Tautomerizer - Predict tautomers based on 80+ rules

PT_02_00 - 1,5 (thio)keto/(thio)enol -
[O,S,Se,Te;X1:1]=[Cz1H0:2][C:5]=[C:6][CX4z0,NX3:3][#1:4]>>[#1:4][O,S,Se,Te;X2:1][Cz1:2]=[C:5][C:6]=[Cz0,N:3]

Select example: C1=CC(C=C(C1=O)C)=O

Run Example

PT_03_00 - simple (aliphatic) imine -
[#1,a,O:5][NX2:1]=[Cz{1-2}:2][CX4R{0-2}:3][#1:4]>>[#1,a,O:5][NX3:1]([#1:4])[Cz:2]=[C:3]

Select example: [C]1(CC[C]CC1)=[N]

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PT_04_00 - special imine -
[Cz0R0X3:1]([C:5])=[C:2][Nz0:3][#1:4]>>[#1:4][Cz0R0X4:1]([C:5])[c:2]=[nz0:3]

Select example: C(CC1=NC=C[NH]1)(C)C

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PT_05_00 - 1,3 aromatic heteroatom H shift -
[#1:4][N:1][C;e6:2]=[O,NX2:3]>>[NX2,nX2:1]=[C,c;e6:2][O,N:3][#1:4]

Select example: CCCN1C(N(C(C2=C1N=C([NH]2)C3=CC(C)(C)N(C3(C)C)O)=O)CCC)=O

Run Example

PT_06_00 - 1,3 heteroatom H shift -
[CX{2-3}z{0-1},N,n,S,s,O,o,Se,Te:1]=[NX2,nX2,CX3,c,P,p:2][N,n,S,O,Se,Te:3][#1:4]>>[#1:4][CX4z{0-1},N,n,S,O,Se,Te:1][NX2,nX2,CX3z{0-1},c,P,p:2]=[N,n,S,s,O,o,Se,Te:3]

Select example: SC1=NC=CN1C

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PT_07_00 - 1,5 (aromatic) heteroatom H shift (1) -
[nX2,NX2,S,O,Se,Te:1]=[C,c,nX2,NX2:6][C,c:5]=[C,c,nX2:2][N,n,S,s,O,o,Se,Te:3][#1:4]>>[#1:4][N,n,S,O,Se,Te:1][C,c,nX2,NX2:6]=[C,c:5][C,c,nX2:2]=[NX2,S,O,Se,Te:3]

Select example: OC1=C(/N=N/C2=CC=C(C=C2)N(C)C)C3=CC=CC=C3C=C1

Run Example

PT_08_00 - 1,5 aromatic heteroatom H shift (2) -
[n,s,o:1]=[c,n:6][c:5]=[c,n:2][n,s,o:3][#1:4]>>[#1:4][n,s,o:1][c,n:6]=[c:5][c,n:2]=[n,s,o:3]

Select example: N2=NC=C1N=C[NH]C1=C2

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PT_09_00 - 1,7 (aromatic) heteroatom H shift -
[nX2,NX2,S,O,Se,Te,Cz0X3:1]=[c,C,NX2,nX2:6][C,c,NX2,nX2:5]=[C,c,NX2,nX2:2][C,c,NX2,nX2:7]=[C,c,NX2,nX2:8][N,n,S,s,O,o,Se,Te,CX4z0:3][#1:4]>>[#1:4][N,n,S,O,Se,Te,Cz0X4:1][C,c,NX2,nX2:6]=[C,c:5][C,c,NX2,nX2:2]=[C,c,NX2,nX2:7][C,c,NX2,nX2:8]=[NX2,S,O,Se,Te,CX3z0:3]

Select example: OC1=C(CN2CCCCC2)C=C(/N=N/C3=CC=C([N+]([O-])=O)C=C3)C4=C1C=CC=C4

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PT_10_00 - 1,9 (aromatic) heteroatom H shift -
[#1:1][n,N,O:2][c,nX2,C:3]=[c,nX2,C:4][c,nX2:5]=[c,nX2:6][c,nX2:7]=[c,nX2:8][c,nX2,C:9]=[n,N,O:10]>>[N,n,O:2]=[C,c,nX2:3][c,nX2:4]=[c,nX2:5][c,nX2:6]=[c,nX2:7][c,nX2:8]=[c,nX2:9][n,O:10][#1:1]

Select example: N1=N[NH]C2=C1C(=NN=C2)NN

Run Example

PT_11_00 - 1,11 (aromatic) heteroatom H shift -
[#1:1][n,N,O:2][c,nX2,C:3]=[c,nX2,C:4][c,nX2:5]=[c,C,nX2:6][c,C,nX2:7]=[c,C,nX2:8][c,nX2,C:9]=[c,C,nX2:10][c,C,nX2:11]=[nX2,NX2,O:12]>>[NX2,nX2,O:2]=[C,c,nX2:3][c,C,nX2:4]=[c,C,nX2:5][c,C,nX2:6]=[c,C,nX2:7][c,C,nX2:8]=[c,C,nX2:9][c,C,nX2:10]=[c,C,nX2:11][nX2,O:12][#1:1]

