List of functional groups recognized by checkmol Current program version: v0.3c Norbert Haider, University of Vienna, 2005 http://merian.pch.univie.ac.at/~nhaider/cheminf/cmmm.html No. functional group name code general structure remarks 001 cation 000000T2 any positive charge 002 anion 000000T1 any negative charge 003 carbonyl compound C2O10000 O ketone or aldehyde R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 004 aldehyde C2O1H000 O R = H, alkyl, aryl R H 005 ketone C2O1C000 O R1 = alkyl, aryl 2 1 2 R = alkyl, aryl R R 006 thiocarbonyl compound C2S10000 S thioketone or thioaldehyde R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 007 thioaldehyde C2S1H000 S R = H, alkyl, aryl R H 008 thioketone C2S1C000 S R1 = alkyl, aryl 2 1 2 R = alkyl, aryl R R 009 imine C2N10000 R3 N R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 3 R = H, alkyl, aryl 010 hydrazone C2N1N000 R3 N 1 R4 R = H, alkyl, aryl N R2 = H, alkyl, aryl R3 = H, alkyl, aryl 1 2 R4 = H, alkyl, aryl R R 011 semicarbazone C2NNC4ON R4 O N R5 1 N 3 R = H, alkyl, aryl R 2 N R = H, alkyl, aryl R3 = H, alkyl, aryl 4 1 2 R = H, alkyl, aryl, R R 5 R = H, alkyl, aryl 012 thiosemicarbazone C2NNC4SN R4 S N R5 1 N 3 R = H, alkyl, aryl R 2 N R = H, alkyl, aryl R3 = H, alkyl, aryl 4 1 2 R = H, alkyl, aryl, R R 5 R = H, alkyl, aryl 013 oxime C2N1OH00 OH N R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 014 oxime ether C2N1OC00 OR3 N R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 3 R = alkyl, aryl 015 ketene C3OC0000 O R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 016 ketene acetal derivative C3OCC000 X Y R1 = H, alkyl, aryl R2 = H, alkyl, aryl X = any hetero atom 1 2 R R Y = any hetero atom 017 carbonyl hydrate C2O2H200 HO OH R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 018 hemiacetal C2O2HC00 3 R O OH R1 = H, alkyl, aryl 2 1 2 R = H, alkyl, aryl R R 3 R = alkyl, aryl 019 acetal C2O2CC00 R3O OR4 R1 = H, alkyl, aryl R2 = H, alkyl, aryl 3 R1 R2 R = alkyl, aryl R4 = alkyl, aryl 4 3 020 hemiaminal C2NOHC10 R R1 = H, alkyl, aryl in a true hemiaminal, R would be H 2 R3O N R5 R = H, alkyl, aryl R3 = H, alkyl, aryl 1 2 R4 = H, alkyl, aryl R R R5 = H, alkyl, aryl 1 021 aminal C2N2CC10 R4 R5 R = H, alkyl, aryl R2 = H, alkyl, aryl 3 6 R N N R R3 = H, alkyl, aryl R4 = H, alkyl, aryl 1 2 R R R5 = H, alkyl, aryl 6 R = H, alkyl, aryl 4 022 thiohemiaminal C2NSHC10 R R1 = H, alkyl, aryl 3 5 2 R S N R R = H, alkyl, aryl R3 = H, alkyl, aryl 1 2 R4 = H, alkyl, aryl R R 5 R = H, alkyl, aryl 023 thioacetal C2S2CC00 R3S SR4 R1 = H, alkyl, aryl R2 = H, alkyl, aryl 3 R1 R2 R = alkyl, aryl 4 R = alkyl, aryl 024 enamine C2CNH000 5 4 R4, R5 = acyl should be types as R R 1 N R = H, acyl, alkyl, aryl enamide R2 = H, acyl, alkyl, aryl 1 3 R 3 R = H, acyl, alkyl, aryl R R4 = H, acyl, alkyl, aryl R2 R5 = H, acyl, alkyl, aryl 025 enol C2COH000 OH 1 R1 = H, acyl, alkyl, aryl R R3 R2 = H, acyl, alkyl, aryl 3 2 R = H, acyl, alkyl, aryl R 026 enolether C2COC000 OR4 1 1 R = H, acyl, alkyl, aryl 2 R 3 R = H, acyl, alkyl, aryl R R3 = H, acyl, alkyl, aryl 2 R4 = alkyl, aryl R 027 hydroxy compound O1H00000 ROH R = alkyl, aryl alcohol or phenol 028 alcohol O1H0C000 ROH R = alkyl 029 prim. alcohol O1H1C000 R OH R = alkyl, aryl 030 sec. alcohol O1H2C000 R2 R1 = alkyl, aryl 1 R2 = alkyl, aryl R OH 031 tert. alcohol O1H3C000 2 R3 R R1 = alkyl, aryl 1 R OH R2 = alkyl, aryl 3 R = alkyl, aryl 032 1,2-diol O1H0CO1H HO OH R1 = H, alkyl, aryl 1 3 R2 = H, alkyl, aryl R R 3 R2 R4 R = H, alkyl, aryl R4 = H, alkyl, aryl 1 033 1,2-aminoalcohol O1H0CN1C HO NH2 R = H, alkyl, aryl 1 3 R2 = H, alkyl, aryl R R 3 R2 R4 R = H, alkyl, aryl R4 = H, alkyl, aryl 034 phenol O1H1A000 OH any aromatic or heteroaromatic ring with an OH substituent 035 1,2-diphenol O1H2A000 OH any aromatic or heteroaromatic ring with two adjacent OH substituents (except tautomeric lactams) OH 036 enediol C2COH200 HO OH R1 = H, alkyl, aryl R2 = H, alkyl, aryl R1 R2 1 037 ether O1C00000 1 O 2 R = alkyl, aryl R R R2 = alkyl, aryl 1 038 dialkylether O1C0CC00 1 O 2 R = alkyl R R R2 = alkyl 1 039 alkylarylether O1C0CA00 1 O 2 R = alkyl R R R2 = aryl 1 040 diarylether O1C0AA00 1 O 2 R = aryl R R R2 = aryl 1 041 thioether S1C00000 1 S 2 R = alkyl, aryl R R R2 = alkyl, aryl 2 042 disulfide S1S1C000 1 1 S R R = alkyl, aryl R S R2 = alkyl, aryl 043 peroxide O1O1C000 2 1 1 O R R = alkyl, aryl R O 2 R = alkyl, aryl 044 hydroperoxide O1O1H000 O R = alkyl, aryl R OH 045 hydrazine derivative N1N10000 2 R R1 = H, acyl, alkyl, aryl 3 R2 = H, acyl, alkyl, aryl 1 N R R N R3 = H, acyl, alkyl, aryl 4 R4 = H, acyl, alkyl, aryl R 046 hydroxylamine N1O1H000 2 R R1 = H, alkyl, aryl 3 R2 = H, alkyl, aryl 1 N R R O R3 = H, alkyl, aryl 3 047 amine N1C00000 R R1 = alkyl, aryl R2 = H, alkyl, aryl N 1 2 R3 = H, alkyl, aryl R R 048 prim. amine N1C10000 RNH R = alkyl, aryl 2 049 prim. aliphat. amine N1C1C000 RNH R = alkyl 2 050 prim. aromat. amine N1C1A000 RNH R = aryl 2 051 sec. amine N1C20000 H R1 = alkyl, aryl N 1 2 R2 = alkyl, aryl R R 052 sec. aliphat. amine N1C2CC00 H R1 = alkyl N 1 2 R2 = alkyl R R 053 sec. mixed amine (aryl alkyl) N1C2AC00 H R1 = alkyl N 1 2 R2 = aryl R R 054 sec. aromat. amine N1C2AA00 H R1 = aryl N R1 R2 R2 = aryl 3 055 tert. amine N1C30000 R R1 = alkyl, aryl R2 = alkyl, aryl N R1 R2 R3 = alkyl, aryl 3 056 tert. aliphat. amine N1C3CC00 R R1 = alkyl R2 = alkyl N R1 R2 R3 = alkyl 3 057 tert. mixed amine N1C3AC00 R R1 = alkyl R2 = aryl N 1 2 R3 = alkyl, aryl R R 3 058 tert. arom_amine N1C3AA00 R R1 = aryl R2 = aryl N R1 R2 R3 = aryl 3 059 quaternary ammonium salt N1C400T2 1 4 R R = alkyl, aryl R + R2 = alkyl, aryl N 3 R1 R2 R = alkyl, aryl 