/usr/share/openbabel/2.3.0/MACCS.txt is in libopenbabel4 2.3.0+dfsg-3ubuntu3.
This file is owned by root:root, with mode 0o644.
The actual contents of the file can be viewed below.
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 | #Comments after SMARTS
# Extracted from RDKit Jul 2008 release (r747) Python/Chem/MACCSKeys.py
#
# Copyright (C) 2001-2006 greg Landrum and Rational Discovery LLC
#
# @@ All Rights Reserved @@
#
#Redistribution and use in source and binary forms, with or without
#modification, are permitted provided that the following conditions are
#met:
#
# * Redistributions of source code must retain the above copyright
# notice, this list of conditions and the following disclaimer.
# * Redistributions in binary form must reproduce the above
# copyright notice, this list of conditions and the following
# disclaimer in the documentation and/or other materials provided
# with the distribution.
# * Neither the name of Rational Discovery nor the names of its
# contributors may be used to endorse or promote products derived
# from this software without specific prior written permission.
#
#THIS SOFTWARE IS PROVIDED BY THE COPYRIGHT HOLDERS AND CONTRIBUTORS
#"AS IS" AND ANY EXPRESS OR IMPLIED WARRANTIES, INCLUDING, BUT NOT
#LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR
#A PARTICULAR PURPOSE ARE DISCLAIMED. IN NO EVENT SHALL THE COPYRIGHT
#OWNER OR CONTRIBUTORS BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL,
#SPECIAL, EXEMPLARY, OR CONSEQUENTIAL DAMAGES (INCLUDING, BUT NOT
#LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES; LOSS OF USE,
#DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER CAUSED AND ON ANY
#THEORY OF LIABILITY, WHETHER IN CONTRACT, STRICT LIABILITY, OR TORT
#(INCLUDING NEGLIGENCE OR OTHERWISE) ARISING IN ANY WAY OUT OF THE USE
#OF THIS SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
# these are SMARTS patterns corresponding to the MDL MACCS keys
1:('?',0), # ISOTOPE
#2:('[#103,#104,#105,#106,#107,#106,#109,#110,#111,#112]',0), # ISOTOPE Not complete
2:('[#103,#104]',0), # ISOTOPE Not complete
3:('[Ge,As,Se,Sn,Sb,Te,Tl,Pb,Bi]',0), # Group IVa,Va,VIa Periods 4-6 (Ge...) *NOTE* spec wrong
4:('[Ac,Th,Pa,U,Np,Pu,Am,Cm,Bk,Cf,Es,Fm,Md,No,Lr]',0), # actinide
5:('[Sc,Ti,Y,Zr,Hf]',0), # Group IIIB,IVB (Sc...) *NOTE* spec wrong
6:('[La,Ce,Pr,Nd,Pm,Sm,Eu,Gd,Tb,Dy,Ho,Er,Tm,Yb,Lu]',0), # Lanthanide
7:('[V,Cr,Mn,Nb,Mo,Tc,Ta,W,Re]',0), # Group VB,VIB,VIIB (V...) *NOTE* spec wrong
8:('[!C;!c;!#1]1~*~*~*~*1',0), # QAAA@1
9:('[Fe,Co,Ni,Ru,Rh,Pd,Os,Ir,Pt]',0), # Group VIII (Fe...)
10:('[Be,Mg,Ca,Sr,Ba,Ra]',0), # Group IIa (Alkaline earth)
11:('*1~*~*~*~*1',0), # 4M Ring *NOTE* Was '*1~*~*~*~1' This and 9 others changed by CM because OB didn't like it
12:('[Cu,Zn,Ag,Cd,Au,Hg]',0), # Group IB,IIB (Cu..)
