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Diffstat (limited to 'data/functional-groups.yaml')
| -rw-r--r-- | data/functional-groups.yaml | 309 |
1 files changed, 309 insertions, 0 deletions
diff --git a/data/functional-groups.yaml b/data/functional-groups.yaml new file mode 100644 index 0000000..eb6e5f4 --- /dev/null +++ b/data/functional-groups.yaml @@ -0,0 +1,309 @@ +Primary_carbon': '[CX4H3][#6]' +Secondary_carbon': '[CX4H2]([#6])[#6]' +Tertiary_carbon': '[CX4H1]([#6])([#6])[#6]' +Quaternary_carbon': '[CX4]([#6])([#6])([#6])[#6]' +Alkene': '[CX3;'([H2]),$([H1][#6]),$(C([#6])[#6])]=[CX3;$([H2]),$([H1][#6]),$(C([#6])[#6])]' +Alkyne': '[CX2]#[CX2]' +Allene': '[CX3]=[CX2]=[CX3]' +Alkylchloride': '[ClX1][CX4]' +Alkylfluoride': '[FX1][CX4]' +Alkylbromide': '[BrX1][CX4]' +Alkyliodide': '[IX1][CX4]' +Alcohol': '[OX2H][CX4;!'(C([OX2H])[O,S,#7,#15])]' +Primary_alcohol': '[OX2H][CX4H2;!'(C([OX2H])[O,S,#7,#15])]' +Secondary_alcohol': '[OX2H][CX4H;!'(C([OX2H])[O,S,#7,#15])]' +Tertiary_alcohol': '[OX2H][CX4D4;!'(C([OX2H])[O,S,#7,#15])]' +Dialkylether': '[OX2]([CX4;!'(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]' +Dialkylthioether': '[SX2]([CX4;!'(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]' +Alkylarylether': '[OX2](c)[CX4;!'(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]' +Diarylether': '[c][OX2][c]' +Alkylarylthioether': '[SX2](c)[CX4;!'(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]' +Diarylthioether': '[c][SX2][c]' +Oxonium': '[O+;!'([O]~[!#6]);!$([S]*~[#7,#8,#15,#16])]' +Amine': '[NX3+0,NX4+;!'([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])]' +Primary_aliph_amine': '[NX3H2+0,NX4H3+;!'([N][!C]);!$([N]*~[#7,#8,#15,#16])]' +Secondary_aliph_amine': '[NX3H1+0,NX4H2+;!'([N][!C]);!$([N]*~[#7,#8,#15,#16])]' +Tertiary_aliph_amine': '[NX3H0+0,NX4H1+;!'([N][!C]);!$([N]*~[#7,#8,#15,#16])]' +Quaternary_aliph_ammonium': '[NX4H0+;!'([N][!C]);!$([N]*~[#7,#8,#15,#16])]' +Primary_arom_amine': '[NX3H2+0,NX4H3+]c' +Secondary_arom_amine': '[NX3H1+0,NX4H2+;!'([N][!c]);!$([N]*~[#7,#8,#15,#16])]' +Tertiary_arom_amine': '[NX3H0+0,NX4H1+;!'([N][!c]);!$([N]*~[#7,#8,#15,#16])]' +Quaternary_arom_ammonium': '[NX4H0+;!'([N][!c]);!$([N]*~[#7,#8,#15,#16])]' +Secondary_mixed_amine': '[NX3H1+0,NX4H2+;'([N]([c])[C]);!$([N]*~[#7,#8,#15,#16])]' +Tertiary_mixed_amine': '[NX3H0+0,NX4H1+;'([N]([c])([C])[#6]);!$([N]*~[#7,#8,#15,#16])]' +Quaternary_mixed_ammonium': '[NX4H0+;'([N]([c])([C])[#6][#6]);!$([N]*~[#7,#8,#15,#16])]' +Ammonium': '[N+;!'([N]~[!#6]);!$(N=*);!$([N]*~[#7,#8,#15,#16])]' +Alkylthiol': '[SX2H][CX4;!'(C([SX2H])~[O,S,#7,#15])]' +Dialkylthioether': '[SX2]([CX4;!'(C([SX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([SX2])[O,S,#7,#15])]' +Alkylarylthioether': '[SX2](c)[CX4;!'(C([SX2])[O,S,#7,#15])]' +Disulfide': '[SX2D2][SX2D2]' +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])]' +1,2-Diol': '[OX2H][CX4;!'