##representation name query iupac_import_enabled [*]OC([*])O[*] |$_R0;;;_R0;;_R0$| acetal [OX2:2][CX4;!$(CO~[!#6]):1][OX2:3] *C([*])=O |$X_p;;_R0;$| acid halide [CX3:1](=[OX1:2])[F,Cl,Br,I:3] OC[*] |$;;_R0$| alcohol [C:1][OH;!$(OC~[!#1!#6]):2] [H]C([*])=O |$;;_R0;$| aldehyde [CX3H1,H2:1]=[OX1;!$(O=C~[!#1!#6]):2] [H]\C([*])=N/O |$;;_R0;;$| aldoxime [CH1:1]=[N:2][OH1:3] [*][H] |$_R0;$| aliphatic [A:1] N[*] |$;_R0$| aliphatic amine [CX4:1][NX3;!$(NC~[!#1!#6!F!Cl!Br!I]);!$(N~[!#1!#6]);!$(Nc):2] aliphatic hetero [!#1!#6;A:1] alkali metal [Li,Na,K,Rb,Cs,Fr:1] alkaline earth metal [Be,Mg,Ca,Sr,Ba,Ra:1] [*][H] |$_R0;$| alkane [*]\C([*])=C(/[*])[*] |$_R0;;_R0;;_R0;_R0$| alkene [C:1]=[C:1] [*]C=C=C[*] |$_R0;;;;_R0$| allene [CX2:1](=[C:2])=[C:2] [H]\C([H])=C(/[H])C([H])([H])[*] |$;;;;;;;;_R0$| allyl [CH2:3]=[CH:2][CH2:1] FALSE [O-]C[*] |$;;_R0$| alkoxide [C:1][O-;!$(OC~[!#1!#6]):2] OC[*] |$;;_R0$| alkoxy [C:1][OX2H0;!$(OC~[!#1!#6]):2] [*]C#C[*] |$_R1;;;_R2$| alkyne [CX2:1]#[CX2:1] [*]* |$_R0;X_p$| alkyl halide [CX4:1][F,Cl,Br,I;!$([F,Cl,Br,I]C~[!#1!#6]):2] [*]N([*])C([*])=O |$_R0;;_R0;;_R0;$| amide [NX3:2][CX3:1]=[OX1:3] [*]\N=C(/[*])N([*])[*] |$_R0;;;_R0;;_R0;_R0$| amidine [NX3:3][C:1]=[NX2:2] [*]N([*])[*] |$_R0;;_R0;_R0$| amine [#6:1][NX3;!$(NC~[!#1!#6!F!Cl!Br!I]);!$(N~[!#1!#6]):2] [*][N+]([*])([*])[*] |$_R0;;_R0;_R0;_R0$| ammonium [#6:1][NX4+:2] [*]C(=O)OC([*])=O |$_R0;;;;;_R0;$| anhydride [CX3:1](=[OX1:2])[OX2:3][CX3:1]=[OX1:2] *N([*])[*] |$Ar_p;;_R0;_R0$| aniline [c:1][NX3;!$(NC~[!#1!#6]);!$(N~[!#1!#6]):2] * any atom [*:1] * |$Ar_p$| aromatic [a:1] aromatic hetero [!#1!#6;a:1] ** |$Ar;X_p$| aryl halide [cX3:1][F,Cl,Br,I:2] [*]N=[N+]=[N-] |$_R0;;;$| azide [$([NX2-:1]-[NX2+:2]#[NX1:3]),$([NX2:1]=[NX2+:2]=[NX1-:3])] [#6][C@@]1([#6])N[C@]1([#6])[#6] |@:1,4| aziridine [C:1]1[C:1][N:2]1 FALSE [*]\N=N\[*] |$_R0;;;_R0$| azo [#6:2]\[N;X2:1]=[N;X2:1]\[#6:2] [*]\N=N\S([*])(=O)=O |$_R0;;;;_R0;;$| azosulfone [N;X2:2]=[N;X2:3][S;X4:1](=[O:5])=[O:4] [O-]\[N+]([*])=N/[*] |$;;_R0;;_R0$| azoxy [#6:1][$([NX2:2]=[NX3+:3]([O-:4])[#6:5]),$([NX2:2]=[NX3+0:3](=[O:4])[#6:5])] [*]CC1=CC=CC=C1 |$_R0;;;;;;;$,c:4,6,t:2| benzyl [CH2]-c1[cH1][cH1][cH1][cH1][cH1]1 FALSE [Br-] bromide [Br-:1] FALSE [*]OC(=O)N([*])[*] |$_R0;;;;;_R0;_R0$| carbamate [NX3,NX4+:2][CX3:1](=[OX1:3])[OX2,OX1-:4] [*]OC(=O)O[*] |$_R0;;;;;_R0$| carbonate [C:1](=[OX1:2])([O:3][#6:4])[O:3][#6:4] [*]C([*])=O |$_R0;;_R0;$| oxo [CX3:1]=[OX1:2] OC([*])=O |$;;_R0;$| carboxylic acid [CX3:1](=[O:2])[OX2H1:3] [O-]C([*])=O |$;;_R0;$| carboxylate [CX3:1](=[O:2])[O-:3] chain [*;R0:1] [Cl-] chloride [Cl-:1] FALSE CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)n1cnc2c(N)ncnc12)C(O)C(=O)NCCC(=O)NCCS[*] |$;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;_R0$| CoA [H]OC([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])[C:2]([H])([H])[S:1])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])C1([H])OC([H])(n2c([H])nc3c(nc([H])nc23)N([H])[H])C([H])(O[H])C1([H])OP(=O)(O[H])O[H] [*]N([*])C#N |$_R0;;_R0;;$| cyanamide [NX3:3][CX2:1]#[NX1:2] [*]N([*])C#N |$_R0;;_R0;;$| cyanimide [NX3:3][CX2:1]#[NX1:2] [*][C-]([*])[N+]#N |$_R0;;_R0;;$| diazo [$([#6:1]=[N+:2]=[N-:3]),$([#6-:1]-[N+:2]#[N:3])] [*][N+]#N |$_R0;;$| diazonium [#6+0:1]-[N+:2]#[N:3] [*]SS[*] |$_R0;;;_R0$| disulfide [#6:1][SX2H0:2][SX2H0:2][#6:1] [*]\C=C\N([*])[*] |$_R0;;;;_R0;_R0$| enamine [NX3;!$(NC~[!#1!#6]):3][CX3:1]=[CX3:2] FALSE O\C=C\[*] |$;;;_R0$| enol [OX2H:3][CX3:2]=[C:1] FALSE [#6][C@@]1([#6])O[C@]1([#6])[#6] |@:1,4| epoxide [C:1]1[C:1][O:2]1 FALSE [*]OC([*])=O |$_R0;;;_R0;$| ester [#6:5][OX2:2][CX3:1](=[O:3])[#6:4] [*]O[*] |$_R0;;_R0$| ether [OD2;!$(OC~[!#1!#6]):2]([#6:1])[#6:1] [F-] fluoride [F-:1] FALSE * |$X_p$| halogen [F,Cl,Br,I:1] [H]C(O)([*])O[*] |$;;;_R1;;_R2$| hemiacetal [C:4][O;X2:3][CH1:1]([#6:2])[OH1;X2:5] * |$Q_p$| hetero [!#1!#6:1] FALSE [*]N([*])N([*])[*] |$_R0;;_R0;;_R0;_R0$| hydrazine [#6:1][NX3:2][NX3:3] [*]N([*])\N=C(\[*])[*] |$_R0;;_R0;;;_R0;_R0$| hydrazone [NX3:3][NX2:2]=[C:1] O[*] |$;_R0$| hydroxyl [#6:1][OH;!$(O[#6]~[!#1!#6]):2] ON([*])[*] |$;;_R0;_R0$| hydroxylamine [NX2:2][OH1:3] [*]N(C([*])=O)C([*])=O |$_R0;;;_R0;;;_R0;$| imide [CX3:1](=[OX1:3])[NX3:2][CX3:1](=[OX1:3]) FALSE [*]\N=C(/[*])[*] |$_R0;;;_R0;_R0$| imine [CX3:1]=[NX2;!$(N~C~[!#1!#6]):3][#6,#1:2] [*]\C([*])=[N+](\[*])[*] |$_R0;;_R0;;_R0;_R0$| iminium [NX3+:2]=[CX3:1] [I-] iodide [I-:1] FALSE [*]N=C=O |$_R0;;;$| isocyanate [NX2:2]=[C:1]=[OX1:3] [*][N+]#[C-] |$_R0;;$| isocyanide [N+:2]#[C-:1] [*][N+]#[C-] |$_R0;;$| isonitrile [N+:2]#[C-:1] [*]N=C=S |$_R0;;;$| isothiocyanate [NX2:2]=[C:1]=[SX1:3] [*]C([*])(O[*])O[*] |$_R1;;_R2;;_R3;;_R4$| ketal [OX2:2][CH0X4;!$(CO~[!#6]):1][OX2:3] [*]C([*])=C=O |$_R0;;_R0;;$| ketene [C:1]=[C:2]=[OX1:3] [*]C([*])=O |$_R0;;_R0;$| ketone [#6:2][CX3:1](=[O:3])[#6:2] O\N=C(\[*])[*] |$;;;_R0;_R0$| ketoxime [C:1](=[N:2][OH1:3])([#6:4])[#6:4] * |$M_p$| metal [!#1!#2!#5!#6!#7!#8!#9!#10!#14!#15!#16!#17!#18!#32!#33!#34!#35!#36!#51!#52!#53!#54!#85!#86:1] metalloid [B,Si,Ge,As,Sb,Te,At:1] [O-][N+]([*])([*])[*] |$;;_R0;_R0;_R0$| N oxide [#7:1][OX1;!$(O[#7]~[!#1!