public void TestToString()
{
PharmacophoreQueryAtom qatom = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
string repr = qatom.ToString();
Assert.AreEqual("aromatic [c1ccccc1]", repr);
}
public void TestMatcherQuery1()
{
Assert.IsNotNull(conformers);
// make a query
var query = new PharmacophoreQuery();
var o = new PharmacophoreQueryAtom("D", "[OX1]");
var n1 = new PharmacophoreQueryAtom("A", "[N]");
var n2 = new PharmacophoreQueryAtom("A", "[N]");
query.Atoms.Add(o);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
var b1 = new PharmacophoreQueryBond(o, n1, 4.0, 4.5);
var b2 = new PharmacophoreQueryBond(o, n2, 4.0, 5.0);
var b3 = new PharmacophoreQueryBond(n1, n2, 5.4, 5.8);
query.Bonds.Add(b1);
query.Bonds.Add(b2);
query.Bonds.Add(b3);
var matcher = new PharmacophoreMatcher(query);
bool firstTime = true;
int i = 0;
var statuses = new bool[100];
foreach (var conf in conformers)
{
if (firstTime)
{
statuses[i] = matcher.Matches(conf, true);
firstTime = false;
}
else
{
statuses[i] = matcher.Matches(conf, false);
}
i++;
}
var hits = new int[18];
int idx = 0;
for (i = 0; i < statuses.Length; i++)
{
if (statuses[i])
{
hits[idx++] = i;
}
}
int[] expected = { 0, 1, 2, 5, 6, 7, 8, 9, 10, 20, 23, 48, 62, 64, 66, 70, 76, 87 };
for (i = 0; i < expected.Length; i++)
{
Assert.AreEqual(expected[i], hits[i], $"Hit {i} didn't match");
}
}
/// <summary>
/// Create a query angle constraint between three query groups.
/// </summary>
/// <remarks>
/// Note that the angle is only considered upto 2 decimal places.
/// </remarks>
/// <param name="atom1">The first pharmacophore group</param>
/// <param name="atom2">The second pharmacophore group</param>
/// <param name="atom3">The third pharmacophore group</param>
/// <param name="lower">The lower bound of the angle between the three groups</param>
/// <param name="upper">The upper bound of the angle between the three groups</param>
public PharmacophoreQueryAngleBond(PharmacophoreQueryAtom atom1, PharmacophoreQueryAtom atom2,
PharmacophoreQueryAtom atom3, double lower, double upper)
: base(new IAtom[] { atom1, atom2, atom3 })
{
this.upper = Round(upper, 2);
this.lower = Round(lower, 2);
}
/// <summary>
/// Create a query angle constraint between three query groups.
/// <para>
/// This constructor allows you to define a query angle constraint
/// such that the angle between the three query groups is exact
/// (i.e., not a range).
/// </para>
/// </summary>
/// <remarks>
/// Note that the angle is only considered upto 2 decimal places.
