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CADDSuite version 1.5
author Marcel Schumann <schumann.marcel@gmail.com>
date Tue, 24 Jul 2012 11:08:49 -0400
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1 #
2 # SMARTS Patterns for Functional Group Classification
3 #
4 # written by Christian Laggner
5 # Copyright 2005 Inte:Ligand Software-Entwicklungs und Consulting GmbH
6 #
7 # Released under the Lesser General Public License (LGPL license)
8 # see http://www.gnu.org/copyleft/lesser.html
9 # Modified from Version 221105
10 #####################################################################################################
11
12 # General Stuff:
13 # These patters were written in an attempt to represent the classification of organic compounds
14 # from the viewpoint of an organic chemist.
15 # They are often very restrictive. This may be generally a good thing, but it also takes some time
16 # for filtering/indexing large compound sets.
17 # For filtering undesired groups (in druglike compounds) one will want to have more general patterns
18 # (e.g. you don't want *any* halide of *any* acid, *neither* aldehyde *nor* formyl esters and amides, ...).
19 #
20
21 # Part I: Carbon
22 # ==============
23
24
25 # I.1: Carbon-Carbon Bonds
26 # ------------------------
27
28 # I.1.1 Alkanes:
29
30 Primary_carbon: [CX4H3][#6]
31
32 Secondary_carbon: [CX4H2]([#6])[#6]
33
34 Tertiary_carbon: [CX4H1]([#6])([#6])[#6]
35
36 Quaternary_carbon: [CX4]([#6])([#6])([#6])[#6]
37
38
39 # I.1.2 C-C double and Triple Bonds
40
41 Alkene: [CX3;$([H2]),$([H1][#6]),$(C([#6])[#6])]=[CX3;$([H2]),$([H1][#6]),$(C([#6])[#6])]
42 # sp2 C may be substituted only by C or H -
43 # does not hit ketenes and allenes, nor enamines, enols and the like
44
45 Alkyne: [CX2]#[CX2]
46 # non-carbon substituents (e.g. alkynol ethers) are rather rare, thus no further discrimination
47
48 Allene: [CX3]=[CX2]=[CX3]
49
50
51 # I.2: One Carbon-Hetero Bond
52 # ---------------------------
53
54
55 # I.2.1 Alkyl Halogenides
56
57 Alkylchloride: [ClX1][CX4]
58 # will also hit chloromethylethers and the like, but no chloroalkenes, -alkynes or -aromats
59 # a more restrictive version can be obtained by modifying the Alcohol string.
60
61 Alkylfluoride: [FX1][CX4]
62
63 Alkylbromide: [BrX1][CX4]
64
65 Alkyliodide: [IX1][CX4]
66
67
68 # I.2.2 Alcohols and Ethers
69
70 Alcohol: [OX2H][CX4;!$(C([OX2H])[O,S,#7,#15])]
71 # nonspecific definition, no acetals, aminals, and the like
72
73 Primary_alcohol: [OX2H][CX4H2;!$(C([OX2H])[O,S,#7,#15])]
74
75 Secondary_alcohol: [OX2H][CX4H;!$(C([OX2H])[O,S,#7,#15])]
76
77 Tertiary_alcohol: [OX2H][CX4D4;!$(C([OX2H])[O,S,#7,#15])]
78
79 Dialkylether: [OX2]([CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]
80 # no acetals and the like; no enolethers
81
82 Dialkylthioether: [SX2]([CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]
83 # no acetals and the like; no enolethers
84
85 Alkylarylether: [OX2](c)[CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]
86 # no acetals and the like; no enolethers
87
88 Diarylether: [c][OX2][c]
89
90 Alkylarylthioether: [SX2](c)[CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]
91
92 Diarylthioether: [c][SX2][c]
93
94 Oxonium: [O+;!$([O]~[!#6]);!$([S]*~[#7,#8,#15,#16])]
95 # can't be aromatic, thus O and not #8
96
97 # I.2.3 Amines
98
99 Amine: [NX3+0,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])]
100 # hits all amines (prim/sec/tert/quart), including ammonium salts, also enamines, but not amides, imides, aminals, ...
101
102 # the following amines include also the protonated forms
103
104 Primary_aliph_amine: [NX3H2+0,NX4H3+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]
105
106 Secondary_aliph_amine: [NX3H1+0,NX4H2+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]
107
108 Tertiary_aliph_amine: [NX3H0+0,NX4H1+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]
109
110 Quaternary_aliph_ammonium: [NX4H0+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]
111
112 Primary_arom_amine: [NX3H2+0,NX4H3+]c
113
114 Secondary_arom_amine: [NX3H1+0,NX4H2+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]
115
116 Tertiary_arom_amine: [NX3H0+0,NX4H1+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]
117
118 Quaternary_arom_ammonium: [NX4H0+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]
119
120 Secondary_mixed_amine: [NX3H1+0,NX4H2+;$([N]([c])[C]);!$([N]*~[#7,#8,#15,#16])]
121
122 Tertiary_mixed_amine: [NX3H0+0,NX4H1+;$([N]([c])([C])[#6]);!$([N]*~[#7,#8,#15,#16])]
123
124 Quaternary_mixed_ammonium: [NX4H0+;$([N]([c])([C])[#6][#6]);!$([N]*~[#7,#8,#15,#16])]
125
126 Ammonium: [N+;!$([N]~[!#6]);!$(N=*);!$([N]*~[#7,#8,#15,#16])]
127 # only C and H substituents allowed. Quaternary or protonated amines
128 # NX4+ or Nv4+ is not recognized by Daylight's depictmatch if less than four C are present
129
130
131 # I.2.4 Others
132
133 Alkylthiol: [SX2H][CX4;!$(C([SX2H])~[O,S,#7,#15])]
134
135 Dialkylthioether: [SX2]([CX4;!$(C([SX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([SX2])[O,S,#7,#15])]
136
137 Alkylarylthioether: [SX2](c)[CX4;!$(C([SX2])[O,S,#7,#15])]
138
139 Disulfide: [SX2D2][SX2D2]
140
141 1,2-Aminoalcohol: [OX2H][CX4;!$(C([OX2H])[O,S,#7,#15,F,Cl,Br,I])][CX4;!$(C([N])[O,S,#7,#15])][NX3;!$(NC=[O,S,N])]
142 # does not hit alpha-amino acids, enaminoalcohols, 1,2-aminoacetals, o-aminophenols, etc.
