RLewis Smarts

7/21/2019 RLewis Smarts

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# $Id: RLewis_smarts.txt 992 2009-02-09 16:14:28Z glandrum $## Various smarts filters collected and contributed# by Richard Lewis##-------------------# GW (GlaxoWellcome) reactives[Br,Cl,I][CX4;CH,CH2] Reactive_alkyl_halides[S,C](=[O,S])[F,Br,Cl,I] Acid_halidesO=CN=[N+]=[N-] CarbazidesCOS(=O)O[C,c] Sulphate_estersCOS(=O)(=O)[C,c] SulphonatesC(=O)OC(=O) Acid_anhydridesOO PeroxidesC(=O)Oc1c(F)c(F)c(F)c(F)c1(F) Pentafluorophenyl_estersC(=O)Oc1ccc(N(=O)=O)cc1 Paranitrophenyl_estersC(=O)Onnn Esters_of_HOBTN=C=[S,O] Isocyanates_&_IsothiocyanantesOS(=O)(=O)C(F)(F)F TriflatesP(=S)(S)S Lawessons_reagent_and_derivativesNP(=O)(N)N phosphoramidescN=[N+]=[N-] Aromatic_azidesC(=O)C[N+,n+] Beta_carbonyl_quaternary_Nitrogen[N;R0][N;R0]C(=O) acylhydrazide

[C+,Cl+,I+,P+,S+] Quaternary_C,Cl,I,P_or_SC=P Phosphoranes[Cl]C([C&R0])=N Chloramidines[N&D2](=O) Nitroso[P,S][Cl,Br,F,I] P/S_HalidesN=C=N Carbodiimide[N+]#[C-] IsonitrileC(=O)N(C(=O))OC(=O) TriacyloximesN#CC[OH] CyanohydrinsN#CC(=O) Acyl_cyanidesS(=O)(=O)C#N Sulfonyl_cyanidesP(OCC)(OCC)(=O)C#N Cyanophosphonates[N;R0]=[N;R0]C#N Azocyanamides

[N;R0]=[N;R0]CC=O Azoalkanals#-------------------#GW bad leads[CD2;R0][CD2;R0][CD2;R0][CD2;R0][CD2;R0][CD2;R0][CD2;R0] Aliphatic_methylene_chains_7_or_more_long#>4[C,S,P](=O)[OH] Compounds_with_4_or_more_acidic_groups[O;R1][C;R1][C;R1][O;R1][C;R1][C;R1][O;R1] Crown_ethersSS Disulphides[SH] ThiolsC1[O,S,N]C1 Epoxides,_Thioepoxides,_Aziridinesc([OH])cc([OH])c([OH]) 2,4,5_trihydroxyphenylc([OH])c([OH])c([OH]) 2,3,4_trihydroxyphenylN=NC(=S)N Hydrazothiourea

SC#N ThiocyanatecC[N+] Benzylic_quaternary_NitrogenC[O,S;R0][C;R0](=S) ThioestersN[CH2]C#N CyanamidesC1(=O)OCC1 Four_membered_lactonesP(=O)([OH])OP(=O)[OH] Di_and_TriphosphatesN1CCC1=O Betalactams#-------------------#GW natural productsO=C1[#6]~[#6]C(=O)[#6]~[#6]1 Quinones


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C=CC=CC=CC=C PolyenesO1CCCCC1OC2CCC3CCCCC3C2 Saponin_derivativesO=C1NCC2CCCCC21 Cytochalasin_derivativesO=C1CCCC(N1)=O Cycloheximide_derivativesO1CCCCC1C2CCCO2 Monensin_derivatives[OH]c1cc([OH])cc2OC(C([OH])Cc21)c3cc([OH])c([OH])cc3 Cyanidol_derivativesC12OCCC(O1)CC2 Squalestatin_derivatives#-------------------# Pfizer filters 6 May 2003c-N(=O)~O Aromatic_Nitro[O,N,S][CH2]N1C(=O)CCC1(=O) Het_ImidesO=C-N!@N Carbonyl_NNC!@N=* Acyclic_Imines[S,P](=O)(=O)OC Alkyl_PS_Esters[$(N!@N),$([N;R0]=[N;R0])] N_N[$(N!@S),$(N~C(~S)-N)] N_S[CH2]=[CH]-[N,O,S] End_VinylS-C#N ThiocyanateS=C-[#6,N,O] Thionyl[Cl,Br,I]-N NXO=CC([$(C(F)(F)F),$(C#N),$(Cl)])=C AB_ketones#-------------------#ParkeDavis_smartsfiltersC#C-[F,Br,I,Cl]

