/// <summary>
/// Atom-atom mapping of the input molecule to the bare container constructed from the InChI connection table.
/// This makes it possible to map the positions of the mobile hydrogens in the InChI back to the input molecule.
/// </summary>
/// <param name="inchiMolGraph">molecule (bare) as defined in InChI</param>
/// <param name="mol">user input molecule</param>
/// <exception cref="CDKException"></exception>
private static void MapInputMoleculeToInChIMolgraph(IAtomContainer inchiMolGraph, IAtomContainer mol)
{
var iter = VentoFoggia.FindIdentical(inchiMolGraph,
AtomMatcher.CreateElementMatcher(), BondMatcher.CreateAnyMatcher())
.MatchAll(mol)
.Limit(1)
.ToAtomMap();
var i = iter.FirstOrDefault();
if (i != null)
{
foreach (var e in i)
{
var src = e.Key;
var dst = e.Value;
var position = src.Id;
dst.Id = position;
Debug.WriteLine("Mapped InChI " + src.Symbol + " " + src.Id + " to " + dst.Symbol + " " + dst.Id);
}
}
else
{
throw new ArgumentException(CANSMI.Create(inchiMolGraph) + " " + CANSMI.Create(mol));
}
}
public static void MakeCanonicalSmileFromRingSystems(string dataFileIn, string dataFileOut)
{
Console.Out.WriteLine("Start make SMILES...");
var data = new List <string>();
var smiles = new SmilesGenerator();
try
{
Console.Out.WriteLine("Start...");
using (var imdl = new EnumerableSDFReader(new StreamReader(dataFileIn), builder))
{
Console.Out.WriteLine("Read File in..");
foreach (var m in imdl)
{
try
{
data.Add((string)smiles.Create(builder.NewAtomContainer(m)));
}
catch (Exception exc1)
{
if (!(exc1 is CDKException || exc1 is IOException))
{
throw;
}
Console.Out.WriteLine("Could not create smile due to: " + exc1.Message);
}
}
}
}
catch (Exception exc)
{
Console.Out.WriteLine("Could not read Molecules from file " + dataFileIn + " due to: " + exc.Message);
}
Console.Out.Write("...ready\nWrite data...");
try
{
using (var fout = new StreamWriter(dataFileOut))
{
for (int i = 0; i < data.Count; i++)
{
try
{
fout.Write(((string)data[i]));
fout.WriteLine();
}
catch (Exception)
{
}
}
Console.Out.WriteLine($"number of smiles: {data.Count}");
}
}
catch (Exception exc3)
{
Console.Out.WriteLine($"Could not write smile in file {dataFileOut} due to: {exc3.Message}");
}
Console.Out.WriteLine("...ready");
}
public void TestSplit()
{
var mol = smilesParser.ParseSmiles("C1CC1C2CCC2");
SpanningTree st = new SpanningTree(mol);
IRingSet rings = st.GetAllRings();
IBond splitBond = null;
for (int i = 0; i < mol.Bonds.Count; i++)
{
if (rings.GetRings(mol.Bonds[i]).Count() == 0)
{
splitBond = mol.Bonds[i];
break;
}
}
var frags = FragmentUtils.SplitMolecule(mol, splitBond);
SmilesGenerator sg = new SmilesGenerator();
var uniqueFrags = new HashSet <string>();
foreach (var frag in frags)
{
uniqueFrags.Add(sg.Create(frag));
}
Assert.AreEqual(2, uniqueFrags.Count);
// You can put the fragments back together with a ring closure and dot
// [CH]12CC1.[CH]12CCC1
Assert.IsTrue(uniqueFrags.IsSupersetOf(new[] { "[CH]1CC1", "[CH]1CCC1" }));
}
/// <summary>
/// Writes the content from molecule to output.
