rdworks 0.25.7__py3-none-any.whl

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Files changed (69) hide show
  1. rdworks/__init__.py +35 -0
  2. rdworks/autograph/__init__.py +4 -0
  3. rdworks/autograph/autograph.py +184 -0
  4. rdworks/autograph/centroid.py +90 -0
  5. rdworks/autograph/dynamictreecut.py +135 -0
  6. rdworks/autograph/nmrclust.py +123 -0
  7. rdworks/autograph/rckmeans.py +74 -0
  8. rdworks/bitqt/__init__.py +1 -0
  9. rdworks/bitqt/bitqt.py +355 -0
  10. rdworks/conf.py +374 -0
  11. rdworks/descriptor.py +36 -0
  12. rdworks/display.py +206 -0
  13. rdworks/ionized.py +170 -0
  14. rdworks/matchedseries.py +260 -0
  15. rdworks/mol.py +1522 -0
  16. rdworks/mollibr.py +887 -0
  17. rdworks/pka.py +38 -0
  18. rdworks/predefined/Asinex_fragment.xml +20 -0
  19. rdworks/predefined/Astex_RO3.xml +16 -0
  20. rdworks/predefined/Baell2010_PAINS/Baell2010A.xml +52 -0
  21. rdworks/predefined/Baell2010_PAINS/Baell2010B.xml +169 -0
  22. rdworks/predefined/Baell2010_PAINS/Baell2010C.xml +1231 -0
  23. rdworks/predefined/Baell2010_PAINS/PAINS-less-than-015-hits.xml +2048 -0
  24. rdworks/predefined/Baell2010_PAINS/PAINS-less-than-150-hits.xml +278 -0
  25. rdworks/predefined/Baell2010_PAINS/PAINS-more-than-150-hits.xml +83 -0
  26. rdworks/predefined/Baell2010_PAINS/makexml.py +70 -0
  27. rdworks/predefined/Brenk2008_Dundee/makexml.py +21 -0
  28. rdworks/predefined/CNS.xml +18 -0
  29. rdworks/predefined/ChEMBL_Walters/BMS.xml +543 -0
  30. rdworks/predefined/ChEMBL_Walters/Dundee.xml +318 -0
  31. rdworks/predefined/ChEMBL_Walters/Glaxo.xml +168 -0
  32. rdworks/predefined/ChEMBL_Walters/Inpharmatica.xml +276 -0
  33. rdworks/predefined/ChEMBL_Walters/LINT.xml +174 -0
  34. rdworks/predefined/ChEMBL_Walters/MLSMR.xml +351 -0
  35. rdworks/predefined/ChEMBL_Walters/PAINS.xml +1446 -0
  36. rdworks/predefined/ChEMBL_Walters/SureChEMBL.xml +501 -0
  37. rdworks/predefined/ChEMBL_Walters/makexml.py +40 -0
  38. rdworks/predefined/Hann1999_Glaxo/Hann1999.xml +168 -0
  39. rdworks/predefined/Hann1999_Glaxo/Hann1999Acid.xml +102 -0
  40. rdworks/predefined/Hann1999_Glaxo/Hann1999Base.xml +6 -0
  41. rdworks/predefined/Hann1999_Glaxo/Hann1999ElPh.xml +6 -0
  42. rdworks/predefined/Hann1999_Glaxo/Hann1999NuPh.xml +6 -0
  43. rdworks/predefined/Hann1999_Glaxo/makexml.py +83 -0
  44. rdworks/predefined/Kazius2005/Kazius2005.xml +114 -0
  45. rdworks/predefined/Kazius2005/makexml.py +66 -0
  46. rdworks/predefined/ZINC_druglike.xml +24 -0
  47. rdworks/predefined/ZINC_fragment.xml +14 -0
  48. rdworks/predefined/ZINC_leadlike.xml +15 -0
  49. rdworks/predefined/fragment.xml +7 -0
  50. rdworks/predefined/ionized/simple_smarts_pattern.csv +57 -0
  51. rdworks/predefined/ionized/smarts_pattern.csv +107 -0
  52. rdworks/predefined/misc/makexml.py +119 -0
  53. rdworks/predefined/misc/reactive-part-2.xml +104 -0
  54. rdworks/predefined/misc/reactive-part-3.xml +74 -0
  55. rdworks/predefined/misc/reactive.xml +321 -0
  56. rdworks/readin.py +312 -0
  57. rdworks/rgroup.py +2173 -0
  58. rdworks/scaffold.py +520 -0
  59. rdworks/std.py +143 -0
  60. rdworks/stereoisomers.py +127 -0
  61. rdworks/tautomers.py +20 -0
  62. rdworks/units.py +63 -0
  63. rdworks/utils.py +495 -0
  64. rdworks/xml.py +260 -0
  65. rdworks-0.25.7.dist-info/METADATA +37 -0
  66. rdworks-0.25.7.dist-info/RECORD +69 -0
  67. rdworks-0.25.7.dist-info/WHEEL +5 -0
  68. rdworks-0.25.7.dist-info/licenses/LICENSE +21 -0
  69. rdworks-0.25.7.dist-info/top_level.txt +1 -0
rdworks/pka.py ADDED
@@ -0,0 +1,38 @@
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+ """This module is an implementation in progress of the decision tree method for pKa prediction.