/// </remarks>
/// <param name="atom1">The first pharmacophore group</param>
/// <param name="atom2">The second pharmacophore group</param>
/// <param name="atom3">The third pharmacophore group</param>
/// <param name="angle">The exact angle between the two groups</param>
public PharmacophoreQueryAngleBond(PharmacophoreQueryAtom atom1, PharmacophoreQueryAtom atom2,
PharmacophoreQueryAtom atom3, double angle)
: base(new PharmacophoreQueryAtom[] { atom1, atom2, atom3 })
{
this.upper = Round(angle, 2);
this.lower = Round(angle, 2);
}
public void TestCNSPcore()
{
var filename = "NCDK.Data.MDL.cnssmarts.sdf";
var ins = ResourceLoader.GetAsStream(filename);
var reader = new EnumerableSDFReader(ins, CDK.Builder);
var query = new PharmacophoreQuery();
var arom = new PharmacophoreQueryAtom("A", "c1ccccc1");
var n1 = new PharmacophoreQueryAtom("BasicAmine", "[NX3;h2,h1,H1,H2;!$(NC=O)]");
var b1 = new PharmacophoreQueryBond(arom, n1, 5.0, 7.0);
query.Atoms.Add(arom);
query.Atoms.Add(n1);
query.Bonds.Add(b1);
var mol = reader.First();
reader.Close();
var matcher = new PharmacophoreMatcher(query);
var status = matcher.Matches(mol);
Assert.IsTrue(status);
var pmatches = matcher.GetMatchingPharmacophoreAtoms();
Assert.AreEqual(1, pmatches.Count);
var upmatches = matcher.GetUniqueMatchingPharmacophoreAtoms();
Assert.AreEqual(1, upmatches.Count);
}
public void TestAngleMatch2()
{
var filename = "NCDK.Data.MDL.cnssmarts.sdf";
var ins = ResourceLoader.GetAsStream(filename);
var reader = new EnumerableSDFReader(ins, CDK.Builder);
var query = new PharmacophoreQuery();
var n1 = new PharmacophoreQueryAtom("BasicAmine", "[NX3;h2,h1,H1,H2;!$(NC=O)]");
var n2 = new PharmacophoreQueryAtom("BasicAmine", "[NX3;h2,h1,H1,H2;!$(NC=O)]");
var n3 = new PharmacophoreQueryAtom("BasicAmine", "[NX3;h2,h1,H1,H2;!$(NC=O)]");
var b1 = new PharmacophoreQueryAngleBond(n1, n2, n3, 89.14);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
query.Atoms.Add(n3);
query.Bonds.Add(b1);
var mol = reader.First();
reader.Close();
var matcher = new PharmacophoreMatcher(query);
var status = matcher.Matches(mol);
Assert.IsTrue(status);
}
private static PharmacophoreAtom NewPCoreAtom(IAtomContainer input, PharmacophoreQueryAtom qatom, string smarts, int[] mapping)
{
var coords = GetEffectiveCoordinates(input, mapping);
var patom = new PharmacophoreAtom(smarts, qatom.Symbol, coords);
// n.b. mapping[] copy is mad by pcore atom
patom.SetMatchingAtoms(mapping);
return(patom);
}
public void TestToString()
{
PharmacophoreQueryAtom qatom1 = new PharmacophoreQueryAtom("Amine", "[CX2]N");
PharmacophoreQueryAtom qatom2 = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
PharmacophoreQueryBond qbond1 = new PharmacophoreQueryBond(qatom1, qatom2, 1.0, 2.0);
string repr = qbond1.ToString();
Assert.AreEqual("DC::Amine [[CX2]N]::aromatic [c1ccccc1]::[1.0 - 2.0] ", repr);
}
public void TestAngleMatch3()
{
Assert.IsNotNull(conformers);
// make a query
var query = new PharmacophoreQuery();
var o = new PharmacophoreQueryAtom("D", "[OX1]");
var n1 = new PharmacophoreQueryAtom("A", "[N]");
var n2 = new PharmacophoreQueryAtom("A", "[N]");
query.Atoms.Add(o);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
var b1 = new PharmacophoreQueryAngleBond(o, n1, n2, 43, 47);
query.Bonds.Add(b1);
var matcher = new PharmacophoreMatcher(query);