Select example: C1=CC=C(C(=C1)\C=C\C(NO)=O)O

Run Example

PT_11_01 - 1,13 (aromatic) heteroatom H shift -
[#1:1][n,N,O:2][c,nX2,C:3]=[c,nX2,C:4][c,nX2,C:5]=[c,nX2,C:6][c,nX2:7]=[c,C,nX2:8][c,C,nX2,NX2:9]=[c,C,nX2:10][c,nX2,C:11]=[c,C,nX2:12][c,C,nX2:13]=[nX2,NX2,O:14]>>[NX2,nX2,O:2]=[c,nX2,C:3][c,nX2,C:4]=[C,c,nX2:5][c,C,nX2:6]=[c,C,nX2,NX2:7][c,C,nX2:8]=[c,C,nX2,NX2:9][c,C,nX2:10]=[c,C,nX2:11][c,C,nX2:12]=[c,C,nX2:13][nX2,O:14][#1:1]

Select example: OC1=CC=C(/N=C2N=C(O)/C(S/2)=C3C(NC4=C/3C=CC=C4)=O)C=C1

Run Example

PT_11_02 - 1,15 (aromatic) heteroatom H shift -
[#1:1][n,N,O:2][c,nX2,C:3]=[c,nX2,C:4][c,nX2,C:5]=[c,nX2,C,NX2:6][c,nX2:7]=[c,C,nX2:8][c,C,nX2,NX2:9]=[c,C,nX2,NX2:10][c,nX2,C:11]=[c,C,nX2:12][c,C,nX2:13]=[c,C,nX2:14][c,C,nX2,NX2:15]=[nX2,NX2,O:16]>>[NX2,nX2,O:2]=[c,nX2,C:3][c,nX2,C:4]=[C,c,nX2:5][c,C,nX2,NX2:6]=[c,C,nX2,NX2:7][c,C,nX2:8]=[c,C,nX2,NX2:9][c,C,nX2,NX2:10]=[c,C,nX2:11][c,C,nX2:12]=[c,C,nX2:13][c,C,nX2:14]=[c,C,nX2,NX2:15][nX2,O,N:16][#1:1]

Select example: O=C1C2=C(C=CC=C2)N=C(/C=C3C(NC4=CC=CC=C\34)=O)N1

Run Example

PT_11_03 - 1,17 (aromatic) heteroatom H shift -
[#1:1][n,N,O:2][c,nX2,C:3]=[c,nX2,C:4][c,nX2,C:5]=[c,nX2,C:6][c,nX2:7]=[c,C,nX2:8][c,C,nX2,NX2:9]=[c,C,nX2:10][c,nX2,C:11]=[c,C,nX2:12][c,C,nX2:13]=[c,C,nX2:14][c,C,nX2:15]=[c,C,nX2:16][c,C,nX2:17]=[nX2,NX2,O:18]>>[NX2,nX2,O:2]=[c,nX2,C:3][c,nX2,C:4]=[C,c,nX2:5][c,C,nX2:6]=[c,C,nX2,NX2:7][c,C,nX2:8]=[c,C,nX2,NX2:9][c,C,nX2:10]=[c,C,nX2:11][c,C,nX2:12]=[c,C,nX2:13][c,C,nX2:14]=[c,C,nX2:15][c,C,nX2:16]=[c,C,nX2:17][nX2,O:18][#1:1]

Select example: O=CC1=C(/C=C\N/C=C\C(C=C/2)=NC2=C/C=N/C=C\3)NC3=C1

Run Example

PT_11_04 - 1,19 (aromatic) heteroatom H shift -
[#1:1][n,N,O:2][c,nX2,C:3]=[c,nX2,C:4][c,nX2,C:5]=[c,nX2,C,NX2:6][c,nX2:7]=[c,C,nX2:8][c,C,nX2,NX2:9]=[c,C,nX2,NX2:10][c,nX2,C:11]=[c,C,nX2:12][c,C,nX2:13]=[c,C,nX2:14][c,C,nX2,NX2:15]=[c,C,nX2:16][c,C,nX2:17]=[c,C,nX2:18][c,C,nX2:19]=[nX2,NX2,O:20]>>[NX2,nX2,O:2]=[c,nX2,C:3][c,nX2,C:4]=[C,c,nX2:5][c,C,nX2,NX2:6]=[c,C,nX2,NX2:7][c,C,nX2:8]=[c,C,nX2,NX2:9][c,C,nX2,NX2:10]=[c,C,nX2:11][c,C,nX2:12]=[c,C,nX2:13][c,C,nX2:14]=[c,C,nX2,NX2:15][c,C,nX2:16]=[c,C,nX2:17][c,C,nX2:18]=[c,C,nX2:19][nX2,O:20][#1:1]

Select example: C1(/C=C2)=N\C(C3=CC=CC=C/43)=NC4=N/C5=CC=C(N5)/N=C(C6=C7C=CC=C6)\N=C7NC2=N1

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PT_12_00 - 1,3 furanones -
[#1:1][O,S,N:2][c,C;z2;r5:3]=[C,c;r5:4][c,C;r5:5]>>[O,S,N:2]=[Cz2r5:3][C&r5R{0-2}:4]([#1:1])[C,c;r5:5]