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+
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+ Crippen, J. Chem. Inf. Model., Vol. 48, No. 10, 2008, 2042-2053.
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+
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+ The SMARTS patterns and pKa values were taken from the supporting information of the paper.
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+ These "MOE SMARTS" were converted to generic SMARTS which relied on use of some recursive SMARTS patterns.
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+ The first data row then describes nodes 1, and then the tree expands out based on decisions of SMARTS-matching:
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+ if node 2 is yes to pattern [#8,#16,#34,#52,#84;H]C(=O) - giving pKa 3.68 and range 5.96
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+ node 3 is no to the same pattern - giving pKa 7.21 and range 17.32
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+ Then nodes 4,5 are under 2 and 6,7 are under 3, etc, etc until the leaf nodes are reached
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+ """
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+
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+
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+ import importlib.resources
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+ from collections import namedtuple
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+ from typing import Union
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+
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+ from rdkit import Chem
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+ from rdkit.Chem import AllChem
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+
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+ datadir = importlib.resources.files('rdworks.predefined')
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+ DecisionTreeNode = namedtuple('DecisionTree', ('node', 'parent', 'child', 'FP', 'SMARTS', 'YN', 'pKa', 'pKa_range'))
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+ decision_tree = []
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+ with open(datadir / "pKa_decision_tree.ext", "r") as f:
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+ for line in f:
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+ if (not line) or line.startswith('#'):
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+ continue
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+ decision_tree.append(DecisionTreeNode(line.strip().split()))
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+
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+
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+ def decision_tree_pKa(rdmol:Chem.Mol) -> Union[float, None]:
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+ pKa = None
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+ for _ in decision_tree:
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+ patt = Chem.MolFromSmarts(_.SMARTS) # make an RDKit query molecule
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+ match = rdmol.HasSubstructMatch(patt) # check if we have a match for our test molecule
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+ # pKa = float(values[6])
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+ # pKa_range = float(values[7])
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+ return pKa
rdworks/predefined/Asinex_fragment.xml ADDED
@@ -0,0 +1,20 @@
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+ <?xml version="1.0" ?>
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+ <Asinext_Fragment combine='AND'>
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+ <descriptor name="MolWt">
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+ <min>120</min>
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+ <max>250</max>
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+ </descriptor>
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+ <descriptor name="LogP">
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+ <max>2.5</max>
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+ </descriptor>
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+ <descriptor name="HAC">
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+ <min>9</min>
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+ <max>18</max>
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+ </descriptor>
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+ <descriptor name="HBA">
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+ <max>7</max>
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+ </descriptor>
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+ <descriptor name="HBD">
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+ <max>4</max>
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+ </descriptor>
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+ </Asinext_Fragment>
rdworks/predefined/Astex_RO3.xml ADDED
@@ -0,0 +1,16 @@
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+ <?xml version="1.0" ?>
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+ <Astext_RO3 combine='AND'>
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+ <!--Astex Rule of 3 -->
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+ <descriptor name="MolWt">
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+ <max>300</max>
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+ </descriptor>
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+ <descriptor name="LogP">
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+ <max>3.0</max>
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+ </descriptor>
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+ <descriptor name="HBD">
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+ <max>3</max>
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+ </descriptor>