bool firstTime = true;
int i = 0;
var statuses = new bool[100];
foreach (var conf in conformers)
{
if (firstTime)
{
statuses[i] = matcher.Matches(conf, true);
firstTime = false;
}
else
{
statuses[i] = matcher.Matches(conf, false);
}
i++;
}
Assert.AreEqual(100, statuses.Length);
var hits = new int[9];
int idx = 0;
for (i = 0; i < statuses.Length; i++)
{
if (statuses[i])
{
hits[idx++] = i;
}
}
int[] expected = { 0, 6, 32, 33, 48, 54, 60, 62, 69 };
for (i = 0; i < expected.Length; i++)
{
Assert.AreEqual(expected[i], hits[i], $"Hit {i} didn't match");
}
}
public void TestLower()
{
PharmacophoreQueryAtom qatom1 = new PharmacophoreQueryAtom("Amine", "[CX2]N");
PharmacophoreQueryAtom qatom2 = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
PharmacophoreQueryBond qbond1 = new PharmacophoreQueryBond(qatom1, qatom2, 1.0, 2.0);
PharmacophoreQueryBond qbond2 = new PharmacophoreQueryBond(qatom1, qatom2, 1.732);
Assert.AreEqual(1.0, qbond1.GetLower(), 0.01);
Assert.AreEqual(1.732, qbond2.GetLower(), 0.01);
}
public void TestToString()
{
PharmacophoreQueryAtom qatom1 = new PharmacophoreQueryAtom("Amine", "[CX2]N");
PharmacophoreQueryAtom qatom2 = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
PharmacophoreQueryAtom qatom3 = new PharmacophoreQueryAtom("blah", "C");
PharmacophoreQueryAngleBond qbond1 = new PharmacophoreQueryAngleBond(qatom1, qatom2, qatom3, 54.735);
string repr = qbond1.ToString();
Assert.AreEqual(repr, "AC::Amine [[CX2]N]::aromatic [c1ccccc1]::blah [C]::[54.74 - 54.74] ");
}
public void TestLower()
{
PharmacophoreQueryAtom qatom1 = new PharmacophoreQueryAtom("Amine", "[CX2]N");
PharmacophoreQueryAtom qatom2 = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
PharmacophoreQueryAtom qatom3 = new PharmacophoreQueryAtom("blah", "C");
PharmacophoreQueryAngleBond qbond1 = new PharmacophoreQueryAngleBond(qatom1, qatom2, qatom3, 54.735);
PharmacophoreQueryAngleBond qbond2 = new PharmacophoreQueryAngleBond(qatom1, qatom2, qatom3, 50, 60);
Assert.AreEqual(54.74, qbond1.GetLower(), 0.01);
Assert.AreEqual(50.00, qbond2.GetLower(), 0.01);
}
public void TestMatchedBonds()
{
Assert.IsNotNull(conformers);
// make a query
var query = new PharmacophoreQuery();
var o = new PharmacophoreQueryAtom("D", "[OX1]");
var n1 = new PharmacophoreQueryAtom("A", "[N]");
var n2 = new PharmacophoreQueryAtom("A", "[N]");
query.Atoms.Add(o);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
var b1 = new PharmacophoreQueryBond(o, n1, 4.0, 4.5);
var b2 = new PharmacophoreQueryBond(o, n2, 4.0, 5.0);
var b3 = new PharmacophoreQueryBond(n1, n2, 5.4, 5.8);
query.Bonds.Add(b1);
query.Bonds.Add(b2);
query.Bonds.Add(b3);
var conf1 = conformers[0];
var matcher = new PharmacophoreMatcher(query);
bool status = matcher.Matches(conf1);
Assert.IsTrue(status);
var bMatches = matcher.GetMatchingPharmacophoreBonds();
Assert.AreEqual(2, bMatches.Count); // 2 since we haven't gotten a unique set
Assert.AreEqual(3, bMatches[0].Count);
var pbond = (PharmacophoreBond)BondRef.Deref(bMatches[0][0]);
var patom1 = (PharmacophoreAtom)AtomRef.Deref(pbond.Begin);
var patom2 = (PharmacophoreAtom)AtomRef.Deref(pbond.End);
Assert.AreEqual("D", patom1.Symbol);
Assert.AreEqual("A", patom2.Symbol);
var bondMap = matcher.GetTargetQueryBondMappings();
Assert.AreEqual(2, bondMap.Count);