Select example: OC1=CC2=CC=CC=C2S1

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PT_13_00 - keten/ynol exchange -
[O,S,Se,Te;X1:1]=[C:2]=[C:3][#1:4]>>[#1:4][O,S,Se,Te;X2:1][C:2]#[C:3]

Select example: O=C=C

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PT_14_00 - ionic nitro/aci-nitro -
[#1:1][C:2][N+:3]([O-:5])=[O:4]>>[C:2]=[N+:3]([O-:5])[O:4][#1:1]

Select example: [N+](C)(=O)[O-]

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PT_15_00 - pentavalent nitro/aci-nitro -
[#1:1][C:2][N:3](=[O:5])=[O:4]>>[C:2]=[N:3](=[O:5])[O:4][#1:1]

Select example: [N+](C)(=O)[O-]

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PT_16_00 - nitroso/oxime -
[#1:1][O;!R:2][N+0z1:3]=[CX3:4]>>[O;!R:2]=[N+0z1:3][CX4:4][#1:1]

Select example: O\N=C\CCC

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PT_17_00 - oxime/nitroso via phenol -
[#1:1][O:2][Nz1:3]=[C:4][C:5]=[C:6][C:7]=[O:8]>>[O:2]=[Nz1:3][c:4]=[c:5][c:6]=[c:7][O:8][#1:1]

Select example: O=C(C=C/1)C=CC1=N/O

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PT_18_00 - cyanic/iso-cyanic acids -
[#1:1][O:2][C:3]#[N:4]>>[O:2]=[C:3]=[N:4][#1:1]

Select example: O=C=N

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PT_19_00 - formamidinesulfonic acid -
[#1:1][O,N:2][C:3]=[S,Se,Te:4]=[O:5]>>[O,N:2]=[C:3][S,Se,Te;v{2-4}:4][O:5][#1:1]

Select example: [S](=O)=CN

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PT_20_00 - isocyanide -
[#1:1][C0:2]#[N0:3]>>[C-:2]#[N+:3][#1:1]

Select example: N#C

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PT_21_00 - phosphonic acid -
[#1:1][O,NX3:2][P;v3:3]>>[O,NX2:2]=[P;v5:3][#1:1]

Select example: O=S(C1=CC=C(CCCC)C=C1)(NP(C2=CC=CC=C2)C3=CC=CC=C3)=O

Run Example

PT_22_00 - imine via imine -
[#1:1][CX4:2][NX2:3]=[CX3:4]>>[CX3:2]=[NX2:3][CX4:4][#1:1]

Select example: CSCCC1=NC(CC)SC1=O

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PT_23_00 - 1,5 furanones -
[#1:1][O,S,NX3:2][cX3;z2;r5:3]=[c;r5:4][c;r5:5]=[c;z{1-2};r5;R{1-2}:6]>>[O,S,NX2:2]=[CX3;z2;r5:3][C;r5:4]=[C;r5:5][Cz{1-2};r5;R{1-2}:6][#1:1]

Select example: CN1C(NC2=NC=CC=C2)=CC=C1

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PT_24_00 - 1,4 N-oxide/N-hydroxide -
[#1:1][OX2:2][N;z{1-2};X3!$(N=O);H0:3][CX3,c,n,NX2;r5:4]=[n,NX2,CX3;r5:5]>>[O&-:2][N+;z{1-2};X3;H0:3]=[c,CX3,n,NX2;r5:4][n,NX3,CX4;r5:5][#1:1]

Select example: [O-][N+]1=NN([H])C2=C1C=CC=C2

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PT_25_00 - 1,6 N-oxide/N-hydroxide(1) -
[#1:1][OX2:2][NX3r5:3][c,C;r5:4]=[c,C;r5:5][CX3,NX2r5:6]=[NX2:7]>>[O&-&H0:2][NX3z2&+;r5:3]=[c,C;r5:4][c,C;r5:5]=[CX3,NX2r5:6][NX3:7][#1:1]

Select example: [O-][N+]1=C(C=CC=C2)C2=NN1[H]

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PT_26_00 - 1,6 N-oxide/N-hydroxide(2) -
[#1:1][O:2][NX3r6:3][C;r6:4]=[C;r6:5][C;z1;r6:6]=[O,NX2,S:7]>>[O&-&H0:2][n&+,N&+;X3;z1;r6:3]=[c,C;r6:4][c,C;r6:5]=[c,C;z1;r6:6][O,NX3,S:7][#1:1]

Select example: O=C1C=CN(O[H])C=C1

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PT_27_00 - acene -
[#1:12][OX2,CX4:1][c:2]1=[cR{2-}a3:3]([c:4])[cR{2-}a3:6]([c:5])=[c:7][cR{2-}a3:8](=[c:9])[cR{2-}a3:11]1=[c:10]>>[#1:12][C:7]1[cR{2-}:6]([c:5])=[cR{2-}:3]([c:4])[C:2](=[O,CX3:1])[cR{2-}:11](=[c:10])[cR{2-}:8]1=[c:9]