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+ <descriptor name="HBA">
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+ <max>3</max>
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+ </descriptor>
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+ </Astext_RO3>
rdworks/predefined/Baell2010_PAINS/Baell2010A.xml ADDED
@@ -0,0 +1,52 @@
1
+ <?xml version="1.0" ?>
2
+ <PAINS combine='OR'>
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+ <!--Filter Family A p.S23-->
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+ <substructure name="(1) ene_six_het_A(483)">
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+ <SMARTS>[#6]-1(-[#6](~[!#6&amp;!#1]~[#6]-[!#6&amp;!#1]-[#6]-1=[!#6&amp;!#1])~[!#6&amp;!#1])=[#6;!R]-[#1]</SMARTS>
6
+ </substructure>
7
+ <substructure name="(2) hzone_phenol_A(479)">
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+ <SMARTS>c:1:c:c(:c(:c:c:1)-[#6]=[#7]-[#7])-[#8]-[#1]</SMARTS>
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+ </substructure>
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+ <substructure name="(3) anil_di_alk_A(478)">
11
+ <SMARTS>[#6](-[#1])(-[#1])-[#7](-[#6](-[#1])-[#1])-c:1:c:c(:c(:c(:c:1)-[$([#1]),$([#6](-[#1])-[#1]),$([#8]-[#6](-[#1])(-[#1])-[#6](-[#1])-[#1])])-[#7])-[#1]</SMARTS>
12
+ </substructure>
13
+ <substructure name="(4) indol_3yl_alk(461)">
14
+ <SMARTS>n:1(c(c(c:2:c:1:c:c:c:c:2-[#1])-[#6;X4]-[#1])-[$([#6](-[#1])-[#1]),$([#6]=,:[!#6&amp;!#1]),$([#6](-[#1])-[#7]),$([#6](-[#1])(-[#6](-[#1])-[#1])-[#6](-[#1])(-[#1])-[#7](-[#1])-[#6](-[#1])-[#1])])-[$([#1]),$([#6](-[#1])-[#1])]</SMARTS>
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+ </substructure>
16
+ <substructure name="(5) quinone_A(370)">
17
+ <SMARTS>[!#6&amp;!#1]=[#6]-1-[#6]=,:[#6]-[#6](=[!#6&amp;!#1])-[#6]=,:[#6]-1</SMARTS>
18
+ </substructure>
19
+ <substructure name="(6) azo_A(324)">
20
+ <SMARTS>[#7;!R]=[#7]</SMARTS>
21
+ </substructure>
22
+ <substructure name="(7) imine_one_A(321)">
23
+ <SMARTS>[#6]-[#6](=[!#6&amp;!#1;!R])-[#6](=[!#6&amp;!#1;!R])-[$([#6]),$([#16](=[#8])=[#8])]</SMARTS>
24
+ </substructure>
25
+ <substructure name="(8) mannich_A(296)">
26
+ <SMARTS>[#7]-[#6;X4]-c:1:c:c:c:c:c:1-[#8]-[#1]</SMARTS>
27
+ </substructure>
28
+ <substructure name="(9) anil_di_alk_B(251)">
29
+ <SMARTS>c:1:c:c(:c:c:c:1-[#7](-[#6;X4])-[#6;X4])-[#6]=[#6]</SMARTS>
30
+ </substructure>
31
+ <substructure name="(10) anil_di_alk_C(246)">
32
+ <SMARTS>c:1:c:c(:c:c:c:1-[#8]-[#6;X4])-[#7](-[#6;X4])-[$([#1]),$([#6;X4])]</SMARTS>
33
+ </substructure>
34
+ <substructure name="(11) ene_rhod_A(235)">
35
+ <SMARTS>[#7]-1-[#6](=[#16])-[#16]-[#6](=[#6])-[#6]-1=[#8]</SMARTS>
36
+ </substructure>
37
+ <substructure name="(12) hzone_phenol_B(215)">
38
+ <SMARTS>c:1(:c:c:c(:c:c:1)-[#6]=[#7]-[#7])-[#8]-[#1]</SMARTS>
39
+ </substructure>
40
+ <substructure name="(13) ene_five_het_A(201)">
41
+ <SMARTS>[#6]-1(=[#6])-[#6]=[#7]-[!#6&amp;!#1]-[#6]-1=[#8]</SMARTS>
42
+ </substructure>
