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[Cdk-commits] SF.net SVN: cdk:[11856] cdk/trunk/src
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From: <raj...@us...> - 2008-08-04 21:16:37
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Revision: 11856
http://cdk.svn.sourceforge.net/cdk/?rev=11856&view=rev
Author: rajarshi
Date: 2008-08-04 21:16:15 +0000 (Mon, 04 Aug 2008)
Log Message:
-----------
Added substructure fingerprinter using the 307 functional group defs from InteLigand
Modified Paths:
--------------
cdk/trunk/src/main/org/openscience/cdk/fingerprint/StandardSubstructureSets.java
cdk/trunk/src/main/org/openscience/cdk/fingerprint/SubstructureFingerprinter.java
cdk/trunk/src/test/org/openscience/cdk/fingerprint/StandardSubstructureSetsTest.java
cdk/trunk/src/test/org/openscience/cdk/fingerprint/SubstructureFingerprinterTest.java
Modified: cdk/trunk/src/main/org/openscience/cdk/fingerprint/StandardSubstructureSets.java
===================================================================
--- cdk/trunk/src/main/org/openscience/cdk/fingerprint/StandardSubstructureSets.java 2008-08-04 20:25:45 UTC (rev 11855)
+++ cdk/trunk/src/main/org/openscience/cdk/fingerprint/StandardSubstructureSets.java 2008-08-04 21:16:15 UTC (rev 11856)
@@ -1,47 +1,47 @@
package org.openscience.cdk.fingerprint;
-import org.openscience.cdk.DefaultChemObjectBuilder;
-import org.openscience.cdk.interfaces.IAtomContainerSet;
-import org.openscience.cdk.smiles.SmilesParser;
+import java.io.BufferedReader;
+import java.io.InputStream;
+import java.io.InputStreamReader;
+import java.util.ArrayList;
+import java.util.List;
/**
* Default sets of atom containers aimed for use with the substructure
*
* @author egonw
*
- * @cdk.module extra
+ * @cdk.module fingerprint
* @cdk.svnrev $Revision$
*/
public class StandardSubstructureSets {
- private static IAtomContainerSet functionalGroupSubstructureSet = null;
+ private static String[] smarts = null;
/**
* @return A set of the functional groups.
* @throws Exception if there is an error parsing SMILES for the functional groups
*/
- public static IAtomContainerSet getFunctionalGroupSubstructureSet() throws Exception {
- if (functionalGroupSubstructureSet == null) {
- functionalGroupSubstructureSet = new org.openscience.cdk.AtomContainerSet();
-
- SmilesParser parser = new SmilesParser(DefaultChemObjectBuilder.getInstance());
- String[] groups = {
- "O=CO", // carboxilyc acid
- "[H]N[H]", // amine
- "O[H]", // hydroxide
- "COC", // alkoxyalkane
- "O=C[H]", // aldehyde
- "O=S(=O)O", // sulfonate
- "O=P(=O)O" // phosphate
- };
- for (String group : groups) {
- functionalGroupSubstructureSet.addAtomContainer(
- parser.parseSmiles(group)
- );
- }
- }
-
- return functionalGroupSubstructureSet;
- }
+ public static String[] getFunctionalGroupSMARTS() throws Exception {
+ if (smarts != null) return smarts;
+
+ String filename = "org/openscience/cdk/fingerprint/data/SMARTS_InteLigand.txt";
+ InputStream ins = StandardSubstructureSets.class.getClassLoader().getResourceAsStream(filename);
+ BufferedReader reader = new BufferedReader(new InputStreamReader(ins));
+
+ List<String> tmp = new ArrayList<String>();
+ String line;
+ while ((line = reader.readLine()) != null) {
+ if (line.startsWith("#") || line.trim().length() == 0) continue;
+ String[] toks = line.split(":");
+ StringBuffer s = new StringBuffer();
+ for (int i = 1; i < toks.length-1; i++) s.append(toks[i]+":");
+ s.append(toks[toks.length-1]);
+ tmp.add(s.toString().trim());
+ }
+ smarts = tmp.toArray(new String[]{});
+ return smarts;
+
+ }
}
Modified: cdk/trunk/src/main/org/openscience/cdk/fingerprint/SubstructureFingerprinter.java
===================================================================
--- cdk/trunk/src/main/org/openscience/cdk/fingerprint/SubstructureFingerprinter.java 2008-08-04 20:25:45 UTC (rev 11855)
+++ cdk/trunk/src/main/org/openscience/cdk/fingerprint/SubstructureFingerprinter.java 2008-08-04 21:16:15 UTC (rev 11856)
@@ -27,10 +27,11 @@
*/
package org.openscience.cdk.fingerprint;
+import org.openscience.cdk.annotations.TestClass;
+import org.openscience.cdk.annotations.TestMethod;
import org.openscience.cdk.exception.CDKException;
import org.openscience.cdk.interfaces.IAtomContainer;
-import org.openscience.cdk.interfaces.IAtomContainerSet;
-import org.openscience.cdk.isomorphism.UniversalIsomorphismTester;
+import org.openscience.cdk.smiles.smarts.SMARTSQueryTool;
import java.util.BitSet;
@@ -38,65 +39,389 @@
* {@link IFingerprinter} that gives a bit set which has a size equal to the number
* of substructures it was constructed from. A set bit indicates that that
* substructure was found at least once in the molecule for which the
- * fingerprint was calculated.
