Table 2.
Examples of the metabolic activation of groups of general chemicals (polycyclic aromatic hydrocarbons, heterocyclic and aromatic amines, insecticides, organic solvents) by human cytochrome P450 enzymes
| General chemical | P450 | Category | Reaction | PMID numbers | References |
|---|---|---|---|---|---|
| N-Acetylaminofluorene (2-acetamidofluorene, 2-AAF) | 1A2 | Acyl arylamine | Hydroxylation, N- (major enzyme, activation) | 8095200, 8313839, 1576936, 2813353, 9705755, 8200083, 10503887, 10517985, 11377247, 11013410, 11473383, 15279838, 11375903, 23432465 | (Aryal et al. 2000; Butler et al. 1989; Edwards et al. 1994; Guengerich 1993; Guengerich et al. 1999; Ioannides and Parke 1993; Josephy et al. 2001; Juchau et al. 1992; Oda et al. 2001; Shimada et al. 2013; Turesky et al. 1999; Turesky et al. 1998; Yamazaki et al. 2004; Yueh et al. 2001) |
| 2-AAF | 1A1 | Acetyl arylamine | Hydroxylation, N- (activation) | 8095200, 8313839, 1576936, 11502724, 15279838, 7955101, 23432465 | (Guengerich 1993; Ioannides and Parke 1993; Juchau et al. 1992; Shimada et al. 1994; Shimada et al. 2013; Shimada et al. 2001a; Yamazaki et al. 2004) |
| 2-Aminoanthracene (2-AA) | 2W1 | Arylamine | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| 2-AA | 1A2 | Arylamine | Hydroxylation, N- (activation) | 23432465 | (Shimada et al. 2013) |
| 2-AA | 2A13 | Arylamine | Hydroxylation, N- (activation) | 23432465 | (Shimada et al. 2013) |
| 2-AA | 2A6 | Arylamine | Hydroxylation, N- (high activity, activation) | 23432465 | (Shimada et al. 2013) |
| 2-AA | 1A1 | Arylamine | Hydroxylation, N- (high activity, activation), major enzyme | 7955101, 11502724, 9705755, 11377247, 10964100, 23432465 | (Oda et al. 2001; Shimada et al. 1994; Shimada et al. 2013; Shimada et al. 2001a; Turesky et al. 1998; Williams et al. 2000) |
| 2-AA | 1B1 | Arylamine | Hydroxylation, N- (high activity, activation) | 8674051, 10964100, 11377247, 11473383, 23432465, 27123158 | (Chun and Kim 2016; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 1996; Shimada et al. 2013; Williams et al. 2000) |
| 6-Aminochrysene | 3A4 | Arylamine | N-Oxidation (high activity, activation) | 2271712, 8330339 | (Brian et al. 1990; Yamazaki et al. 1993) |
| 6-Aminochrysene | 1A1 | Arylamine | Oxidation (high activity and activation) | 7955101, 8961944, 11502724, 9685642 | (Guengerich and Shimada 1998; Shimada et al. 1994; Shimada et al. 2001a; Shou et al. 1996a) |
| 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) | 2A13 | Heterocyclic amine | Activation | 23432465 | (Shimada et al. 2013) |
| MeIQ | 2A6 | Heterocyclic amine | Activation | 23432465 | (Shimada et al. 2013) |
| MeIQ | 2W1 | Heterocyclic amine | Activation | 24278521 | (Eun et al. 2010) |
| MeIQ | 1A1 | Heterocyclic amine | Hydroxylation, N- (activation) | 7955101, 9152602, 11502724, 9705755, 8200083, 11377247, 11473383 | (Edwards et al. 1994; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 1994; Shimada et al. 1997b; Shimada et al. 2001a; Turesky et al. 1998) |