var mapping = bondMap[0];
// get the 'BondRef' for lookup
var value = mapping[bMatches[0][0]];
Assert.AreEqual(b1, value);
}
static void Main()
{
var matcher = new PharmacophoreMatcher();
#region
QueryAtomContainer query = new QueryAtomContainer(ChemObjectBuilder.Instance);
PharmacophoreQueryAtom o = new PharmacophoreQueryAtom("D", "[OX1]");
PharmacophoreQueryAtom n1 = new PharmacophoreQueryAtom("A", "[N]");
PharmacophoreQueryAtom n2 = new PharmacophoreQueryAtom("A", "[N]");
query.Atoms.Add(o);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
PharmacophoreQueryBond b1 = new PharmacophoreQueryBond(o, n1, 4.0, 4.5);
PharmacophoreQueryBond b2 = new PharmacophoreQueryBond(o, n2, 4.0, 5.0);
PharmacophoreQueryBond b3 = new PharmacophoreQueryBond(n1, n2, 5.4, 5.8);
query.Bonds.Add(b1);
query.Bonds.Add(b2);
query.Bonds.Add(b3);
string filename = "/Users/rguha/pcore1.sdf";
using (var srm = new FileStream(filename, FileMode.Open))
{
foreach (var conformers in new IEnumerableMDLConformerReader(srm, ChemObjectBuilder.Instance))
{
bool firstTime = true;
foreach (var conf in conformers)
{
bool status;
if (firstTime)
{
status = matcher.Matches(conf, true);
firstTime = false;
}
else
{
status = matcher.Matches(conf, false);
}
if (status)
{
// OK, matched. Do something
}
}
#endregion
}
}
}
public void TestMatches()
{
PharmacophoreQueryAtom qatom = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
PharmacophoreAtom patom1 = new PharmacophoreAtom("c1ccccc1", "aromatic", Vector3.Zero);
PharmacophoreAtom patom2 = new PharmacophoreAtom("c1ccccc1", "hydrophobic", Vector3.Zero);
PharmacophoreAtom patom3 = new PharmacophoreAtom("Cc1ccccc1", "aromatic", Vector3.Zero);
PharmacophoreAtom patom4 = new PharmacophoreAtom("[CX2]N", "amine", Vector3.Zero);
Assert.IsTrue(qatom.Matches(patom1));
Assert.IsFalse(qatom.Matches(patom2));
Assert.IsTrue(qatom.Matches(patom3));
Assert.IsFalse(qatom.Matches(patom4));
}
public void TestMatches()
{
PharmacophoreAtom patom1 = new PharmacophoreAtom("[CX2]N", "Amine", Vector3.Zero);
PharmacophoreAtom patom2 = new PharmacophoreAtom("c1ccccc1", "Aromatic", new Vector3(1, 1, 1));
PharmacophoreBond pbond = new PharmacophoreBond(patom1, patom2);
PharmacophoreQueryAtom qatom1 = new PharmacophoreQueryAtom("Amine", "[CX2]N");
PharmacophoreQueryAtom qatom2 = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
PharmacophoreQueryBond qbond1 = new PharmacophoreQueryBond(qatom1, qatom2, 1.0, 2.0);
PharmacophoreQueryBond qbond2 = new PharmacophoreQueryBond(qatom1, qatom2, 1.732);
PharmacophoreQueryBond qbond3 = new PharmacophoreQueryBond(qatom1, qatom2, 0.1, 1.0);
Assert.IsTrue(qbond1.Matches(pbond));
Assert.IsTrue(qbond2.Matches(pbond));
Assert.IsFalse(qbond3.Matches(pbond));
}
public void TestGetterSetter()
{
var query = new PharmacophoreQuery();
var arom = new PharmacophoreQueryAtom("A", "c1ccccc1");
var n1 = new PharmacophoreQueryAtom("BasicAmine", "[NX3;h2,h1,H1,H2;!$(NC=O)]");
var b1 = new PharmacophoreQueryBond(arom, n1, 5.0, 7.0);
query.Atoms.Add(arom);
query.Atoms.Add(n1);
query.Bonds.Add(b1);
var matcher = new PharmacophoreMatcher();
matcher.SetPharmacophoreQuery(query);
var retQuery = matcher.GetPharmacophoreQuery();
Assert.AreEqual(2, retQuery.Atoms.Count);
Assert.AreEqual(1, retQuery.Bonds.Count);
}
/// <summary>
/// string representation of this query.
