder(atoml) == BondOrder.Single)
{
foreach (var atomR in reactant.GetConnectedAtoms(atoml))
{
if (atom1s != null && atom1s.Contains(atomR))
{
continue;
}
if (atomCheck(atomR))
{
atomi.IsReactiveCenter = true;
atoml.IsReactiveCenter = true;
atomR.IsReactiveCenter = true;
reactant.GetBond(atomR, atoml).IsReactiveCenter = true;;
}
}
}
}
}
}
}
public void TestAutomatic_Set_Active_Atom()
{
// Ionize(>C=O): C=CCC(=O)CC -> C=CCC(=O*)CC, without setting the
// reactive center
IAtomContainer reactant = builder.NewAtomContainer();//CreateFromSmiles("C=CCC(=O)CC")
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("O"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.Atoms.Add(builder.NewAtom("C"));
reactant.AddBond(reactant.Atoms[0], reactant.Atoms[1], BondOrder.Double);
reactant.AddBond(reactant.Atoms[1], reactant.Atoms[2], BondOrder.Single);
reactant.AddBond(reactant.Atoms[2], reactant.Atoms[3], BondOrder.Single);
reactant.AddBond(reactant.Atoms[3], reactant.Atoms[4], BondOrder.Double);
reactant.AddBond(reactant.Atoms[3], reactant.Atoms[5], BondOrder.Single);
reactant.AddBond(reactant.Atoms[5], reactant.Atoms[6], BondOrder.Single);
AddExplicitHydrogens(reactant);
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(reactant);
CDK.LonePairElectronChecker.Saturate(reactant);
var setOfReactants = ChemObjectBuilder.Instance.NewAtomContainerSet();
setOfReactants.Add(reactant);
/* initiate */
MakeSureAtomTypesAreRecognized(reactant);
IReactionProcess type = new ElectronImpactNBEReaction();
var setOfReactions = type.Initiate(setOfReactants, null);
Assert.AreEqual(1, setOfReactions.Count);
Assert.AreEqual(1, setOfReactions[0].Products.Count);
IAtomContainer molecule = setOfReactions[0].Products[0];
Assert.AreEqual(1, molecule.Atoms[4].FormalCharge.Value);
Assert.AreEqual(1, molecule.GetConnectedSingleElectrons(molecule.Atoms[4]).Count());
}
private static void SetActiveCenters(IAtomContainer reactant, CheckReactantAtom checkReactantAtom, CheckAtom checkAtom, CheckBond checkBond)
{
foreach (var atomi in reactant.Atoms)
{
if (checkReactantAtom(reactant, atomi))
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (checkBond(bondi))
{
IAtom atomj = bondi.GetOther(atomi);
if (checkAtom(atomj) && !reactant.GetConnectedSingleElectrons(atomj).Any())
{
atomi.IsReactiveCenter = true;
atomj.IsReactiveCenter = true;
bondi.IsReactiveCenter = true;
}
}
}
}
}
}
private static void SetActiveCenters(IAtomContainer reactant, string atomSymbol, int charge)
{
foreach (var atomi in reactant.Atoms)
{
if (reactant.GetConnectedSingleElectrons(atomi).Count() == 1 && atomi.FormalCharge == charge)
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.Order == BondOrder.Single)
{
IAtom atomj = bondi.GetOther(atomi);
if (atomj.FormalCharge == 0)
{
foreach (var bondj in reactant.GetConnectedBonds(atomj))
{