- *
+ * fingerprint was calculated. The fingerprint currently supports 307
+ * substructures, listed below:
+ *
+
+ * <table>
+ * <thead>
+ * <tr>
+ * <td>Bit positionh</td><td>Description</td><td>Pattern</td>
+ * </tr>
+ * </thead>
+ * <tbody>
+ * <tr><td>0</td><td>Primary carbon</td><td>[CX4H3][#6]</td></tr>
+ * <tr><td>1</td><td>Secondary carbon</td><td>[CX4H2]([#6])[#6]</td></tr>
+ * <tr><td>2</td><td>Tertiary carbon</td><td>[CX4H1]([#6])([#6])[#6]</td></tr>
+ * <tr><td>3</td><td>Quaternary carbon</td><td>[CX4]([#6])([#6])([#6])[#6]</td></tr>
+ * <tr><td>4</td><td>Alkene</td><td>[CX3;$([H2]),$([H1][#6]),$(C([#6])[#6])]=[CX3;$([H2]),$([H1][#6]),$(C([#6])[#6])]</td></tr>
+ * <tr><td>5</td><td>Alkyne</td><td>[CX2]#[CX2]</td></tr>
+ * <tr><td>6</td><td>Allene</td><td>[CX3]=[CX2]=[CX3]</td></tr>
+ * <tr><td>7</td><td>Alkylchloride</td><td>[ClX1][CX4]</td></tr>
+ * <tr><td>8</td><td>Alkylfluoride</td><td>[FX1][CX4]</td></tr>
+ * <tr><td>9</td><td>Alkylbromide</td><td>[BrX1][CX4]</td></tr>
+ * <tr><td>10</td><td>Alkyliodide</td><td>[IX1][CX4]</td></tr>
+ * <tr><td>11</td><td>Alcohol</td><td>[OX2H][CX4;!$(C([OX2H])[O,S,#7,#15])]</td></tr>
+ * <tr><td>12</td><td>Primary alcohol</td><td>[OX2H][CX4H2;!$(C([OX2H])[O,S,#7,#15])]</td></tr>
+ * <tr><td>13</td><td>Secondary alcohol</td><td>[OX2H][CX4H;!$(C([OX2H])[O,S,#7,#15])]</td></tr>
+ * <tr><td>14</td><td>Tertiary alcohol</td><td>[OX2H][CX4D4;!$(C([OX2H])[O,S,#7,#15])]</td></tr>
+ * <tr><td>15</td><td>Dialkylether</td><td>[OX2]([CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]</td></tr>
+ * <tr><td>16</td><td>Dialkylthioether</td><td>[SX2]([CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]</td></tr>
+ * <tr><td>17</td><td>Alkylarylether</td><td>[OX2](c)[CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]</td></tr>
+ * <tr><td>18</td><td>Diarylether</td><td>[c][OX2][c]</td></tr>
+ * <tr><td>19</td><td>Alkylarylthioether</td><td>[SX2](c)[CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]</td></tr>
+ * <tr><td>20</td><td>Diarylthioether</td><td>[c][SX2][c]</td></tr>
+ * <tr><td>21</td><td>Oxonium</td><td>[O+;!$([O]~[!#6]);!$([S]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>22</td><td>Amine</td><td>[NX3+0,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>23</td><td>Primary aliph amine</td><td>[NX3H2+0,NX4H3+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>24</td><td>Secondary aliph amine</td><td>[NX3H1+0,NX4H2+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>25</td><td>Tertiary aliph amine</td><td>[NX3H0+0,NX4H1+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>26</td><td>Quaternary aliph ammonium</td><td>[NX4H0+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>27</td><td>Primary arom amine</td><td>[NX3H2+0,NX4H3+]c</td></tr>
+ * <tr><td>28</td><td>Secondary arom amine</td><td>[NX3H1+0,NX4H2+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>29</td><td>Tertiary arom amine</td><td>[NX3H0+0,NX4H1+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>30</td><td>Quaternary arom ammonium</td><td>[NX4H0+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>31</td><td>Secondary mixed amine</td><td>[NX3H1+0,NX4H2+;$([N]([c])[C]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>32</td><td>Tertiary mixed amine</td><td>[NX3H0+0,NX4H1+;$([N]([c])([C])[#6]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>33</td><td>Quaternary mixed ammonium</td><td>[NX4H0+;$([N]([c])([C])[#6][#6]);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>34</td><td>Ammonium</td><td>[N+;!$([N]~[!#6]);!$(N=*);!$([N]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>35</td><td>Alkylthiol</td><td>[SX2H][CX4;!$(C([SX2H])~[O,S,#7,#15])]</td></tr>
+ * <tr><td>36</td><td>Dialkylthioether</td><td>[SX2]([CX4;!$(C([SX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([SX2])[O,S,#7,#15])]</td></tr>
+ * <tr><td>37</td><td>Alkylarylthioether</td><td>[SX2](c)[CX4;!$(C([SX2])[O,S,#7,#15])]</td></tr>
+ * <tr><td>38</td><td>Disulfide</td><td>[SX2D2][SX2D2]</td></tr>
+ * <tr><td>39</td><td>1,2-Aminoalcohol</td><td>[OX2H][CX4;!$(C([OX2H])[O,S,#7,#15,F,Cl,Br,I])][CX4;!$(C([N])[O,S,#7,#15])][NX3;!$(NC=[O,S,N])]</td></tr>
+ * <tr><td>40</td><td>1,2-Diol</td><td>[OX2H][CX4;!$(C([OX2H])[O,S,#7,#15])][CX4;!$(C([OX2H])[O,S,#7,#15])][OX2H]</td></tr>
+ * <tr><td>41</td><td>1,1-Diol</td><td>[OX2H][CX4;!$(C([OX2H])([OX2H])[O,S,#7,#15])][OX2H]</td></tr>
+ * <tr><td>42</td><td>Hydroperoxide</td><td>[OX2H][OX2]</td></tr>
+ * <tr><td>43</td><td>Peroxo</td><td>[OX2D2][OX2D2]</td></tr>
+ * <tr><td>44</td><td>Organolithium compounds</td><td>[LiX1][#6,#14]</td></tr>
+ * <tr><td>45</td><td>Organomagnesium compounds</td><td>[MgX2][#6,#14]</td></tr>
+ * <tr><td>46</td><td>Organometallic compounds</td><td>[!#1;!#5;!#6;!#7;!#8;!#9;!#14;!#15;!#16;!#17;!#33;!#34;!#35;!#52;!#53;!#85]~[#6;!-]</td></tr>
+ * <tr><td>47</td><td>Aldehyde</td><td>[$([CX3H][#6]),$([CX3H2])]=[OX1]</td></tr>
+ * <tr><td>48</td><td>Ketone</td><td>[#6][CX3](=[OX1])[#6]</td></tr>
+ * <tr><td>49</td><td>Thioaldehyde</td><td>[$([CX3H][#6]),$([CX3H2])]=[SX1]</td></tr>
+ * <tr><td>50</td><td>Thioketone</td><td>[#6][CX3](=[SX1])[#6]</td></tr>
+ * <tr><td>51</td><td>Imine</td><td>[NX2;$([N][#6]),$([NH]);!$([N][CX3]=[#7,#8,#15,#16])]=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])]</td></tr>
+ * <tr><td>52</td><td>Immonium</td><td>[NX3+;!$([N][!#6]);!$([N][CX3]=[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>53</td><td>Oxime</td><td>[NX2](=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2H]</td></tr>
+ * <tr><td>54</td><td>Oximether</td><td>[NX2](=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2][#6;!$(C=[#7,#8])]</td></tr>