Select example: C=C1C=CC([H])C=C1

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PT_27_01 - thiophene analogue of acene -
[#1:12][O:11][c:10]1=[c;a3;r5:9]([c,s;r5:6])[c;a3;r5:8]([c,s;r5:7])=[c:5][c;a3:4]([c,s:1])=[c;a3:3]1[c,s:2]>>[#1:12][C:5]1[c;a2:4]([c,s:1])=[c;a2:3]([c,s:2])[C:10](=[O:11])[c;a2;r5:9]([c,s;r5:6])=[c;a2;r5:8]1[c,s;r5:7]

Select example: O=C1C(C=CS2)=C2CC3=C1SC=C3

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PT_28_00 - nitro/aci-nitro via aromatic ring (1): 1,7 H-shift -
[#1:1][CX4:2][c;r6:3]=[c;r6:4][c;r6:5]=[c;r6:6][N+:7]([O-:9])=[O:8]>>[CX3:2]=[C;r6:3][C;r6:4]=[C;r6:5][C;r6:6]=[N+:7]([O-:9])[O:8][#1:1]

Select example: [O-][N+](C1=CC=C(C([H])(C#N)C#N)C=C1)=O

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PT_29_00 - nitro/aci-nitro via aromatic ring (2): 1,5 H-shift -
[#1:1][CX4:2][c;r6:3]=[c;r6:4][NX3+:5]([O-:7])=[O:6]>>[CX3:2]=[C;r6:3][C;r6:4]=[NX3+:5]([O-:7])[O:6][#1:1]

Select example: [O-][N+](C1=C(C[H])C=CC=C1)=O

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PT_29_01 - o-tolualdehyde -
[#1:1][CX4:2][c;r6:3]=[c;r6:4][CX3:5]([#1:7])=[OX1:6]>>[CX3:2]=[C;r6:3][C;r6:4]=[CX3:5]([#1:7])[OX2:6][#1:1]

Select example: CC1=C(C=O)C=C(C)C=C1C=O

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PT_30_00 - nitramide/N-nitronic acid -
[#1:1][N:2][N+:3]([O-:5])=[O:4]>>[N:2]=[N+:3]([O-:5])[O:4][#1:1]

Select example: CN([H])[N+]([O-])=O

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PT_31_00 - sulfone-based aliphatic compounds -
[#1:1][CX4z1:2]1[CX3:3]=[CX3:4][CX3:5]=[CX3;!a:6][SX4:7]1(=[O])(=[O])>>[CX3z1;!a:2]1=[CX3:3][CX3:4]=[CX3:5][CX4:6]([#1:1])[SX4:7]1(=[O])(=[O])

Select example: O=S1(C(C(C)C)=CC=CC(C)1[H])=O

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PT_32_00 - nitrile/keteneimine: 1,3 H-shift -
[#1:1][CX4;$([C][CX{3-4}]=,-[OX{1-2}]):2][CX2:3]#[NX1:4]>>[CX3;$([C][CX{3-4}]=,-[OX{1-2}]):2]=[C:3]=[NX2:4][#1:1]

Select example: N#CCC(O)/C=C/C1=CC=CC=C1

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PT_33_00 - nitrile/keteneimine: 1,5 H-shift -
[#1:1][CX4:2][CX3:3]=[C;$([CX3][CX{2-3}]=,#[N,O]):4][CX2:5]#[NX1:6]>>[CX3:2]=[CX3:3][C;$([CX3][CX{2-3}]=,#[N,O]):4]=[C:5]=[NX2:6][#1:1]

Select example: O=C(OCC)C/C(C)=C(C#N)/C#N

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PT_34_00 - triad phosphorus-carbon -
[#1:1][CX4:2][PX4:3]=[C;$([CX{2-3}z2]~[PX{3-4}]):4]>>[CX3:2]=[PX4:3][C;$([CX{3-4}z2]~[PX{3-4}]):4][#1:1]

Select example: [H]CP(C1=CC=CC=C1)(C2=CC=CC=C2)=CP(C3=CC=CC=C3)C4=CC=CC=C4

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PT_35_00 - sulfenyl/sulfinyl (1,2 H shift) -
[Sv2X2:1][OX2:2][#1:3]>>[Sv4X3:1]([#1:3])=[OX1:2]

Select example: [H]OSC1=CC=CC=C1

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PT_36_00 - oxime/nitrone (1,2 H shift) -
[CX3:1]=[NX2:2][OX2:3][#1:4]>>[CX3:1]=[NX3+:2]([OX1-:3])[#1:4]

Select example: CN(C1)C[C@@H]2/C([C@H]1CN(C)C2)=[N+]([O-])\[H]

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PT_37_00 - sulfenyl /S-oxide ( 1,4 H shift) -
[NX2:1]=[CX3z{2-3}:2][SX2:3][OX2:4][#1:5]>>[#1:5][NX3:1][CX3z{2-3}:2]=[SX2+:3][OX-:4]

Select example: [H]OSC1=NC=CN1

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PT_38_00 - sila-hemiaminal/silanoic amide -
[#1:1][CX4;!a:2][CX3;!a:3]=[NX3+:4][SiX4-:5]([NX3:7])([NX3:8])=[O:6]>>[CX3;!a:2]=[CX3;!a:3][NX3:4][SiX4:5]([NX3:7])([NX3:8])[OX2:6][#1:1]

Select example: [H]CC(C=C(C)N(C1=C(C(C)C)C=CC=C1C(C)C)[Si-]2(N)=O)=[N+]2C3=C(C(C)C)C=CC=C3C(C)C