if (bondj.Equals(bondi))
{
continue;
}
if (bondj.Order == BondOrder.Single)
{
IAtom atomk = bondj.GetOther(atomj);
if (atomk.Symbol.Equals(atomSymbol, StringComparison.Ordinal) && atomk.FormalCharge == 0)
{
atomi.IsReactiveCenter = true;
atomj.IsReactiveCenter = true;
atomk.IsReactiveCenter = true;
bondi.IsReactiveCenter = true;
bondj.IsReactiveCenter = true;
}
}
}
}
}
}
}
}
}
public int CalculateNumberOfImplicitHydrogens(IAtom atom, IAtomContainer container, bool throwExceptionForUnknowAtom)
{
return(this.CalculateNumberOfImplicitHydrogens(atom, container.GetBondOrderSum(atom),
container.GetConnectedSingleElectrons(atom).Count(), container.GetConnectedBonds(atom),
throwExceptionForUnknowAtom));
}
internal IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents, int length, bool checkPrev, AtomCheck atomCheck)
{
CheckInitiateParams(reactants, agents);
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(reactant);
Aromaticity.CDKLegacy.Apply(reactant);
AllRingsFinder arf = new AllRingsFinder();
IRingSet ringSet = arf.FindAllRings(reactant);
for (int ir = 0; ir < ringSet.Count; ir++)
{
IRing ring = (IRing)ringSet[ir];
for (int jr = 0; jr < ring.Atoms.Count; jr++)
{
IAtom aring = ring.Atoms[jr];
aring.IsInRing = true;
}
}
// if the parameter hasActiveCenter is not fixed yet, set the active centers
IParameterReaction ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant, length, checkPrev, atomCheck);
}
HOSECodeGenerator hcg = new HOSECodeGenerator();
foreach (var atomi in reactant.Atoms)
{
if (atomi.IsReactiveCenter && reactant.GetConnectedSingleElectrons(atomi).Count() == 1)
{
IEnumerable <IAtom> atom1s = null;
if (checkPrev)
{
hcg.GetSpheres(reactant, atomi, length - 1, true);
atom1s = hcg.GetNodesInSphere(length - 1);
}
hcg.GetSpheres(reactant, atomi, length, true);
foreach (var atoml in hcg.GetNodesInSphere(length))
{
if (atoml != null &&
atoml.IsReactiveCenter &&
!atoml.IsInRing &&
(atoml.FormalCharge ?? 0) == 0 &&
!atoml.AtomicNumber.Equals(AtomicNumbers.H) &&
reactant.GetMaximumBondOrder(atoml) == BondOrder.Single)
{
foreach (var atomR in reactant.GetConnectedAtoms(atoml))
{
if (atom1s != null && atom1s.Contains(atomR))
{
continue;
}
if (reactant.GetBond(atomR, atoml).IsReactiveCenter &&
atomR.IsReactiveCenter &&
atomCheck(atomR))
{
var atomList = new List <IAtom>
{
atomR,
atomi,
atoml
};
var bondList = new List <IBond>
{
reactant.GetBond(atomR, atoml)
};
var moleculeSet = reactant.Builder.NewChemObjectSet <IAtomContainer>();
moleculeSet.Add(reactant);
var reaction = Mechanism.Initiate(moleculeSet, atomList, bondList);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
}
}
}
}
return(setOfReactions);
}
/// <summary>
/// Reads atoms, bonds etc from atom container and converts to format
/// InChI library requires, then places call for the library to generate
/// the InChI.