+ * <tr><td>55</td><td>Acetal</td><td>[OX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]</td></tr>
+ * <tr><td>56</td><td>Hemiacetal</td><td>[OX2H][CX4;!$(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]</td></tr>
+ * <tr><td>57</td><td>Aminal</td><td>[NX3v3;!$(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][NX3v3;!$(NC=[#7,#8,#15,#16])][#6]</td></tr>
+ * <tr><td>58</td><td>Hemiaminal</td><td>[NX3v3;!$(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][OX2H]</td></tr>
+ * <tr><td>59</td><td>Thioacetal</td><td>[SX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][SX2][#6;!$(C=[O,S,N])]</td></tr>
+ * <tr><td>60</td><td>Thiohemiacetal</td><td>[SX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][OX2H]</td></tr>
+ * <tr><td>61</td><td>Halogen acetal like</td><td>[NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>62</td><td>Acetal like</td><td>[NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1,NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>63</td><td>Halogenmethylen ester and similar</td><td>[NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>64</td><td>NOS methylen ester and similar</td><td>[NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>65</td><td>Hetero methylen ester and similar</td><td>[NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1,NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>66</td><td>Cyanhydrine</td><td>[NX1]#[CX2][CX4;$([CH2]),$([CH]([CX2])[#6]),$(C([CX2])([#6])[#6])][OX2H]</td></tr>
+ * <tr><td>67</td><td>Chloroalkene</td><td>[ClX1][CX3]=[CX3]</td></tr>
+ * <tr><td>68</td><td>Fluoroalkene</td><td>[FX1][CX3]=[CX3]</td></tr>
+ * <tr><td>69</td><td>Bromoalkene</td><td>[BrX1][CX3]=[CX3]</td></tr>
+ * <tr><td>70</td><td>Iodoalkene</td><td>[IX1][CX3]=[CX3]</td></tr>
+ * <tr><td>71</td><td>Enol</td><td>[OX2H][CX3;$([H1]),$(C[#6])]=[CX3]</td></tr>
+ * <tr><td>72</td><td>Endiol</td><td>[OX2H][CX3;$([H1]),$(C[#6])]=[CX3;$([H1]),$(C[#6])][OX2H]</td></tr>
+ * <tr><td>73</td><td>Enolether</td><td>[OX2]([#6;!$(C=[N,O,S])])[CX3;$([H0][#6]),$([H1])]=[CX3]</td></tr>
+ * <tr><td>74</td><td>Enolester</td><td>[OX2]([CX3]=[OX1])[#6X3;$([#6][#6]),$([H1])]=[#6X3;!$(C[OX2H])]</td></tr>
+ * <tr><td>75</td><td>Enamine</td><td>[NX3;$([NH2][CX3]),$([NH1]([CX3])[#6]),$([N]([CX3])([#6])[#6]);!$([N]*=[#7,#8,#15,#16])][CX3;$([CH]),$([C][#6])]=[CX3]</td></tr>
+ * <tr><td>76</td><td>Thioenol</td><td>[SX2H][CX3;$([H1]),$(C[#6])]=[CX3]</td></tr>
+ * <tr><td>77</td><td>Thioenolether</td><td>[SX2]([#6;!$(C=[N,O,S])])[CX3;$(C[#6]),$([CH])]=[CX3]</td></tr>
+ * <tr><td>78</td><td>Acylchloride</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[ClX1]</td></tr>
+ * <tr><td>79</td><td>Acylfluoride</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[FX1]</td></tr>
+ * <tr><td>80</td><td>Acylbromide</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[BrX1]</td></tr>
+ * <tr><td>81</td><td>Acyliodide</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[IX1]</td></tr>
+ * <tr><td>82</td><td>Acylhalide</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>83</td><td>Carboxylic acid</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>84</td><td>Carboxylic ester</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>85</td><td>Lactone</td><td>[#6][#6X3R](=[OX1])[#8X2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>86</td><td>Carboxylic anhydride</td><td>[CX3;$([H0][#6]),$([H1])](=[OX1])[#8X2][CX3;$([H0][#6]),$([H1])](=[OX1])</td></tr>
+ * <tr><td>87</td><td>Carboxylic acid derivative</td><td>[$([#6X3H0][#6]),$([#6X3H])](=[!#6])[!#6]</td></tr>
+ * <tr><td>88</td><td>Carbothioic acid</td><td>[CX3;!R;$([C][#6]),$([CH]);$([C](=[OX1])[$([SX2H]),$([SX1-])]),$([C](=[SX1])[$([OX2H]),$([OX1-])])]</td></tr>
+ * <tr><td>89</td><td>Carbothioic S ester</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[SX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>90</td><td>Carbothioic S lactone</td><td>[#6][#6X3R](=[OX1])[#16X2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>91</td><td>Carbothioic O ester</td><td>[CX3;$([H0][#6]),$([H1])](=[SX1])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>92</td><td>Carbothioic O lactone</td><td>[#6][#6X3R](=[SX1])[#8X2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>93</td><td>Carbothioic halide</td><td>[CX3;$([H0][#6]),$([H1])](=[SX1])[FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>94</td><td>Carbodithioic acid</td><td>[CX3;!R;$([C][#6]),$([CH]);$([C](=[SX1])[SX2H])]</td></tr>
+ * <tr><td>95</td><td>Carbodithioic ester</td><td>[CX3;!R;$([C][#6]),$([CH]);$([C](=[SX1])[SX2][#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>96</td><td>Carbodithiolactone</td><td>[#6][#6X3R](=[SX1])[#16X2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>97</td><td>Amide</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>98</td><td>Primary amide</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[NX3H2]</td></tr>
+ * <tr><td>99</td><td>Secondary amide</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3H1][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>100</td><td>Tertiary amide</td><td>[CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>101</td><td>Lactam</td><td>[#6R][#6X3R](=[OX1])[#7X3;$([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>102</td><td>Alkyl imide</td><td>[#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H0]([#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])</td></tr>
+ * <tr><td>103</td><td>N hetero imide</td><td>[#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H0]([!#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])</td></tr>
+ * <tr><td>104</td><td>Imide acidic</td><td>[#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H1][#6X3;$([H0][#6]),$([H1])](=[OX1])</td></tr>