(C([OX2H])[O,S,#7,#15])][CX4;!$(C([OX2H])[O,S,#7,#15])][OX2H]' +1,1-Diol': '[OX2H][CX4;!'(C([OX2H])([OX2H])[O,S,#7,#15])][OX2H]' +Hydroperoxide': '[OX2H][OX2]' +Peroxo': '[OX2D2][OX2D2]' +Organolithium_compounds': '[LiX1][#6,#14]' +Organomagnesium_compounds': '[MgX2][#6,#14]' +Organometallic_compounds': '[!#1;!#5;!#6;!#7;!#8;!#9;!#14;!#15;!#16;!#17;!#33;!#34;!#35;!#52;!#53;!#85]~[#6;!-]' +Aldehyde': '['([CX3H][#6]),$([CX3H2])]=[OX1]' +Ketone': '[#6][CX3](=[OX1])[#6]' +Thioaldehyde': '['([CX3H][#6]),$([CX3H2])]=[SX1]' +Thioketone': '[#6][CX3](=[SX1])[#6]' +Imine': '[NX2;'([N][#6]),$([NH]);!$([N][CX3]=[#7,#8,#15,#16])]=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])]' +Immonium': '[NX3+;!'([N][!#6]);!$([N][CX3]=[#7,#8,#15,#16])]' +Oxime': '[NX2](=[CX3;'([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2H]' +Oximether': '[NX2](=[CX3;'([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2][#6;!$(C=[#7,#8])]' +Acetal': '[OX2]([#6;!'(C=[O,S,N])])[CX4;!$(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]' +Hemiacetal': '[OX2H][CX4;!'(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]' +Aminal': '[NX3v3;!'(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][NX3v3;!$(NC=[#7,#8,#15,#16])][#6] ' +Hemiaminal': '[NX3v3;!'(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][OX2H]' +Thioacetal': '[SX2]([#6;!'(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][SX2][#6;!$(C=[O,S,N])]' +Thiohemiacetal': '[SX2]([#6;!'(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][OX2H]' +Halogen_acetal_like': '[NX3v3,SX2,OX2;!'(*C=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]' +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])]' +Halogenmethylen_ester_and_similar': '[NX3v3,SX2,OX2;'(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]' +NOS_methylen_ester_and_similar': '[NX3v3,SX2,OX2;'(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]' +Hetero_methylen_ester_and_similar': '[NX3v3,SX2,OX2;'(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1,NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]' +Cyanhydrine': '[NX1]#[CX2][CX4;'([CH2]),$([CH]([CX2])[#6]),$(C([CX2])([#6])[#6])][OX2H]' +Chloroalkene': '[ClX1][CX3]=[CX3]' +Fluoroalkene': '[FX1][CX3]=[CX3]' +Bromoalkene': '[BrX1][CX3]=[CX3]' +Iodoalkene': '[IX1][CX3]=[CX3]' +Enol': '[OX2H][CX3;'([H1]),$(C[#6])]=[CX3]' +Endiol': '[OX2H][CX3;'([H1]),$(C[#6])]=[CX3;$([H1]),$(C[#6])][OX2H]' +Enolether': '[OX2]([#6;!'(C=[N,O,S])])[CX3;$([H0][#6]),$([H1])]=[CX3]' +Enolester': '[OX2]([CX3]=[OX1])[#6X3;'([#6][#6]),$([H1])]=[#6X3;!$(C[OX2H])]' +Enamine': '[NX3;'([NH2][CX3]),$([NH1]([CX3])[#6]),$([N]([CX3])([#6])[#6]);!$([N]*=[#7,#8,#15,#16])][CX3;$([CH]),$([C][#6])]=[CX3]' +Thioenol': '[SX2H][CX3;'([H1]),$(C[#6])]=[CX3]' +Thioenolether': '[SX2]([#6;!'