/// </summary>
/// <param name="atomContainer">AtomContainer to generate InChI for.</param>
/// <param name="ignore"></param>
private void GenerateInChIFromCDKAtomContainer(IAtomContainer atomContainer, bool ignore)
{
this.ReferringAtomContainer = atomContainer;
// Check for 3d coordinates
bool all3d = true;
bool all2d = true;
foreach (var atom in atomContainer.Atoms)
{
if (all3d && atom.Point3D == null)
{
all3d = false;
}
if (all2d && atom.Point2D == null)
{
all2d = false;
}
}
var atomMap = new Dictionary <IAtom, NInchiAtom>();
foreach (var atom in atomContainer.Atoms)
{
// Get coordinates
// Use 3d if possible, otherwise 2d or none
double x, y, z;
if (all3d)
{
var p = atom.Point3D.Value;
x = p.X;
y = p.Y;
z = p.Z;
}
else if (all2d)
{
var p = atom.Point2D.Value;
x = p.X;
y = p.Y;
z = 0.0;
}
else
{
x = 0.0;
y = 0.0;
z = 0.0;
}
// Chemical element symbol
var el = atom.Symbol;
// Generate InChI atom
var iatom = Input.Add(new NInchiAtom(x, y, z, el));
atomMap[atom] = iatom;
// Check if charged
var charge = atom.FormalCharge.Value;
if (charge != 0)
{
iatom.Charge = charge;
}
// Check whether isotopic
var isotopeNumber = atom.MassNumber;
if (isotopeNumber != null)
{
iatom.IsotopicMass = isotopeNumber.Value;
}
// Check for implicit hydrogens
// atom.HydrogenCount returns number of implicit hydrogens, not
// total number
// Ref: Posting to cdk-devel list by Egon Willighagen 2005-09-17
int?implicitH = atom.ImplicitHydrogenCount;
// set implicit hydrogen count, -1 tells the inchi to determine it
iatom.ImplicitH = implicitH ?? -1;
// Check if radical
int count = atomContainer.GetConnectedSingleElectrons(atom).Count();
if (count == 0)
{
// TODO - how to check whether singlet or undefined multiplicity
}
else if (count == 1)
{
iatom.Radical = INCHI_RADICAL.Doublet;
}
else if (count == 2)
{
iatom.Radical = INCHI_RADICAL.Triplet;
}
else
{
throw new CDKException("Unrecognised radical type");
}
}
// Process bonds
var bondMap = new Dictionary <IBond, NInchiBond>();
foreach (var bond in atomContainer.Bonds)
{
// Assumes 2 centre bond
var at0 = atomMap[bond.Begin];
var at1 = atomMap[bond.End];
// Get bond order
INCHI_BOND_TYPE order;
var bo = bond.Order;
if (!ignore && bond.IsAromatic)
{
order = INCHI_BOND_TYPE.Altern;
}
else if (bo == BondOrder.Single)
{
order = INCHI_BOND_TYPE.Single;
}
else if (bo == BondOrder.Double)
{
order = INCHI_BOND_TYPE.Double;
}
else if (bo == BondOrder.Triple)
{
order = INCHI_BOND_TYPE.Triple;
}
else
{
throw new CDKException("Failed to generate InChI: Unsupported bond type");
}
// Create InChI bond
var ibond = new NInchiBond(at0, at1, order);
bondMap[bond] = ibond;
Input.Add(ibond);
// Check for bond stereo definitions
var stereo = bond.Stereo;
// No stereo definition
if (stereo == BondStereo.None)
{
ibond.BondStereo = INCHI_BOND_STEREO.None;
}
// Bond ending (fat end of wedge) below the plane
else if (stereo == BondStereo.Down)
{
ibond.BondStereo = INCHI_BOND_STEREO.Single1Down;
}
// Bond ending (fat end of wedge) above the plane
else if (stereo == BondStereo.Up)
{
ibond.BondStereo = INCHI_BOND_STEREO.Single1Up;
}
// Bond starting (pointy end of wedge) below the plane
else if (stereo == BondStereo.DownInverted)
{
ibond.BondStereo = INCHI_BOND_STEREO.Single2Down;
}
// Bond starting (pointy end of wedge) above the plane
else if (stereo == BondStereo.UpInverted)
{
ibond.BondStereo = INCHI_BOND_STEREO.Single2Up;
}
else if (stereo == BondStereo.EOrZ)
{
ibond.BondStereo = INCHI_BOND_STEREO.DoubleEither;