/// </summary>
/// <param name="molecule">Molecule of which the data is given as output.</param>
public void WriteAtomContainer(IAtomContainer molecule)
{
SmilesGenerator sg = new SmilesGenerator();
if (useAromaticityFlag.IsSet)
{
sg = sg.Aromatic();
}
string smiles = "";
try
{
smiles = sg.Create(molecule);
Debug.WriteLine($"Generated SMILES: {smiles}");
writer.Write(smiles);
writer.Write('\n');
writer.Flush();
Debug.WriteLine("file flushed...");
}
catch (Exception exc)
{
if (exc is CDKException | exc is IOException)
{
Trace.TraceError($"Error while writing Molecule: {exc.Message}");
Debug.WriteLine(exc);
}
else
{
throw;
}
}
}
// private IAtomContainer CreateBenzaldehyde() {
// Molecule result = new DefaultMolecule();
// Atom c1 = result.Atoms.Add("C");
// Atom c2 = result.Atoms.Add("C");
// Atom c3 = result.Atoms.Add("C");
// Atom c4 = result.Atoms.Add("C");
// Atom c5 = result.Atoms.Add("C");
// Atom c6 = result.Atoms.Add("C");
// Atom c7 = result.Atoms.Add("C");
// Atom o8 = result.Atoms.Add("O");
//
// result.Connect(c1, c2, 1);
// result.Connect(c2, c3, 2);
// result.Connect(c3, c4, 1);
// result.Connect(c4, c5, 2);
// result.Connect(c5, c6, 1);
// result.Connect(c6, c1, 2);
// result.Connect(c7, c1, 1);
// result.Connect(c7, o8, 2);
//
// return result;
// }
//
// private IAtomContainer CreateBenzoicAcid() {
// Molecule result = CreateBenzaldehyde();
//
// result.Connect(result.Atoms[6], result.Atoms.Add("O"), 1);
//
// return result;
// }
//
// private IAtomContainer CreateBlockedBenzaldehyde() {
// Molecule result = CreateBenzaldehyde();
//
// result.Connect(result.Atoms[6], result.Atoms.Add("H"), 1);
//
// return result;
// }
// private Molecule Create4Toluene() {
// Molecule result = new DefaultMolecule();
// Atom c1 = result.Atoms.Add("C");
// Atom c2 = result.Atoms.Add("C");
// Atom c3 = result.Atoms.Add("C");
// Atom c4 = result.Atoms.Add("C");
// Atom c5 = result.Atoms.Add("C");
// Atom c6 = result.Atoms.Add("C");
// Atom c7 = result.Atoms.Add("C");
//
// result.Connect(c1, c2, 1);
// result.Connect(c2, c3, 2);
// result.Connect(c3, c4, 1);
// result.Connect(c4, c5, 2);
// result.Connect(c5, c6, 1);
// result.Connect(c6, c1, 2);
// result.Connect(c7, c4, 1);
//
// return result;
// }
public static IAtomContainer CreateSimpleImine()
{
IAtomContainer result = builder.NewAtomContainer();
IAtom c1 = builder.NewAtom("C");
IAtom c2 = builder.NewAtom("N");
result.Atoms.Add(c1);
result.Atoms.Add(c2);
IBond bond = builder.NewBond(c1, c2, BondOrder.Double);
result.Bonds.Add(bond);
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(result);
var adder = CDK.HydrogenAdder;
adder.AddImplicitHydrogens(result);
Aromaticity.CDKLegacy.Apply(result);
SmilesGenerator sg = new SmilesGenerator();
string oldSmiles = sg.Create(result);
Console.Out.WriteLine("SimpleImine " + oldSmiles);
return(result);
}
public void InliningReactionsWithRadicals()
{
IChemObjectBuilder bldr = ChemObjectBuilder.Instance;
SmilesParser smipar = new SmilesParser(bldr);
IReaction reaction = smipar.ParseReactionSmiles("[CH2]CO.CC(=O)O>[H+]>CCOC(=O)C.O |^1:0| ethyl esterification");