#6]):2] [*]C#N |$_R0;;$| nitrile [NX1:2]#[CX2:1] [O-][N+]([*])=O |$;;_R0;$| nitro [#6:1][$([NX3:2](=[O:3])=[O:3]),$([NX3+:1](=[O:3])[O-:3])] [*]N=O |$_R0;;$| nitroso [NX2:1]=[OX1:2] nonmetal [#1,#2,#6,#7,#8,F,#10,#15,#16,Cl,#18,#34,Br,#36,I,#54,#86:1] O\N=C(\[*])[*] |$;;;_R0;_R0$| oxime [C:1]=[N:2][OH1:3] [*]OO[*] |$_R0;;;_R0$| peroxide [OX2,OX1-][OX2,OX1-] O[*] |$;Ar_p$| phenol [c:1][OX2H:2] FALSE [O-][*] |$;Ar_p$| phenoxide [c:1][OX1-:2] O[*] |$;Ar_p$| phenoxy [c:1][OX2H0;!$(OC~[!#1!#6]):2] [*]C1=CC=CC=C1 |$_R0;;;;;;$,c:3,5,t:1| phenyl [cH1]1[cH1][cH1][cH1][cH1]c1 FALSE [*]P([*])[*] |$_R0;;_R0;_R0$| phosphine [#1,#6:1][P;!$(P#6~[!#1!#6]):2]([#1,#6:1])[#1,#6:1] NC([*])=O |$;;_R0;$| primary amide [NX3H2:2][CX3:1]=[OX1:3] N[*] |$;_R0$| primary amine [#6:1][#7;A;H2X3;!$(NC~[!#1!#6!F!Cl!Br!I])!$(N~[!#1!#6]):2] [*+][H] protonated [*H1,H2,H3,H4+:1] [*][N+]([*])([*])[*] |$_R0;;_R0;_R0;_R0$| quaternary amino [#6X4:1][NX4H0;!$(NC~[!#1!#6]):2] ring [*;R:1] [*]NC([*])=O |$_R0;;;_R0;$| secondary amide [NX3H1:2][CX3:1]=[OX1:3] [*]N[*] |$_R0;;_R0$| secondary amine [#6:1][NX3H1;!$(NC~[!#1!#6!F!Cl!Br!I]);!$(N~[!#1!#6]):2] [*]S[*] |$_R0;;_R0$| sulfide [#6:1][SX2H0;!$(SC~[!#1!#6]):2][#6:1] FALSE [*]N([*])S([*])(=O)=O |$_R0;;_R0;;_R0;;$| sulfonamide [#6:1][$([SX4:2]([NX3:3])(=[OX1:4])(=[OX1:4])),$([SX4+2:2]([NX3:3])([OX1-:4])([OX1-:4]))] [*]S([*])(=O)=O |$_R0;;_R0;;$| sulfone [$([SX4:2](=[OX1:3])(=[OX1:3])([#6:1])[#6:1]),$([SX4+2:2]([OX1-:3])([OX1-:3])([#6:1])[#6:1])] OS([*])(=O)=O |$;;_R0;;$| sulfonic acid [#6:1][$([SX4:2](=[OX1:4])(=[OX1:4])[OX2H,OX1H0-:3]),$([SX4+2:2]([OX1-:4])([OX1-:4])[OX2H,OX1H0-:3])] [*]S([*])=O |$_R0;;_R0;$| sulfoxide [$([#SX3:2](=[OX1:3])([#6:1])[#6:2]),$([SX3+:2]([OX1-:3])([#6:1])[#6:1])] [*]N([*])C([*])=O |$_R0;;_R0;;_R0;$| tertiary amide [NX3H0:2][CX3:1]=[OX1:3] [*]N([*])[*] |$_R0;;_R0;_R0$| tertiary amine [#6:1][NX3H0;!$(NC~[!#1!#6!F!Cl!Br!I]):2] [*]N([*])[*] |$_R0;;_R0;_R0$| tertiary amino [#6:1][NX3H0;!$(NC~[!#1!#6!F!Cl!Br!I]):2] [*]N([*])C([*])=S |$_R0;;_R0;;_R0;$| thioamide [NX3:2][CX3:1]=[SX1:3] SC([*])=S |$;;_R0;$| thiocarboxide [CX3:1](=[S:2])[SX2H1:3] [S-]C([*])=S |$;;_R0;$| thiocarboxylate [CX3:1](=[S:2])[S-:3] [*]SC([*])=O |$_R0;;;_R0;$| thioester [#6:5][SX2:2][CX3:1](=[O:3])[#6:4] S[*] |$;_R0$| thiol [#6:1][SH;!$(S[#6]~[!#1!#6]):2] [*]N([*])C(=S)N([*])[*] |$_R0;;_R0;;;;_R0;_R0$| thiourea [NX3:2][CX3:1](=[SX1:3])[NX3:2] [*]N([*])C(=O)N([*])[*] |$_R0;;_R0;;;;_R0;_R0$| urea [NX3:2][CX3:1](=[OX1:3])[NX3:2] [H]\C([H])=C(/[H])[*] |$;;;;;_R0$| vinyl [CX3H2:1]=[CX3H1:1]