}
else if (stereo == BondStereo.UpOrDown)
{
ibond.BondStereo = INCHI_BOND_STEREO.Single1Either;
}
else if (stereo == BondStereo.UpOrDownInverted)
{
ibond.BondStereo = INCHI_BOND_STEREO.Single2Either;
}
// Bond with undefined stereochemistry
else if (stereo == BondStereo.None)
{
if (order == INCHI_BOND_TYPE.Single)
{
ibond.BondStereo = INCHI_BOND_STEREO.Single1Either;
}
else if (order == INCHI_BOND_TYPE.Double)
{
ibond.BondStereo = INCHI_BOND_STEREO.DoubleEither;
}
}
}
// Process tetrahedral stereo elements
foreach (var stereoElem in atomContainer.StereoElements)
{
if (stereoElem is ITetrahedralChirality chirality)
{
var stereoType = chirality.Stereo;
var atC = atomMap[chirality.ChiralAtom];
var at0 = atomMap[chirality.Ligands[0]];
var at1 = atomMap[chirality.Ligands[1]];
var at2 = atomMap[chirality.Ligands[2]];
var at3 = atomMap[chirality.Ligands[3]];
var p = INCHI_PARITY.Unknown;
if (stereoType == TetrahedralStereo.AntiClockwise)
{
p = INCHI_PARITY.Odd;
}
else if (stereoType == TetrahedralStereo.Clockwise)
{
p = INCHI_PARITY.Even;
}
else
{
throw new CDKException("Unknown tetrahedral chirality");
}
var jniStereo = new NInchiStereo0D(atC, at0, at1, at2, at3, INCHI_STEREOTYPE.Tetrahedral, p);
Input.Stereos.Add(jniStereo);
}
else if (stereoElem is IDoubleBondStereochemistry dbStereo)
{
var surroundingBonds = dbStereo.Bonds;
if (surroundingBonds[0] == null || surroundingBonds[1] == null)
{
throw new CDKException("Cannot generate an InChI with incomplete double bond info");
}
var stereoType = dbStereo.Stereo;
IBond stereoBond = dbStereo.StereoBond;
NInchiAtom at0 = null;
NInchiAtom at1 = null;
NInchiAtom at2 = null;
NInchiAtom at3 = null;
// TODO: I should check for two atom bonds... or maybe that should happen when you
// create a double bond stereochemistry
if (stereoBond.Contains(surroundingBonds[0].Begin))
{
// first atom is A
at1 = atomMap[surroundingBonds[0].Begin];
at0 = atomMap[surroundingBonds[0].End];
}
else
{
// first atom is X
at0 = atomMap[surroundingBonds[0].Begin];
at1 = atomMap[surroundingBonds[0].End];
}
if (stereoBond.Contains(surroundingBonds[1].Begin))
{
// first atom is B
at2 = atomMap[surroundingBonds[1].Begin];
at3 = atomMap[surroundingBonds[1].End];
}
else
{
// first atom is Y
at2 = atomMap[surroundingBonds[1].End];
at3 = atomMap[surroundingBonds[1].Begin];
}
var p = INCHI_PARITY.Unknown;
if (stereoType == DoubleBondConformation.Together)
{
p = INCHI_PARITY.Odd;
}
else if (stereoType == DoubleBondConformation.Opposite)
{
p = INCHI_PARITY.Even;
}
else
{
throw new CDKException("Unknown double bond stereochemistry");
}
var jniStereo = new NInchiStereo0D(null, at0, at1, at2, at3, INCHI_STEREOTYPE.DoubleBond, p);
Input.Stereos.Add(jniStereo);
}
else if (stereoElem is ExtendedTetrahedral extendedTetrahedral)
{
TetrahedralStereo winding = extendedTetrahedral.Winding;
// The peripherals (p<i>) and terminals (t<i>) are referring to
// the following atoms. The focus (f) is also shown.
//
// p0 p2
// \ /
// t0 = f = t1
// / \
// p1 p3
var terminals = extendedTetrahedral.FindTerminalAtoms(atomContainer);
var peripherals = extendedTetrahedral.Peripherals.ToArray();
// InChI API is particular about the input, each terminal atom
// needs to be present in the list of neighbors and they must
// be at index 1 and 2 (i.e. in the middle). This is true even
// of explicit atoms. For the implicit atoms, the terminals may
// be in the peripherals already and so we correct the winding
// and reposition as needed.