143
144 1,2-Diol: [OX2H][CX4;!$(C([OX2H])[O,S,#7,#15])][CX4;!$(C([OX2H])[O,S,#7,#15])][OX2H]
145 # does not hit alpha-hydroxy acids, enolalcohols, 1,2-hydroxyacetals, 1,2-diphenols, etc.
146
147 1,1-Diol: [OX2H][CX4;!$(C([OX2H])([OX2H])[O,S,#7,#15])][OX2H]
148
149 Hydroperoxide: [OX2H][OX2]
150 #does not neccessarily have to be connected to a carbon atom, includes also hydrotrioxides
151
152 Peroxo: [OX2D2][OX2D2]
153
154 Organolithium_compounds: [LiX1][#6,#14]
155
156 Organomagnesium_compounds: [MgX2][#6,#14]
157 # not restricted to Grignard compounds, also dialkyl Mg
158
159 Organometallic_compounds: [!#1;!#5;!#6;!#7;!#8;!#9;!#14;!#15;!#16;!#17;!#33;!#34;!#35;!#52;!#53;!#85]~[#6;!-]
160 # very general, includes all metals covalently bound to carbon
161
162
163 # I.3: Two Carbon-Hetero Bonds (Carbonyl and Derivatives)
164 # ----------------------------
165
166 # I.3.1 Double Bond to Hetero
167
168 Aldehyde: [$([CX3H][#6]),$([CX3H2])]=[OX1]
169 # hits aldehydes including formaldehyde
170
171 Ketone: [#6][CX3](=[OX1])[#6]
172 # does not include oxo-groups connected to a (hetero-) aromatic ring
173
174 Thioaldehyde: [$([CX3H][#6]),$([CX3H2])]=[SX1]
175
176 Thioketone: [#6][CX3](=[SX1])[#6]
177 # does not include thioxo-groups connected to a (hetero-) aromatic ring
178
179 Imine: [NX2;$([N][#6]),$([NH]);!$([N][CX3]=[#7,#8,#15,#16])]=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])]
180 # nitrogen is not part of an amidelike strukture, nor of an aromatic ring, but can be part of an aminal or similar
181
182 Immonium: [NX3+;!$([N][!#6]);!$([N][CX3]=[#7,#8,#15,#16])]
183
184 Oxime: [NX2](=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2H]
185
186 Oximether: [NX2](=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2][#6;!$(C=[#7,#8])]
187 # ether, not ester or amide; does not hit isoxazole
188
189
190 # I.3.2. Two Single Bonds to Hetero
191
192 Acetal: [OX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]
193 # does not hit hydroxy-methylesters, ketenacetals, hemiacetals, orthoesters, etc.
194
195 Hemiacetal: [OX2H][CX4;!$(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]
196
197 Aminal: [NX3v3;!$(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][NX3v3;!$(NC=[#7,#8,#15,#16])][#6]
198 # Ns are not part of an amide or similar. v3 ist to exclude nitro and similar groups
199
200 Hemiaminal: [NX3v3;!$(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][OX2H]
201
202 Thioacetal: [SX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][SX2][#6;!$(C=[O,S,N])]
203
204 Thiohemiacetal: [SX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][OX2H]
205
206 Halogen_acetal_like: [NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]
207 # hits chloromethylenethers and other reactive alkylating agents
208
209 Acetal_like: [NX3v3,SX2,OX2;!$(*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])]
210 # includes all of the above and other combinations (S-C-N, hydrates, ...), but still no aminomethylenesters and similar
211
212 Halogenmethylen_ester_and_similar: [NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]
213 # also reactive alkylating agents. Acid does not have to be carboxylic acid, also S- and P-based acids allowed
214
215 NOS_methylen_ester_and_similar: [NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]
216 # Same as above, but N,O or S instead of halogen. Ester/amide allowed only on one side
217
218 Hetero_methylen_ester_and_similar: [NX3v3,SX2,OX2;$(**=[#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])]
219 # Combination of the last two patterns
220
221 Cyanhydrine: [NX1]#[CX2][CX4;$([CH2]),$([CH]([CX2])[#6]),$(C([CX2])([#6])[#6])][OX2H]
222
223
224 # I.3.3 Single Bond to Hetero, C=C Double Bond (Enols and Similar)
225
226 Chloroalkene: [ClX1][CX3]=[CX3]
227
228 Fluoroalkene: [FX1][CX3]=[CX3]
229
230 Bromoalkene: [BrX1][CX3]=[CX3]
231
232 Iodoalkene: [IX1][CX3]=[CX3]
233
234 Enol: [OX2H][CX3;$([H1]),$(C[#6])]=[CX3]
235 # no phenols
236
237 Endiol: [OX2H][CX3;$([H1]),$(C[#6])]=[CX3;$([H1]),$(C[#6])][OX2H]
238 # no 1,2-diphenols, ketenacetals, ...