43
+ <substructure name="(14) anil_di_alk_D(198)">
44
+ <SMARTS>c:1:c:c(:c:c:c:1-[#7](-[#6;X4])-[#6;X4])-[#6;X4]-[$([#8]-[#1]),$([#6]=[#6]-[#1]),$([#7]-[#6;X4])]</SMARTS>
45
+ </substructure>
46
+ <substructure name="(15) imine_one_isatin(189)">
47
+ <SMARTS>[#8]=[#6]-2-[#6](=!@[#7]-[#7])-c:1:c:c:c:c:c:1-[#7]-2</SMARTS>
48
+ </substructure>
49
+ <substructure name="(16) anil_di_alk_E(186)">
50
+ <SMARTS>[#6](-[#1])-[#7](-[#6](-[#1])-[#1])-c:1:c(:c(:c(:c(:c:1-[#1])-[$([#1]),$([#6](-[#1])-[#1])])-[#6](-[#1])-[$([#1]),$([#6]-[#1])])-[#1])-[#1]</SMARTS>
51
+ </substructure>
52
+ </PAINS>
rdworks/predefined/Baell2010_PAINS/Baell2010B.xml ADDED
@@ -0,0 +1,169 @@
1
+ <?xml version="1.0" ?>
2
+ <PAINSb>
3
+ <!--Filter Family B S23-S25-->
4
+ <substructure name="(1) thiaz_ene_A(128)">
5
+ <SMARTS>[#6]-1(=[#6](-[$([#1]),$([#6](-[#1])-[#1]),$([#6]=[#8])])-[#16]-[#6](-[#7]-1-[$([#1]),$([#6]-[#1]),$([#6]:[#6])])=[#7;!R])-[$([#6](-[#1])-[#1]),$([#6]:[#6])]</SMARTS>
6
+ </substructure>
7
+ <substructure name="(2) pyrrole_A(118)">
8
+ <SMARTS>n2(-[#6]:1:[!#1]:[#6]:[#6]:[#6]:[#6]:1)c(cc(c2-[#6;X4])-[#1])-[#6;X4]</SMARTS>
9
+ </substructure>
10
+ <substructure name="(3) catechol_A(92)">
11
+ <SMARTS>c:1:c:c(:c(:c:c:1)-[#8]-[#1])-[#8]-[#1]</SMARTS>
12
+ </substructure>
13
+ <substructure name="(4) ene_five_het_B(90)">
14
+ <SMARTS>[#6]-1(=[#6])-[#6](-[#7]=[#6]-[#16]-1)=[#8]</SMARTS>
15
+ </substructure>
16
+ <substructure name="(5) imine_one_fives(89)">
17
+ <SMARTS>[#6]-1=[!#1]-[!#6&amp;!#1]-[#6](-[#6]-1=[!#6&amp;!#1;!R])=[#8]</SMARTS>
18
+ </substructure>
19
+ <substructure name="(6) ene_five_het_C(85)">
20
+ <SMARTS>[#6]-1(-[#6](-[#6]=[#6]-[!#6&amp;!#1]-1)=[#6])=[!#6&amp;!#1]</SMARTS>
21
+ </substructure>
22
+ <substructure name="(7) hzone_pipzn(79)">
23
+ <SMARTS>[#6]-[#7]-1-[#6](-[#1])(-[#1])-[#6](-[#1])(-[#1])-[#7](-[#6](-[#1])(-[#1])-[#6]-1(-[#1])-[#1])-[#7]=[#6](-[#1])-[#6]:[!#1]</SMARTS>
24
+ </substructure>
25
+ <substructure name="(8) keto_keto_beta_A(68)">
26
+ <SMARTS>c:1-2:c(:c:c:c:c:1)-[#6](=[#8])-[#6;X4]-[#6]-2=[#8]</SMARTS>
27
+ </substructure>
28
+ <substructure name="(9) hzone_pyrrol(64)">
29
+ <SMARTS>n1(-[#6])c(c(-[#1])c(c1-[#6]=[#7]-[#7])-[#1])-[#1]</SMARTS>
30
+ </substructure>
31
+ <substructure name="(10) ene_one_ene_A(57)">
32
+ <SMARTS>[#6]=!@[#6](-[!#1])-@[#6](=!@[!#6&amp;!#1])-@[#6](=!@[#6])-[!#1]</SMARTS>
33
+ </substructure>
34
+ <substructure name="(11) cyano_ene_amine_A(56)">
35
+ <SMARTS>[#6](-[#6]#[#7])(-[#6]#[#7])-[#6](-[#7](-[#1])-[#1])=[#6]-[#6]#[#7]</SMARTS>
36
+ </substructure>
37
+ <substructure name="(12) ene_five_one_A(55)">
38
+ <SMARTS>c:1-2:c(:c:c:c:c:1)-[#6](=[#8])-[#6](=[#6])-[#6]-2=[#8]</SMARTS>
39
+ </substructure>
40
+ <substructure name="(13) cyano_pyridone_A(54)">
41
+ <SMARTS>[#6]-1(=[!#1]-[!#1]=[!#1]-[#7](-[#6]-1=[#16])-[#1])-[#6]#[#7]</SMARTS>
42
+ </substructure>
43
+ <substructure name="(14) anil_alk_ene(51)">
44
+ <SMARTS>c:1:c:c-2:c(:c:c:1)-[#6]-3-[#6](-[#6]-[#7]-2)-[#6]-[#6]=[#6]-3</SMARTS>