C(-[O;H1])(-C#N)C(-O)-C-N(=O)=OC(=N)-SC(=O)-C(-O)-N-C=OC(=O)-C(=C)-C(=O)C(=O)-C(=N)C(=O)-C([F,Br,I,Cl])-C(=O)C(=O)-C([F,Br,I,Cl])=C([F,Br,I,Cl])-C(=O)C(=O)-C=C-C(=O)C(=O)-N(-O)-C(=O)C(=O)-N(-S)-C(=O)[C;!R](=O)-[N;!R]-[C;!R](=O)C(=O)-N-N(=O)

C(=O)-N-N-C(=O)C(=O)-O-N-C(=O)C(=O)-SC(=O)-S-C(=S)C(=S)-S[C;H1](=O)C([F,Br,I,Cl])=N[C;H2]-[C;H2]-[C;H2]-[C;H2]-[C;H2]-[C;H2]-[C;H2]C-N=OC-S(=O)(=O)-OC1-C-C(=O)-O1C=C(-S)-S(=O)[C;!R]=[C;!R]-[C;!R](-O)

C=C-C(=N)[C;!R]=[C;!R]-[C;!R](=O)C=C-C(=O)-C=CC=C-C(=S)C=C-C(=S)-SC=C-C([F,Br,I,Cl])=C([F,Br,I,Cl])C=C-C=NC=C-N([C,c])([C,c])C=C-N(=O)(=O)C=C-N(O)(=O)


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C=C-OC=C-O-C(=O)[C;!R]=[C;!R]-[S;!R]C=C-S(=O)(=O)C=N-C(-O)C=N-C(=O)C=N-NC=N-N=CC=N-OC=N-O-C(=O)C=N=ON#C-SN(=O)-C([F,Br,I,Cl])[N!H0]-[C!H0]-[N!H0]N(O)=C-C-N(=O)N-C(-S)=N-S(=O)(=O)N-C(=N)-SN-C(=O)-O-c1ccccc1N-C(=S)N-C(=S)-NN-C=CN-O-C(=O)N1-C-C1N1-N-C(=O)-N-N1

N=C(-N)-C(=N)-NN=C(-O)-NN=C(-S)-C(=N)-NN=C([F,Br,I,Cl])N=C-C(=O)N=C-SN=C=NN=C=ON=C=SO-C(=O)-O-NO-C([F,Br,I,Cl])=SO-C=CO-N=C-C=N-O

PS(=O)(=O)-C([F,Br,I,Cl])S(=O)(=O)OS-C#NS-C(=C)-SS-C(=N)-NS-C(=N)-SS-C(=S)-NS-N-C(=O)[S;H][Si][N;H2]-S[N;H]-[C;H]-[N;H]

c-C(-O)(-O)-cc-C(-[O;H])[!O]c-S(=O)(=O)-C=Cc-S(=O)(=O)-On1(=O)c([F,Br,I,Cl])cccc1n1c([F,Br,I,Cl])cccc1n1c([F,Br,I,Cl])ncccc1C1-C-O-C-O-C1C=Sc=S


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S=C-SC=C-N(=O)(=O)C=C-N(=O)(-O)C(=O)-C(=N)C=C-SC(-S)(-S)(-S)(-S)S(-O)(-O)(-O)(-O)S(=O)(=O)-C-N(=O)(=O)S(=O)(=O)-C-N(=O)(-O)N#C-SC=N-OC=N-S=NS-C(=O)-SS-C(=N)-SS-C(=N)(=N)N(=O)(=O)N(=O)(-O)N(-O)(-O)C1-S-C-S1N=C=SN=C=NC1-N=N1C([F,Br,Cl,I])-SC(-S)(-S)=C(-S)(-S)

C(=N)-C=N-OC(-C#N)(-C#N)C-O-N=OC=C-NC=N-S(=O)(=O)N-N=ON-C(=O)-SS-C#NN-C(=O)-C(=O)-Nc=NC1-O-C-O-C1C=N-N-S(=O)(=O)[C;!R](=O)-[C;!R](=O)