/// </summary>
/// <returns>string representation of this query</returns>
public override string ToString()
{
var stringBuilder = new StringBuilder();
stringBuilder.Append("PharmacophoreQuery(").Append(this.GetHashCode()).Append(", ");
stringBuilder.Append("#A:").Append(Atoms.Count).Append(", ");
stringBuilder.Append("#EC:").Append(GetElectronContainers().Count()).Append(", ");
foreach (var atom in Atoms)
{
PharmacophoreQueryAtom qatom = (PharmacophoreQueryAtom)atom;
stringBuilder.Append(qatom.Symbol).Append(", ");
}
foreach (var bond in Bonds)
{
stringBuilder.Append(bond.ToString()).Append(", ");
}
stringBuilder.Append(')');
return(stringBuilder.ToString());
}
public void TestMatchingBonds()
{
var filename = "NCDK.Data.MDL.cnssmarts.sdf";
var ins = ResourceLoader.GetAsStream(filename);
EnumerableSDFReader reader = new EnumerableSDFReader(ins, CDK.Builder);
PharmacophoreQuery query = new PharmacophoreQuery();
PharmacophoreQueryAtom arom = new PharmacophoreQueryAtom("A", "c1ccccc1");
PharmacophoreQueryAtom n1 = new PharmacophoreQueryAtom("BasicAmine", "[NX3;h2,h1,H1,H2;!$(NC=O)]");
PharmacophoreQueryBond b1 = new PharmacophoreQueryBond(arom, n1, 5.0, 7.0);
query.Atoms.Add(arom);
query.Atoms.Add(n1);
query.Bonds.Add(b1);
IAtomContainer mol = (IAtomContainer)reader.First();
reader.Close();
PharmacophoreMatcher matcher = new PharmacophoreMatcher(query);
bool status = matcher.Matches(mol);
Assert.IsTrue(status);
var pmatches = matcher.GetMatchingPharmacophoreAtoms();
Assert.AreEqual(1, pmatches.Count);
var upmatches = matcher.GetUniqueMatchingPharmacophoreAtoms();
Assert.AreEqual(1, upmatches.Count);
var bmatches = matcher.GetMatchingPharmacophoreBonds();
Assert.AreEqual(1, bmatches.Count);
var bmatch = bmatches[0];
Assert.AreEqual(1, bmatch.Count);
PharmacophoreBond pbond = (PharmacophoreBond)BondRef.Deref(bmatch[0]);
Assert.AreEqual(5.63, pbond.BondLength, 0.01);
}
public void TestMatches()
{
PharmacophoreAtom patom1 = new PharmacophoreAtom("[CX2]N", "Amine", new Vector3(1, 1, 1));
PharmacophoreAtom patom2 = new PharmacophoreAtom("c1ccccc1", "Aromatic", Vector3.Zero);
PharmacophoreAtom patom3 = new PharmacophoreAtom("C", "Blah", new Vector3(1, 0, 0));
PharmacophoreAngleBond pbond = new PharmacophoreAngleBond(patom1, patom2, patom3);
PharmacophoreQueryAtom qatom1 = new PharmacophoreQueryAtom("Amine", "[CX2]N");
PharmacophoreQueryAtom qatom2 = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
PharmacophoreQueryAtom qatom3 = new PharmacophoreQueryAtom("blah", "C");
PharmacophoreQueryAngleBond qbond1 = new PharmacophoreQueryAngleBond(qatom1, qatom2, qatom3, 54.735);
PharmacophoreQueryAngleBond qbond2 = new PharmacophoreQueryAngleBond(qatom1, qatom2, qatom3, 50, 60);
PharmacophoreQueryAngleBond qbond3 = new PharmacophoreQueryAngleBond(qatom1, qatom2, qatom3, 60, 80);
PharmacophoreQueryBond qbond4 = new PharmacophoreQueryBond(qatom1, qatom2, 1, 2);
Assert.IsTrue(qbond1.Matches(pbond));
Assert.IsTrue(qbond2.Matches(pbond));
Assert.IsFalse(qbond3.Matches(pbond));
Assert.IsFalse(qbond4.Matches(pbond));
}
public PharmacophoreQueryTest()
{
query = new PharmacophoreQuery();
PharmacophoreQueryAtom o = new PharmacophoreQueryAtom("D", "[OX1]");
PharmacophoreQueryAtom n1 = new PharmacophoreQueryAtom("A", "[N]");
PharmacophoreQueryAtom n2 = new PharmacophoreQueryAtom("A", "[N]");