SmilesGenerator smigen = new SmilesGenerator(SmiFlavors.CxSmiles);
// convert to molecule
IAtomContainer mol = ReactionManipulator.ToMolecule(reaction);
Assert.AreEqual("[CH2]CO.CC(=O)O.[H+].CCOC(=O)C.O |^1:0|", smigen.Create(mol));
Assert.AreEqual("[CH2]CO.CC(=O)O>[H+]>CCOC(=O)C.O |^1:0|", smigen.CreateReactionSMILES(ReactionManipulator.ToReaction(mol)));
}
public void TestIndoleAgainstItself()
{
IAtomContainer indole = TestMoleculeFactory.MakeIndole();
AddImplicitHydrogens(indole);
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(indole);
Aromaticity.CDKLegacy.Apply(indole);
SmilesGenerator generator = new SmilesGenerator().Aromatic();
string indoleSmiles = generator.Create(indole);
var smilesParser = CDK.SmilesParser;
indole = smilesParser.ParseSmiles(indoleSmiles);
SMARTSQueryTool querytool = new SMARTSQueryTool(indoleSmiles, ChemObjectBuilder.Instance);
Assert.IsTrue(querytool.Matches(indole));
}
public override IReadOnlyDictionary <string, int> GetRawFingerprint(IAtomContainer atomContainer)
{
aromaticity.Apply(atomContainer);
var smiles = ReplaceDigits(gen.Create(atomContainer));
var map = new Dictionary <string, int>();
for (int i = 0, l = smiles.Length - n + 1; i < l; i++)
{
string subsmi = smiles.Substring(i, n);
if (!map.TryGetValue(subsmi, out int count))
{
map[subsmi] = 1;
}
else
{
map[subsmi] = count + 1;
}
}
return(map);
}
public static List <IReaction> SplitReaction(IReaction rxn, IDictionary <IAtom, IAtom> map)
{
var rctPrdPairs = from rct in rxn.Reactants
from prd in rxn.Products
select new { rct, prd };
var mappedPairs = rctPrdPairs.Where(pair => {
if (map.Count == 0)
{
return(true);
}
else if (pair.rct.Atoms.Any(rctAtom => {
if (map.ContainsKey(rctAtom) && pair.prd.Atoms.Contains(map[rctAtom]))
{
return(true);
}
else
{
return(false);
}
}))
{
return(true);
}
else
{
return(false);
}
});
return(mappedPairs.Select(mp => {
var newRxn = ChemObjectBuilder.Instance.NewReaction();
newRxn.Reactants.Add(AtomContainerManipulator.CopyAndSuppressedHydrogens(mp.rct));
newRxn.Products.Add(AtomContainerManipulator.CopyAndSuppressedHydrogens(mp.prd));
newRxn.SetProperty(CDKPropertyName.SMILES, sg.Create(newRxn));
return newRxn;
}).ToList());
}
public static void ExtractUniqueRingSystemsFromFile(string dataFile)
{
Console.Out.WriteLine("****** EXTRACT UNIQUE RING SYSTEMS ******");
Console.Out.WriteLine($"From file: {dataFile}");
Dictionary <string, string> hashRingSystems = new Dictionary <string, string>();
SmilesGenerator smilesGenerator = new SmilesGenerator();
int counterRings = 0;
int counterMolecules = 0;
int counterUniqueRings = 0;
IRingSet ringSet = null;
string key = "";
IAtomContainer ac = null;
string molfile = dataFile + "_UniqueRings";
try
{
using (var fout = new FileStream(molfile, FileMode.Create))
using (var mdlw = new MDLV2000Writer(fout))
{
try
{
Console.Out.WriteLine("Start...");
using (var fin = new StreamReader(dataFile))
using (var imdl = new EnumerableSDFReader(fin, builder))
{
Console.Out.WriteLine("Read File in..");
foreach (var m in imdl)