C(=O)-N-O-C(=O)C1(=O)-C=C-C(=O)-C=C1BONOON(~O)~OC1(O)CC(O)CO1C1(O)C(O)CCO1C1(O)CC(O)CCO1N=[N+]=NN-C#N[C;!R]=N-N=[C;!R]N(C)(C)-[C;H2]-[C;H2]([F,Br,I,Cl])[C;a]-[N;H1]-[N;H2]

[C;a]-[C;H2]([F,Br,I,Cl])[S;!R]-[C;!R]-[O;!R]N1-C-O1[C;H2]-O-S(=O)(=O)-CC1-C-O1c1-[N;a]-c([F,Br,I,Cl])-c-c-c1C=[C;H0]([F,Br,I,Cl])([F,Br,I,Cl])[N+]#NON#COOO


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[N+]#N-* diazonium[C,c]-[S;D2]-[O,N] SON# 5. S, P, Si, N halides[Cl,Br,I,F][S,P,Si,N] Unstable_halide# added v2.53[Cl,Br,I]CC[S,N] Mustards# 6. sulphonates, sulphinates, Silicates[Si]-O-* silicateS(O[C,c,N,n])(~O)[C,c,N,n] sulphate# 7. N-O systems# acyclic nitroamino; removes N-nitroso (and N-nitrate, but the latter is no great loss)[N;R0](~N)~O acyclic nitroamino# nitrateN(~O)(~O)(~O)-* nitrate# nitro#>4[C,c]-N(=O)~O more_than_4_nitros[N+]([O-])(=C)-* nitrone[!$([C,c]-N(=O)~O);$([!O]~[N;R0]=O)] N-oxide# 8. acyclic aminalN([H,C;X4])([H,C;X4])-[C;R0;X4]-N[C;X4]([H,C;X4])([H,C;X4]) acyclic_aminal# 9. acyclic cyanohydrinN#C[C;R0;X4]O[!$(O=[C,S])] acyclic_cyanohydrin# 10. acyclic enol; gets rid even of stabilised enols but this was acceptable to

chemists[C;R0](=[C;R0])-[S,O,N;R0][!$(O=[C,S])] acyclic_enol[O-]-[C;R0]=[C;R0] acyclic_enolate[C;R0](=[C;R0])-[OH] acyclic enol# 11. metals and other elements[Be,B,Al,Ti,Cr,Mn,Fe,Co,Ni,Cu,Pd,Ag,Sn,Pt,Au,Hg,Pb,Bi,As,Sb,Gd,Te] metals_and_other_elements# 13. labile estersO=CON1C(=O)CCC1=O labile_esterO=COn1cncc1 labile_esterFc1c(OC=O)c(F)c(F)c(F)c1F labile_ester# 14. quarternary S[S;D2][C;R0](C)(C)C quarternary_S

# 15. hydrocarbon tails[C;R0;X4]!@[CH]!@[CH]!@[CH]!@[CH]!@[CH]!@[CH]!@[CH]!@[CH]!@[CH]!@[CH][CH2] 10_alkyl_chain# 16. aldehydes[CH]=O aldehyde#-------------------#1. hydrocarbon tails#1010 shtail [C;R0;X4][CH2][CH2][CH2][CH2][C;R0;X4] S[C;R0;X4]!@[CH2]!@[CH2]!@[CH2]!@[CH2]!@[CH2]!@[C;R0;X4] (CH2)6_alkyl_chain_Q# 2. Se (2.5)#Selenium se [Se,se] S# 3. S-compounds (2.5)[S;D2;R0]-[S;D2] Disulphide_bond_Q

[SH] thiol_Q[S,s;D2]C[S,s;D2] masked_aldehyde_Q[$([S,s]~[S,s]~[C,c]=S),$([S,s]~[C,c](=S)~[S,s,N]),$([S;D2;R0]-S~O)] thiolating_agent_Q# 4. N-alkyl heterocycles[n+]-C pyridinium_Q# 5. benzamidines[NH]=C([NH2])c benzamidine_Q# 6. hydroxamatesO=CN[OH] hydroxamate_Q