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PT_39_00 - nitrone/azoxy or Behrend rearrangement -
[CX3,NX2:1]=[NX3+:2]([O-:3])[CX4:4][#1:5]>>[#1:5][CX4,NX3:1][NX3+:2]([O-:3])=[CX3:4]

Select example: [O-]/[N+](C(C1=CC=CC=C1)[H])=C\C2=CC=C(C)C=C2

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PT_40_00 - tetrad phosphorus-carbon -
[#1:1][PX4:2]=[C;$([CX3][PX4+]):3][CX3z1:4]=[O:5]>>[PX3:2][C;$([CX3][PX4+]):3]=[CX3z1:4][OX2:5][#1:1]

Select example: CC(C([P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)=P([H])(C4=CC=CC=C4)C5=CC=CC=C5)=O

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PT_41_00 - pyridine 1-oxide/1-hydroxypyridine -
[#1:1][SX2,NX3,OX2;!R:2][CX3,c;r{5-6}:3]=[NX3+r{5-6}:4][OX1-:5]>>[SX1,NX2,OX1;!R:2]=[CX3,c;r{5-6}:3][NX3r{5-6}:4][OX2:5][#1:1]

Select example: [O-][N+]1=C(O)C=CC=C1

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PT_42_00 - △3-/△4-pyrro(thio/seleno)lin-2-one -
[#1:1][CX4:4]1[NX3,O,S,Se:5][CX3:6](=[O:7])[CX3:2]=[CX3;a0:3]1>>[#1:1][CX4:2]1[CX3;a0:3]=[CX3:4][NX3,O,S,Se:5][CX3:6]1=[O:7]

Select example: O=C1C(C(C)(C)C)=CC(S1)C2=NC=CC=C2

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PT_43_00 - isobenzofuran/phthalan -
[#1:1][CX4:2][c:5]1=[c:9]2[c:8]=[c:7][c:6]=[c:11][c:10]2=[c:4][#8:3]1>>[#1:1][CX4:4]1[#8:3][CX3:5](=[CX3!c:2])[c:9]2=[c:10]1[c:11]=[c:6][c:7]=[c:8]2

Select example: C12=C(CC3=CC=CC=C3)OC=C1C=CC=C2

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PT_44_00 - 2-subsituted-pyrrole -
[#1:7][CX4;$([C][C]#[N]),$([C][C](=[O])[O]):6][c:5]1=[cR1:4][c:3]=[c:2][nX3:1]1>>[#1:7][CX4R1:4]1[CX3:3]=[CX3:2][NX3:1][CX3:5]1=[CX3;$([C][C]#[N]),$([C][C](=[O])[O]):6]

Select example: N#CCC1=CC=C(CC#N)N1C2=CC=CC=C2

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PT_45_00 - isopropylidenecycloalkane/isopropylcycloalkene -
[#1:1][CX4:2]([CH3:3])([CH3:4])[CX3R1r{5-8}!c;z0:5]=[CX3R1r{5-8}!c:6][CR{1-};!c:7]>>[CX3:2]([CH3:3])([CH3:4])=[CX3R1r{5-8};z0:5][CX4R1r{5-8}:6]([CR{1-}:7])[#1:1]

Select example: C/C(C)=C1CCCC/1

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PT_46_00 - 4-picoline -
[#1:8][CX4;$(C[S](=[O])[O]):7][C:1]1=[C:6][C:5]=[NX2+0:4][C:3]=[C:2]1>>[#1:8][N:4]1[C:3]=[C:2][C:1](=[CX3;$(C[S](=[O])[O]):7])[C:6]=[C:5]1

Select example: C(C1=C2C=CC=CC2=NC=C1)S(O)=O

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PT_47_00 - isoindole/isoindolenine -
[#1:10][CX4:8]1[#7X2:9]=[CX3:7][c:6]2=[c:5]1[c:4]=[c:3][c:2]=[c:1]2>>[#1:10][#7X3:9]1[c:7]=[c:6]2[c:1]=[c:2][c:3]=[c:4][c:5]2=[c:8]1

Select example: CC1=CC=C(C2=C(NC(C)=C12)C)C

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PT_48_00 - benzofuranone -
[#1:12][OX2:10][c:2]1=[c:3][c:4]=[c:5][c:6]2=[c:1]1[C:8](=[O:11])[O:7][C:9]2>>[OX1:10]=[C:2]1[C:3]=[C:4][CX4:5]([#1:12])[C:6]2=[C:1]1[C:8](=[O:11])[O:7][C:9]2

Select example: CCOC(=O)C1=CC2=C(C(=O)OC2(C)C)C(O)=C1

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PT_49_00 - N-hydroxyindole -
[#1:9][OX2:8][NX3R1r5:1]([aR{1-}r{5-}:2])[cR1r5:5]=[cR1r5:4]([aR{1-}r{5-}:3])[CX3:6]=[O:7]>>[OX1-:8][NX3+R1r5:1]([a,AR{1-}r{5-}:2])=[CR1r5:5][CX3R1r5:4]([a,AR{1-}r{5-}:3])=[CX3:6][OX2:7][#1:9]

