/// <summary>
/// Build CDK BitSetFingerprints from an AtomContainer
/// including the overall fingerprint and a fingerprint for each fragment
/// </summary>
/// <param name="molfile"></param>
/// <param name="fpTypeInt"></param>
/// <param name="fpSubtype"></param>
/// <param name="fpLen"></param>
/// <returns></returns>
public static List <BitSetFingerprint> BuildBitSetFingerprints(
string molfile,
bool includeOverallFingerprint,
FingerprintType fpType,
int fpSubtype = -1,
int fpLen = -1)
{
IAtomContainer mol2;
BitSetFingerprint fp;
string smiles;
int fi, fi2;
IAtomContainer mol = MolfileToAtomContainer(molfile);
List <BitSetFingerprint> fpList = new List <BitSetFingerprint>();
int pseudoCount = RemovePseudoAtoms(mol);
//mol = AtomContainerToSmilesAndBack(mol, out smiles); // need this for kekulization?
mol = RemoveIsotopesStereoExplicitHydrogens(mol); // additional normalization for fingerprint
List <IAtomContainer> frags = FragmentMolecule(mol, true); // get fragments filtering out small and common frags
if (includeOverallFingerprint && frags.Count > 1) // include overall fingerprint for multiple fragments
{
fp = // generate a fingerprint
CdkFingerprint.BuildBitSetFingerprint(mol, fpType, fpSubtype, fpLen);
fpList.Add(fp);
}
for (fi = 0; fi < frags.Count; fi++)
{
mol2 = frags[fi];
fp = CdkFingerprint.BuildBitSetFingerprint(
mol2,
fpType,
fpSubtype,
fpLen);
for (fi2 = 0; fi2 < fpList.Count; fi2++) // see if a dup fp
{
if (fp.Equals(fpList[fi2]))
{
break;
}
}
if (fi2 < fpList.Count)
{
continue; // skip if dup
}
fpList.Add(fp);
}
return(fpList);
}
/// <summary>
/// Build a CDK BitSetFingerprint for the largest fragment in an AtomContainer
/// </summary>
/// <param name="mol"></param>
/// <param name="fpTypeInt"></param>
/// <param name="fpSubtype"></param>
/// <param name="fpLen"></param>
/// <returns></returns>
public static BitSetFingerprint BuildBitSetFingerprintForLargestFragment(
IAtomContainer mol,
FingerprintType fpType,
int fpSubtype = -1,
int fpLen = -1)
{
string smiles;
mol = GetLargestMoleculeFragment(mol);
int pseudoCount = RemovePseudoAtoms(mol);
//mol = AtomContainerToSmilesAndBack(mol, out smiles); // need this for kekulization
mol = RemoveIsotopesStereoExplicitHydrogens(mol); // additional normalization for fingerprint
BitSetFingerprint bfp = CdkFingerprint.BuildBitSetFingerprint(
mol,
fpType,
fpSubtype,
fpLen);
return(bfp);
}
static INativeMolMx 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.Atoms.Count <= 1)
{
throw new Exception("Atom count <= 1");
}
int pseudoCount = CdkMol.RemovePseudoAtoms(mol);
mol = CdkMol.AtomContainerToSmilesAndBack(mol, out molSmiles);
InChIGeneratorFactory igf = InChIGeneratorFactory.Instance;
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.ReturnStatus + ": " + ig.Message;
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.InChI;
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.Atoms.Count;
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.InChI;
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.Instance;
AtomContainerSet acs = (AtomContainerSet)ConnectivityChecker.PartitionIntoMolecules(mol);
PartitionIntoMoleculesTime += TimeOfDay.Delta(ref t0);
acc = acs.Count;
for (aci = 0; aci < acc; aci++)
{
mol2 = acs[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;
}