+ * <tr><td>105</td><td>Thioamide</td><td>[$([CX3;!R][#6]),$([CX3H;!R])](=[SX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>106</td><td>Thiolactam</td><td>[#6R][#6X3R](=[SX1])[#7X3;$([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>107</td><td>Oximester</td><td>[#6X3;$([H0][#6]),$([H1])](=[OX1])[#8X2][#7X2]=,:[#6X3;$([H0]([#6])[#6]),$([H1][#6]),$([H2])]</td></tr>
+ * <tr><td>108</td><td>Amidine</td><td>[NX3;!$(NC=[O,S])][CX3;$([CH]),$([C][#6])]=[NX2;!$(NC=[O,S])]</td></tr>
+ * <tr><td>109</td><td>Hydroxamic acid</td><td>[CX3;$([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>110</td><td>Hydroxamic acid ester</td><td>[CX3;$([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>111</td><td>Imidoacid</td><td>[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>112</td><td>Imidoacid cyclic</td><td>[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>113</td><td>Imidoester</td><td>[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>114</td><td>Imidolactone</td><td>[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>115</td><td>Imidothioacid</td><td>[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])]</td></tr>
+ * <tr><td>116</td><td>Imidothioacid cyclic</td><td>[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])]</td></tr>
+ * <tr><td>117</td><td>Imidothioester</td><td>[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>118</td><td>Imidothiolactone</td><td>[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>119</td><td>Amidine</td><td>[#7X3v3;!$(N([#6X3]=[#7X2])C=[O,S])][CX3R0;$([H1]),$([H0][#6])]=[NX2v3;!$(N(=[#6X3][#7X3])C=[O,S])]</td></tr>
+ * <tr><td>120</td><td>Imidolactam</td><td>[#6][#6X3R;$([H0](=[NX2;!$(N(=[#6X3][#7X3])C=[O,S])])[#7X3;!$(N([#6X3]=[#7X2])C=[O,S])]),$([H0](-[NX3;!$(N([#6X3]=[#7X2])C=[O,S])])=,:[#7X2;!$(N(=[#6X3][#7X3])C=[O,S])])]</td></tr>
+ * <tr><td>121</td><td>Imidoylhalide</td><td>[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>122</td><td>Imidoylhalide cyclic</td><td>[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>123</td><td>Amidrazone</td><td>[$([$([#6X3][#6]),$([#6X3H])](=[#7X2v3])[#7X3v3][#7X3v3]),$([$([#6X3][#6]),$([#6X3H])]([#7X3v3])=[#7X2v3][#7X3v3])]</td></tr>
+ * <tr><td>124</td><td>Alpha aminoacid</td><td>[NX3,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[OX2H,OX1-]</td></tr>
+ * <tr><td>125</td><td>Alpha hydroxyacid</td><td>[OX2H][C][CX3](=[OX1])[OX2H,OX1-]</td></tr>
+ * <tr><td>126</td><td>Peptide middle</td><td>[NX3;$([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]</td></tr>
+ * <tr><td>127</td><td>Peptide C term</td><td>[NX3;$([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[OX2H,OX1-]</td></tr>
+ * <tr><td>128</td><td>Peptide N term</td><td>[NX3,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]</td></tr>
+ * <tr><td>129</td><td>Carboxylic orthoester</td><td>[#6][OX2][CX4;$(C[#6]),$([CH])]([OX2][#6])[OX2][#6]</td></tr>
+ * <tr><td>130</td><td>Ketene</td><td>[CX3]=[CX2]=[OX1]</td></tr>
+ * <tr><td>131</td><td>Ketenacetal</td><td>[#7X2,#8X3,#16X2;$(*[#6,#14])][#6X3]([#7X2,#8X3,#16X2;$(*[#6,#14])])=[#6X3]</td></tr>
+ * <tr><td>132</td><td>Nitrile</td><td>[NX1]#[CX2]</td></tr>
+ * <tr><td>133</td><td>Isonitrile</td><td>[CX1-]#[NX2+]</td></tr>
+ * <tr><td>134</td><td>Vinylogous carbonyl or carboxyl derivative</td><td>[#6X3](=[OX1])[#6X3]=,:[#6X3][#7,#8,#16,F,Cl,Br,I]</td></tr>
+ * <tr><td>135</td><td>Vinylogous acid</td><td>[#6X3](=[OX1])[#6X3]=,:[#6X3][$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>136</td><td>Vinylogous ester</td><td>[#6X3](=[OX1])[#6X3]=,:[#6X3][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>137</td><td>Vinylogous amide</td><td>[#6X3](=[OX1])[#6X3]=,:[#6X3][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>138</td><td>Vinylogous halide</td><td>[#6X3](=[OX1])[#6X3]=,:[#6X3][FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>139</td><td>Carbonic acid dieester</td><td>[#6;!$(C=[O,N,S])][#8X2][#6X3](=[OX1])[#8X2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>140</td><td>Carbonic acid esterhalide</td><td>[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[OX1])[OX2][FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>141</td><td>Carbonic acid monoester</td><td>[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[OX1])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>142</td><td>Carbonic acid derivatives</td><td>[!#6][#6X3](=[!#6])[!#6]</td></tr>
+ * <tr><td>143</td><td>Thiocarbonic acid dieester</td><td>[#6;!$(C=[O,N,S])][#8X2][#6X3](=[SX1])[#8X2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>144</td><td>Thiocarbonic acid esterhalide</td><td>[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[SX1])[OX2][FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>145</td><td>Thiocarbonic acid monoester</td><td>[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[SX1])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>146</td><td>Urea</td><td>[#7X3;!$([#7][!#6])][#6X3](=[OX1])[#7X3;!$([#7][!#6])]</td></tr>
+ * <tr><td>147</td><td>Thiourea</td><td>[#7X3;!$([#7][!#6])][#6X3](=[SX1])[#7X3;!$([#7][!#6])]</td></tr>
+ * <tr><td>148</td><td>Isourea</td><td>[#7X2;!$([#7][!#6])]=,:[#6X3]([#8X2&!$([#8][!#6]),OX1-])[#7X3;!$([#7][!#6])]</td></tr>
+ * <tr><td>149</td><td>Isothiourea</td><td>[#7X2;!$([#7][!#6])]=,:[#6X3]([#16X2&!$([#16][!#6]),SX1-])[#7X3;!$([#7][!#6])]</td></tr>
+ * <tr><td>150</td><td>Guanidine</td><td>[N;v3X3,v4X4+][CX3](=[N;v3X2,v4X3+])[N;v3X3,v4X4+]</td></tr>
+ * <tr><td>151</td><td>Carbaminic acid</td><td>[NX3]C(=[OX1])[O;X2H,X1-]</td></tr>
+ * <tr><td>152</td><td>Urethan</td><td>[#7X3][#6](=[OX1])[#8X2][#6]</td></tr>