var t0Bonds = OnlySingleBonded(atomContainer.GetConnectedBonds(terminals[0]));
var t1Bonds = OnlySingleBonded(atomContainer.GetConnectedBonds(terminals[1]));
// first if there are two explicit atoms we need to replace one
// with the terminal atom - the configuration does not change
if (t0Bonds.Count == 2)
{
var orgBond = t0Bonds[0];
t0Bonds.RemoveAt(0);
var replace = orgBond.GetOther(terminals[0]);
for (int i = 0; i < peripherals.Length; i++)
{
if (replace == peripherals[i])
{
peripherals[i] = terminals[0];
}
}
}
if (t1Bonds.Count == 2)
{
var orgBond = t0Bonds[0];
t1Bonds.RemoveAt(0);
var replace = orgBond.GetOther(terminals[1]);
for (int i = 0; i < peripherals.Length; i++)
{
if (replace == peripherals[i])
{
peripherals[i] = terminals[1];
}
}
}
// the neighbor attached to each terminal atom that we will
// define the configuration of
var t0Neighbor = t0Bonds[0].GetOther(terminals[0]);
var t1Neighbor = t1Bonds[0].GetOther(terminals[1]);
// we now need to move all the atoms into the correct positions
// everytime we exchange atoms the configuration inverts
for (int i = 0; i < peripherals.Length; i++)
{
if (i != 0 && t0Neighbor == peripherals[i])
{
Swap(peripherals, i, 0);
winding = winding.Invert();
}
else if (i != 1 && terminals[0] == peripherals[i])
{
Swap(peripherals, i, 1);
winding = winding.Invert();
}
else if (i != 2 && terminals[1] == peripherals[i])
{
Swap(peripherals, i, 2);
winding = winding.Invert();
}
else if (i != 3 && t1Neighbor == peripherals[i])
{
Swap(peripherals, i, 3);
winding = winding.Invert();
}
}
var parity = INCHI_PARITY.Unknown;
if (winding == TetrahedralStereo.AntiClockwise)
{
parity = INCHI_PARITY.Odd;
}
else if (winding == TetrahedralStereo.Clockwise)
{
parity = INCHI_PARITY.Even;
}
else
{
throw new CDKException("Unknown extended tetrahedral chirality");
}
NInchiStereo0D jniStereo = new NInchiStereo0D(atomMap[extendedTetrahedral.Focus],
atomMap[peripherals[0]], atomMap[peripherals[1]], atomMap[peripherals[2]],
atomMap[peripherals[3]], INCHI_STEREOTYPE.Allene, parity);
Input.Stereos.Add(jniStereo);
}
}
try
{
Output = NInchiWrapper.GetInchi(Input);
}
catch (NInchiException jie)
{
throw new CDKException("Failed to generate InChI: " + jie.Message, jie);
}
}
/// <summary>
/// Initiate process.
/// It is needed to call the addExplicitHydrogensToSatisfyValency
/// from the class tools.HydrogenAdder.
/// </summary>
/// <param name="reactants">reactants of the reaction.</param>
/// <param name="agents">agents of the reaction (Must be in this case null).</param>
/// <exception cref="CDKException"> Description of the Exception</exception>
public IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents)
{
Debug.WriteLine("initiate reaction: SharingChargeDBReaction");
if (reactants.Count != 1)
{
throw new CDKException("SharingChargeDBReaction only expects one reactant");
}
if (agents != null)
{
throw new CDKException("SharingChargeDBReaction don't expects agents");
}
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
// if the parameter hasActiveCenter is not fixed yet, set the active centers
var ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant);
}
foreach (var atomi in reactant.Atoms)
{
if (atomi.IsReactiveCenter && atomi.FormalCharge == 1)
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.IsReactiveCenter && bondi.Order != BondOrder.Single)
{
IAtom atomj = bondi.GetOther(atomi);
if (atomj.IsReactiveCenter && atomj.FormalCharge == 0)
{
if (!reactant.GetConnectedSingleElectrons(atomj).Any())