45
+ </substructure>
46
+ <substructure name="(15) amino_acridine_A(46)">
47
+ <SMARTS>c:1:c:2:c(:c:c:c:1):n:c:3:c(:c:2-[#7]):c:c:c:c:3</SMARTS>
48
+ </substructure>
49
+ <substructure name="(16) ene_five_het_D(46)">
50
+ <SMARTS>[#6]-1(=[#6])-[#6](=[#8])-[#7]-[#7]-[#6]-1=[#8]</SMARTS>
51
+ </substructure>
52
+ <substructure name="(17) thiophene_amino_Aa(45)">
53
+ <SMARTS>[#7](-[#1])(-[#1])-c:1:c(:c(:c(:s:1)-[!#1])-[!#1])-[#6]=[#8]</SMARTS>
54
+ </substructure>
55
+ <substructure name="(18) ene_five_het_E(44)">
56
+ <SMARTS>[#7]-[#6]=!@[#6]-2-[#6](=[#8])-c:1:c:c:c:c:c:1-[!#6&amp;!#1]-2</SMARTS>
57
+ </substructure>
58
+ <substructure name="(19) sulfonamide_A(43)">
59
+ <SMARTS>c:1(:c(:c(:c(:c(:c:1-[#8]-[#1])-[F,Cl,Br,I])-[#1])-[F,Cl,Br,I])-[#1])-[#16](=[#8])(=[#8])-[#7]</SMARTS>
60
+ </substructure>
61
+ <substructure name="(20) thio_ketone(43)">
62
+ <SMARTS>[#6]-[#6](=[#16])-[#6]</SMARTS>
63
+ </substructure>
64
+ <substructure name="(21) sulfonamide_B(41)">
65
+ <SMARTS>c:1:c:c(:c:c:c:1-[#8]-[#1])-[#7](-[#1])-[#16](=[#8])=[#8]</SMARTS>
66
+ </substructure>
67
+ <substructure name="(22) anil_no_alk(40)">
68
+ <SMARTS>c:1(:c(:c(:c(:c(:c:1-[#1])-[#1])-[$([#8]),$([#7]),$([#6](-[#1])-[#1])])-[#1])-[#1])-[#7](-[#1])-[#1]</SMARTS>
69
+ </substructure>
70
+ <substructure name="(23) thiophene_amino_Ab(40)">
71
+ <SMARTS>[$([#1]),$([#6](-[#1])-[#1]),$([#6]:[#6])]-c:1:c(:c(:c(:s:1)-[#7](-[#1])-[#6](=[#8])-[#6])-[#6](=[#8])-[#8])-[$([#6]:1:[#6]:[#6]:[#6]:[#6]:[#6]:1),$([#6]:1:[#16]:[#6]:[#6]:[#6]:1)]</SMARTS>
72
+ </substructure>
73
+ <substructure name="(24) het_pyridiniums_A(39)">
74
+ <SMARTS>[#7+]:1(:[#6]:[#6]:[!#1]:c:2:c:1:c(:c(-[$([#1]),$([#7])]):c:c:2)-[#1])-[$([#6](-[#1])(-[#1])-[#1]),$([#8;X1]),$([#6](-[#1])(-[#1])-[#6](-[#1])=[#6](-[#1])-[#1]),$([#6](-[#1])(-[#1])-[#6](-[#1])(-[#1])-[#8]-[#1]),$([#6](-[#1])(-[#1])-[#6](=[#8])-[#6]),$([#6](-[#1])(-[#1])-[#6](=[#8])-[#7](-[#1])-[#6]:[#6]),$([#6](-[#1])(-[#1])-[#6](-[#1])(-[#1])-[#1])]</SMARTS>
75
+ </substructure>
76
+ <substructure name="(25) anthranil_one_A(38)">
77
+ <SMARTS>c:1:c:c:c:c(:c:1-[#7](-[#1])-[!$([#6]=[#8])])-[#6](-[#6]:[#6])=[#8]</SMARTS>
78
+ </substructure>
79
+ <substructure name="(26) cyano_imine_A(37)">
80
+ <SMARTS>[#7](-[#1])-[#7]=[#6](-[#6]#[#7])-[#6]=[!#6&amp;!#1;!R]</SMARTS>
81
+ </substructure>
82
+ <substructure name="(27) diazox_sulfon_A(36)">
83
+ <SMARTS>[#7](-c:1:c:c:c:c:c:1)-[#16](=[#8])(=[#8])-[#6]:2:[#6]:[#6]:[#6]:[#6]:3:[#7]:[$([#8]),$([#16])]:[#7]:[#6]:2:3</SMARTS>
84
+ </substructure>
85
+ <substructure name="(28) hzone_anil_di_alk(35)">
86
+ <SMARTS>[#6](-[#1])(-[#1])-[#7](-[#6](-[#1])-[#1])-c:1:c(:c(:c(:c(:c:1-[#1])-[#1])-[#6](-[#1])=[#7]-[#7]-[$([#6](=[#8])-[#6](-[#1])(-[#1])-[#16]-[#6]:[#7]),$([#6](=[#8])-[#6](-[#1])(-[#1])-[!#1]:[!#1]:[#7]),$([#6](=[#8])-[#6]:[#6]-[#8]-[#1]),$([#6]:[#7]),$([#6](-[#1])(-[#1])-[#6](-[#1])-[#8]-[#1])])-[#1])-[#1]</SMARTS>
87
+ </substructure>
88
+ <substructure name="(29) rhod_sat_A(33)">