(C=[N,O,S])])[CX3;$(C[#6]),$([CH])]=[CX3]' +Acylchloride': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[ClX1] ' +Acylfluoride': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[FX1] ' +Acylbromide': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[BrX1] ' +Acyliodide': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[IX1]' +Acylhalide': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[FX1,ClX1,BrX1,IX1]' +Carboxylic_acid': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[$([OX2H]),$([OX1-])]' +Carboxylic_ester': ' [CX3;'([R0][#6]),$([H1R0])](=[OX1])[OX2][#6;!$(C=[O,N,S])]' +Lactone': '[#6][#6X3R](=[OX1])[#8X2][#6;!'(C=[O,N,S])]' +Carboxylic_anhydride': '[CX3;'([H0][#6]),$([H1])](=[OX1])[#8X2][CX3;$([H0][#6]),$([H1])](=[OX1])' +Carboxylic_acid_derivative': '['([#6X3H0][#6]),$([#6X3H])](=[!#6])[!#6]' +Carbothioic_acid': '[CX3;!R;'([C][#6]),$([CH]);$([C](=[OX1])[$([SX2H]),$([SX1-])]),$([C](=[SX1])[$([OX2H]),$([OX1-])])]' +Carbothioic_S_ester': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[SX2][#6;!$(C=[O,N,S])]' +Carbothioic_S_lactone': '[#6][#6X3R](=[OX1])[#16X2][#6;!'(C=[O,N,S])]' +Carbothioic_O_ester': '[CX3;'([H0][#6]),$([H1])](=[SX1])[OX2][#6;!$(C=[O,N,S])]' +Carbothioic_O_lactone': '[#6][#6X3R](=[SX1])[#8X2][#6;!'(C=[O,N,S])]' +Carbothioic_halide': '[CX3;'([H0][#6]),$([H1])](=[SX1])[FX1,ClX1,BrX1,IX1]' +Carbodithioic_acid': '[CX3;!R;'([C][#6]),$([CH]);$([C](=[SX1])[SX2H])]' +Carbodithioic_ester': '[CX3;!R;'([C][#6]),$([CH]);$([C](=[SX1])[SX2][#6;!$(C=[O,N,S])])]' +Carbodithiolactone': '[#6][#6X3R](=[SX1])[#16X2][#6;!'(C=[O,N,S])]' +Amide': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Primary_amide': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[NX3H2]' +Secondary_amide': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[#7X3H1][#6;!$(C=[O,N,S])]' +Tertiary_amide': '[CX3;'([R0][#6]),$([H1R0])](=[OX1])[#7X3H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])]' +Lactam': '[#6R][#6X3R](=[OX1])[#7X3;'([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Alkyl_imide': '[#6X3;'([H0][#6]),$([H1])](=[OX1])[#7X3H0]([#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])' +N_hetero_imide': '[#6X3;'([H0][#6]),$([H1])](=[OX1])[#7X3H0]([!#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])' +Imide_acidic': '[#6X3;'([H0][#6]),$([H1])](=[OX1])[#7X3H1][#6X3;$([H0][#6]),$([H1])](=[OX1])' +Thioamide': '['([CX3;!R][#6]),$([CX3H;!R])](=[SX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Thiolactam': '[#6R][#6X3R](=[SX1])[#7X3;'([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Oximester': '[#6X3;'([H0][#6]),$([H1])](=[OX1])[#8X2][#7X2]=,:[#6X3;$([H0]([#6])[#6]),$([H1][#6]),$([H2])]' +Amidine': '[NX3;!'(NC=[O,S])][CX3;$([CH]),$([C][#6])]=[NX2;!$(NC=[O,S])]' +Hydroxamic_acid': '[CX3;'([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][$([OX2H]),$([OX1-])]' +Hydroxamic_acid_ester': '[CX3;'([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][OX2][#6;!