Select example: ON1C(C)=C(C2=C1C=CC=C2)C(NC(C)(C)C)=O

Run Example

RC_03_00 - 5_exo_trig -
[#1:1][O,N,S,Se,Te:2][#6R1;!c:3]1[*:4]~[*:7]~[R1:6][O,N,S,Se,Te;R:5]1>>[O,N,S,Se,Te:2]=[C;!R:3][R{0-1}:4]~[R{0-1}:7][!R:6][O,N,S,Se,Te:5][#1:1]

Select example: O[C@@H]1[C@@H](CO)O[C@H](O)[C@@H]1O

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RC_03_03 - boronic acids/oxaborole -
[#1:1][OX2:2][BX3:3]([OX2])[cr6:4][cr6:5][CX3:6]=[OX1:7]>>[OX2:2]1[BX3:3]([OX2])[cr{5-6}:4][cr{5-6}:5][CX4:6]1[OX2:7][#1:1]

Select example: OB(O[H])C1=C(C=O)C(F)=CC=C1

Run Example

RC_03_04 - 5_exo_trig -
[#1:1][OX2:2][CX4;!R:3][CX4:4][CX4:5][CX3;!c:6]=[CX3!c;$([C][CX3](=[OX1])[OX2]):7]>>[OX2:2]1[CX4:3][CX4:4][CX4:5][CX4:6]1[CX4;$([C][CX3](=[OX1])[OX2]):7][#1:1]

Select example: OCCC(C)/C(N)=C/C(OC)=O

Run Example

RC_04_01 - 6_exo_trig -
[O,N,S,Se,Te:2]=[C;!R:3][!R:4]~[R{0-1}:7]~[R{0-1}:8]~[!R:6][O,N,S,Se,Te:5][#1:1]>>[#1:1][O,N,S,Se,Te:2][#6R1;!c:3]1[*;R1:4]~[*:7]~[*:8]~[R1:6][O,N,S,Se,Te;R:5]1

Select example: O[C@@H](CO)[C@@H](O)[C@@H](O)C=O

Run Example

RC_04_02 - 6_exo_trig -
[O,N,S,Se,Te:2]=[C;!R:3][!R:4]~[!R:7]~[R{0-1}:8]~[R{0-1}:6][O,N,S,Se,Te;!R:5][#1:1]>>[#1:1][O,N,S,Se,Te:2][#6R1;!c:3]1[*;R1:4]~[*;R1:7]~[*:8]~[R:6][O,N,S,Se,Te;R1:5]1

Select example: CC(CC(C1=C(OC2=C(C1=O)C=CC=C2)O[H])C3=CC=CC=C3)=O

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RC_04_04 - 6_exo_trig -
[#1:1][NX3!R:2][SX4:3](=[O:4])(=[O:5])[c:6]=[c:7][NX3:8][CX3!c:9]=[CX3!c:10]>>[NX3:2]1[SX4:3](=[O:4])(=[O:5])[c:6]=[c:7][NX3:8][CX4:9]1[CX4:10][#1:1]

Select example: O=S(C(C=CC=C1)=C1N/C=C/C(C2=CC=CC=C2)=O)(N[H])=O

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RC_09_00 - 5_endo_trig -
[#1:1][N;R1;X3:3]1[!a:4]~[R:6][O,N,S,Se,Te;R:5][#6R;z2;X4:2]1>>[C;!R;z1;X3:2]=[N;!R,X2;+0:3][*:4]~[*:6][O,N,S,Se,Te;!R:5][#1:1]

Select example: CC(C)(CO)/N=C/C1=CC=CC=C1

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RC_10_00 - 6_endo_trig -
[#1:1][N;R1;X3:3]1[!a:4]~[*:7]~[*;R1:6][O,N,S,Se,Te;R:5][#6R;z2;X4:2]1>>[C;!R;z1;X3:2]=[N;!R;+0:3][R{0-1}:4]~[*;R{0-1}:7]~[!R:6][O,N,S,Se,Te:5][#1:1]

Select example: OCC1=C(/N=C/C2=CC=CC=C2)C=CC=C1

Run Example

RC_12_00 - 5_endo_tet or iminophosphorane/benzoxazaphospholine -
[OX2;R:2]1[*R:3]~[*R:4][NX3:5]([#1:1])[PX5R;z2:6]1>>[#1:1][O;!R:2][*:3]~[*:4][NX2;!R;+0:5]=[PX4;!R;z1:6]

Select example: OC1=C(N=P(C2=CC=CC=C2)(CC)CC)C=C(CCCC)C=C1

Run Example

RC_13_00 - 6_endo_dig -
[OX:2]=[CX2;z2:3]=[NX2;!R:4][c;R{0-1};!$(*=[#7,#8,#16]):5]~[c;R{0-1}:6]!:[C;R{0-1}:7][NX3;!R:8][#1:1]>>[O:2]=[CX3;z3;R:3]1[NX3;R:4]([#1:1])[c;R{1-2};!$(*=[#7,#8,#16]):5]~[c;R{1-3}:6]!:[C;R{1-2}:7][NX3;R:8]1