13:('[O,o]~[N,n](~[C,c])~[C,c]',0), # ON(C)C
14:('[S,s]-[S,s]',0), # S-S
15:('[O,o]~[C,c](~[O,o])~[O,o]',0), # OC(O)O
16:('[!C;!c;!#1]1~*~*~*1',0), # QAA@1
17:('[C,c]#[C,c]',0), #CTC
18:('[B,Al,Ga,In,Tl]',0), # Group IIIA (B...) *NOTE* spec wrong
19:('*1~*~*~*~*~*~*~*1',0), # 7M Ring
20:('[Si]',0), #Si
21:('[C,c]=[C,c](~[!C;!c;!#1])~[!C;!c;!#1]',0), # C=C(Q)Q
22:('*1~*~*~*1',0), # 3M Ring
23:('[N,n]~[C,c](~[O,o])~[O,o]',0), # NC(O)O
24:('[N,n]-[O,o]',0), # N-O
25:('[N,n]~[C,c](~[N,n])~[N,n]',0), # NC(N)N
26:('[C,c]=;@[C,c](@*)@*',0), # C$=C($A)$A
27:('[I]',0), # I
28:('[!C;!c;!#1]~[CH2]~[!C;!c;!#1]',0), # QCH2Q
29:('P',0),# P
30:('[C,c]~[!C;!c;!#1](~[C,c])(~[C,c])~*',0), # CQ(C)(C)A
31:('[!C;!c;!#1]~[F,Cl,Br,I]',0), # QX
32:('[C,c]~[S,s]~[N,n]',0), # CSN
33:('[N,n]~[S,s]',0), # NS
34:('[CH2]=*',0), # CH2=A
35:('[Li,Na,K,Rb,Cs,Fr]',0), # Group IA (Alkali Metal)
36:('[$(S@*),$(s@*)]',0), # S Heterocycle
37:('[N,n]~[C,c](~[O,o])~[N,n]',0), # NC(O)N
38:('[N,n]~[C,c](~[C,c])~[N,n]',0), # NC(C)N
39:('[O,o]~[S,s](~[O,o])~[O,o]',0), # OS(O)O
40:('[S,s]-[O,o]',0), # S-O
41:('[C,c]#[N,n]',0), # CTN
42:('F',0), # F
43:('[!C;!c;!#1;H,H2,H3,H4]~*~[!C;!c;!#1;H,H2,H3,H4]',0), # QHAQH FIX: possibly incomplete
44:('?',0), # OTHER
45:('[C,c]=[C,c]~[N,n]',0), # C=CN
46:('Br',0), # BR
47:('[S,s]~*~[N,n]',0), # SAN
48:('[O,o]~[!C;!c;!#1](~[O,o])(~[O,o])~*',0), # OQ(O)O
49:('[-,-2,-3,-4,+,+2,+3,+4]',0), # CHARGE FIX: possibly incomplete
50:('[C,c]=[C,c](~[C,c])~[C,c]',0), # C=C(C)C
51:('[C,c]~[S,s]~[O,o]',0), # CSO
52:('[N,n]~[N,n]',0), # NN
53:('[!#6;!#1;!H0]~*~*~*~[!#6;!#1;!H0]',0), # QHAAAQH FIX: possibly incomplete
54:('[!#6;!#1;!H0]~*~*~[!#6;!#1;!H0]',0), # QHAAQH FIX: possibly incomplete
55:('[O,o]~[S,s]~[O,o]',0), #OSO
56:('[O,o]~[N,n](~[O,o])~[C,c]',0), # ON(O)C
57:('[$(O@*),$(o@*)]',0), # O Heterocycle
58:('[!C;!c;!#1]~[S,s]~[!C;!c;!#1]',0), # QSQ
59:('[S,s]!:*:*',0), # Snot%A%A
60:('[S,s]=[O,o]',0), # S=O
61:('*~[S,s](~*)~*',0), # AS(A)A
62:('*@*!@*@*',0), # A$!A$A
63:('[N,n]=[O,o]',0), # N=O
64:('*@*!@[S,s]',0), # A$A!S
65:('[C,c]:[N,n]',0), # C%N
66:('[C,c]~[C,c](~[C,c])(~[C,c])~*',0), # CC(C)(C)A
67:('[!C;!c;!#1]~[S,s]',0), # QS
68:('[!#6;!#1;!H0]~[!#6;!#1;!H0]',0), # QHQH FIX: possibly incomplete
69:('[!C;!c;!#1]~[!#6;!#1;!H0]',0), # QQH FIX: possibly incomplete
70:('[!C;!c;!#1]~[N,n]~[!C;!c;!#1]',0), # QNQ
71:('[N,n]~[O,o]',0), # NO
72:('[O,o]~*~*~[O,o]',0), # OAAO
73:('[S,s]=*',0), # S=A
74:('[CH3]~*~[CH3]',0), # CH3ACH3
75:('*!@[N,n]@*',0), # A!N$A
76:('[C,c]=[C,c](~*)~*',0), # C=C(A)A
77:('[N,n]~*~[N,n]',0), # NAN
78:('[C,c]=[N,n]',0), # C=N
79:('[N,n]~*~*~[N,n]',0), # NAAN
80:('[N,n]~*~*~*~[N,n]',0), # NAAAN
81:('[S,s]~*(~*)~*',0), # SA(A)A
82:('*~[CH2]~[!#6;!#1;!H0]',0), # ACH2QH
83:('[!C;!c;!#1]1~*~*~*~*~*1',0), # QAAAA@1
84:('[NH2]',0), #NH2
85:('[C,c]~[N,n](~[C,c])~[C,c]',0), # CN(C)C
86:('[CH2][!C;!c;!#1][CH2]',0), # CH2QCH2
87:('[F,Cl,Br,I]!@*@*',0), # X!A$A
88:('[S,s]',0), # S
89:('[O,o]~*~*~*~[O,o]',0), # OAAAO
90:('[!#6;!#1;!H0]~*~*~[CH2]~*',0), # QHAACH2A