query.Atoms.Add(o);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
PharmacophoreQueryBond b1 = new PharmacophoreQueryBond(o, n1, 4.0, 4.5);
PharmacophoreQueryBond b2 = new PharmacophoreQueryBond(o, n2, 4.0, 5.0);
PharmacophoreQueryBond b3 = new PharmacophoreQueryBond(n1, n2, 5.4, 5.8);
query.Bonds.Add(b1);
query.Bonds.Add(b2);
query.Bonds.Add(b3);
}
public void MultiSmartsQuery()
{
var query = new PharmacophoreQuery();
var rings = new PharmacophoreQueryAtom("A", "c1ccccc1|C1CCCC1");
var o1 = new PharmacophoreQueryAtom("Hd", "[OX1]");
var b1 = new PharmacophoreQueryBond(rings, o1, 3.5, 5.8);
query.Atoms.Add(rings);
query.Atoms.Add(o1);
query.Bonds.Add(b1);
var matcher = new PharmacophoreMatcher();
matcher.SetPharmacophoreQuery(query);
var filename = "NCDK.Data.PCore.multismartpcore.sdf";
var ins = ResourceLoader.GetAsStream(filename);
var reader = new EnumerableSDFReader(ins, CDK.Builder);
var enumerator = reader.GetEnumerator();
enumerator.MoveNext();
var mol = enumerator.Current;
Assert.IsTrue(matcher.Matches(mol));
Assert.AreEqual(1, matcher.GetUniqueMatchingPharmacophoreAtoms().Count);
Assert.AreEqual(2, matcher.GetUniqueMatchingPharmacophoreAtoms()[0].Count);
enumerator.MoveNext();
mol = enumerator.Current;
Assert.IsTrue(matcher.Matches(mol));
Assert.AreEqual(2, matcher.GetUniqueMatchingPharmacophoreAtoms().Count);
Assert.AreEqual(2, matcher.GetUniqueMatchingPharmacophoreAtoms()[0].Count);
Assert.AreEqual(2, matcher.GetUniqueMatchingPharmacophoreAtoms()[1].Count);
enumerator.MoveNext();
mol = enumerator.Current;
reader.Close();
Assert.IsFalse(matcher.Matches(mol));
}
public void TestInvalidQuery()
{
var query = new PharmacophoreQuery();
var o = new PharmacophoreQueryAtom("D", "[OX1]");
var n1 = new PharmacophoreQueryAtom("A", "[N]");
var n2 = new PharmacophoreQueryAtom("A", "[NX3]");
query.Atoms.Add(o);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
var b1 = new PharmacophoreQueryBond(o, n1, 4.0, 4.5);
var b2 = new PharmacophoreQueryBond(o, n2, 4.0, 5.0);
var b3 = new PharmacophoreQueryBond(n1, n2, 5.4, 5.8);
query.Bonds.Add(b1);
query.Bonds.Add(b2);
query.Bonds.Add(b3);
var matcher = new PharmacophoreMatcher(query);
matcher.Matches(conformers[0]);
}
public void TestMatchedAtoms()
{
Assert.IsNotNull(conformers);
// make a query
var query = new PharmacophoreQuery();
var o = new PharmacophoreQueryAtom("D", "[OX1]");
var n1 = new PharmacophoreQueryAtom("A", "[N]");
var n2 = new PharmacophoreQueryAtom("A", "[N]");
query.Atoms.Add(o);
query.Atoms.Add(n1);
query.Atoms.Add(n2);
var b1 = new PharmacophoreQueryBond(o, n1, 4.0, 4.5);
var b2 = new PharmacophoreQueryBond(o, n2, 4.0, 5.0);
var b3 = new PharmacophoreQueryBond(n1, n2, 5.4, 5.8);
query.Bonds.Add(b1);
query.Bonds.Add(b2);
query.Bonds.Add(b3);
var conf1 = conformers[0];
var matcher = new PharmacophoreMatcher(query);
bool status = matcher.Matches(conf1);
Assert.IsTrue(status);
var pmatches = matcher.GetMatchingPharmacophoreAtoms();
Assert.AreEqual(2, pmatches.Count);
var upmatches = matcher.GetUniqueMatchingPharmacophoreAtoms();
Assert.AreEqual(1, upmatches.Count);
}
public void TestGetSmarts()
{
PharmacophoreQueryAtom qatom = new PharmacophoreQueryAtom("aromatic", "c1ccccc1");
Assert.AreEqual("c1ccccc1", qatom.Smarts);
}
/// <summary>
/// Create a query distance constraint between two query groups.