239
240 Enolether: [OX2]([#6;!$(C=[N,O,S])])[CX3;$([H0][#6]),$([H1])]=[CX3]
241 # finds also endiodiethers, but not enolesters, no aromats
242
243 Enolester: [OX2]([CX3]=[OX1])[#6X3;$([#6][#6]),$([H1])]=[#6X3;!$(C[OX2H])]
244
245
246 Enamine: [NX3;$([NH2][CX3]),$([NH1]([CX3])[#6]),$([N]([CX3])([#6])[#6]);!$([N]*=[#7,#8,#15,#16])][CX3;$([CH]),$([C][#6])]=[CX3]
247 # does not hit amines attached to aromatic rings, nor may the nitrogen be aromatic
248
249 Thioenol: [SX2H][CX3;$([H1]),$(C[#6])]=[CX3]
250
251 Thioenolether: [SX2]([#6;!$(C=[N,O,S])])[CX3;$(C[#6]),$([CH])]=[CX3]
252
253
254 # I.4: Three Carbon-Hetero Bonds (Carboxyl and Derivatives)
255 # ------------------------------
256
257 Acylchloride: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[ClX1]
258
259 Acylfluoride: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[FX1]
260
261 Acylbromide: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[BrX1]
262
263 Acyliodide: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[IX1]
264
265 Acylhalide: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[FX1,ClX1,BrX1,IX1]
266 # all of the above
267
268
269 # The following contains all simple carboxylic combinations of O, N, S, & Hal -
270 # - acids, esters, amides, ... as well as a few extra cases (anhydride, hydrazide...)
271 # Cyclic structures (including aromats) like lactones, lactames, ... got their own
272 # definitions. Structures where both heteroatoms are part of an aromatic ring
273 # (oxazoles, imidazoles, ...) were excluded.
274
275 Carboxylic_acid: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[$([OX2H]),$([OX1-])]
276 # includes carboxylate anions
277
278 Carboxylic_ester: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[OX2][#6;!$(C=[O,N,S])]
279 # does not hit anhydrides or lactones
280
281 Lactone: [#6][#6X3R](=[OX1])[#8X2][#6;!$(C=[O,N,S])]
282 # may also be aromatic
283
284 Carboxylic_anhydride: [CX3;$([H0][#6]),$([H1])](=[OX1])[#8X2][CX3;$([H0][#6]),$([H1])](=[OX1])
285 # anhydride formed by two carboxylic acids, no mixed anhydrides (e.g. between carboxylic acid and sulfuric acid); may be part of a ring, even aromatic
286
287 Carboxylic_acid_derivative: [$([#6X3H0][#6]),$([#6X3H])](=[!#6])[!#6]
288 # includes most of the structures of I.4 and many more, also 1,3-heteroaromatics such as isoxazole
289
290 Carbothioic_acid: [CX3;!R;$([C][#6]),$([CH]);$([C](=[OX1])[$([SX2H]),$([SX1-])]),$([C](=[SX1])[$([OX2H]),$([OX1-])])]
291 # hits both tautomeric forms, as well as anions
292
293 Carbothioic_S_ester: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[SX2][#6;!$(C=[O,N,S])]
294
295 Carbothioic_S_lactone: [#6][#6X3R](=[OX1])[#16X2][#6;!$(C=[O,N,S])]
296 # may also be aromatic
297
298 Carbothioic_O_ester: [CX3;$([H0][#6]),$([H1])](=[SX1])[OX2][#6;!$(C=[O,N,S])]
299
300 Carbothioic_O_lactone: [#6][#6X3R](=[SX1])[#8X2][#6;!$(C=[O,N,S])]
301
302 Carbothioic_halide: [CX3;$([H0][#6]),$([H1])](=[SX1])[FX1,ClX1,BrX1,IX1]
303
304 Carbodithioic_acid: [CX3;!R;$([C][#6]),$([CH]);$([C](=[SX1])[SX2H])]
305
306 Carbodithioic_ester: [CX3;!R;$([C][#6]),$([CH]);$([C](=[SX1])[SX2][#6;!$(C=[O,N,S])])]
307
308 Carbodithiolactone: [#6][#6X3R](=[SX1])[#16X2][#6;!$(C=[O,N,S])]
309
310
311 Amide: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
312 # does not hit lactames
313
314 Primary_amide: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[NX3H2]
315
316 Secondary_amide: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3H1][#6;!$(C=[O,N,S])]
317
318 Tertiary_amide: [CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])]
319
320 Lactam: [#6R][#6X3R](=[OX1])[#7X3;$([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
321 # cyclic amides, may also be aromatic
322
323 Alkyl_imide: [#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H0]([#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])
324 # may be part of a ring, even aromatic. only C allowed at central N. May also be triacyl amide
325
326 N_hetero_imide: [#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H0]([!#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])
327 # everything else than H or C at central N
328
329 Imide_acidic: [#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H1][#6X3;$([H0][#6]),$([H1])](=[OX1])
330 # can be deprotonated
331
332 Thioamide: [$([CX3;!R][#6]),$([CX3H;!R])](=[SX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
333 # does not hit thiolactames
334
335 Thiolactam: [#6R][#6X3R](=[SX1])[#7X3;$([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
336 # cyclic thioamides, may also be aromatic
337
338
339 Oximester: [#6X3;$([H0][#6]),$([H1])](=[OX1])[#8X2][#7X2]=,:[#6X3;$([H0]([#6])[#6]),$([H1][#6]),$([H2])]
340 # may also be part of a ring / aromatic
341
342 Amidine: [NX3;!$(NC=[O,S])][CX3;$([CH]),$([C][#6])]=[NX2;!$(NC=[O,S])]
343 # only basic amidines, not as part of aromatic ring (e.g. imidazole)
344
345 Hydroxamic_acid: [CX3;$([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][$([OX2H]),$([OX1-])]
346
347 Hydroxamic_acid_ester: [CX3;$([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][OX2][#6;!$(C=[O,N,S])]
348 # does not hit anhydrides of carboxylic acids withs hydroxamic acids
349
350
351 Imidoacid: [CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]
352 # not cyclic
353
354 Imidoacid_cyclic: [#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]
355 # the enamide-form of lactames. may be aromatic like 2-hydroxypyridine
356
357 Imidoester: [CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]
358 # esters of the above structures. no anhydrides.
359
360 Imidolactone: [#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]
361 # no oxazoles and similar
362
363 Imidothioacid: [CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])]
364 # not cyclic
365
366 Imidothioacid_cyclic: [#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])]
367 # the enamide-form of thiolactames. may be aromatic like 2-thiopyridine
368
369 Imidothioester: [CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]
370 # thioesters of the above structures. no anhydrides.