Select example: O=C=NC1=C(C(N([H])C2=NN=NN2)=O)C=CC=C1

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RC_14_00 - thiadiazoline rearrangement -
[#1:1][NX3:2][CX{2-3}:3][NX3:4][CX3;R1:5]1[SX2;R1:6][NX3;R1:7][CX3;R1:8](=[O:9])[NX2:10]=1>>[NX3;R:2]1[CX{2-3};R:3][NX3;R:4][CX3;R:5](=[NX2:10][CX3:8](=[O:9])[NX3:7][#1:1])[SX2;R1:6]1

Select example: O=C1N=C(SN1C)N(/C(N([H])C)=N/C2=CC=C(C=C2)C)C3=CC=CC=C3

Run Example

RC_15_00 - 5_exo_trig (1,4 H shift) -
[#1:1][NX3,OX2:2][CX4!R:3][CX4:4][CX4:5][CX3!c:6]=[NX3+:7][OX1-:8]>>[NX3,OX2:2]1[CX4:3][CX4:4][CX4:5][CX4:6]1[NX3:7][OX2:8][#1:1]

Select example: [O-]/[N+](CC1=CC=CC=C1)=C\C2C(OC(C)(C)O2)CO[H]

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RC_16_00 - boryl-borate -
[#1:1][OX2:2][CX4:3][PX3:4][CX4:5][OX2:6][BX3:7]>>[OX2:2]1[CX4:3][PX3:4][CX4:5][OX2:6][BX4-:7]1.[#1+:1]

Select example: [H]OCP1COB(C2=CC=CC=C2)OC1

Run Example

RC_17_00 - boryl-borate (ion-complex) -
[OX2:2]1[CX4:3][PX4;$(P=[O,S,Se]):4][CX4:5][OX2:6][BX4-:7]1.[#1:1][NX4+:8]>>[#1:1][OX2:2][CX4:3][PX4;$(P=[O,S,Se]):4][CX4:5][OX2:6][BX4-:7][NX4+:8]

Select example: O=P1(C2=CC=CC=C2)CO[B-](C3=CC=CC=C3)(C4=CC=CC=C4)OC1.C[N+]([H])(C)C

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RC_18_00 - hydroxyphosphorane -
[#1:1][OX2:2][CX4:3][c:4]=[c:5][P:6]=[OX1:7]>>[OX2:2]1[CX4:3][c:4]=[c:5][P:6]1[OX2:7][#1:1]

Select example: CC(C)(O)c1ccccc1P3(=O)OC(C)(C)c2ccccc23

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RC_19_00 - nitroolefin/1,2-oxazine N-oxide -
[#1:1][CX4:2]([NX3+:3]([O-:5])=[O:4])[CX4:6][CX4:7][CX3:8]=[CX3:9]>>[CX3:2](=[NX3+:3]([O-:5])[O:4]1)[CX4:6][CX4:7][CX4:8]1[CX4:9][#1:1]

Select example: [O-]/[N+](O)=C(C)/C(C1=CC=CC=C1)C2COCC=C2N3CCCCC3

Run Example

RC_20_00 - 5_endo_trig: 1,4 H-shift or aminoethyl nitrone/imidazolidin-1-ol -
[#1:1][OX2,NX3:2][CX4!R,CD4!R2:3][CX4:4][NX3+:5]([OX1-:7])=[CX3:6]>>[OX2,NX3:2]1[CX4:3][CX4:4][NX3:5]([OX2:7][#1:1])[CX4:6]1

Select example: [O-]/[N+](C(CN(C1=CC=C(C=C1)C)[H])C2=CC=CC=C2)=C\C3=CC=C(C=C3)Cl

Run Example

RC_21_00 - cyclobutane/enamine -
[#1:1][CX4:2]([NX3+:3]([O-:5])=[O:4])[CX4:6][CX4:7][CX3:8]=[CX3:9]>>[CX4:2]1([NX3+:3]([O-:5])=[O:4])[CX4:6][CX4:7][CX4:8]1[CX4:9][#1:1]

Select example: O=[N+](C[C@@H](C(Cl)(Cl)Cl)[C@H]4CCCC=C4N5CCN(CC5)C)[O-]

Run Example

RC_22_00 - 5_endo_trig: 1,5 H-shift -
[#1:1][OX2:2][NX2:3]=[CX3:4][CX4:5][NX3+:6]([OX1-:7])=[CX3:8]>>[OX1-:2][NX3+:3]1=[CX3:4][CX4:5][NX3:6]([OX2:7][#1:1])[CX4:8]1

Select example: C=C(OC)/C=[N+]([O-])/C(C)/C(C)=N/O

Run Example

RC_23_00 - 6_endo_trig: 1,4 H-shift -
[#1:1][OX2:2][CX4:3][CX4:4][CX4:5][NX3+:6]([OX1-:7])=[CX3:8]>>[OX2:2]1[CX4:3][CX4:4][CX4:5][NX3:6]([OX2:7][#1:1])[CX4:8]1

Select example: CC1([N+]([O-])=CC2=CC=CC=C2)C([H])(CO)CCC1

Run Example

RC_24_00 - λ5/λ3-phosphane -
[#1:12][O:10][C:9][cr6:6]=[cr6:1][PX3z0:7]>>[#1:12][PX5z1:7]1[O:10][C:9][cr{5-6}:6]=[cr{5-6}:1]1