89
+ <SMARTS>[#7]-1-[#6](=[#16])-[#16]-[#6;X4]-[#6]-1=[#8]</SMARTS>
90
+ </substructure>
91
+ <substructure name="(30) hzone_enamin(30)">
92
+ <SMARTS>[#7](-[#1])-[#7]=[#6]-[#6](-[$([#1]),$([#6])])=[#6](-[#6])-!@[$([#7]),$([#8]-[#1])]</SMARTS>
93
+ </substructure>
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+ <substructure name="(31) pyrrole_B(29)">
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+ <SMARTS>n2(-[#6]:1:[!#1]:[#6]:[#6]:[#6]:[#6]:1)c(cc(c2-[#6]:[#6])-[#1])-[#6;X4]</SMARTS>
96
+ </substructure>
97
+ <substructure name="(32) thiophene_hydroxy(28)">
98
+ <SMARTS>s1ccc(c1)-[#8]-[#1]</SMARTS>
99
+ </substructure>
100
+ <substructure name="(33) cyano_pyridone_B(27)">
101
+ <SMARTS>[#6]-1(=[#6](-[#6](=[#8])-[#7]-[#6](=[#7]-1)-[!#6&amp;!#1])-[#6]#[#7])-[#6]</SMARTS>
102
+ </substructure>
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+ <substructure name="(34) imine_one_sixes(27)">
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+ <SMARTS>[#6]-1(-[#6](=[#8])-[#7]-[#6](=[#8])-[#7]-[#6]-1=[#8])=[#7]</SMARTS>
105
+ </substructure>
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+ <substructure name="(35) dyes5A(27)">
107
+ <SMARTS>[#6](-[#1])(-[#1])-[#7]([#6]:[#6])~[#6][#6]=,:[#6]-[#6]~[#6][#7]</SMARTS>
108
+ </substructure>
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+ <substructure name="(36) naphth_amino_A(25)">
110
+ <SMARTS>c:2:c:1:c:c:c:c-3:c:1:c(:c:c:2)-[#7]-[#6]=[#7]-3</SMARTS>
111
+ </substructure>
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+ <substructure name="(37) naphth_amino_B(25)">
113
+ <SMARTS>c:2:c:1:c:c:c:c-3:c:1:c(:c:c:2)-[#7](-[#6;X4]-[#7]-3-[#1])-[#1]</SMARTS>
114
+ </substructure>
115
+ <substructure name="(38) ene_one_ester(24)">
116
+ <SMARTS>[#6]-[#6](=[#8])-[#6](-[#1])=[#6](-[#7](-[#1])-[#6])-[#6](=[#8])-[#8]-[#6]</SMARTS>
117
+ </substructure>
118
+ <substructure name="(39) thio_dibenzo(23)">
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+ <SMARTS>[#16]=[#6]-1-[#6]=,:[#6]-[!#6&amp;!#1]-[#6]=,:[#6]-1</SMARTS>
120
+ </substructure>
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+ <substructure name="(40) cyano_cyano_A(23)">
122
+ <SMARTS>[#6](-[#6]#[#7])(-[#6]#[#7])-[#6](-[$([#6]#[#7]),$([#6]=[#7])])-[#6]#[#7]</SMARTS>
123
+ </substructure>
124
+ <substructure name="(41) hzone_acyl_naphthol(22)">
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+ <SMARTS>c:1:2:c(:c(:c(:c(:c:1:c(:c(:c(:c:2-[#1])-[#8]-[#1])-[#6](=[#8])-[#7](-[#1])-[#7]=[#6])-[#1])-[#1])-[#1])-[#1])-[#1]</SMARTS>
126
+ </substructure>
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+ <substructure name="(42) het_65_A(21)">
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+ <SMARTS>[#8]=[#6]-c2c1nc(-[#6](-[#1])-[#1])cc(-[#8]-[#1])n1nc2</SMARTS>
129
+ </substructure>
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+ <substructure name="(43) imidazole_A(19)">
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+ <SMARTS>n:1:c(:n(:c(:c:1-c:2:c:c:c:c:c:2)-c:3:c:c:c:c:c:3)-[#1])-[#6]:[!#1]</SMARTS>