{
counterMolecules = counterMolecules + 1;
IRingSet ringSetM = Cycles.FindSSSR(m).ToRingSet();
if (counterMolecules % 1000 == 0)
{
Console.Out.WriteLine("Molecules:" + counterMolecules);
}
if (ringSetM.Count > 0)
{
var ringSystems = RingPartitioner.PartitionRings(ringSetM);
for (int i = 0; i < ringSystems.Count; i++)
{
ringSet = (IRingSet)ringSystems[i];
ac = builder.NewAtomContainer();
var containers = RingSetManipulator.GetAllAtomContainers(ringSet);
foreach (var container in containers)
{
ac.Add(container);
}
counterRings = counterRings + 1;
// Only connection is important
for (int j = 0; j < ac.Atoms.Count; j++)
{
(ac.Atoms[j]).Symbol = "C";
}
try
{
key = smilesGenerator.Create(builder.NewAtomContainer(ac));
}
catch (CDKException e)
{
Trace.TraceError(e.Message);
return;
}
if (hashRingSystems.ContainsKey(key))
{
}
else
{
counterUniqueRings = counterUniqueRings + 1; hashRingSystems[key] = "1";
try
{
mdlw.Write(builder.NewAtomContainer(ac));
}
catch (Exception emdl)
{
if (!(emdl is ArgumentException || emdl is CDKException))
{
throw;
}
}
}
}
}
}
}
}
catch (Exception exc)
{
Console.Out.WriteLine($"Could not read Molecules from file {dataFile} due to: {exc.Message}");
}
}
}
catch (Exception ex2)
{
Console.Out.WriteLine($"IOError:cannot write file due to: {ex2.ToString()}");
}
Console.Out.WriteLine($"READY Molecules:{counterMolecules} RingSystems:{counterRings} UniqueRingsSystem:{counterUniqueRings}");
Console.Out.WriteLine($"HashtableKeys:{hashRingSystems.Count}");
}
static string SmiGen(IAtomContainer mol)
{
return(sg.Create(mol));
}
/// <summary>
/// Internal - create a canonical SMILES string temporarily adjusting to default
/// hydrogen count. This method may be moved to the SMILESGenerator in future.
/// </summary>
/// <param name="mol">molecule</param>
/// <param name="ordering">ordering output</param>
/// <returns>SMILES</returns>
/// <exception cref="CDKException">SMILES could be generate</exception>
private string CreateCanonicalSmiles(IAtomContainer mol, int[] ordering)
{
// backup parts we will strip off
var hcntBackup = new int?[mol.Atoms.Count];
var idxs = new Dictionary <IAtom, int>();
for (int i = 0; i < mol.Atoms.Count; i++)
{
hcntBackup[i] = mol.Atoms[i].ImplicitHydrogenCount;
idxs[mol.Atoms[i]] = i;
}
var bondedValence = new int[mol.Atoms.Count];
for (int i = 0; i < mol.Bonds.Count; i++)
{
var bond = mol.Bonds[i];
bondedValence[idxs[bond.Begin]] += bond.Order.Numeric();
bondedValence[idxs[bond.End]] += bond.Order.Numeric();
}
// http://www.opensmiles.org/opensmiles.html#orgsbst
for (int i = 0; i < mol.Atoms.Count; i++)
{
var atom = mol.Atoms[i];
atom.ImplicitHydrogenCount = 0;
switch (atom.AtomicNumber)
{
case 5: // B
if (bondedValence[i] <= 3)
{
atom.ImplicitHydrogenCount = 3 - bondedValence[i];
}
break;
case 6: // C
if (bondedValence[i] <= 4)
{
atom.ImplicitHydrogenCount = 4 - bondedValence[i];
}
break;
case 7: // N
case 15: // P
if (bondedValence[i] <= 3)
{
atom.ImplicitHydrogenCount = 3 - bondedValence[i];
}
else if (bondedValence[i] <= 5)
{
atom.ImplicitHydrogenCount = 5 - bondedValence[i];