$(C=[O,N,S])]' +Imidoacid': '[CX3R0;'([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]' +Imidoacid_cyclic': '[#6R][#6X3R](=,:[#7X2;'([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])] ' +Imidoester': '[CX3R0;'([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]' +Imidolactone': '[#6R][#6X3R](=,:[#7X2;'([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]' +Imidothioacid': '[CX3R0;'([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])]' +Imidothioacid_cyclic': '[#6R][#6X3R](=,:[#7X2;'([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])] ' +Imidothioester': '[CX3R0;'([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]' +Imidothiolactone': '[#6R][#6X3R](=,:[#7X2;'([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]' +Amidine': '[#7X3v3;!'(N([#6X3]=[#7X2])C=[O,S])][CX3R0;$([H1]),$([H0][#6])]=[NX2v3;!$(N(=[#6X3][#7X3])C=[O,S])]' +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;!$(N(=[#6X3][#7X3])C=[O,S])])] ' +Imidoylhalide': '[CX3R0;'([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]' +Imidoylhalide_cyclic': '[#6R][#6X3R](=,:[#7X2;'([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]' + ' +Amidrazone': '['([$([#6X3][#6]),$([#6X3H])](=[#7X2v3])[#7X3v3][#7X3v3]),$([$([#6X3][#6]),$([#6X3H])]([#7X3v3])=[#7X2v3][#7X3v3])]' +Alpha_aminoacid': '[NX3,NX4+;!'([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[OX2H,OX1-]' +Alpha_hydroxyacid': '[OX2H][C][CX3](=[OX1])[OX2H,OX1-]' +Peptide_middle': '[NX3;'([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]' +Peptide_C_term': '[NX3;'([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[OX2H,OX1-]' +Peptide_N_term': '[NX3,NX4+;!'([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]' +Carboxylic_orthoester': '[#6][OX2][CX4;'(C[#6]),$([CH])]([OX2][#6])[OX2][#6] ' +Ketene': '[CX3]=[CX2]=[OX1]' +Ketenacetal': '[#7X2,#8X3,#16X2;'(*[#6,#14])][#6X3]([#7X2,#8X3,#16X2;$(*[#6,#14])])=[#6X3]' +Nitrile': '[NX1]#[CX2]' +Isonitrile': '[CX1-]#[NX2+]' +Vinylogous_carbonyl_or_carboxyl_derivative': '[#6X3](=[OX1])[#6X3]=,:[#6X3][#7,#8,#16,F,Cl,Br,I]' +Vinylogous_acid': '[#6X3](=[OX1])[#6X3]=,:[#6X3]['([OX2H]),$([OX1-])]' +Vinylogous_ester': '[#6X3](=[OX1])[#6X3]=,:[#6X3][#6;!'(C=[O,N,S])]' +Vinylogous_amide': '[#6X3](=[OX1])[#6X3]=,:[#6X3][#7X3;'([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Vinylogous_halide': '[#6X3](=[OX1])[#6X3]=,:[#6X3][FX1,ClX1,BrX1,IX1]' +Carbonic_acid_dieester': '[#6;!'(C=[O,N,S])][#8X2][#6X3](=[OX1])[#8X2][#6;!$(C=[O,N,S])]' +Carbonic_acid_esterhalide': '[#6;!'(C=[O,N,S])][OX2;!R][CX3](=[OX1])[OX2][FX1,ClX1,BrX1,IX1]' +Carbonic_acid_monoester': '[#6;!'(C=[O,N,S])][OX2;!R][CX3](=[OX1])[$([OX2H]),$([OX1-])]' +Carbonic_acid_derivatives': '[!#6][#6X3](=[!#6])[!#6]' +Thiocarbonic_acid_dieester': '[#6;!'(C=[O,N,S])][#8X2][#6X3](=[SX1])[#8X2][#6;!