{
var atomList = new List <IAtom>
{
atomj,
atomi
};
var bondList = new List <IBond>
{
bondi
};
var moleculeSet = reactant.Builder.NewChemObjectSet <IAtomContainer>();
moleculeSet.Add(reactant);
var reaction = Mechanism.Initiate(moleculeSet, atomList, bondList);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
}
}
}
}
return(setOfReactions);
}
internal IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents, string atomSymbol, int charge)
{
CheckInitiateParams(reactants, agents);
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
// if the parameter hasActiveCenter is not fixed yet, set the active centers
IParameterReaction ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant, atomSymbol, charge);
}
foreach (var atomi in reactants[0].Atoms)
{
if (atomi.IsReactiveCenter && reactant.GetConnectedSingleElectrons(atomi).Count() == 1 &&
atomi.FormalCharge == charge)
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.IsReactiveCenter && bondi.Order == BondOrder.Single)
{
IAtom atomj = bondi.GetOther(atomi);
if (atomj.IsReactiveCenter && atomj.FormalCharge == 0)
{
foreach (var bondj in reactant.GetConnectedBonds(atomj))
{
if (bondj.Equals(bondi))
{
continue;
}
if (bondj.IsReactiveCenter &&
bondj.Order == BondOrder.Single)
{
IAtom atomk = bondj.GetOther(atomj);
if (atomk.IsReactiveCenter && atomk.Symbol.Equals(atomSymbol, StringComparison.Ordinal) &&
atomk.FormalCharge == 0)
{
var atomList = new List <IAtom>
{
atomi,
atomj,
atomk
};
var bondList = new List <IBond>
{
bondi,
bondj
};
IChemObjectSet <IAtomContainer> moleculeSet = reactant.Builder.NewChemObjectSet <IAtomContainer>();
moleculeSet.Add(reactant);
IReaction reaction = Mechanism.Initiate(moleculeSet, atomList, bondList);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
}
}
}
}
}
}
return(setOfReactions);
}
/// <summary>
/// Write the atoms of a molecule. We pass in the order of atoms since for compatibility we
/// have shifted all hydrogens to the back.
/// </summary>
/// <param name="mol">molecule</param>
/// <param name="atoms">the atoms of a molecule in desired output order</param>
/// <param name="idxs">index lookup</param>
/// <param name="atomToStereo">tetrahedral stereo lookup</param>
/// <exception cref="IOException">low-level IO error</exception>
/// <exception cref="CDKException">inconsistent state etc</exception>
private void WriteAtomBlock(IAtomContainer mol, IAtom[] atoms, Dictionary <IChemObject, int> idxs, Dictionary <IAtom, ITetrahedralChirality> atomToStereo)
{
if (mol.Atoms.Count == 0)
{
return;
}
var dim = GetNumberOfDimensions(mol);
writer.Write("BEGIN ATOM\n");
int atomIdx = 0;
foreach (var atom in atoms)
{
var elem = NullAsZero(atom.AtomicNumber);
var chg = NullAsZero(atom.FormalCharge);
var mass = NullAsZero(atom.MassNumber);
var hcnt = NullAsZero(atom.ImplicitHydrogenCount);
var elec = mol.GetConnectedSingleElectrons(atom).Count();
int rad = 0;
switch (elec)
{
case 1: // 2
rad = MDLV2000Writer.SpinMultiplicity.Monovalent.Value;
break;
case 2: // 1 or 3? Information loss as to which
rad = MDLV2000Writer.SpinMultiplicity.DivalentSinglet.Value;
break;
}
int expVal = 0;
foreach (var bond in mol.GetConnectedBonds(atom))
{
if (bond.Order == BondOrder.Unset)
{
throw new CDKException($"Unsupported bond order: {bond.Order}");
}
expVal += bond.Order.Numeric();
}
string symbol = GetSymbol(atom, elem);
int rnum = -1;
if (symbol[0] == 'R')
{
var matcher = R_GRP_NUM.Match(symbol);
if (matcher.Success)