}
break;
case 8: // O
if (bondedValence[i] <= 2)
{
atom.ImplicitHydrogenCount = 2 - bondedValence[i];
}
break;
case 16: // S
if (bondedValence[i] <= 2)
{
atom.ImplicitHydrogenCount = 2 - bondedValence[i];
}
else if (bondedValence[i] <= 4)
{
atom.ImplicitHydrogenCount = 4 - bondedValence[i];
}
else if (bondedValence[i] <= 6)
{
atom.ImplicitHydrogenCount = 6 - bondedValence[i];
}
break;
case 9: // F
case 17: // Cl
case 35: // Br
case 53: // I
if (bondedValence[i] <= 1)
{
atom.ImplicitHydrogenCount = 1 - bondedValence[i];
}
break;
default:
atom.ImplicitHydrogenCount = 0;
break;
}
}
string smi = null;
try
{
smi = smigen.Create(mol, ordering);
}
finally
{
// restore
for (int i = 0; i < mol.Atoms.Count; i++)
{
mol.Atoms[i].ImplicitHydrogenCount = hcntBackup[i];
}
}
return(smi);
}
private List <IAtomContainer> Run(IAtomContainer atomContainer)
{
var fragments = new List <IAtomContainer>();
if (atomContainer.Bonds.Count < 3)
{
return(fragments);
}
var splitableBonds = GetSplitableBonds(atomContainer);
if (splitableBonds.Count == 0)
{
return(fragments);
}
Debug.WriteLine("Got " + splitableBonds.Count + " splittable bonds");
string tmpSmiles;
foreach (var bond in splitableBonds)
{
var parts = FragmentUtils.SplitMolecule(atomContainer, bond);
// make sure we don't add the same fragment twice
foreach (var partContainer in parts)
{
AtomContainerManipulator.ClearAtomConfigurations(partContainer);
foreach (var atom in partContainer.Atoms)
{
atom.ImplicitHydrogenCount = null;
}
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(partContainer);
CDK.HydrogenAdder.AddImplicitHydrogens(partContainer);
Aromaticity.CDKLegacy.Apply(partContainer);
tmpSmiles = smilesGenerator.Create(partContainer);
if (partContainer.Atoms.Count >= MinimumFragmentSize && !fragMap.ContainsKey(tmpSmiles))
{
fragments.Add(partContainer);
fragMap[tmpSmiles] = partContainer;
}
}
}
// try and partition the fragments
var tmp = new List <IAtomContainer>(fragments);
foreach (var fragment in fragments)
{
if (fragment.Bonds.Count < 3 || fragment.Atoms.Count < MinimumFragmentSize)
{
continue;
}
if (GetSplitableBonds(fragment).Count == 0)
{
continue;
}
var frags = Run(fragment);
if (frags.Count == 0)
{
continue;
}
foreach (var frag in frags)
{
if (frag.Bonds.Count < 3)
{
continue;
}
AtomContainerManipulator.ClearAtomConfigurations(frag);
foreach (var atom in frag.Atoms)
{
atom.ImplicitHydrogenCount = null;
}
AtomContainerManipulator.PercieveAtomTypesAndConfigureAtoms(frag);
CDK.HydrogenAdder.AddImplicitHydrogens(frag);
Aromaticity.CDKLegacy.Apply(frag);
tmpSmiles = smilesGenerator.Create(frag);
if (frag.Atoms.Count >= MinimumFragmentSize && !fragMap.ContainsKey(tmpSmiles))
{
tmp.Add(frag);
fragMap[tmpSmiles] = frag;
}
}
}
fragments = new List <IAtomContainer>(tmp);
return(fragments);
}
public static string MolToSmiles(IAtomContainer mol)
{
var gen = new SmilesGenerator();
return(gen.Create(mol));
}
/// <summary>
/// Find all enabled abbreviations in the provided molecule. They are not
/// added to the existing Sgroups and may need filtering.
