static ICdkMol CdkMolUtil => StaticCdkMol.I; // static molecule shortcut for utility methods
/// <summary>
/// Build UniChem Data
/// Note that this routine takes about 14 secs the first time it's called, faster thereafter.
/// </summary>
/// <param name="mol"></param>
/// <returns></returns>
public static UniChemData BuildUniChemData(
IAtomContainer mol)
{
IAtomContainer mol2;
InChIGenerator ig = null;
string molSmiles, fragSmiles = "", molFile = "";
int acc, fi, ci;
//if (Lex.StartsWith(molString, "InChI="))
//{
// sourceInchi = molString;
// mol = CdkMol.InChIToAtomContainer(sourceInchi);
//}
//else // assume molfile otherwise
//{
// molfile = molString;
// mol = CdkMol.MolfileToAtomContainer(molfile);
//}
if (mol.getAtomCount() <= 1)
{
throw new Exception("Atom count <= 1");
}
int pseudoCount = CdkMol.RemovePseudoAtoms(mol);
mol = CdkMol.AtomContainerToSmilesAndBack(mol, out molSmiles);
InChIGeneratorFactory igf = InChIGeneratorFactory.getInstance();
try
{
//string options = "/KET /15T"; // options to include keto-enol and 1,5-tautomerism (not recognized by CDK)
ig = igf.getInChIGenerator(mol); //, options);
}
catch (Exception ex) // may fail for some complex mols (e.g. CorpId 12345, a MDL V3000 mol with a CF3 Sgroup/alias)
{
throw new Exception(ex.Message, ex);
}
//{
// try // try to simplify the molfile so that InChI can handle it
// {
// //if (Lex.IsUndefined(molfile)) throw ex;
// string molfile2 = SimplifyMolfileForInChIGeneration(molile);
// mol = CdkMol.MolfileToAtomContainer(molfile2);
// mol = CdkMol.AtomContainerToSmilesAndBack(mol, out molSmiles);
// ig = igf.getInChIGenerator(mol);
// }
// catch (Exception ex2)
// {
// throw new Exception(ex2.Message, ex);
// }
//}
if (!IsAcceptableInchiStatus(ig))
{
string errMsg = "InChI generation " + ig.getReturnStatus() + ": " + ig.getMessage();
molFile = CdkMol.AtomContainerToMolfile(mol); // debug
throw new Exception(errMsg);
}
// Populate the UniChem object
UniChemData icd = new UniChemData();
//icd.Molfile = molfile;
icd.AtomContainer = mol;
icd.InChIString = ig.getInchi();
icd.InChIKey = ig.getInchiKey();
icd.CanonSmiles = molSmiles;
// Build and store fingerprint
mol = CdkMol.InChIToAtomContainer(icd.InChIString);
//int hydRemovedCnt = CdkMol.RemoveHydrogensBondedToPositiveNitrogens(mol);
mol = CdkMol.RemoveIsotopesStereoExplicitHydrogens(mol); // additional normalization for fingerprint
BitSetFingerprint fp = // generate a fingerprint
CdkFingerprint.BuildBitSetFingerprint(mol, FingerprintType.MACCS, -1, -1);
icd.Fingerprint = fp;
if (ConnectivityChecker.isConnected(mol))
{
return(icd); // single fragment
}
//string mf = CdkMol.GetMolecularFormula(mol);
//AtomContainerSet acs = (AtomContainerSet)ConnectivityChecker.partitionIntoMolecules(mol);
List <IAtomContainer> frags = CdkMol.FragmentMolecule(mol, true); // get fragments filtering out small and common frags
for (fi = 0; fi < frags.Count; fi++)
{
mol2 = frags[fi];
int atomCnt = mol2.getAtomCount();
if (atomCnt <= 1)
{
continue;
}
try
{