371
372 Imidothiolactone: [#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]
373 # no thioxazoles and similar
374
375 Amidine: [#7X3v3;!$(N([#6X3]=[#7X2])C=[O,S])][CX3R0;$([H1]),$([H0][#6])]=[NX2v3;!$(N(=[#6X3][#7X3])C=[O,S])]
376 # only basic amidines, not substituted by carbonyl or thiocarbonyl, not as part of a ring
377
378 Imidolactam: [#6][#6X3R;$([H0](=[NX2;!$(N(=[#6X3][#7X3])C=[O,S])])[#7X3;!$(N([#6X3]=[#7X2])C=[O,S])]),$([H0](-[NX3;!$(N([#6X3]=[#7X2])C=[O,S])])=,:[#7X2;!$(N(=[#6X3][#7X3])C=[O,S])])]
379 # one of the two C~N bonds is part of a ring (may be aromatic), but not both - thus no imidazole
380
381 Imidoylhalide: [CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]
382 # not cyclic
383
384 Imidoylhalide_cyclic: [#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]
385 # may also be aromatic
386
387 # may be ring, aromatic, substituted with carbonyls, hetero, ...
388 # (everything else would get too complicated)
389
390 Amidrazone: [$([$([#6X3][#6]),$([#6X3H])](=[#7X2v3])[#7X3v3][#7X3v3]),$([$([#6X3][#6]),$([#6X3H])]([#7X3v3])=[#7X2v3][#7X3v3])]
391 # hits both tautomers. as above, it may be ring, aromatic, substituted with carbonyls, hetero, ...
392
393
394 Alpha_aminoacid: [NX3,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[OX2H,OX1-]
395 # N may be alkylated, but not part of an amide (as in peptides), ionic forms are included
396 # includes also non-natural aminoacids with double-bonded or two aliph./arom. substituents at alpha-C
397 # N may not be aromatic as in 1H-pyrrole-2-carboxylic acid
398
399 Alpha_hydroxyacid: [OX2H][C][CX3](=[OX1])[OX2H,OX1-]
400
401 Peptide_middle: [NX3;$([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]
402 # finds peptidic structures which are neither C- nor N-terminal. Both neighbours must be amino-acids/peptides
403
404 Peptide_C_term: [NX3;$([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[OX2H,OX1-]
405 # finds C-terminal amino acids
406
407 Peptide_N_term: [NX3,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]
408 # finds N-terminal amino acids. As above, N may be substituted, but not part of an amide-bond.
409
410
411 Carboxylic_orthoester: [#6][OX2][CX4;$(C[#6]),$([CH])]([OX2][#6])[OX2][#6]
412 # hits also anhydride like struktures (e. g. HC(OMe)2-OC=O residues)
413
414 Ketene: [CX3]=[CX2]=[OX1]
415
416 Ketenacetal: [#7X2,#8X3,#16X2;$(*[#6,#14])][#6X3]([#7X2,#8X3,#16X2;$(*[#6,#14])])=[#6X3]
417 # includes aminals, silylacetals, ketenesters, etc. C=C DB is not aromatic, everything else may be
418
419 Nitrile: [NX1]#[CX2]
420 # includes cyanhydrines
421
422 Isonitrile: [CX1-]#[NX2+]
423
424
425 Vinylogous_carbonyl_or_carboxyl_derivative: [#6X3](=[OX1])[#6X3]=,:[#6X3][#7,#8,#16,F,Cl,Br,I]
426 # may be part of a ring, even aromatic
427
428 Vinylogous_acid: [#6X3](=[OX1])[#6X3]=,:[#6X3][$([OX2H]),$([OX1-])]
429
430 Vinylogous_ester: [#6X3](=[OX1])[#6X3]=,:[#6X3][#6;!$(C=[O,N,S])]
431
432 Vinylogous_amide: [#6X3](=[OX1])[#6X3]=,:[#6X3][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
433
434 Vinylogous_halide: [#6X3](=[OX1])[#6X3]=,:[#6X3][FX1,ClX1,BrX1,IX1]
435
436
437
438 # I.5: Four Carbon-Hetero Bonds (Carbonic Acid and Derivatives)
439 # -----------------------------
440
441 Carbonic_acid_dieester: [#6;!$(C=[O,N,S])][#8X2][#6X3](=[OX1])[#8X2][#6;!$(C=[O,N,S])]
442 # may be part of a ring, even aromatic
443
444 Carbonic_acid_esterhalide: [#6;!$(C=[O,N,S])][OX2;!R][CX3](=[OX1])[OX2][FX1,ClX1,BrX1,IX1]
445
446 Carbonic_acid_monoester: [#6;!$(C=[O,N,S])][OX2;!R][CX3](=[OX1])[$([OX2H]),$([OX1-])]
447 # unstable
448
449 Carbonic_acid_derivatives: [!#6][#6X3](=[!#6])[!#6]
450
451
452 Thiocarbonic_acid_dieester: [#6;!$(C=[O,N,S])][#8X2][#6X3](=[SX1])[#8X2][#6;!$(C=[O,N,S])]
453 # may be part of a ring, even aromatic
454
455 Thiocarbonic_acid_esterhalide: [#6;!$(C=[O,N,S])][OX2;!R][CX3](=[SX1])[OX2][FX1,ClX1,BrX1,IX1]
456
457 Thiocarbonic_acid_monoester: [#6;!$(C=[O,N,S])][OX2;!R][CX3](=[SX1])[$([OX2H]),$([OX1-])]
458
459
460 Urea:[#7X3;!$([#7][!#6])][#6X3](=[OX1])[#7X3;!$([#7][!#6])]
461 # no check whether part of imide, biuret, etc. Aromatic structures are only hit if
462 # both N share no double bonds, like in the dioxo-form of uracil