/// </summary>
/// <param name="mol">molecule</param>
/// <returns>list of new abbreviation Sgroups</returns>
public IList <Sgroup> Generate(IAtomContainer mol)
{
// mark which atoms have already been abbreviated or are
// part of an existing Sgroup
var usedAtoms = new HashSet <IAtom>();
var sgroups = mol.GetCtabSgroups();
if (sgroups != null)
{
foreach (var sgroup in sgroups)
{
foreach (var atom in sgroup.Atoms)
{
usedAtoms.Add(atom);
}
}
}
var newSgroups = new List <Sgroup>();
// disconnected abbreviations, salts, common reagents, large compounds
if (!usedAtoms.Any())
{
try
{
var copy = AtomContainerManipulator.CopyAndSuppressedHydrogens(mol);
string cansmi = usmigen.Create(copy);
if (disconnectedAbbreviations.TryGetValue(cansmi, out string label) && !disabled.Contains(label) && ContractToSingleLabel)
{
var sgroup = new Sgroup
{
Type = SgroupType.CtabAbbreviation,
Subscript = label
};
foreach (var atom in mol.Atoms)
{
sgroup.Atoms.Add(atom);
}
return(new[] { sgroup });
}
else if (cansmi.Contains("."))
{
var parts = ConnectivityChecker.PartitionIntoMolecules(mol);
// leave one out
Sgroup best = null;
for (int i = 0; i < parts.Count; i++)
{
var a = parts[i];
var b = a.Builder.NewAtomContainer();
for (int j = 0; j < parts.Count; j++)
{
if (j != i)
{
b.Add(parts[j]);
}
}
var sgroup1 = GetAbbr(a);
var sgroup2 = GetAbbr(b);
if (sgroup1 != null && sgroup2 != null && ContractToSingleLabel)
{
var combined = new Sgroup();
label = null;
foreach (var atom in sgroup1.Atoms)
{
combined.Atoms.Add(atom);
}
foreach (var atom in sgroup2.Atoms)
{
combined.Atoms.Add(atom);
}
if (sgroup1.Subscript.Length > sgroup2.Subscript.Length)
{
combined.Subscript = sgroup1.Subscript + String_Interpunct + sgroup2.Subscript;
}
else
{
combined.Subscript = sgroup2.Subscript + String_Interpunct + sgroup1.Subscript;
}
combined.Type = SgroupType.CtabAbbreviation;
return(new[] { combined });
}
if (sgroup1 != null && (best == null || sgroup1.Atoms.Count > best.Atoms.Count))
{
best = sgroup1;
}
if (sgroup2 != null && (best == null || sgroup2.Atoms.Count < best.Atoms.Count))
{
best = sgroup2;
}
}
if (best != null)
{
newSgroups.Add(best);
foreach (var atom in best.Atoms)
{
usedAtoms.Add(atom);
}
}
}
}
catch (CDKException)
{
}
}
var fragments = GenerateFragments(mol);
var sgroupAdjs = new MultiDictionary <IAtom, Sgroup>();
foreach (var frag in fragments)
{
try
{
var smi = usmigen.Create(AtomContainerManipulator.CopyAndSuppressedHydrogens(frag));
if (!connectedAbbreviations.TryGetValue(smi, out string label) || disabled.Contains(label))
{
continue;
}
bool overlap = false;
// note: first atom is '*'
var numAtoms = frag.Atoms.Count;
var numBonds = frag.Bonds.Count;
for (int i = 1; i < numAtoms; i++)
{
if (usedAtoms.Contains(frag.Atoms[i]))
{
overlap = true;
break;
}
}
// overlaps with previous assignment
if (overlap)
{
continue;
}
// create new abbreviation Sgroup
var sgroup = new Sgroup
{
Type = SgroupType.CtabAbbreviation,
Subscript = label
};
var attachBond = frag.Bonds[0].GetProperty <IBond>(PropertyName_CutBond);
IAtom attachAtom = null;
sgroup.Bonds.Add(attachBond);
for (int i = 1; i < numAtoms; i++)
{
var atom = frag.Atoms[i];
usedAtoms.Add(atom);
sgroup.Atoms.Add(atom);
if (attachBond.Begin.Equals(atom))