{
symbol = "R#";
rnum = int.Parse(matcher.Groups[1].Value, NumberFormatInfo.InvariantInfo);
}
}
writer.Write(++atomIdx)
.Write(' ')
.Write(symbol)
.Write(' ');
var p2d = atom.Point2D;
var p3d = atom.Point3D;
switch (dim)
{
case 0:
writer.Write("0 0 0 ");
break;
case 2:
if (p2d != null)
{
writer.Write(p2d.Value.X).WriteDirect(' ')
.Write(p2d.Value.Y).WriteDirect(' ')
.Write("0 ");
}
else
{
writer.Write("0 0 0 ");
}
break;
case 3:
if (p3d != null)
{
writer.Write(p3d.Value.X).WriteDirect(' ')
.Write(p3d.Value.Y).WriteDirect(' ')
.Write(p3d.Value.Z).WriteDirect(' ');
}
else
{
writer.Write("0 0 0 ");
}
break;
}
writer.Write(NullAsZero(atom.GetProperty <int>(CDKPropertyName.AtomAtomMapping)));
if (chg != 0 && chg >= -15 && chg <= 15)
{
writer.Write(" CHG=").Write(chg);
}
if (mass != 0)
{
writer.Write(" MASS=").Write(mass);
}
if (rad > 0 && rad < 4)
{
writer.Write(" RAD=").Write(rad);
}
if (rnum >= 0)
{
writer.Write(" RGROUPS=(1 ").Write(rnum).Write(")");
}
// determine if we need to write the valence
if (MDLValence.ImplicitValence(elem, chg, expVal) - expVal != hcnt)
{
int val = expVal + hcnt;
if (val <= 0 || val > 14)
{
val = -1; // -1 is 0
}
writer.Write(" VAL=").Write(val);
}
if (atomToStereo.TryGetValue(atom, out ITetrahedralChirality stereo))
{
switch (GetLocalParity(idxs, stereo))
{
case TetrahedralStereo.Clockwise:
writer.Write(" CFG=1");
break;
case TetrahedralStereo.AntiClockwise:
writer.Write(" CFG=2");
break;
default:
break;
}
}
writer.Write('\n');
}
writer.Write("END ATOM\n");
}
/// <summary>
/// Initiate process.
/// It is needed to call the addExplicitHydrogensToSatisfyValency
/// from the class tools.HydrogenAdder.
/// </summary>
/// <exception cref="CDKException"></exception>
/// <param name="reactants">reactants of the reaction.</param>
/// <param name="agents">agents of the reaction (Must be in this case null).</param>
public IReactionSet Initiate(IChemObjectSet <IAtomContainer> reactants, IChemObjectSet <IAtomContainer> agents)
{
CheckInitiateParams(reactants, agents);
IReactionSet setOfReactions = reactants.Builder.NewReactionSet();
IAtomContainer reactant = reactants[0];
// if the parameter hasActiveCenter is not fixed yet, set the active centers
var ipr = base.GetParameterClass(typeof(SetReactionCenter));
if (ipr != null && !ipr.IsSetParameter)
{
SetActiveCenters(reactant);
}
foreach (var atomi in reactant.Atoms)
{
if (atomi.IsReactiveCenter &&
atomi.FormalCharge == 1)
{
foreach (var bondi in reactant.GetConnectedBonds(atomi))
{
if (bondi.IsReactiveCenter && bondi.Order == BondOrder.Single)
{
IAtom atomj = bondi.GetOther(atomi);
if (atomj.IsReactiveCenter &&
(atomj.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atomj).Any())
{
foreach (var bondj in reactant.GetConnectedBonds(atomj))
{
if (bondj.Equals(bondi))
{
continue;
}
if (bondj.IsReactiveCenter &&
bondj.Order == BondOrder.Single)
{
IAtom atomk = bondj.GetOther(atomj);
if (atomk.IsReactiveCenter &&
(atomk.FormalCharge ?? 0) == 0 &&
!reactant.GetConnectedSingleElectrons(atomk).Any() &&
atomk.AtomicNumber.Equals(AtomicNumbers.H)
)
{
var atomList = new List <IAtom>
{
atomi,
atomj,
atomk
};
var bondList = new List <IBond>
{
bondi,
bondj
};
var moleculeSet = reactant.Builder.NewChemObjectSet <IAtomContainer>();
moleculeSet.Add(reactant);
var reaction = Mechanism.Initiate(moleculeSet, atomList, bondList);
if (reaction == null)
{
continue;
}
else
{
setOfReactions.Add(reaction);
}
}
}
}
}
}
}
}
}
return(setOfReactions);
}