463
464 Thiourea: [#7X3;!$([#7][!#6])][#6X3](=[SX1])[#7X3;!$([#7][!#6])]
465
466 Isourea: [#7X2;!$([#7][!#6])]=,:[#6X3]([#8X2&!$([#8][!#6]),OX1-])[#7X3;!$([#7][!#6])]
467 # O may be substituted. no check whether further amide-like bonds are present. Aromatic
468 # structures are only hit if single bonded N shares no additional double bond, like in
469 # the 1-hydroxy-3-oxo form of uracil
470
471 Isothiourea: [#7X2;!$([#7][!#6])]=,:[#6X3]([#16X2&!$([#16][!#6]),SX1-])[#7X3;!$([#7][!#6])]
472
473 Guanidine: [N;v3X3,v4X4+][CX3](=[N;v3X2,v4X3+])[N;v3X3,v4X4+]
474 # also hits guanidinium salts. v3 and v4 to avoid nitroamidines
475
476 Carbaminic_acid: [NX3]C(=[OX1])[O;X2H,X1-]
477 # quite unstable, unlikely to be found. Also hits salts
478
479 Urethan: [#7X3][#6](=[OX1])[#8X2][#6]
480 # also hits when part of a ring, no check whether the last C is part of carbonyl
481
482 Biuret: [#7X3][#6](=[OX1])[#7X3][#6](=[OX1])[#7X3]
483
484 Semicarbazide: [#7X3][#7X3][#6X3]([#7X3;!$([#7][#7])])=[OX1]
485
486 Carbazide: [#7X3][#7X3][#6X3]([#7X3][#7X3])=[OX1]
487
488 Semicarbazone: [#7X2](=[#6])[#7X3][#6X3]([#7X3;!$([#7][#7])])=[OX1]
489
490 Carbazone: [#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[OX1]
491
492 Thiosemicarbazide: [#7X3][#7X3][#6X3]([#7X3;!$([#7][#7])])=[SX1]
493
494 Thiocarbazide: [#7X3][#7X3][#6X3]([#7X3][#7X3])=[SX1]
495
496 Thiosemicarbazone: [#7X2](=[#6])[#7X3][#6X3]([#7X3;!$([#7][#7])])=[SX1]
497
498 Thiocarbazone: [#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[SX1]
499
500
501 Isocyanate: [NX2]=[CX2]=[OX1]
502
503 Cyanate: [OX2][CX2]#[NX1]
504
505 Isothiocyanate: [NX2]=[CX2]=[SX1]
506
507 Thiocyanate: [SX2][CX2]#[NX1]
508
509 Carbodiimide: [NX2]=[CX2]=[NX2]
510
511 Orthocarbonic_derivatives: [CX4H0]([O,S,#7])([O,S,#7])([O,S,#7])[O,S,#7,F,Cl,Br,I]
512 # halogen allowed just once, to avoid mapping to -OCF3 and similar groups (much more
513 # stable as for example C(OCH3)4)
514
515
516 # I.6 Aromatics
517 # -------------
518
519 # I know that this classification is not very logical, arylamines are found under I.2 ...
520
521 Phenol: [OX2H][c]
522
523 1,2-Diphenol: [OX2H][c][c][OX2H]
524
525 Arylchloride: [Cl][c]
526
527 Arylfluoride: [F][c]
528
529 Arylbromide: [Br][c]
530
531 Aryliodide: [I][c]
532
533 Arylthiol: [SX2H][c]
534
535 Iminoarene: [c]=[NX2;$([H1]),$([H0][#6;!$([C]=[N,S,O])])]
536 # N may be substituted with H or C, but not carbonyl or similar
537 # aromatic atom is always C, not S or P (these are not planar when substituted)
538
539 Oxoarene: [c]=[OX1]
540
541 Thioarene: [c]=[SX1]
542
543 Hetero_N_basic_H: [nX3H1+0]
544 # as in pyrole. uncharged to exclude pyridinium ions
545
546 Hetero_N_basic_no_H: [nX3H0+0]
547 # as in N-methylpyrole. uncharged to exclude pyridinium ions
548
549 Hetero_N_nonbasic: [nX2,nX3+]
550 # as in pyridine, pyridinium
551
552 Hetero_O: [o]
553
554 Hetero_S: [sX2]
555 # X2 because Daylight's depictmatch falsely describes C1=CS(=O)C=C1 as aromatic
556 # (is not planar because of lonepair at S)
557
558 Heteroaromatic: [a;!c]
559
560
561 # Part II: N, S, P, Si, B
562 # =======================
563
564
565 # II.1 Nitrogen
566 # -------------
567
568 Nitrite: [NX2](=[OX1])[O;$([X2]),$([X1-])]
569 # hits nitrous acid, its anion, esters, and other O-substituted derivatives
570
571 Thionitrite: [SX2][NX2]=[OX1]
572
573 Nitrate: [$([NX3](=[OX1])(=[OX1])[O;$([X2]),$([X1-])]),$([NX3+]([OX1-])(=[OX1])[O;$([X2]),$([X1-])])]
574 # hits nitric acid, its anion, esters, and other O-substituted derivatives
575
576 Nitro: [$([NX3](=O)=O),$([NX3+](=O)[O-])][!#8]
577 # hits nitro groups attached to C,N, ... but not nitrates
578
579 Nitroso: [NX2](=[OX1])[!#7;!#8]
580 # no nitrites, no nitrosamines
581
582 Azide: [NX1]~[NX2]~[NX2,NX1]
583 # hits both mesomeric forms, also anion
584
585 Acylazide: [CX3](=[OX1])[NX2]~[NX2]~[NX1]
586
587 Diazo: [$([#6]=[NX2+]=[NX1-]),$([#6-]-[NX2+]#[NX1])]
588
589 Diazonium: [#6][NX2+]#[NX1]
590
591 Nitrosamine: [#7;!$(N*=O)][NX2]=[OX1]
592
593 Nitrosamide: [NX2](=[OX1])N-*=O
594 # includes nitrososulfonamides
595
596 N-Oxide: [$([#7+][OX1-]),$([#7v5]=[OX1]);!$([#7](~[O])~[O]);!$([#7]=[#7])]
597 # Hits both forms. Won't hit azoxy, nitro, nitroso, or nitrate.