{
attachAtom = attachBond.End;
}
else if (attachBond.End.Equals(atom))
{
attachAtom = attachBond.Begin;
}
}
if (attachAtom != null)
{
sgroupAdjs.Add(attachAtom, sgroup);
}
newSgroups.Add(sgroup);
}
catch (CDKException)
{
// ignore
}
}
if (!ContractOnHetero)
{
return(newSgroups);
}
// now collapse
foreach (var attach in mol.Atoms)
{
if (usedAtoms.Contains(attach))
{
continue;
}
// skip charged or isotopic labelled, C or R/*, H, He
if ((attach.FormalCharge != null && attach.FormalCharge != 0) ||
attach.MassNumber != null ||
attach.AtomicNumber == 6 ||
attach.AtomicNumber < 2)
{
continue;
}
var hcount = attach.ImplicitHydrogenCount.Value;
var xatoms = new HashSet <IAtom>();
var xbonds = new HashSet <IBond>();
var newbonds = new HashSet <IBond>();
xatoms.Add(attach);
var nbrSymbols = new List <string>();
var todelete = new HashSet <Sgroup>();
foreach (var sgroup in sgroupAdjs[attach])
{
if (ContainsChargeChar(sgroup.Subscript))
{
continue;
}
if (sgroup.Bonds.Count != 1)
{
continue;
}
var xbond = sgroup.Bonds.First();
xbonds.Add(xbond);
foreach (var a in sgroup.Atoms)
{
xatoms.Add(a);
}
if (attach.Symbol.Length == 1 &&
char.IsLower(sgroup.Subscript[0]))
{
if (ChemicalElement.OfSymbol(attach.Symbol + sgroup.Subscript[0]) != ChemicalElement.R)
{
goto continue_collapse;
}
}
nbrSymbols.Add(sgroup.Subscript);
todelete.Add(sgroup);
}
int numSGrpNbrs = nbrSymbols.Count;
foreach (var bond in mol.GetConnectedBonds(attach))
{
if (!xbonds.Contains(bond))
{
var nbr = bond.GetOther(attach);
// contract terminal bonds
if (mol.GetConnectedBonds(nbr).Count() == 1)
{
if (nbr.MassNumber != null ||
(nbr.FormalCharge != null && nbr.FormalCharge != 0))
{
newbonds.Add(bond);
}
else if (nbr.AtomicNumber == 1)
{
hcount++;
xatoms.Add(nbr);
}
else if (nbr.AtomicNumber > 0)
{
nbrSymbols.Add(NewSymbol(nbr.AtomicNumber, nbr.ImplicitHydrogenCount.Value, false));
xatoms.Add(nbr);
}
}
else
{
newbonds.Add(bond);
}
}
}
// reject if no symbols
// reject if no bonds (<1), except if all symbols are identical... (HashSet.size==1)
// reject if more that 2 bonds
if (!nbrSymbols.Any() ||
newbonds.Count < 1 && (new HashSet <string>(nbrSymbols).Count != 1) ||
newbonds.Count > 2)
{
continue;
}
// create the symbol
var sb = new StringBuilder();
sb.Append(NewSymbol(attach.AtomicNumber, hcount, newbonds.Count == 0));
string prev = null;
int count = 0;
nbrSymbols.Sort((o1, o2) =>
{
int cmp = o1.Length.CompareTo(o2.Length);
if (cmp != 0)
{
return(cmp);
}
return(o1.CompareTo(o2));
});
foreach (string nbrSymbol in nbrSymbols)
{
if (nbrSymbol.Equals(prev))
{
count++;
}
else
{
bool useParen = count == 0 || CountUpper(prev) > 1 || (prev != null && nbrSymbol.StartsWith(prev));
AppendGroup(sb, prev, count, useParen);
prev = nbrSymbol;
count = 1;
}
}
AppendGroup(sb, prev, count, false);
// remove existing
foreach (var e in todelete)
{
newSgroups.Remove(e);
}
// create new
var newSgroup = new Sgroup
{
Type = SgroupType.CtabAbbreviation,
Subscript = sb.ToString()
};
foreach (var bond in newbonds)
{
newSgroup.Bonds.Add(bond);
}
foreach (var atom in xatoms)
{
newSgroup.Atoms.Add(atom);
}
newSgroups.Add(newSgroup);
foreach (var a in xatoms)
{
usedAtoms.Add(a);
}
continue_collapse:
;
}
return(newSgroups);
}