132
+ </substructure>
133
+ <substructure name="(44) ene_cyano_A(19)">
134
+ <SMARTS>[#6](-[#6]#[#7])(-[#6]#[#7])=[#6]-c:1:c:c:c:c:c:1</SMARTS>
135
+ </substructure>
136
+ <substructure name="(45) anthranil_acid_A(19)">
137
+ <SMARTS>c:1(:c:c:c:c:c:1-[#7](-[#1])-[#7]=[#6])-[#6](=[#8])-[#8]-[#1]</SMARTS>
138
+ </substructure>
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+ <substructure name="(46) dyes3A(19)">
140
+ <SMARTS>[#7+]([#6]:[#6])=,:[#6]-[#6](-[#1])=[#6]-[#7](-[#6;X4])-[#6]</SMARTS>
141
+ </substructure>
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+ <substructure name="(47) dhp_bis_amino_CN(19)">
143
+ <SMARTS>[#7](-[#1])(-[#1])-[#6]-1=[#6](-[#6]#[#7])-[#6](-[#1])(-[#6]:[#6])-[#6](=[#6](-[#7](-[#1])-[#1])-[#16]-1)-[#6]#[#7]</SMARTS>
144
+ </substructure>
145
+ <substructure name="(48) het_6_tetrazine(18)">
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+ <SMARTS>[#7]~[#6]:1:[#7]:[#7]:[#6](:[$([#7]),$([#6]-[#1]),$([#6]-[#7]-[#1])]:[$([#7]),$([#6]-[#7])]:1)-[$([#7]-[#1]),$([#8]-[#6](-[#1])-[#1])]</SMARTS>
147
+ </substructure>
148
+ <substructure name="(49) ene_one_hal(17)">
149
+ <SMARTS>[#6]-[#6]=[#6](-[F,Cl,Br,I])-[#6](=[#8])-[#6]</SMARTS>
150
+ </substructure>
151
+ <substructure name="(50) cyano_imine_B(17)">
152
+ <SMARTS>[#6](-[#6]#[#7])(-[#6]#[#7])=[#7]-[#7](-[#1])-c:1:c:c:c:c:c:1</SMARTS>
153
+ </substructure>
154
+ <substructure name="(51) thiaz_ene_B(17)">
155
+ <SMARTS>[#6]-1(=[#6](-!@[#6](=[#8])-[#7]-[#6](-[#1])-[#1])-[#16]-[#6](-[#7]-1-[$([#6](-[#1])(-[#1])-[#6](-[#1])=[#6](-[#1])-[#1]),$([#6]:[#6])])=[#16])-[$([#7]-[#6](=[#8])-[#6]:[#6]),$([#7](-[#1])-[#1])]</SMARTS>
156
+ </substructure>
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+ <substructure name="(52) ene_rhod_B(16)">
158
+ <SMARTS>[#16]-1-[#6](=[#8])-[#7]-[#6](=[#8])-[#6]-1=[#6](-[#1])-[$([#6]-[#35]),$([#6]:[#6](-[#1]):[#6](-[F,Cl,Br,I]):[#6]:[#6]-[F,Cl,Br,I]),$([#6]:[#6](-[#1]):[#6](-[#1]):[#6]-[#16]-[#6](-[#1])-[#1]),$([#6]:[#6]:[#6]:[#6]:[#6]:[#6]:[#6]:[#6]:[#6]:[#6]-[#8]-[#6](-[#1])-[#1]),$([#6]:1:[#6](-[#6](-[#1])-[#1]):[#7](-[#6](-[#1])-[#1]):[#6](-[#6](-[#1])-[#1]):[#6]:1)]</SMARTS>
159
+ </substructure>
160
+ <substructure name="(53) thio_carbonate_A(15)">
161
+ <SMARTS>[#8]-1-[#6](-[#16]-c:2:c-1:c:c:c(:c:2)-[$([#7]),$([#8])])=[$([#8]),$([#16])]</SMARTS>
162
+ </substructure>
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+ <substructure name="(54) anil_di_alk_furan_A(15)">
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+ <SMARTS>[#7](-[#6](-[#1])-[#1])(-[#6](-[#1])-[#1])-c:1:c(:c(:c(:o:1)-[#6]=[#7]-[#7](-[#1])-[#6]=[!#6&amp;!#1])-[#1])-[#1]</SMARTS>
165
+ </substructure>
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+ <substructure name="(55) ene_five_het_F(15)">
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+ <SMARTS>c:1(:c:c:c:c:c:1)-[#6](-[#1])=!@[#6]-3-[#6](=[#8])-c:2:c:c:c:c:c:2-[#16]-3</SMARTS>
168
+ </substructure>
169
+ </PAINSb>