598
599
600 Hydrazine: [NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])]
601 # no hydrazides
602
603 Hydrazone: [NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX2]=[#6]
604
605 Hydroxylamine: [NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][OX2;$([H1]),$(O[#6;!$(C=[N,O,S])])]
606 # no discrimination between O-, N-, and O,N-substitution
607
608
609 # II.2 Sulfur
610 # -----------
611
612 Sulfon: [$([SX4](=[OX1])(=[OX1])([#6])[#6]),$([SX4+2]([OX1-])([OX1-])([#6])[#6])]
613 # can't be aromatic, thus S and not #16
614
615 Sulfoxide: [$([SX3](=[OX1])([#6])[#6]),$([SX3+]([OX1-])([#6])[#6])]
616
617 Sulfonium: [S+;!$([S]~[!#6]);!$([S]*~[#7,#8,#15,#16])]
618 # can't be aromatic, thus S and not #16
619
620 Sulfuric_acid: [SX4](=[OX1])(=[OX1])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]
621 # includes anions
622
623 Sulfuric_monoester: [SX4](=[OX1])(=[OX1])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]
624
625 Sulfuric_diester: [SX4](=[OX1])(=[OX1])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]
626
627 Sulfuric_monoamide: [SX4](=[OX1])(=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]
628
629 Sulfuric_diamide: [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])])]
630
631 Sulfuric_esteramide: [SX4](=[OX1])(=[OX1])([#7X3][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]
632
633 Sulfuric_derivative: [SX4D4](=[!#6])(=[!#6])([!#6])[!#6]
634 # everything else (would not be a "true" derivative of sulfuric acid, if one of the substituents were less electronegative
635 # than sulfur, but this should be very very rare, anyway)
636
637
638
639 #### sulfurous acid and derivatives missing!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
640
641
642
643
644 Sulfonic_acid: [SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[$([OX2H]),$([OX1-])]
645
646 Sulfonamide: [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])])]
647
648 Sulfonic_ester: [SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[OX2][#6;!$(C=[O,N,S])]
649
650 Sulfonic_halide: [SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[FX1,ClX1,BrX1,IX1]
651
652 Sulfonic_derivative: [SX4;$([H1]),$([H0][#6])](=[!#6])(=[!#6])[!#6]
653 # includes all of the above and many more
654 # for comparison: this is what "all sulfonic derivatives but not the ones above" would look like:
655 # [$([SX4;$([H1]),$([H0][#6])](=[!#6])(=[!#6;!O])[!#6]),$([SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[!$([FX1,ClX1,BrX1,IX1]);!$([#6]);!$([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])])])])]
656
657
658 Sulfinic_acid: [SX3;$([H1]),$([H0][#6])](=[OX1])[$([OX2H]),$([OX1-])]
659
660 Sulfinic_amide: [SX3;$([H1]),$([H0][#6])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
661
662 Sulfinic_ester: [SX3;$([H1]),$([H0][#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]
663
664 Sulfinic_halide: [SX3;$([H1]),$([H0][#6])](=[OX1])[FX1,ClX1,BrX1,IX1]
665
666 Sulfinic_derivative: [SX3;$([H1]),$([H0][#6])](=[!#6])[!#6]
667
668 Sulfenic_acid: [SX2;$([H1]),$([H0][#6])][$([OX2H]),$([OX1-])]
669
670 Sulfenic_amide: [SX2;$([H1]),$([H0][#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
671
672 Sulfenic_ester: [SX2;$([H1]),$([H0][#6])][OX2][#6;!$(C=[O,N,S])]
673
674 Sulfenic_halide: [SX2;$([H1]),$([H0][#6])][FX1,ClX1,BrX1,IX1]
675
676 Sulfenic_derivative: [SX2;$([H1]),$([H0][#6])][!#6]
677
678
679 # II.3 Phosphorous
680 # ----------------
681
682 Phosphine: [PX3;$([H3]),$([H2][#6]),$([H1]([#6])[#6]),$([H0]([#6])([#6])[#6])]
683 # similar to amine, but less restrictive: includes also amide- and aminal-analogues
684
685 Phosphine_oxide: [PX4;$([H3]=[OX1]),$([H2](=[OX1])[#6]),$([H1](=[OX1])([#6])[#6]),$([H0](=[OX1])([#6])([#6])[#6])]
686
687 Phosphonium: [P+;!$([P]~[!#6]);!$([P]*~[#7,#8,#15,#16])]
688 # similar to Ammonium
689
690 Phosphorylen: [PX4;$([H3]=[CX3]),$([H2](=[CX3])[#6]),$([H1](=[CX3])([#6])[#6]),$([H0](=[CX3])([#6])([#6])[#6])]
691
692
693 # conventions for the following acids and derivatives:
694 # acids find protonated and deprotonated acids
695 # esters do not find mixed anhydrides ( ...P-O-C(=O))
696 # derivatives: subtituents which go in place of the OH and =O are not H or C (may also be O,
697 # thus including acids and esters)
698
699 Phosphonic_acid: [PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]
700 # includes anions
701
702 Phosphonic_monoester: [PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]
703
704 Phosphonic_diester: [PX4;$([H1]),$([H0][#6])](=[OX1])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]
705
706 Phosphonic_monoamide: [PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
707
708 Phosphonic_diamide: [PX4;$([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;!$(C=[O,N,S])])]
709
710 Phosphonic_esteramide: [PX4;$([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])])]
711
712 Phosphonic_acid_derivative: [PX4;$([H1]),$([H0][#6])](=[!#6])([!#6])[!#6]
713 # all of the above and much more
714
715
716 Phosphoric_acid: [PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]
717 # includes anions
718
719 Phosphoric_monoester: [PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]
720
721 Phosphoric_diester: [PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]
722
723 Phosphoric_triester: [PX4D4](=[OX1])([OX2][#6;!$(C=[O,N,S])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]
724
725 Phosphoric_monoamide: [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])])]
726