| MeIQ | 1B1 | Heterocyclic amine | Hydroxylation, N- (activation) | 8674051, 10964100, 9152602, 10426814, 11377247, 11473383, 9721189, 11502724, 11719446, 23432465, 27123158 | (Chun and Kim 2016; Chun et al. 2001; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 1994; Shimada et al. 1997b; Shimada et al. 2013; Shimada et al. 2001a; Shimada et al. 1999; Shimada et al. 1998; Williams et al. 2000) |
| 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) | 2A13 | Heterocyclic amine | Activation | 23432465 | (Shimada et al. 2013) |
| MeIQx | 2A6 | Heterocyclic amine | Activation (weaker activation) | 23432465 | (Shimada et al. 2013) |
| MeIQx | 1B1 | Heterocyclic amine | Activation (weaker activation) | 23432465, 27123158 | (Shimada et al. 2013) |
| MeIQx | 1A1 | Heterocyclic amine | Hydroxylation, N- (activation) | 7955101, 9705755, 8200083, 11377247, 11473383, 11502724, 17627018 | (Bendaly et al. 2007; Edwards et al. 1994; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 1994; Shimada et al. 2001a; Turesky et al. 1998) |
| MeIQx | 1A2 | Heterocyclic amine | Hydroxylation, N- (major enzyme, high activity and activation) | 7955101, 9705755, 8200083, 11377247, 11473383, 9111224, 10220313, 11258970, 11453738, 12351158, 14744142, 14725854, 28879062 | (Delannée et al. 2017; Edwards et al. 1994; Hammons et al. 1997; Josephy et al. 2001; Kim and Guengerich 2004; Langouët et al. 2001; Oda et al. 2001; Parikh et al. 1999; Shimada et al. 1994; Turesky et al. 1998; Turesky et al. 2002; Turesky et al. 2001; Zhou et al. 2004) |
| 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) | 2D6 | Heterocyclic amine | Hydroxylation, N- (activation) | 11377247 | (Oda et al. 2001) |
| Trp-P-1 | 2E1 | Heterocyclic amine | Hydroxylation, N- (activation) | 11377247 | (Oda et al. 2001) |
| Trp-P-1 | 3A4 | Heterocyclic amine | Hydroxylation, N- (high activation) | 11377247 | (Oda et al. 2001) |
| Trp-P-1 | 2C9 | Heterocyclic amine | Oxidation (activation) | 11377247 | (Oda et al. 2001) |
| Trp-P-1 | 2W1 | Heterocyclic amine | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| Trp-P-1 | 2A13 | Heterocyclic amine | Activation (weaker activation) | 23432465 | (Shimada et al. 2013) |
| Trp-P-1 | 2A6 | Heterocyclic amine | Activation (weaker activation) | 23432465 | (Shimada et al. 2013) |
| Trp-P-1 | 2W1 | Heterocyclic amine | Oxidation (activation) | 24278521 | (Eun et al. 2010) |
| Trp-P-1 | 1A2 | Heterocyclic amine | Hydroxylation, N- (major enzyme, activation) | 11377247, 7955101, 9705755, 11473383, 8961944 | (Josephy et al. 2001; Oda et al. 2001; Shimada et al. 1994; Shou et al. 1996a; Turesky et al. 1998) |
| Trp-P-1 | 1A1 | Heterocyclic amine | Hydroxylation, N- (high activation) | 7955101, 8200083, 11377247, 11502724, 11473383, 9705755 | (Edwards et al. 1994; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 1994; Shimada et al. 2001a; Turesky et al. 1998) |
| 2-Aminofluorene (2-AF) | 2W1 | Arylamine | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| 2-AF | 2A6 | Arylamine | Hydroxylation, N- (activation) | 23432465 | (Shimada et al. 2013) |
| 2-AF | 2A13 | Arylamine | Hydroxylation, N- (major enzyme, high activity, activation) | 23432465 | (Shimada et al. 2013) |