$(C=[O,N,S])]' +Thiocarbonic_acid_esterhalide': '[#6;!'(C=[O,N,S])][OX2;!R][CX3](=[SX1])[OX2][FX1,ClX1,BrX1,IX1]' +Thiocarbonic_acid_monoester': '[#6;!'(C=[O,N,S])][OX2;!R][CX3](=[SX1])[$([OX2H]),$([OX1-])]' +Urea:[#7X3;!'([#7][!#6])][#6X3](=[OX1])[#7X3;!$([#7][!#6])]' +Thiourea': '[#7X3;!'([#7][!#6])][#6X3](=[SX1])[#7X3;!$([#7][!#6])]' +Isourea': '[#7X2;!'([#7][!#6])]=,:[#6X3]([#8X2&!$([#8][!#6]),OX1-])[#7X3;!$([#7][!#6])]' +Isothiourea': '[#7X2;!'([#7][!#6])]=,:[#6X3]([#16X2&!$([#16][!#6]),SX1-])[#7X3;!$([#7][!#6])]' +Guanidine': '[N;v3X3,v4X4+][CX3](=[N;v3X2,v4X3+])[N;v3X3,v4X4+]' +Carbaminic_acid': '[NX3]C(=[OX1])[O;X2H,X1-]' +Urethan': '[#7X3][#6](=[OX1])[#8X2][#6]' +Biuret': '[#7X3][#6](=[OX1])[#7X3][#6](=[OX1])[#7X3]' +Semicarbazide': '[#7X3][#7X3][#6X3]([#7X3;!'([#7][#7])])=[OX1]' +Carbazide': '[#7X3][#7X3][#6X3]([#7X3][#7X3])=[OX1]' +Semicarbazone': '[#7X2](=[#6])[#7X3][#6X3]([#7X3;!'([#7][#7])])=[OX1]' +Carbazone': '[#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[OX1]' +Thiosemicarbazide': '[#7X3][#7X3][#6X3]([#7X3;!'([#7][#7])])=[SX1]' +Thiocarbazide': '[#7X3][#7X3][#6X3]([#7X3][#7X3])=[SX1]' +Thiosemicarbazone': '[#7X2](=[#6])[#7X3][#6X3]([#7X3;!'([#7][#7])])=[SX1]' +Thiocarbazone': '[#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[SX1]' +Isocyanate': '[NX2]=[CX2]=[OX1]' +Cyanate': '[OX2][CX2]#[NX1]' +Isothiocyanate': '[NX2]=[CX2]=[SX1]' +Thiocyanate': '[SX2][CX2]#[NX1]' +Carbodiimide': '[NX2]=[CX2]=[NX2]' +Orthocarbonic_derivatives': '[CX4H0]([O,S,#7])([O,S,#7])([O,S,#7])[O,S,#7,F,Cl,Br,I]' +Phenol': '[OX2H][c]' +1,2-Diphenol': '[OX2H][c][c][OX2H]' +Arylchloride': '[Cl][c]' +Arylfluoride': '[F][c]' +Arylbromide': '[Br][c]' +Aryliodide': '[I][c]' +Arylthiol': '[SX2H][c]' +Iminoarene': '[c]=[NX2;'([H1]),$([H0][#6;!$([C]=[N,S,O])])]' +Oxoarene': '[c]=[OX1]' +Thioarene': '[c]=[SX1]' +Hetero_N_basic_H': '[nX3H1+0]' +Hetero_N_basic_no_H': '[nX3H0+0]' +Hetero_N_nonbasic': '[nX2,nX3+]' +Hetero_O': '[o]' +Hetero_S': '[sX2]' +Heteroaromatic': '[a;!c]' +Nitrite': '[NX2](=[OX1])[O;'([X2]),$([X1-])]' +Thionitrite': '[SX2][NX2]=[OX1]' +Nitrate': '['([NX3](=[OX1])(=[OX1])[O;$([X2]),$([X1-])]),$([NX3+]([OX1-])(=[OX1])[O;$([X2]),$([X1-])])] ' +Nitro': '['([NX3](=O)=O),$([NX3+](=O)[O-])][!#8]' +Nitroso': '[NX2](=[OX1])[!#7;!#8]' +Azide': '[NX1]~[NX2]~[NX2,NX1]' +Acylazide': '[CX3](=[OX1])[NX2]~[NX2]~[NX1]' +Diazo': '['([#6]=[NX2+]=[NX1-]),$([#6-]-[NX2+]#[NX1])] ' +Diazonium': '[#6][NX2+]#[NX1]' +Nitrosamine': '[#7;!'(N*=O)][NX2]=[OX1]' +Nitrosamide': '[NX2](=[OX1])N-*=O' +N-Oxide': '['([#7+][OX1-]),$([#7v5]=[OX1]);!$([#7](~[O])~[O]);!$([#7]=[#7])] ' +Hydrazine': '[NX3;'([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])]' +Hydrazone': '[NX3;'([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX2]=[#6]' +Hydroxylamine': '[NX3;'([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][OX2;$([H1]),$(O[#6;!