727 Phosphoric_diamide: [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])])]
728
729 Phosphoric_triamide: [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])])]
730
731 Phosphoric_monoestermonoamide: [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;!$(C=[O,N,S])])]
732
733 Phosphoric_diestermonoamide: [PX4D4](=[OX1])([OX2][#6;!$(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;!$(C=[O,N,S])])]
734
735 Phosphoric_monoesterdiamide: [PX4D4](=[OX1])([OX2][#6;!$(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])])]
736
737 Phosphoric_acid_derivative: [PX4D4](=[!#6])([!#6])([!#6])[!#6]
738
739
740 Phosphinic_acid: [PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[$([OX2H]),$([OX1-])]
741
742 Phosphinic_ester: [PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]
743
744 Phosphinic_amide: [PX4;$([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])])]
745
746 Phosphinic_acid_derivative: [PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[!#6])[!#6]
747
748
749 Phosphonous_acid: [PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]
750
751 Phosphonous_monoester: [PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]
752
753 Phosphonous_diester: [PX3;$([H1]),$([H0][#6])]([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]
754
755 Phosphonous_monoamide: [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])])]
756
757 Phosphonous_diamide: [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])])]
758
759 Phosphonous_esteramide: [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;!$(C=[O,N,S])])]
760
761 Phosphonous_derivatives: [PX3;$([D2]),$([D3][#6])]([!#6])[!#6]
762
763
764 Phosphinous_acid: [PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][$([OX2H]),$([OX1-])]
765
766 Phosphinous_ester: [PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][OX2][#6;!$(C=[O,N,S])]
767
768 Phosphinous_amide: [PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]
769
770 Phosphinous_derivatives: [PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][!#6]
771
772
773 # II.4 Silicon
774 # ------------
775
776 Quart_silane: [SiX4]([#6])([#6])([#6])[#6]
777 # four C-substituents. non-reactive, non-toxic, in experimental phase for drug development
778
779 Non-quart_silane: [SiX4;$([H1]([#6])([#6])[#6]),$([H2]([#6])[#6]),$([H3][#6]),$([H4])]
780 # has 1-4 hydride(s), reactive. Daylight's depictmatch does not add hydrogens automatically to
781 # the free positions at Si, thus Hs had to be added implicitly
782
783 Silylmonohalide: [SiX4]([FX1,ClX1,BrX1,IX1])([#6])([#6])[#6]
784 # reagents for inserting protection groups
785
786 Het_trialkylsilane: [SiX4]([!#6])([#6])([#6])[#6]
787 # mostly acid-labile protection groups such as trimethylsilyl-ethers
788
789 Dihet_dialkylsilane: [SiX4]([!#6])([!#6])([#6])[#6]
790
791 Trihet_alkylsilane: [SiX4]([!#6])([!#6])([!#6])[#6]
792
793 Silicic_acid_derivative: [SiX4]([!#6])([!#6])([!#6])[!#6]
794 # four substituent which are neither C nor H
795
796
797 # II.5 Boron
798 # ----------
799
800 Trialkylborane: [BX3]([#6])([#6])[#6]
801 # also carbonyls allowed
802
803 Boric_acid_derivatives: [BX3]([!#6])([!#6])[!#6]
804 # includes acids, esters, amides, ... H-substituent at B is very rare.
805
806 Boronic_acid_derivative: [BX3]([!#6])([!#6])[!#6]
807 # # includes acids, esters, amides, ...
808
809 Borohydride: [BH1,BH2,BH3,BH4]
810 # at least one H attached to B
811
812 Quaternary_boron: [BX4]
813 # mostly borates (negative charge), in complex with Lewis-base
814
815
816
817 # Part III: Some Special Patterns
818 # ===============================
819
820
821 # III.1 Chains
822 # ------------
823
824 # some simple chains
825
826
827
828 # III.2 Rings
829 # -----------
830
831 Aromatic: a
832
833 Heterocyclic: [!#6;!R0]
834 # may be aromatic or not
835
836 Epoxide: [OX2r3]1[#6r3][#6r3]1
837 # toxic/reactive. may be annelated to aromat, but must not be aromatic itself (oxirane-2,3-dione)
838
839 NH_aziridine: [NX3H1r3]1[#6r3][#6r3]1
840 # toxic/reactive according to Maybridge's garbage filter
841
842 Spiro: [D4R;$(*(@*)(@*)(@*)@*)]
843 # at least two different rings can be found which are sharing just one atom.
844 # these two rings can be connected by a third ring, so it matches also some
845 # bridged systems, like morphine
846
847 Annelated_rings: [R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]
848 # two different rings sharing exactly two atoms
849
850 Bridged_rings: [R;$(*(@*)(@*)@*);!$([D4R;$(*(@*)(@*)(@*)@*)]);!$([R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])])]
851 # part of two or more rings, not spiro, not annelated -> finds bridgehead atoms,
852 # but only if they are not annelated at the same time - otherwise impossible (?)
853 # to distinguish from non-bridgehead annelated atoms
854
855 # some basic ring-patterns (just size, no other information):
856
857
858
859
860
861 # III.3 Sugars and Nucleosides/Nucleotides, Steroids
862 # --------------------------------------------------
863
864 # because of the large variety of sugar derivatives, different patterns can be applied.
865 # The choice of patterns and their combinations will depend on the contents of the database
866 # e.g. natural products, nucleoside analoges with modified sugars, ... as well as on the
867 # desired restriction
868
869
870 Sugar_pattern_1: [OX2;$([r5]1@C@C@C(O)@C1),$([r6]1@C@C@C(O)@C(O)@C1)]
871 # 5 or 6-membered ring containing one O and at least one (r5) or two (r6) oxygen-substituents.