+ * <tr><td>153</td><td>Biuret</td><td>[#7X3][#6](=[OX1])[#7X3][#6](=[OX1])[#7X3]</td></tr>
+ * <tr><td>154</td><td>Semicarbazide</td><td>[#7X3][#7X3][#6X3]([#7X3;!$([#7][#7])])=[OX1]</td></tr>
+ * <tr><td>155</td><td>Carbazide</td><td>[#7X3][#7X3][#6X3]([#7X3][#7X3])=[OX1]</td></tr>
+ * <tr><td>156</td><td>Semicarbazone</td><td>[#7X2](=[#6])[#7X3][#6X3]([#7X3;!$([#7][#7])])=[OX1]</td></tr>
+ * <tr><td>157</td><td>Carbazone</td><td>[#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[OX1]</td></tr>
+ * <tr><td>158</td><td>Thiosemicarbazide</td><td>[#7X3][#7X3][#6X3]([#7X3;!$([#7][#7])])=[SX1]</td></tr>
+ * <tr><td>159</td><td>Thiocarbazide</td><td>[#7X3][#7X3][#6X3]([#7X3][#7X3])=[SX1]</td></tr>
+ * <tr><td>160</td><td>Thiosemicarbazone</td><td>[#7X2](=[#6])[#7X3][#6X3]([#7X3;!$([#7][#7])])=[SX1]</td></tr>
+ * <tr><td>161</td><td>Thiocarbazone</td><td>[#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[SX1]</td></tr>
+ * <tr><td>162</td><td>Isocyanate</td><td>[NX2]=[CX2]=[OX1]</td></tr>
+ * <tr><td>163</td><td>Cyanate</td><td>[OX2][CX2]#[NX1]</td></tr>
+ * <tr><td>164</td><td>Isothiocyanate</td><td>[NX2]=[CX2]=[SX1]</td></tr>
+ * <tr><td>165</td><td>Thiocyanate</td><td>[SX2][CX2]#[NX1]</td></tr>
+ * <tr><td>166</td><td>Carbodiimide</td><td>[NX2]=[CX2]=[NX2]</td></tr>
+ * <tr><td>167</td><td>Orthocarbonic derivatives</td><td>[CX4H0]([O,S,#7])([O,S,#7])([O,S,#7])[O,S,#7,F,Cl,Br,I]</td></tr>
+ * <tr><td>168</td><td>Phenol</td><td>[OX2H][c]</td></tr>
+ * <tr><td>169</td><td>1,2-Diphenol</td><td>[OX2H][c][c][OX2H]</td></tr>
+ * <tr><td>170</td><td>Arylchloride</td><td>[Cl][c]</td></tr>
+ * <tr><td>171</td><td>Arylfluoride</td><td>[F][c]</td></tr>
+ * <tr><td>172</td><td>Arylbromide</td><td>[Br][c]</td></tr>
+ * <tr><td>173</td><td>Aryliodide</td><td>[I][c]</td></tr>
+ * <tr><td>174</td><td>Arylthiol</td><td>[SX2H][c]</td></tr>
+ * <tr><td>175</td><td>Iminoarene</td><td>[c]=[NX2;$([H1]),$([H0][#6;!$([C]=[N,S,O])])]</td></tr>
+ * <tr><td>176</td><td>Oxoarene</td><td>[c]=[OX1]</td></tr>
+ * <tr><td>177</td><td>Thioarene</td><td>[c]=[SX1]</td></tr>
+ * <tr><td>178</td><td>Hetero N basic H</td><td>[nX3H1+0]</td></tr>
+ * <tr><td>179</td><td>Hetero N basic no H</td><td>[nX3H0+0]</td></tr>
+ * <tr><td>180</td><td>Hetero N nonbasic</td><td>[nX2,nX3+]</td></tr>
+ * <tr><td>181</td><td>Hetero O</td><td>[o]</td></tr>
+ * <tr><td>182</td><td>Hetero S</td><td>[sX2]</td></tr>
+ * <tr><td>183</td><td>Heteroaromatic</td><td>[a;!c]</td></tr>
+ * <tr><td>184</td><td>Nitrite</td><td>[NX2](=[OX1])[O;$([X2]),$([X1-])]</td></tr>
+ * <tr><td>185</td><td>Thionitrite</td><td>[SX2][NX2]=[OX1]</td></tr>
+ * <tr><td>186</td><td>Nitrate</td><td>[$([NX3](=[OX1])(=[OX1])[O;$([X2]),$([X1-])]),$([NX3+]([OX1-])(=[OX1])[O;$([X2]),$([X1-])])]</td></tr>
+ * <tr><td>187</td><td>Nitro</td><td>[$([NX3](=O)=O),$([NX3+](=O)[O-])][!#8]</td></tr>
+ * <tr><td>188</td><td>Nitroso</td><td>[NX2](=[OX1])[!#7;!#8]</td></tr>
+ * <tr><td>189</td><td>Azide</td><td>[NX1]~[NX2]~[NX2,NX1]</td></tr>
+ * <tr><td>190</td><td>Acylazide</td><td>[CX3](=[OX1])[NX2]~[NX2]~[NX1]</td></tr>
+ * <tr><td>191</td><td>Diazo</td><td>[$([#6]=[NX2+]=[NX1-]),$([#6-]-[NX2+]#[NX1])]</td></tr>
+ * <tr><td>192</td><td>Diazonium</td><td>[#6][NX2+]#[NX1]</td></tr>
+ * <tr><td>193</td><td>Nitrosamine</td><td>[#7;!$(N*=O)][NX2]=[OX1]</td></tr>
+ * <tr><td>194</td><td>Nitrosamide</td><td>[NX2](=[OX1])N-*=O</td></tr>
+ * <tr><td>195</td><td>N-Oxide</td><td>[$([#7+][OX1-]),$([#7v5]=[OX1]);!$([#7](~[O])~[O]);!$([#7]=[#7])]</td></tr>
+ * <tr><td>196</td><td>Hydrazine</td><td>[NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])]</td></tr>
+ * <tr><td>197</td><td>Hydrazone</td><td>[NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX2]=[#6]</td></tr>
+ * <tr><td>198</td><td>Hydroxylamine</td><td>[NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][OX2;$([H1]),$(O[#6;!$(C=[N,O,S])])]</td></tr>
+ * <tr><td>199</td><td>Sulfon</td><td>[$([SX4](=[OX1])(=[OX1])([#6])[#6]),$([SX4+2]([OX1-])([OX1-])([#6])[#6])]</td></tr>
+ * <tr><td>200</td><td>Sulfoxide</td><td>[$([SX3](=[OX1])([#6])[#6]),$([SX3+]([OX1-])([#6])[#6])]</td></tr>
+ * <tr><td>201</td><td>Sulfonium</td><td>[S+;!$([S]~[!#6]);!$([S]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>202</td><td>Sulfuric acid</td><td>[SX4](=[OX1])(=[OX1])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>203</td><td>Sulfuric monoester</td><td>[SX4](=[OX1])(=[OX1])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>204</td><td>Sulfuric diester</td><td>[SX4](=[OX1])(=[OX1])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>205</td><td>Sulfuric monoamide</td><td>[SX4](=[OX1])(=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>206</td><td>Sulfuric diamide</td><td>[SX4](=[OX1])(=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>207</td><td>Sulfuric esteramide</td><td>[SX4](=[OX1])(=[OX1])([#7X3][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>208</td><td>Sulfuric derivative</td><td>[SX4D4](=[!#6])(=[!#6])([!#6])[!#6]</td></tr>
+ * <tr><td>209</td><td>Sulfonic acid</td><td>[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>210</td><td>Sulfonamide</td><td>[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>211</td><td>Sulfonic ester</td><td>[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>212</td><td>Sulfonic halide</td><td>[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>213</td><td>Sulfonic derivative</td><td>[SX4;$([H1]),$([H0][#6])](=[!#6])(=[!#6])[!#6]</td></tr>