4 R = alkyl, aryl 060 N-oxide N0O10000 the N-O bond may be formulated as O a double bond O + 1 N + R = alkyl, aryl 2 1 N 3 R = alkyl, aryl R R 3 R2 R = alkyl, aryl 061 halogen deriv. XX000000 RX X = F, Cl, Br, I R = alkyl, alkenyl, aryl 062 alkyl halide XX00C000 RX X = F, Cl, Br, I R = alkyl 063 alkyl fluoride XF00C000 RF R = alkyl 064 alkyl chloride XC00C000 RCl R = alkyl 065 alkyl bromide XB00C000 RBr R = alkyl 066 alkyl iodide XI00C000 RI R = alkyl 067 aryl halide XX00A000 RX X = F, Cl, Br, I R = aryl 068 aryl fluoride XF00A000 RF R = aryl 069 aryl chloride XC00A000 RCl R = aryl 070 aryl bromide XB00A000 RBr R = aryl 071 aryl iodide XI00A000 RI R = aryl 072 organometallic compound 000000MX R M M = any metal R = alkyl, aryl 073 organolithium compound 000000ML RLi R = alkyl, aryl 074 organomagnesium compound 000000MM RMg R = alkyl, aryl 075 carboxylic acid deriv. C3O20000 O R = H, alkyl, aryl X = any hetero atom R X 076 carboxylic acid C3O2H000 O R = H, alkyl, aryl R OH 077 carboxylic acid salt C3O200T1 O R = H, alkyl, aryl R O 078 carboxylic acid ester C3O2C000 O 2 R1 = H, alkyl, aryl R 1 R2 = alkyl, aryl R O 079 lactone C3O2CZ00 O a cyclic ester (any ring size) O 080 carboxylic acid amide C3ONC000 O 2 R1 = H, alkyl, aryl 1 R 2 R N R = H, alkyl, aryl 3 3 R = H, alkyl, aryl R 081 carboxylic acid prim. amide C3ONC100 O R = H, alkyl, aryl R NH 2 082 carboxylic acid sec. amide C3ONC200 O 2 R1 = H, alkyl, aryl 1 R 2 R N R = alkyl, aryl H 083 carboxylic acid tert. amide C3ONC300 O 2 R1 = H, alkyl, aryl 1 R 2 R N R = alkyl, aryl 3 3 R = alkyl, aryl R 084 lactam C3ONCZ00 O a cyclic amide (any ring size) R N R = H, alkyl, aryl 085 carboxylic acid hydrazide C3ONN100 4 O R R1 = H, alkyl, aryl R2 = H, alkyl, aryl 1 N 3 R N R R3 = H, alkyl, aryl 4 2 R = H, alkyl, aryl R 086 carboxylic acid azide C3ONN200 O R = H, alkyl, aryl + R N N N 087 hydroxamic acid C3ONOH00 O R = H, alkyl, aryl OH R N H 088 carboxylic acid amidine C3N2H000 R4 N R1 = H, alkyl, aryl 3 R2 = H, alkyl, aryl 1 R R N R3 = H, alkyl, aryl 4 2 R = H, alkyl, aryl R 089 carboxylic acid amidrazone C3NNN100 5 R 4 N R R1 = H, alkyl, aryl R2 = H, alkyl, aryl 1 N 3 R N R R3 = H, alkyl, aryl 4 2 R = H, alkyl, aryl R 5 R = H, alkyl, aryl 090 nitrile C3N00000 RCN R = H, alkyl, aryl 091 acyl halide C3OXX000 O R = H, alkyl, aryl X = F, Cl, Br, I R X 092 acyl fluoride C3OXF000 O R = H, alkyl, aryl R F 093 acyl chloride C3OXC000 O R = H, alkyl, aryl R Cl 094 acyl bromide C3OXB000 O R = H, alkyl, aryl R Br 095 acyl iodide C3OXI000 O R = H, alkyl, aryl R I 096 acyl cyanide C2OC3N00 O R = H, alkyl, aryl R C N 097 imido ester C3NOC000 R3 N 2 R1 = H, alkyl, aryl R 2 R1 O R = alkyl, aryl 3 R = H, alkyl, aryl 098 imidoyl halide C3NXX000 R2 N R1 = H, alkyl, aryl 1 2 R X R = H, alkyl, aryl X = F, Cl, Br, I 099 thiocarboxylic acid deriv.