Select example: OC(C(F)(F)F)(C(F)(F)F)C(C=CC=C1)=C1P2([H])(C3=CC=CC=C3)C4=C(C(O2)(C(F)(F)F)C(F)(F)F)C=CC=C4

Run Example

VT_01_00 - monothio-o-benzoquinone/benzoxathiete -
[OX1:1]=[CX3R1:2][CX3R1:3]=[SX{1-2}z{0-1};!R:4]>>[OX2:1]1[c:2]=[c:3][SX{2-3}z{1-2}:4]1

Select example: O=C1C(C=C(C=C1)C)=S

Run Example

VT_01_01 - α-dithione and 1,2-dithiete -
[SX1:1]=[CX3:2][CX3:3]=[SX1]>>[SX2:1]1[C:2]=[C:3][SX2:4]1

Select example: S=C(C1=CC=C(N(C)C)C=C1)C(C2=CC=C(N(C)C)C=C2)=S

Run Example

VT_02_00 - tetrazole–azide -
[NX2,nX2:1]=[CX3,cz{2-3}:2][NX2z1:3]=[NX2z2+:4]=[NX1-:5]>>[NX3:1]1[Cz{2-3}:2]=[NX2z1:3][NX2z2:4]=[NX2z2:5]1

Select example: CC(C=CC=C1C)=C1OC2=NN=NN2C(OCC(Cl)(Cl)Cl)=O

Run Example

VT_03_00 - isothiocyanate-triazinethione -
[SX1:1]=[Cz2X2:2]=[NX2:3][cr6:4]=[cr6:5][NX2:6]=[NX2:7]>>[SX1:1]=[Cz3X3:2]1[NX2:3]=[C:4][C:5]=[NX2:6][NX3:7]1

Select example: S=C=NC1=C(/N=N/C(C)(C)C)C=CC=C1

Run Example

VT_04_00 - tetrazine/azodiazo -
[NX3:1]1[N:2]=[CR2:3]2[C:4]=[C:5][C:6]=[CR2:7]2[N:8]=[N:9]1>>[NX2:1]=[NX2:2][C:3]1=[C:4][C:5]=[C:6][C:7]1=[NX2+:8]=[NX1-:9]

Select example: C12=CC=CC1=NN(C3=CC=CC=C3)N=N2

Run Example

VT_05_00 - 1,2,3-triazole/diazoamidine -
[nX3;$([n][C]#[N]),$([n][N+](=[O])[O-]),$([n][SX4](=[O])=[O]):1]1[c:2]=[c:3][nX2:4]=[nX2:5]1>>[NX2;$([N][C]#[N]),$([N][N+](=[O])[O-]),$([N][SX4](=[O])=[O]):1]=[C:2][C:3]=[NX2+:4]=[NX1-:5]

Select example: CC1=C(C)N(C#N)N=N1

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VT_06_00 - norcaradiene–cycloheptatriene or benzene-oxide–oxepin -
[CX4,OX2,NX3:1]1[CX4:2]2[CX3:3]=[CX3:4][CX3:5]=[CX3:6][CX4:7]21>>[CX4,OX2,NX3:1]1[CX3:2]=[CX3:3][CX3:4]=[CX3:5][CX3:6]=[CX3:7]1

Select example: FC(C1(C#N)C2C1C=CC=C2)(F)F

Run Example

VT_07_00 - phospha-münchnones -
[PX4:1]=[CX3:2][NX3:3][CX3:4]=[OX1:5]>>[PX5:1]1[CX3-:2][NX3+:3]=[CX3:4][OX2:5]1

Select example: O=C(C1=CC=CC=C1)N(C)C(C2=CC=CC=C2)=P(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5

Run Example

VT_08_00 - 1,2,3,4-tetrazinium/azodiazonium -
[NX2:1]=[NX2:2][cr6:3][cr6:4][NX2+:5]#[NX1:6]>>[NX3+:1]1=[NX2:2][cr6:3][cr6:4][NX2:5]=[NX2:6]1

Select example: CC(/N=N/C1=C([N+]#N)C=CC=C1)(C)C.FB(F)F.[F-]

Run Example

VT_09_00 - diazaphosphazole/phosphinoimine -
[NX3:10][Pv3:9]([NX3:11])[N:8]=[CX3:7][c:5]1=[N:4][c:3]=[c:2][c:1]=[c:6]1>>[NX3:10][Pv5:9]1([NX3:11])=[N:8][CX3:7]=[C:5]2[N:4]1[C:3]=[C:2][C:1]=[C:6]2

Select example: CC(C)N(C(C)C)P1(N(C(C)C)C(C)C)=NC(C2=CC=CC=C2)=C3N1C=CC=C3

Run Example

VT_10_00 - phosphine/phosphonium salt -
[NX2z1:9]=[NX2:8][c:6]1=[c:1]([c:2]=[c:3][c:4]=[c:5]1)[PX3:7]>>[PX4+:7]1[Nz2:9][N-:8][c:6]2=[c:1]1[c:2]=[c:3][c:4]=[c:5]2

Select example: C1(P(C2=C(/N=N/C3=CC=CC=C3)C=CC=C2)C4=CC=CC=C4)=CC=CC=C1

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