$(C=[N,O,S])])]' +Sulfon': '['([SX4](=[OX1])(=[OX1])([#6])[#6]),$([SX4+2]([OX1-])([OX1-])([#6])[#6])]' +Sulfoxide': '['([SX3](=[OX1])([#6])[#6]),$([SX3+]([OX1-])([#6])[#6])]' +Sulfonium': '[S+;!'([S]~[!#6]);!$([S]*~[#7,#8,#15,#16])]' +Sulfuric_acid': '[SX4](=[OX1])(=[OX1])(['([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]' +Sulfuric_monoester': '[SX4](=[OX1])(=[OX1])(['([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]' +Sulfuric_diester': '[SX4](=[OX1])(=[OX1])([OX2][#6;!'(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]' +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]),$([OX1-])]' +Sulfuric_diamide': '[SX4](=[OX1])(=[OX1])([#7X3;'([H2]),$([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])])]' +Sulfuric_esteramide': '[SX4](=[OX1])(=[OX1])([#7X3][#6;!'(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]' +Sulfuric_derivative': '[SX4D4](=[!#6])(=[!#6])([!#6])[!#6]' +Sulfonic_acid': '[SX4;'([H1]),$([H0][#6])](=[OX1])(=[OX1])[$([OX2H]),$([OX1-])]' +Sulfonamide': '[SX4;'([H1]),$([H0][#6])](=[OX1])(=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Sulfonic_ester': '[SX4;'([H1]),$([H0][#6])](=[OX1])(=[OX1])[OX2][#6;!$(C=[O,N,S])]' +Sulfonic_halide': '[SX4;'([H1]),$([H0][#6])](=[OX1])(=[OX1])[FX1,ClX1,BrX1,IX1]' +Sulfonic_derivative': '[SX4;'([H1]),$([H0][#6])](=[!#6])(=[!#6])[!#6]' +Sulfinic_acid': '[SX3;'([H1]),$([H0][#6])](=[OX1])[$([OX2H]),$([OX1-])]' +Sulfinic_amide': '[SX3;'([H1]),$([H0][#6])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Sulfinic_ester': '[SX3;'([H1]),$([H0][#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]' +Sulfinic_halide': '[SX3;'([H1]),$([H0][#6])](=[OX1])[FX1,ClX1,BrX1,IX1]' +Sulfinic_derivative': '[SX3;'([H1]),$([H0][#6])](=[!#6])[!#6]' +Sulfenic_acid': '[SX2;'([H1]),$([H0][#6])][$([OX2H]),$([OX1-])]' +Sulfenic_amide': '[SX2;'([H1]),$([H0][#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Sulfenic_ester': '[SX2;'([H1]),$([H0][#6])][OX2][#6;!$(C=[O,N,S])]' +Sulfenic_halide': '[SX2;'([H1]),$([H0][#6])][FX1,ClX1,BrX1,IX1]' +Sulfenic_derivative': '[SX2;'([H1]),$([H0][#6])][!#6]' +Phosphine': '[PX3;'([H3]),$([H2][#6]),$([H1]([#6])[#6]),$([H0]([#6])([#6])[#6])]' +Phosphine_oxide': '[PX4;'([H3]=[OX1]),$([H2](=[OX1])[#6]),$([H1](=[OX1])([#6])[#6]),$([H0](=[OX1])([#6])([#6])[#6])]' +Phosphonium': '[P+;!'([P]~[!#6]);!$([P]*~[#7,#8,#15,#16])]' +Phosphorylen': '[PX4;'([H3]=[CX3]),$([H2](=[CX3])[#6]),$([H1](=[CX3])([#6])[#6]),$([H0](=[CX3])([#6])([#6])[#6])]' +Phosphonic_acid': '[PX4;'([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]' +Phosphonic_monoester': '[PX4;'([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]' +Phosphonic_diester': '[PX4;'([H1]),$([H0][#6])](=[OX1])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]' +Phosphonic_monoamide': '[PX4;'([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +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;!