872
873 Sugar_pattern_2: [OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]
874 # 5 or 6-membered ring containing one O and an acetal-like bond at postion 2.
875
876 Sugar_pattern_combi: [OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C(O)@C1)]
877 # combination of the two above
878
879 Sugar_pattern_2_reducing: [OX2;$([r5]1@C(!@[OX2H1])@C@C@C1),$([r6]1@C(!@[OX2H1])@C@C@C@C1)]
880 # 5 or 6-membered cyclic hemi-acetal
881
882 Sugar_pattern_2_alpha: [OX2;$([r5]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]
883 # 5 or 6-membered cyclic hemi-acetal
884
885 Sugar_pattern_2_beta: [OX2;$([r5]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]
886 # 5 or 6-membered cyclic hemi-acetal
887
888 ##Poly_sugar_1: ([OX2;$([r5]1@C@C@C(O)@C1),$([r6]1@C@C@C(O)@C(O)@C1)].[OX2;$([r5]1@C@C@C(O)@C1),$([r6]1@C@C@C(O)@C(O)@C1)])
889 # pattern1 occours more than once (in same molecule, but moieties don't have to be adjacent!)
890
891 ##Poly_sugar_2: ([OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)].[OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)])
892 # pattern2 occours more than once (in same molecule, but moieties don't have to be adjacent!)
893
894
895 # III.4 Everything else...
896 # ------------------------
897
898 Conjugated_double_bond: *=*[*]=,#,:[*]
899
900 Conjugated_tripple_bond: *#*[*]=,#,:[*]
901
902 Cis_double_bond: */[D2]=[D2]\*
903 # only one single-bonded substituent on each DB-atom. no aromats.
904 # only found when character of DB is explicitely stated.
905
906 Trans_double_bond: */[D2]=[D2]/*
907 # analog
908
909 Mixed_anhydrides: [$(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))][#8X2][$(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))]
910 # should hits all combinations of two acids
911
912 Halogen_on_hetero: [FX1,ClX1,BrX1,IX1][!#6]
913
914 Halogen_multi_subst: [F,Cl,Br,I;!$([X1]);!$([X0-])]
915 # Halogen which is not mono-substituted nor an anion, e.g. chlorate.
916 # Most of these cases should be also filtered by Halogen_on_hetero.
917
918 Trifluoromethyl: [FX1][CX4;!$([H0][Cl,Br,I]);!$([F][C]([F])([F])[F])]([FX1])([FX1])
919 # C with three F attached, connected to anything which is not another halogen
920
921 C_ONS_bond: [#6]~[#7,#8,#16]
922 # probably all drug-like molecules have at least one O, N, or S connected to a C -> nice filter
923
924 ## Mixture: (*).(*)
925 # two or more seperate parts, may also be salt
926 # component-level grouping is not yet supported in Open Babel Version 2.0
927
928
929 Charged: [!+0]
930
931 Anion: [-1,-2,-3,-4,-5,-6,-7]
932
933 Kation: [+1,+2,+3,+4,+5,+6,+7]
934
935 Salt: ([-1,-2,-3,-4,-5,-6,-7]).([+1,+2,+3,+4,+5,+6,+7])
936 # two or more seperate components with opposite charges
937
938 ##Zwitterion: ([-1,-2,-3,-4,-5,-6,-7].[+1,+2,+3,+4,+5,+6,+7])
939 # both negative and positive charges somewhere within the same molecule.
940
941 1,3-Tautomerizable: [$([#7X2,OX1,SX1]=*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=*),$([#7X3,OX2,SX2;!H0]*:n)]
942 # 1,3 migration of H allowed. Includes keto/enol and amide/enamide.
943 # Aromatic rings must stay aromatic - no keto form of phenol
944
945 1,5-Tautomerizable: [$([#7X2,OX1,SX1]=,:**=,:*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=**=*),$([#7X3,OX2,SX2;!H0]*=,:**:n)]
946
947 Rotatable_bond: [!$(*#*)&!D1]-!@[!$(*#*)&!D1]
948 # taken from http://www.daylight.com/support/contrib/smarts/content.html
949
950 Michael_acceptor: [CX3]=[CX3][$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-])]
951 # the classical case: C=C near carbonyl, nitrile, nitro, or similar
952 # Oxo-heteroaromats and similar are not included.
953
954 Dicarbodiazene: [CX3](=[OX1])[NX2]=[NX2][CX3](=[OX1])
955 # Michael-like acceptor, see Mitsunobu reaction
956
957 # H-Bond_donor:
958
959 # H-Bond_acceptor:
960
961 # Pos_ionizable:
962
963 # Neg_ionizable:
964
965 # Unlikely_ions:
966 # O+,N-,C+,C-, ...
967
968 CH-acidic: [$([CX4;!$([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)]
969 # C-H alpha to carbony, nitro or similar, C is not double-bonded, only C, H, S,P=O and nitro substituents allowed.
970 # pentadiene is included. acids, their salts, prim./sec. amides, and imides are excluded.
971 # hits also CH-acidic_strong
972
973 CH-acidic_strong: [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-])]
974 # same as above (without pentadiene), but carbonyl or similar on two or three sides
975
976 Chiral_center_specified: [$([*@](~*)(~*)(*)*),$([*@H](*)(*)*),$([*@](~*)(*)*),$([*@H](~*)~*)]
977 # Hits atoms with tetrahedral chirality, if chiral center is specified in the SMILES string
978 # depictmach does not find oxonium, sulfonium, or sulfoxides!
979
980 # Chiral_center_unspecified: [$([*@?](~*)(~*)(*)*),$([*@?H](*)(*)*),$([*@?](~*)(*)*),$([*@?H](~*)~*)]
981 # Hits atoms with tetrahedral chirality, if chiral center is not specified in the SMILES string
982 # "@?" (unspecified chirality) is not yet supported in Open Babel Version 2.0
983