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# 7. Hydrazines[NH;R0][NH;R0] hydrazine_Q# 8. tricarbonyls[$(O=C[CH](C=O)C=O),$(N#C[CH](-C=O)-C=O)] tricarbonyls_Q# 9. phosphinatesP(=O)(O[H,C])O[H,C] phosphinate_Q# 10. Michaels acceptors; 2.51 change to allow anything rather than C,c attachedto Beta-C.[$(N#C-C=[CH][C,c]),$([CH](=[C;R0]-[CH]=O)),$([CH](=[C,R]-C(=O)-C));!$([CH]1=CC(=O)C=CC1=*);!$([CH]1=CC(=O)C(=[N,O])C=C1);!$([CH](=C-C=O)-C=O)] Michaels_acceptors_Q# added v2.52 enyne acceptors[$(N#C-C#C[C,c]),$(C#C-[CH]=O),$(C(#C-C(=O)-[C,c]))] Michaels_acceptors1_Q# 11. electrophiles for Cys[$(N#CSc1sc(nc1)N),$([S,Se]1C(N)C(=O)[#6][#6]1)] electrophiles_for_Cys_Q# 12. imines[!$(O=[C,S])][N;R0]=[C;R0]([C,c])[C,c] imines_Q# 13. perhalo ketonesO=CC([Cl,Br,I,F])([Cl,Br,I,F])[Cl,Br,I,F] perhalketones_Q# 14. thioesters[#6]SC(=O) thioester_Q#-------------------# other useful queries[$(O([CX4,c])!@[CH,CH2]!@O[CX4,c])] acetal

C(=O)Cl acid_chloride[$(C#N),$([C,N,S]=O)][CH2,CH][$([C,N,S]=O),$(C#N)] acidic_CHC(=O)[Cl,Br] acyl_halide[CX4][OH] any_alcohol[CX4;H2][OH] primary_alcohol[CX4;H][OH] secondary_alcohol[CX4;H0][OH] tertiary_alcohol[#6][CH]=O aldehyde[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])]=[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])] alkene[CX4][Cl,Br,I] alkyl_halideC#C alkyne[Cl,Br,I][CH]C=C allyl_halide

cCC(=O)[OH] alpha_aryl_caC([Cl,Br,I])([Cl,Br,I])([Cl,Br,I])C(=O)[OH] alpha_trihalo_ca[#6]C(=O)C(=O)[OH] alpha_keto_caC=CC(=O)[OH] alpha_beta_unsat_caN#C-C(=O)[OH] alpha_cyano_caN(~O)(~O)-C-C(=O)[OH] alpha_nitro_ca[ND3]([CX4,c,H])([CX4,c,H])[CX4][$([CH]),$(C([CX4,c]))]=O alpha_amino_ket_or_ald[OH][CX4][$([CH]),$(C([CX4,c]))]=O alpha_hydroxy_ket_or_ald[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])]=C-[$([CH]),$(C([CX4,c]))]=O alpha_beta_ket_or_ald[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])]=C-C#N alpha_beta_CN[OH][CX4][Cl,Br,I] alpha_halo_hydroxyl

[Cl,Br,I][$([CX4][CH]=O),$([CX4]C(=O)[CX4,c])] alpha_halo_ket_or_ald[OH][CX4][$([NH2]),$([NH][CX4]),$(N([CX4])[CX4])] alpha_amino_hydroxylO=C([c,CX4])[$([NH2]),$([NH][c,CX4]),$(N([c,CX4])[c,CX4])] amide[$([NH2][CX4]),$([$([NH]([CX4])[CX4]);!$([NH]([CX4])[CX4][O,N]);!$([NH]([CX4])[CX4][O,N])]),$([ND3]([CX4])([CX4])[CX4])] any_amine[$([NH2]),$([NH][c,CX4]),$(N([c,CX4])[c,CX4]);!$(NC=O)][CX4]C(=O)[OH] amino_acidO(C(=O)[#6])(C(=O)[#6]) anhydridec[NH,NH2] anilinec-[ND3]([#6])[#6] aniline_disub