+ * <tr><td>214</td><td>Sulfinic acid</td><td>[SX3;$([H1]),$([H0][#6])](=[OX1])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>215</td><td>Sulfinic amide</td><td>[SX3;$([H1]),$([H0][#6])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>216</td><td>Sulfinic ester</td><td>[SX3;$([H1]),$([H0][#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>217</td><td>Sulfinic halide</td><td>[SX3;$([H1]),$([H0][#6])](=[OX1])[FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>218</td><td>Sulfinic derivative</td><td>[SX3;$([H1]),$([H0][#6])](=[!#6])[!#6]</td></tr>
+ * <tr><td>219</td><td>Sulfenic acid</td><td>[SX2;$([H1]),$([H0][#6])][$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>220</td><td>Sulfenic amide</td><td>[SX2;$([H1]),$([H0][#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>221</td><td>Sulfenic ester</td><td>[SX2;$([H1]),$([H0][#6])][OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>222</td><td>Sulfenic halide</td><td>[SX2;$([H1]),$([H0][#6])][FX1,ClX1,BrX1,IX1]</td></tr>
+ * <tr><td>223</td><td>Sulfenic derivative</td><td>[SX2;$([H1]),$([H0][#6])][!#6]</td></tr>
+ * <tr><td>224</td><td>Phosphine</td><td>[PX3;$([H3]),$([H2][#6]),$([H1]([#6])[#6]),$([H0]([#6])([#6])[#6])]</td></tr>
+ * <tr><td>225</td><td>Phosphine oxide</td><td>[PX4;$([H3]=[OX1]),$([H2](=[OX1])[#6]),$([H1](=[OX1])([#6])[#6]),$([H0](=[OX1])([#6])([#6])[#6])]</td></tr>
+ * <tr><td>226</td><td>Phosphonium</td><td>[P+;!$([P]~[!#6]);!$([P]*~[#7,#8,#15,#16])]</td></tr>
+ * <tr><td>227</td><td>Phosphorylen</td><td>[PX4;$([H3]=[CX3]),$([H2](=[CX3])[#6]),$([H1](=[CX3])([#6])[#6]),$([H0](=[CX3])([#6])([#6])[#6])]</td></tr>
+ * <tr><td>228</td><td>Phosphonic acid</td><td>[PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>229</td><td>Phosphonic monoester</td><td>[PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>230</td><td>Phosphonic diester</td><td>[PX4;$([H1]),$([H0][#6])](=[OX1])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>231</td><td>Phosphonic monoamide</td><td>[PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>232</td><td>Phosphonic diamide</td><td>[PX4;$([H1]),$([H0][#6])](=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>233</td><td>Phosphonic esteramide</td><td>[PX4;$([H1]),$([H0][#6])](=[OX1])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>234</td><td>Phosphonic acid derivative</td><td>[PX4;$([H1]),$([H0][#6])](=[!#6])([!#6])[!#6]</td></tr>
+ * <tr><td>235</td><td>Phosphoric acid</td><td>[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>236</td><td>Phosphoric monoester</td><td>[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>237</td><td>Phosphoric diester</td><td>[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>238</td><td>Phosphoric triester</td><td>[PX4D4](=[OX1])([OX2][#6;!$(C=[O,N,S])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>239</td><td>Phosphoric monoamide</td><td>[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>240</td><td>Phosphoric diamide</td><td>[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>241</td><td>Phosphoric triamide</td><td>[PX4D4](=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>242</td><td>Phosphoric monoestermonoamide</td><td>[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>243</td><td>Phosphoric diestermonoamide</td><td>[PX4D4](=[OX1])([OX2][#6;!$(C=[O,N,S])])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>244</td><td>Phosphoric monoesterdiamide</td><td>[PX4D4](=[OX1])([OX2][#6;!$(C=[O,N,S])])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>245</td><td>Phosphoric acid derivative</td><td>[PX4D4](=[!#6])([!#6])([!#6])[!#6]</td></tr>
+ * <tr><td>246</td><td>Phosphinic acid</td><td>[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>247</td><td>Phosphinic ester</td><td>[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>248</td><td>Phosphinic amide</td><td>[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>249</td><td>Phosphinic acid derivative</td><td>[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[!#6])[!#6]</td></tr>
+ * <tr><td>250</td><td>Phosphonous acid</td><td>[PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>251</td><td>Phosphonous monoester</td><td>[PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>252</td><td>Phosphonous diester</td><td>[PX3;$([H1]),$([H0][#6])]([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>253</td><td>Phosphonous monoamide</td><td>[PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>254</td><td>Phosphonous diamide</td><td>[PX3;$([H1]),$([H0][#6])]([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>255</td><td>Phosphonous esteramide</td><td>[PX3;$([H1]),$([H0][#6])]([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>256</td><td>Phosphonous derivatives</td><td>[PX3;$([D2]),$([D3][#6])]([!#6])[!#6]</td></tr>
+ * <tr><td>257</td><td>Phosphinous acid</td><td>[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][$([OX2H]),$([OX1-])]</td></tr>
+ * <tr><td>258</td><td>Phosphinous ester</td><td>[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][OX2][#6;!$(C=[O,N,S])]</td></tr>
+ * <tr><td>259</td><td>Phosphinous amide</td><td>[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]</td></tr>
+ * <tr><td>260</td><td>Phosphinous derivatives</td><td>[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][!#6]</td></tr>
+ * <tr><td>261</td><td>Quart silane</td><td>[SiX4]([#6])([#6])([#6])[#6]</td></tr>
+ * <tr><td>262</td><td>Non-quart silane</td><td>[SiX4;$([H1]([#6])([#6])[#6]),$([H2]([#6])[#6]),$([H3][#6]),$([H4])]</td></tr>
+ * <tr><td>263</td><td>Silylmonohalide</td><td>[SiX4]([FX1,ClX1,BrX1,IX1])([#6])([#6])[#6]</td></tr>
+ * <tr><td>264</td><td>Het trialkylsilane</td><td>[SiX4]([!#6])([#6])([#6])[#6]</td></tr>
+ * <tr><td>265</td><td>Dihet dialkylsilane</td><td>[SiX4]([!#6])([!#6])([#6])[#6]</td></tr>
+ * <tr><td>266</td><td>Trihet alkylsilane</td><td>[SiX4]([!#6])([!#6])([!#6])[#6]</td></tr>