$(C=[O,N,S])])]' +Phosphonic_esteramide': '[PX4;'([H1]),$([H0][#6])](=[OX1])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Phosphonic_acid_derivative': '[PX4;'([H1]),$([H0][#6])](=[!#6])([!#6])[!#6]' +Phosphoric_acid': '[PX4D4](=[OX1])(['([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]' +Phosphoric_monoester': '[PX4D4](=[OX1])(['([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]' +Phosphoric_diester': '[PX4D4](=[OX1])(['([OX2H]),$([OX1-])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]' +Phosphoric_triester': '[PX4D4](=[OX1])([OX2][#6;!'(C=[O,N,S])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]' +Phosphoric_monoamide': '[PX4D4](=[OX1])(['([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Phosphoric_diamide': '[PX4D4](=[OX1])(['([OX2H]),$([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])])]' +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;!$(C=[O,N,S])])]' +Phosphoric_monoestermonoamide': '[PX4D4](=[OX1])(['([OX2H]),$([OX1-])])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Phosphoric_diestermonoamide': '[PX4D4](=[OX1])([OX2][#6;!'(C=[O,N,S])])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +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])])]' +Phosphoric_acid_derivative': '[PX4D4](=[!#6])([!#6])([!#6])[!#6]' +Phosphinic_acid': '[PX4;'([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[$([OX2H]),$([OX1-])]' +Phosphinic_ester': '[PX4;'([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]' +Phosphinic_amide': '[PX4;'([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Phosphinic_acid_derivative': '[PX4;'([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[!#6])[!#6]' +Phosphonous_acid': '[PX3;'([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]' +Phosphonous_monoester': '[PX3;'([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]' +Phosphonous_diester': '[PX3;'([H1]),$([H0][#6])]([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]' +Phosphonous_monoamide': '[PX3;'([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +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;!$(C=[O,N,S])])]' +Phosphonous_esteramide': '[PX3;'([H1]),$([H0][#6])]([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Phosphonous_derivatives': '[PX3;'([D2]),$([D3][#6])]([!#6])[!#6]' +Phosphinous_acid': '[PX3;'([H2]),$([H1][#6]),$([H0]([#6])[#6])][$([OX2H]),$([OX1-])]' +Phosphinous_ester': '[PX3;'([H2]),$([H1][#6]),$([H0]([#6])[#6])][OX2][#6;!$(C=[O,N,S])]' +Phosphinous_amide': '[PX3;'([H2]),$([H1][#6]),$([H0]([#6])[#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]' +Phosphinous_derivatives': '[PX3;'([H2]),$([H1][#6]),$([H0]([#6])[#6])][!#6]' +Quart_silane': '[SiX4]([#6])([#6])([#6])[#6]' +Non-quart_silane': '[SiX4;'([H1]([#6])([#6])[#6]),$([H2]([#6])[#6]),$([H3][#6]),$([H4])]' +Silylmonohalide': '[SiX4]([FX1,ClX1,BrX1,IX1])([#6])([#6])[#6]' +Het_trialkylsilane': '[SiX4]([!