91:('[!#6;!#1;!H0]~*~*~*~[CH2]~*',0), # QHAAACH2A
92:('[O,o]~[C,c](~[N,n])~[C,c]',0), # OC(N)C
93:('[!C;!c;!#1]~[CH3]',0), # QCH3
94:('[!C;!c;!#1]~[N,n]',0), # QN
95:('[N,n]~*~*~[O,o]',0), # NAAO
96:('*1~*~*~*~*~*1',0), # 5 M ring
97:('[N,n]~*~*~*~[O,o]',0), # NAAAO
98:('[!C;!c;!#1]1~*~*~*~*~*~*1',0), # QAAAAA@1
99:('[C,c]=[C,c]',0), # C=C
100:('*~[CH2]~[N,n]',0), # ACH2N
101:('[r8,r9,r10,r11,r12]',0), # 8M Ring or larger FIX: This is not exhaustive and it appears that oelib doesn't do this right
102:('[!C;!c;!#1]~[O,o]',0), # QO
103:('Cl',0), # CL
104:('[!#6;!#1;!H0]~*~[CH2]~*',0), # QHACH2A
105:('[!C;!c;!#1]@*(@*)@*',0), # A$A($A)$A
106:('[!C;!c;!#1]~*(~[!C;!c;!#1])~[!C;!c;!#1]',0), # QA(Q)Q
107:('[F,Cl,Br,I]~*(~*)~*',0), # XA(A)A
108:('[CH3]~*~*~*~[CH2]~*',0), # CH3AAACH2A
109:('*~[CH2]~[O,o]',0), # ACH2O
110:('[N,n]~[C,c]~[O,o]',0), # NCO
111:('[N,n]~*~[CH2]~*',0), # NACH2A
112:('*~*(~*)(~*)~*',0), # AA(A)(A)A
113:('[O,o]!:*:*',0), # Onot%A%A
114:('[CH3]~[CH2]~*',0), # CH3CH2A
115:('[CH3]~*~[CH2]~*',0), # CH3ACH2A
116:('[CH3]~*~*~[CH2]~*',0), # CH3AACH2A
117:('[N,n]~*~[O,o]',0), # NAO
118:('*~[CH2]~[CH2]~*',1), # ACH2CH2A > 1
119:('[N,n]=*',0), # N=A
120:('[!C;!c;R]',1), # Heterocyclic atom > 1
121:('[$(N@*),$(n@*)]',0), # N Heterocycle
122:('*~[N,n](~*)~*',0), # AN(A)A
123:('[O,o]~[C,c]~[O,o]',0), # OCO
124:('[!C;!c;!#1]~[!C;!c;!#1]',0), # QQ
125:('?',0), # Aromatic Ring > 1
126:('*!@[O,o]!@*',0), # A!O!A
127:('*@*!@[O,o]',1), # A$A!O > 1
128:('*~[CH2]~*~*~*~[CH2]~*',0), # ACH2AAACH2A
129:('*~[CH2]~*~*~[CH2]~*',0), # ACH2AACH2A
130:('[!C;!c;!#1]~[!C;!c;!#1]',1), # QQ > 1 (&...)
131:('[!#6;!#1;!H0]',1), # QH > 1
132:('[O,o]~*~[CH2]~*',0), # OACH2A
133:('*@*!:[N,n]',0), # A$A!N
134:('[F,Cl,Br,I]',0), # X (HALOGEN)
135:('[N,n]!:*:*',0), # Nnot%A%A
136:('[O,o]=*',1), # O=A>1 FIX: maybe not right key
137:('[!C;!c;R]',0), # Heterocycle
138:('[!C;!c;!#1]~[CH2]~*',1), # QCH2A>1 (&...)
139:('[OH,OH2,OH3]',0), # OH
140:('[O,o]',3), # O > 3
141:('[CH3]',2), # CH3 > 2
142:('[N,n]',1), # N > 1
143:('*@*!@[O,o]',0), # A$A!O
144:('*!:*:*!:*',0), # Anot%A%Anot%A
145:('*1~*~*~*~*~*~*1',1), # 6M ring > 1
146:('[O,o]',2), # O > 2
147:('*~[CH2]~[CH2]~*',0), # ACH2CH2A
148:('*~[!C;!c;!#1](~*)~*',0), # AQ(A)A
149:('[CH3]',1), # CH3 > 1
150:('*!@*@*!@*',0), # A!A$A!A
151:('[N!H0]',0), # NH
152:('[O,o]~[C,c](~[C,c])~[C,c]',0), # OC(C)C
153:('[!C;!c;!#1]~[CH2]~*',0), # QCH2A
154:('[C,c]=[O,o]',0), # C=O
155:('*!@[CH2]!@*',0), # A!CH2!A
156:('[N,n]~*(~*)~*',0), # NA(A)A
157:('[C,c]-[O,o]',0), # C-O
158:('[C,c]-[N,n]',0), # C-N
159:('[O,o]',1), # O>1
160:('[CH3]',0), #CH3
161:('[N,n]',0), # N
162:('a',0), # Aromatic
163:('*1~*~*~*~*~*~*1',0), # 6M Ring
164:('[O,o]',0), # O
165:('[R]',0), # Ring
166:('?',0), # Fragments FIX: this should be (*).(*), but that doesn't work properly in oelib
# Output with SMILES "CNO"
#> 24: N-O 68: QHQH 69: QQH 71: NO 93: QCH3 94: QN 102: QO
#124: QQ 131: QH > 1*2 139: OH 151: NH 158: C-N 160: CH3 161: N 164: O
|