+ * <tr><td>267</td><td>Silicic acid derivative</td><td>[SiX4]([!#6])([!#6])([!#6])[!#6]</td></tr>
+ * <tr><td>268</td><td>Trialkylborane</td><td>[BX3]([#6])([#6])[#6]</td></tr>
+ * <tr><td>269</td><td>Boric acid derivatives</td><td>[BX3]([!#6])([!#6])[!#6]</td></tr>
+ * <tr><td>270</td><td>Boronic acid derivative</td><td>[BX3]([!#6])([!#6])[!#6]</td></tr>
+ * <tr><td>271</td><td>Borohydride</td><td>[BH1,BH2,BH3,BH4]</td></tr>
+ * <tr><td>272</td><td>Quaternary boron</td><td>[BX4]</td></tr>
+ * <tr><td>273</td><td>Aromatic</td><td>a</td></tr>
+ * <tr><td>274</td><td>Heterocyclic</td><td>[!#6;!R0]</td></tr>
+ * <tr><td>275</td><td>Epoxide</td><td>[OX2r3]1[#6r3][#6r3]1</td></tr>
+ * <tr><td>276</td><td>NH aziridine</td><td>[NX3H1r3]1[#6r3][#6r3]1</td></tr>
+ * <tr><td>277</td><td>Spiro</td><td>[D4R;$(*(@*)(@*)(@*)@*)]</td></tr>
+ * <tr><td>278</td><td>Annelated rings</td><td>[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]</td></tr>
+ * <tr><td>279</td><td>Bridged rings</td><td>[R;$(*(@*)(@*)@*);!$([D4R;$(*(@*)(@*)(@*)@*)]);!$([R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])])]</td></tr>
+ * <tr><td>280</td><td>Sugar pattern 1</td><td>[OX2;$([r5]1@C@C@C(O)@C1),$([r6]1@C@C@C(O)@C(O)@C1)]</td></tr>
+ * <tr><td>281</td><td>Sugar pattern 2</td><td>[OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]</td></tr>
+ * <tr><td>282</td><td>Sugar pattern combi</td><td>[OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C(O)@C1)]</td></tr>
+ * <tr><td>283</td><td>Sugar pattern 2 reducing</td><td>[OX2;$([r5]1@C(!@[OX2H1])@C@C@C1),$([r6]1@C(!@[OX2H1])@C@C@C@C1)]</td></tr>
+ * <tr><td>284</td><td>Sugar pattern 2 alpha</td><td>[OX2;$([r5]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]</td></tr>
+ * <tr><td>285</td><td>Sugar pattern 2 beta</td><td>[OX2;$([r5]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]</td></tr>
+ * <tr><td>286</td><td>Conjugated double bond</td><td>*=*[*]=,#,:[*]</td></tr>
+ * <tr><td>287</td><td>Conjugated tripple bond</td><td>*#*[*]=,#,:[*]</td></tr>
+ * <tr><td>288</td><td>Cis double bond</td><td>*/[D2]=[D2]/*</td></tr>
+ * <tr><td>289</td><td>Trans double bond</td><td>*/[D2]=[D2]/*</td></tr>
+ * <tr><td>290</td><td>Mixed anhydrides</td><td>[$(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))][#8X2][$(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))]</td></tr>
+ * <tr><td>291</td><td>Halogen on hetero</td><td>[FX1,ClX1,BrX1,IX1][!#6]</td></tr>
+ * <tr><td>292</td><td>Halogen multi subst</td><td>[F,Cl,Br,I;!$([X1]);!$([X0-])]</td></tr>
+ * <tr><td>293</td><td>Trifluoromethyl</td><td>[FX1][CX4;!$([H0][Cl,Br,I]);!$([F][C]([F])([F])[F])]([FX1])([FX1])</td></tr>
+ * <tr><td>294</td><td>C ONS bond</td><td>[#6]~[#7,#8,#16]</td></tr>
+ * <tr><td>295</td><td>Charged</td><td>[!+0]</td></tr>
+ * <tr><td>296</td><td>Anion</td><td>[-1,-2,-3,-4,-5,-6,-7]</td></tr>
+ * <tr><td>297</td><td>Kation</td><td>[+1,+2,+3,+4,+5,+6,+7]</td></tr>
+ * <tr><td>298</td><td>Salt</td><td>([-1,-2,-3,-4,-5,-6,-7]).([+1,+2,+3,+4,+5,+6,+7])</td></tr>
+ * <tr><td>299</td><td>1,3-Tautomerizable</td><td>[$([#7X2,OX1,SX1]=*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=*),$([#7X3,OX2,SX2;!H0]*:n)]</td></tr>
+ * <tr><td>300</td><td>1,5-Tautomerizable</td><td>[$([#7X2,OX1,SX1]=,:**=,:*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=**=*),$([#7X3,OX2,SX2;!H0]*=,:**:n)]</td></tr>
+ * <tr><td>301</td><td>Rotatable bond</td><td>[!$(*#*)&!D1]-!@[!$(*#*)&!D1]</td></tr>
+ * <tr><td>302</td><td>Michael acceptor</td><td>[CX3]=[CX3][$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-])]</td></tr>
+ * <tr><td>303</td><td>Dicarbodiazene</td><td>[CX3](=[OX1])[NX2]=[NX2][CX3](=[OX1])</td></tr>
+ * <tr><td>304</td><td>CH-acidic</td><td>[$([CX4;!$([H0]);!$(C[!#6;!$([P,S]=O);!$(N(~O)~O)])][$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-]);!$(*[S,O,N;H1,H2]);!$([*+0][S,O;X1-])]),$([CX4;!$([H0])]1[CX3]=[CX3][CX3]=[CX3]1)]</td></tr>
+ * <tr><td>305</td><td>CH-acidic strong</td><td>[CX4;!$([H0]);!$(C[!#6;!$([P,S]=O);!$(N(~O)~O)])]([$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-]);!$(*[S,O,N;H1,H2]);!$([*+0][S,O;X1-])])[$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-]);!$(*[S,O,N;H1,H2]);!$([*+0][S,O;X1-])]</td></tr>
+ * <tr><td>306</td><td>Chiral center specified</td><td>[$([*@](~*)(~*)(*)*),$([*@H](*)(*)*),$([*@](~*)(*)*),$([*@H](~*)~*)]</td></tr>
+ * </tbody></table>
+ *
+ *
* @author egonw
* @cdk.created 2005-12-30
*
* @cdk.keyword fingerprint
* @cdk.keyword similarity
*
- * @cdk.module extra
+ * @cdk.module fingerprint
* @cdk.svnrev $Revision$
*/
+@TestClass("org.openscience.cdk.fingerprint.SubstructureFingerprinterTest")
public class SubstructureFingerprinter implements IFingerprinter {
- private IAtomContainerSet substructureSet;
+ private String[] smarts;
/**
* Set up the fingerprinter to use the fragments from {@link org.openscience.cdk.fingerprint.StandardSubstructureSets}.
*/
+ @TestMethod("testFingerprint")
public SubstructureFingerprinter() {
try {
- this.substructureSet = StandardSubstructureSets.getFunctionalGroupSubstructureSet();
+ smarts = StandardSubstructureSets.getFunctionalGroupSMARTS();
} catch (Exception e) {
- substructureSet = null;
+ smarts = null;
}
}
/**
* Set up the fingerprinter to use a user-defined set of fragments.
*
- * @param substructureSet The collection of fragments to look for
+ * @param smarts The collection of fragments to look for
*/
- public SubstructureFingerprinter(IAtomContainerSet substructureSet) {
- this.substructureSet = substructureSet;
+ @TestMethod("testUserFunctionalGroups")
+ public SubstructureFingerprinter(String[] smarts) {
+ this.smarts = smarts;
}
/**
* Calculates the substructure fingerprint for the given AtomContainer.