mol2 = CdkMol.AtomContainerToSmilesAndBack(mol2, out fragSmiles);
}
catch (Exception ex)
{
AtomContainerToSmilesAndBackErrorCount++; // just count error and ignore
}
ig = igf.getInChIGenerator(mol2);
if (!IsAcceptableInchiStatus(ig))
{
continue;
}
string childInChIString = ig.getInchi();
string childInChIKey = ig.getInchiKey();
string childFIKHB = UniChemUtil.GetFIKHB(childInChIKey);
mol2 = CdkMol.InChIToAtomContainer(childInChIString); // convert from inchi
mol2 = CdkMol.RemoveIsotopesStereoExplicitHydrogens(mol2); // additional normalization for fingerprint
fp = // generate a fingerprint for the fragment
CdkFingerprint.BuildBitSetFingerprint(mol2, FingerprintType.MACCS, -1, -1);
for (ci = 0; ci < icd.Children.Count; ci++) // see if a dup child
{
if (icd.Children[ci].ChildFIKHB == childFIKHB)
{
break;
}
}
if (ci < icd.Children.Count)
{
continue; // skip if dup
}
UniChemFIKHBHierarchy icdChild = new UniChemFIKHBHierarchy();
icdChild.ParentFIKHB = icd.GetFIKHB();
icdChild.ChildFIKHB = childFIKHB;
icdChild.InChIString = childInChIString;
icdChild.CanonSmiles = fragSmiles;
icdChild.Fingerprint = fp;
icd.Children.Add(icdChild);
}
return(icd);
}
/// <summary>
/// BuildFingerprints
/// </summary>
public static void BuildFingerprints(
UniChemData icd)
{
IAtomContainer mol, mol2;
InChIGenerator ig = null;
int acc, aci, ci;
icd.Children.Clear();
string parentFIKHB = icd.GetFIKHB();
DateTime t0 = DateTime.Now;
mol = CdkMol.InChIToAtomContainer(icd.InChIString);
icd.CanonSmiles = CdkMol.AtomContainerToSmiles(mol);
InChIToAtomContainerTime += TimeOfDay.Delta(ref t0);
BitSetFingerprint fp = // generate a fingerprint
CdkFingerprint.BuildBitSetFingerprint(mol, FingerprintType.MACCS, -1, -1);
BuildFinterprintTime1 += TimeOfDay.Delta(ref t0);
icd.Fingerprint = fp;
if (ConnectivityChecker.isConnected(mol))
{
return; // single fragment
}
InChIGeneratorFactory igf = InChIGeneratorFactory.getInstance();
AtomContainerSet acs = (AtomContainerSet)ConnectivityChecker.partitionIntoMolecules(mol);
PartitionIntoMoleculesTime += TimeOfDay.Delta(ref t0);
acc = acs.getAtomContainerCount();
for (aci = 0; aci < acc; aci++)
{
mol2 = acs.getAtomContainer(aci);
GetAtomContainerTime += TimeOfDay.Delta(ref t0);
ig = igf.getInChIGenerator(mol2);
if (!IsAcceptableInchiStatus(ig))
{
continue;
}
string childKey = ig.getInchiKey();
string childFIKHB = UniChemUtil.GetFIKHB(childKey);
InChIGeneratorTime += TimeOfDay.Delta(ref t0);
fp = // generate a fingerprint for the fragment
CdkFingerprint.BuildBitSetFingerprint(mol2, FingerprintType.MACCS, -1, -1);
BuildFinterprintTime2 += TimeOfDay.Delta(ref t0);
for (ci = 0; ci < icd.Children.Count; ci++) // see if a dup child
{
if (icd.Children[ci].ChildFIKHB == childFIKHB)
{
break;
}
}
if (ci < icd.Children.Count)
{
continue; // skip if dup
}
UniChemFIKHBHierarchy fikhbHier = new UniChemFIKHBHierarchy();
fikhbHier.ParentFIKHB = parentFIKHB;
fikhbHier.ChildFIKHB = childFIKHB;
fikhbHier.CanonSmiles = CdkMol.AtomContainerToSmiles(mol2);
fikhbHier.Fingerprint = fp;
icd.Children.Add(fikhbHier);
}
return;
}