/// <para>
/// This constructor allows you to define a query distance constraint
/// such that the distance between the two query groups is exact
/// (i.e., not a range).
/// </para>
/// </summary>
/// <remarks>
/// Note that the distance is only considered upto 2 decimal places.
/// </remarks>
/// <param name="atom1">The first pharmacophore group</param>
/// <param name="atom2">The second pharmacophore group</param>
/// <param name="distance">The exact distance between the two groups</param>
/// <seealso cref="PharmacophoreQueryBond(PharmacophoreQueryAtom, PharmacophoreQueryAtom, double, double)"/>
public PharmacophoreQueryBond(PharmacophoreQueryAtom atom1, PharmacophoreQueryAtom atom2, double distance)
: base(atom1, atom2)
{
this.upper = Round(distance, 2);
this.lower = Round(distance, 2);
}
/// <summary>
/// Create a query distance constraint between two query groups.
/// </summary>
/// <remarks>
/// Note that the distance is only considered upto 2 decimal places.
/// </remarks>
/// <param name="atom1">The first pharmacophore group</param>
/// <param name="atom2">The second pharmacophore group</param>
/// <param name="lower">The lower bound of the distance between the two groups</param>
/// <param name="upper">The upper bound of the distance between the two groups</param>
/// <seealso cref="PharmacophoreQueryBond(PharmacophoreQueryAtom,PharmacophoreQueryAtom,double)"/>
public PharmacophoreQueryBond(PharmacophoreQueryAtom atom1, PharmacophoreQueryAtom atom2, double lower, double upper)
: base(atom1, atom2)
{
this.upper = Round(upper, 2);
this.lower = Round(lower, 2);
}
private static void ProcessAngleConstraint(XElement child, Dictionary <string, string> local,
Dictionary <string, string> global, PharmacophoreQuery ret)
{
double lower;
XAttribute tmp;
tmp = child.Attribute("lower");
if (tmp == null)
{
throw new CDKException("Must have a 'lower' attribute");
}
else
{
lower = double.Parse(tmp.Value, NumberFormatInfo.InvariantInfo);
}
// we may not have an upper bound specified
double upper;
tmp = child.Attribute("upper");
if (tmp != null)
{
upper = double.Parse(tmp.Value, NumberFormatInfo.InvariantInfo);
}
else
{
upper = lower;
}
// now get the three groups for this distance
var grouprefs = child.Elements().ToReadOnlyList();
if (grouprefs.Count != 3)
{
throw new CDKException("An angle constraint can only refer to 3 groups.");
}
string id1 = grouprefs[0].Attribute("id")?.Value;
string id2 = grouprefs[1].Attribute("id")?.Value;
string id3 = grouprefs[2].Attribute("id")?.Value;
// see if it's a local def, else get it from the global list
string smarts1, smarts2, smarts3;
if (local.ContainsKey(id1))
{
smarts1 = local[id1];
}
else if (global.ContainsKey(id1))
{
smarts1 = global[id1];
}
else
{
throw new CDKException("Referring to a non-existant group definition");
}
if (local.ContainsKey(id2))
{
smarts2 = local[id2];
}
else if (global.ContainsKey(id2))
{
smarts2 = global[id2];
}
else
{
throw new CDKException("Referring to a non-existant group definition");
}
if (local.ContainsKey(id3))
{
smarts3 = local[id3];
}
else if (global.ContainsKey(id3))
{
smarts3 = global[id3];
}
else
{