*/
- public BitSet getFingerprint(IAtomContainer atomContainer) throws Exception {
-
- if (substructureSet == null) {
+ @TestMethod("testUerFunctionalGroups,testFingerprint")
+ public BitSet getFingerprint(IAtomContainer atomContainer) throws Exception {
+ if (smarts == null) {
throw new CDKException("No substructures were defined");
}
-
- int bitsetLength = substructureSet.getAtomContainerCount();
- BitSet fingerPrint = new BitSet(bitsetLength);
-
- IAtomContainer substructure;
- for (int i=0; i<bitsetLength; i++) {
- substructure = substructureSet.getAtomContainer(i);
- if (UniversalIsomorphismTester.isSubgraph(atomContainer, substructure))
- fingerPrint.set(i, true);
- }
-
- return fingerPrint;
- }
- public int getSize() {
- return substructureSet.getAtomContainerCount();
+ int bitsetLength = smarts.length;
+ BitSet fingerPrint = new BitSet(bitsetLength);
+
+ SMARTSQueryTool sqt = new SMARTSQueryTool("C");
+ for (int i = 0; i < smarts.length; i++) {
+ String pattern = smarts[i];
+
+ sqt.setSmarts(pattern);
+ boolean status = sqt.matches(atomContainer);
+ if (status) fingerPrint.set(i, true);
+ }
+ return fingerPrint;
+ }
+
+ @TestMethod("getSize")
+ public int getSize() {
+ return smarts.length;
}
}
Modified: cdk/trunk/src/test/org/openscience/cdk/fingerprint/StandardSubstructureSetsTest.java
===================================================================
--- cdk/trunk/src/test/org/openscience/cdk/fingerprint/StandardSubstructureSetsTest.java 2008-08-04 20:25:45 UTC (rev 11855)
+++ cdk/trunk/src/test/org/openscience/cdk/fingerprint/StandardSubstructureSetsTest.java 2008-08-04 21:16:15 UTC (rev 11856)
@@ -30,20 +30,18 @@
import org.junit.Assert;
import org.junit.Test;
import org.openscience.cdk.NewCDKTestCase;
-import org.openscience.cdk.interfaces.IAtomContainerSet;
/**
- * @cdk.module test-extra
+ * @cdk.module test-fingerprint
*/
public class StandardSubstructureSetsTest extends NewCDKTestCase {
@Test public void testGetFunctionalGroupSubstructureSet() throws Exception {
- IAtomContainerSet set = null;
- set = StandardSubstructureSets.getFunctionalGroupSubstructureSet();
-
- Assert.assertNotNull(set);
- Assert.assertEquals(8, set.getAtomContainerCount());
- }
+ String[] smarts = null;
+ smarts = StandardSubstructureSets.getFunctionalGroupSMARTS();
+ Assert.assertNotNull(smarts);
+ Assert.assertEquals(307, smarts.length);
+ }
}
Modified: cdk/trunk/src/test/org/openscience/cdk/fingerprint/SubstructureFingerprinterTest.java
===================================================================
--- cdk/trunk/src/test/org/openscience/cdk/fingerprint/SubstructureFingerprinterTest.java 2008-08-04 20:25:45 UTC (rev 11855)
+++ cdk/trunk/src/test/org/openscience/cdk/fingerprint/SubstructureFingerprinterTest.java 2008-08-04 21:16:15 UTC (rev 11856)
@@ -27,82 +27,61 @@
*/
package org.openscience.cdk.fingerprint;
-import java.util.BitSet;
-
import org.junit.Assert;
import org.junit.Test;
+import org.openscience.cdk.DefaultChemObjectBuilder;
import org.openscience.cdk.NewCDKTestCase;
-import org.openscience.cdk.interfaces.IAminoAcid;
-import org.openscience.cdk.interfaces.IAtomContainerSet;
-import org.openscience.cdk.interfaces.IMolecule;
+import org.openscience.cdk.interfaces.IAtomContainer;
import org.openscience.cdk.smiles.SmilesParser;
-import org.openscience.cdk.templates.AminoAcids;
-import org.openscience.cdk.templates.MoleculeFactory;
-import org.openscience.cdk.tools.manipulator.AminoAcidManipulator;
+import java.util.BitSet;
+
/**
- * @cdk.module test-extra
+ * @cdk.module test-fingerprint
*/
public class SubstructureFingerprinterTest extends NewCDKTestCase {
-
- @Test public void testFunctionalGroups() throws Exception {
- BitSet bitset = null;
- IAtomContainerSet set = null;
- set = StandardSubstructureSets.getFunctionalGroupSubstructureSet();
- IFingerprinter printer = new SubstructureFingerprinter(set);
- IMolecule pinene = MoleculeFactory.makeAlphaPinene();
- bitset = printer.getFingerprint(pinene);
-
- Assert.assertNotNull(set);
- Assert.assertNotNull(bitset);
- // none of the functional groups is found in this molecule
- for (int i=0; i<set.getAtomContainerCount(); i++) {
- Assert.assertFalse(bitset.get(i));
- }
- }
-
- public void testFunctionalGroups_matchAll() throws Exception {
- BitSet bitset = null;
- IAtomContainerSet set = null;
- set = StandardSubstructureSets.getFunctionalGroupSubstructureSet();
+ @Test
+ public void testSize() throws Exception {
+ SubstructureFingerprinter fp = new SubstructureFingerprinter();
+ Assert.assertEquals(307, fp.getSize());
+ }
+
+ @Test public void testUserFunctionalGroups() throws Exception {
+ String[] smarts = {"c1ccccc1", "[CX4H3][#6]", "[CX2]#[CX2]"};
+ IFingerprinter printer = new SubstructureFingerprinter(smarts);
+ Assert.assertEquals(3, printer.getSize());
- IFingerprinter printer = new SubstructureFingerprinter(set);
- IMolecule matchesAll = new SmilesParser(org.openscience.cdk.DefaultChemObjectBuilder.getInstance()).parseSmiles("C(C(=O)O)C(N([H])[H])C(O[H])C(COC)C(C(=O)[H])C(S(=O)(=O)O)C(P(=O)(=O)O)");
- bitset = printer.getFingerprint(matchesAll);
- System.out.println("BitSet: " + bitset);
-
- Assert.assertNotNull(set);
- Assert.assertNotNull(bitset);
- // all funtional groups are found in this molecule
- Assert.assertEquals(set.getAtomContainerCount(), bitset.cardinality());
- }
-
- public void testAminoAcids() throws Exception {
- BitSet bitset = null;
- IAtomContainerSet set = null;
- set = StandardSubstructureSets.getFunctionalGroupSubstructureSet();
+ SmilesParser sp = new SmilesParser(DefaultChemObjectBuilder.getInstance());
+ IAtomContainer mol1 = sp.parseSmiles("c1ccccc1CCC");
+ BitSet fp = printer.getFingerprint(mol1);
+ Assert.assertNotNull(fp);
- IAminoAcid[] aas = AminoAcids.createAAs();
- IFingerprinter printer = new SubstructureFingerprinter(set);
+ Assert.assertTrue(fp.get(0));
+ Assert.assertTrue(fp.get(1));
+ Assert.assertFalse(fp.get(2));
- Assert.assertNotNull(set);
+ mol1 = sp.parseSmiles("C=C=C");
+ fp = printer.getFingerprint(mol1);
+ Assert.assertNotNull(fp);
+ Assert.assertFalse(fp.get(0));
+ Assert.assertFalse(fp.get(1));
+ Assert.assertFalse(fp.get(2));
+ }
- // test whether all molecules have an amine and carboxylic acid group
- for (int i=0; i<aas.length; i++) {
- AminoAcidManipulator.addAcidicOxygen(aas[i]);
- IMolecule aminoAcid = aas[i].getBuilder().newMolecule(aas[i]);
- addExplicitHydrogens(aminoAcid);
+ @Test
+ public void testFingerprint() throws Exception {
+ IFingerprinter printer = new SubstructureFingerprinter();
+ Assert.assertEquals(307, printer.getSize());
- Assert.assertNotNull(aminoAcid);
- bitset = printer.getFingerprint(aminoAcid);
- Assert.assertNotNull(bitset);
- System.out.println("AA: " + aas[i].getProperty(AminoAcids.RESIDUE_NAME));
- System.out.println(" -> " + bitset);
- Assert.assertTrue(bitset.get(0)); // carboxylic acid group
- if (!aas[i].getProperty(AminoAcids.RESIDUE_NAME).equals("PRO"))
- Assert.assertTrue(bitset.get(1)); // amine group
- }
- }
+ SmilesParser sp = new SmilesParser(DefaultChemObjectBuilder.getInstance());
+ IAtomContainer mol1 = sp.parseSmiles("c1ccccc1CCC");
+ BitSet fp = printer.getFingerprint(mol1);
+ Assert.assertNotNull(fp);
+ Assert.assertTrue(fp.get(273));
+ Assert.assertTrue(fp.get(0));
+ Assert.assertTrue(fp.get(1));
+ Assert.assertFalse(fp.get(100));
+ }
}
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