#6])([#6])([#6])[#6]' +Dihet_dialkylsilane': '[SiX4]([!#6])([!#6])([#6])[#6]' +Trihet_alkylsilane': '[SiX4]([!#6])([!#6])([!#6])[#6]' +Silicic_acid_derivative': '[SiX4]([!#6])([!#6])([!#6])[!#6]' +Trialkylborane': '[BX3]([#6])([#6])[#6] ' +Boric_acid_derivatives': '[BX3]([!#6])([!#6])[!#6]' +Boronic_acid_derivative': '[BX3]([!#6])([!#6])[!#6]' +Borohydride': '[BH1,BH2,BH3,BH4]' +Quaternary_boron': '[BX4]' +Aromatic': 'a' +Heterocyclic': '[!#6;!R0]' +Epoxide': '[OX2r3]1[#6r3][#6r3]1' +NH_aziridine': '[NX3H1r3]1[#6r3][#6r3]1' +Spiro': '[D4R;'(*(@*)(@*)(@*)@*)]' +Annelated_rings': '[R;'(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]' +Bridged_rings': '[R;'(*(@*)(@*)@*);!$([D4R;$(*(@*)(@*)(@*)@*)]);!$([R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])])]' +Sugar_pattern_1': '[OX2;'([r5]1@C@C@C(O)@C1),$([r6]1@C@C@C(O)@C(O)@C1)]' +Sugar_pattern_2': '[OX2;'([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]' +Sugar_pattern_combi': '[OX2;'([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C(O)@C1)]' +Sugar_pattern_2_reducing': '[OX2;'([r5]1@C(!@[OX2H1])@C@C@C1),$([r6]1@C(!@[OX2H1])@C@C@C@C1)]' +Sugar_pattern_2_alpha': '[OX2;'([r5]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]' +Sugar_pattern_2_beta': '[OX2;'([r5]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]' +Conjugated_double_bond': '*=*[*]=,#,:[*]' +Conjugated_tripple_bond': '*#*[*]=,#,:[*]' +Cis_double_bond': '*/[D2]=[D2]\*' +Trans_double_bond': '*/[D2]=[D2]/*' +Mixed_anhydrides': '['(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))][#8X2][$(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))]' +Halogen_on_hetero': '[FX1,ClX1,BrX1,IX1][!#6]' +Halogen_multi_subst': '[F,Cl,Br,I;!'([X1]);!$([X0-])]' +Trifluoromethyl': '[FX1][CX4;!'([H0][Cl,Br,I]);!$([F][C]([F])([F])[F])]([FX1])([FX1])' +C_ONS_bond': '[#6]~[#7,#8,#16]' +Charged': '[!+0]' +Anion': '[-1,-2,-3,-4,-5,-6,-7]' +Kation': '[+1,+2,+3,+4,+5,+6,+7]' +Salt': '([-1,-2,-3,-4,-5,-6,-7]).([+1,+2,+3,+4,+5,+6,+7])' +1,3-Tautomerizable': '['([#7X2,OX1,SX1]=*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=*),$([#7X3,OX2,SX2;!H0]*:n)]' +1,5-Tautomerizable': '['([#7X2,OX1,SX1]=,:**=,:*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=**=*),$([#7X3,OX2,SX2;!H0]*=,:**:n)]' +Rotatable_bond': '[!'(*#*)&!D1]-!@[!$(*#*)&!D1]' +Michael_acceptor': '[CX3]=[CX3]['([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-])]' +Dicarbodiazene': '[CX3](=[OX1])[NX2]=[NX2][CX3](=[OX1])' +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;!$([H0])]1[CX3]=[CX3][CX3]=[CX3]1)]' +CH-acidic_strong': '[CX4;!'([H0]);!$(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-])]' +Chiral_center_specified': '['([*@](~*)(~*)(*)*),$([*@H](*)(*)*),$([*@](~*)(*)*),$([*@H](~*)~*)]' + ' |