throw new CDKException("Referring to a non-existant group definition");
}
// now see if we already have a correpsondiong pcore atom
// else create a new atom
if (!ContainsPatom(ret, id1))
{
PharmacophoreQueryAtom pqa = new PharmacophoreQueryAtom(id1, smarts1);
ret.Atoms.Add(pqa);
}
if (!ContainsPatom(ret, id2))
{
PharmacophoreQueryAtom pqa = new PharmacophoreQueryAtom(id2, smarts2);
ret.Atoms.Add(pqa);
}
if (!ContainsPatom(ret, id3))
{
PharmacophoreQueryAtom pqa = new PharmacophoreQueryAtom(id3, smarts3);
ret.Atoms.Add(pqa);
}
// now add the constraint as a bond
IAtom a1 = null, a2 = null;
IAtom a3 = null;
foreach (var queryAtom in ret.Atoms)
{
if (queryAtom.Symbol.Equals(id1, StringComparison.Ordinal))
{
a1 = queryAtom;
}
if (queryAtom.Symbol.Equals(id2, StringComparison.Ordinal))
{
a2 = queryAtom;
}
if (queryAtom.Symbol.Equals(id3, StringComparison.Ordinal))
{
a3 = queryAtom;
}
}
ret.Bonds.Add(new PharmacophoreQueryAngleBond((PharmacophoreQueryAtom)a1, (PharmacophoreQueryAtom)a2,
(PharmacophoreQueryAtom)a3, lower, upper));
}
/// <summary>
/// Write out one or more pharmacophore queries in the CDK XML format.
/// </summary>
/// <param name="queries">The pharmacophore queries</param>
/// <param name="output">The Stream to write to</param>
/// <exception cref="IOException">if there is a problem writing the XML document</exception>
public static void WritePharmacophoreDefinition(PharmacophoreQuery[] queries, Stream output)
{
var root = new XElement("pharmacophoreContainer");
root.SetAttributeValue("version", "1.0");
foreach (var query in queries)
{
var pcore = new XElement("pharmacophore");
var description = query.GetProperty <string>("description");
if (description != null)
{
pcore.SetAttributeValue("description", description);
}
var name = query.Title;
if (name != null)
{
pcore.SetAttributeValue("name", name);
}
// we add the pcore groups for this query as local to the group
foreach (var atom in query.Atoms)
{
var group = new XElement("group");
group.SetAttributeValue("id", atom.Symbol);
group.Value = ((PharmacophoreQueryAtom)atom).Smarts;
pcore.Add(group);
}
// now add the constraints
foreach (var bond in query.Bonds)
{
XElement elem = null;
switch (bond)
{
case PharmacophoreQueryBond dbond:
{
elem = new XElement("distanceConstraint");
elem.SetAttributeValue("lower", dbond.GetLower().ToString(NumberFormatInfo.InvariantInfo));
elem.SetAttributeValue("upper", dbond.GetUpper().ToString(NumberFormatInfo.InvariantInfo));
elem.SetAttributeValue("units", "A");
}
break;
case PharmacophoreQueryAngleBond dbond:
{
elem = new XElement("angleConstraint");
elem.SetAttributeValue("lower", dbond.GetLower().ToString(NumberFormatInfo.InvariantInfo));
elem.SetAttributeValue("upper", dbond.GetUpper().ToString(NumberFormatInfo.InvariantInfo));
elem.SetAttributeValue("units", "degrees");
}
break;
}
// now add the group associated with this constraint
foreach (var iAtom in bond.Atoms)
{
PharmacophoreQueryAtom atom = (PharmacophoreQueryAtom)iAtom;
var gelem = new XElement("groupRef");
gelem.SetAttributeValue("id", atom.Symbol);
if (elem != null)
{
elem.Add(gelem);
}
}
pcore.Add(elem);
}
root.Add(pcore);
}
var doc = new XDocument(root);
doc.Save(output);
}