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c aromaticc-[F,Cl,Br,I] aryl_halidec-[Br,I] aryl_heavy_halideFcaa[F,Cl,Br,I,$([C,N,S]=O)] active_aryl_fluoridecB([OH])[OH] aryl_boronate[N;R0;D2]~[N;R0]~[N;R0;D1] azide[N;D2]([C,c;!$(C=[O,S,N])])=[N;D2]-[C,c;!$(C=[O,S,N])] azo[OH][CX4][CX4][Cl,Br,I] beta_halo_hydroxyl[OH][CX4][CX4][$([NH2]),$([NH][CX4]),$(N([CX4])[CX4])] beta_amino_hydroxyl[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])]=C[CX4]C(=O)[OH] beta_gamma_unsat_ca[CX4]([OH])[CX4]C(=O)[OH] beta_hydroxy_ca[CX4]([Cl,Br,I])[CX4]C(=O)[OH] beta_halo_ca[#6]C(=O)[CX4]C(=O)[OH] beta_keto_ca[#6]C(=O)[CX4]C(=O)O[$([#6]);!$(C=[O,S,N])] beta_keto_ester[$([NH2]),$([NH][c,CX4]),$(N([c,CX4])[c,CX4])]C(=O)O[$([#6]);!$(C=[O,S,N])] carbamate[$([NH2]),$([NH][c,CX4]),$(N([c,CX4])[c,CX4])]C(=O)[OH] carbamic_acidC(=O)[OH] carboxylic_acidO([CX4,c])C(=O)O[CX4,c] carbonate[$([CX4,c][CH]=O),$([CX4,c]C(=O)[CX4,c])] carbonylClC(=O)O[CX4,c] chloroformate[CX4,c]-C#N cyanideN[CX4]C(=O)N[CX4]C(=O) dipeptide[S;D2]-[S;D2] disulphide

[$([S;D2]([CX4,c])!@[CH,CH2]!@[S;D2][CX4,c])] dithioacetal[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])]=[$([CX3][$([NH2]),$([NH][CX4]),$([N;R0]([CX4])[CX4])]);!$(CC=[O,S,N]);!$(C[O,S])] enamine[$([CX3]C(=O)[CX4,c]);!$(CC=[S,N]);!$(C[O,S,N])]=[$([CX3]C(=O)[CX4,c]);!$(CC=[S,N]);!$(C[N,S])] enedione[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])]=[$([CX3][OH]);!$(CC=[O,S,N]);!$(C[N,S])]enol[$([CX3]);!$(CC=[O,S,N]);!$(C[O,S,N])]=[$([CX3]O[CX4]);!$(CC=[O,S,N]);!$(C[N,S])] enol_etherO1[CX4][CX4]1 epoxide[$([#6]);!$(C=[O,S,N])]C(=O)O[$([#6]);!$(C=[O,S,N])] ester[$(O([$([CX4,c]);!$(C[O,N,S])])[$([CX4,c]);!$(C[O,N,S])]);!$(O1[CX4][CX4]1)] ether

[OH][CH,CH2]O[CX4,c] hemiacetalO([#6])-C([#6])([#6])-[OH] hemiketal[OH][$([NX3]([C;!$(C=[O,S,N])])[C;!$(C=[O,S,N])]),$([NH][CX4])] hydroxylamine[$([NH;R0]([C;!$(C=[O,S,N])]))][$([NH;R0][C;!$(C=[O,S,N])])] hydrazineC=N[NH2] hydrazoneC=NC=O imide[$([C;R0]=[N;R0]);!$(C(~[N,O,S])(~[N,O,S]));!$([C;R0]=[N;R0]~[N,O,n])] imineC#N-[#6] isocyanideO=C=N-[#6] isocyanateS=C=N-[#6] isothiocyanateO([CX4,c])-C([CX4,c])([CX4,c])-O([CX4,c]) ketal[CX4,c]C(=O)[CX4,c] ketone[C;R0;X4]!@[CX4]!@[CX4]!@[CX4]!@[CX4]!@[CX4]!@[C;R0;X4] long_chain

[$([C;R1]);!$(C(N)N)](=O)@[$([NH][c,CX4]),$(N([c,CX4])[c,CX4])] lactam[$([C;R1]);!$(C(O)N);!$(C(O)O)](=O)@[$(O);!$(O(C=O))] lactoneOC(=O)CC(=O)[OH] malonic_acid[r8,r9,r10,r11,r12,r13,r14] macrocycle*-C#N nitrile*-N(=O)(~O) nitro[N;D4] nquatOC(=O)C(=O)O oxalylC=[N;R0]-[OH] oximeO~O peroxide


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