| 2-AF | 1A2 | Arylamine | Hydroxylation, N- (major enzyme, high activity and activation) | 2334931, 7955101, 8095200, 8313839, 1576936, 9705755, 8200083, 10503887, 10964100, 11377247, 11013410, 2803520, 10815771, 23432465 | (Aoyama et al. 1989; Aryal et al. 2000; Edwards et al. 1994; Guengerich 1993; Ioannides and Parke 1993; Juchau et al. 1992; Lozano et al. 2000; McManus et al. 1990; Oda et al. 2001; Shimada et al. 1994; Shimada et al. 2013; Turesky et al. 1999; Turesky et al. 1998; Williams et al. 2000) |
| 2-AF | 1B1 | Arylamine | Hydroxylation, N- (weaker activation) | 23432465, 27123158 | (Chun and Kim 2016; Shimada et al. 2013) |
| 2-Amino-6-methyldipyrido[1,2-a,3,2’-d]-imidazole (Glu-P-1) | 1A2 | Heterocyclic amine | Hydroxylation, N- (high activity, major enzyme, activation) | 7955101, 9705755, 10503887, 10517985, 11377247, 2803520, 14744142, 14725854 | (Aoyama et al. 1989; Guengerich et al. 1999; Kim and Guengerich 2004; Oda et al. 2001; Shimada et al. 1994; Turesky et al. 1999; Turesky et al. 1998; Zhou et al. 2004) |
| 2-Amino-3-methylimidazo[4,5-f]quinoline (IQ) | 2A13 | Heterocyclic amine | Activation | 23432465 | (Shimada et al. 2013) |
| IQ | 2A6 | Heterocyclic amine | Activation (weaker activation) | 23432465 | (Shimada et al. 2013) |
| IQ | 2W1 | Heterocyclic amine | Activation | 24278521 | (Eun et al. 2010) |
| IQ | 1B1 | Heterocyclic amine | Activation | 23432465, 27123158 | (Chun and Kim 2016; Shimada et al. 2013) |
| IQ | 1A1 | Heterocyclic amine | Hydroxylation, N- (activation) | 7955101, 9705755, 8200083, 11377247, 11473383, 9918136, 8095200 | (Edwards et al. 1994; Guengerich 1993; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 1994; Turesky et al. 1998; Williams et al. 1998) |
| IQ | 1A2 | Heterocyclic amine | Hydroxylation, N- (high activity, major enzyme, activation) | 9675256, 7955101, 8200083, 11377247, 9111224, 9918136, 14744142, 14725854, 11038156 | (Barceló et al. 1998; Edwards et al. 1994; Hammons et al. 1997; Kim and Guengerich 2004; Miranda et al. 2000; Oda et al. 2001; Shimada et al. 1994; Williams et al. 1998; Zhou et al. 2004) |
| 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, PhIP | 2C9 | Heterocyclic amine | Hydroxylation, N2- (activation) | 11377247 | (Oda et al. 2001) |
| PhIP | 2D6 | Heterocyclic amine | Hydroxylation, N2- (activation) | 11377247 | (Oda et al. 2001) |
| PhIP | 2E1 | Heterocyclic amine | Hydroxylation, N2- (low or no activation) | 11377247 | (Oda et al. 2001) |
| PhIP | 1A1 | Heterocyclic amine | Hydroxylation, N2- (activation) | 11502724, 8961944, 9705755, 9855011, 8200083, 11377247, 11473383, 15279838, 9111224, 8095200 | (Crofts et al. 1998; Edwards et al. 1994; Guengerich 1993; Hammons et al. 1997; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 2001a; Shou et al. 1996a; Turesky et al. 1998; Yamazaki et al. 2004) |
| PhIP | 1A2 | Heterocyclic amine | Hydroxylation, N2- (high activity, major enzyme, major reaction, activation) | 1913651, 7955101, 9705755, 8200083, 11377247, 11473383, 10220313, 11258970, 11453738, 12351158, 14725854, 15279838, 16167840 | (Cheung et al. 2005a; Edwards et al. 1994; Josephy et al. 2001; Langouët et al. 2001; Oda et al. 2001; Parikh et al. 1999; Shimada et al. 1994; Shimada and Guengerich 1991; Turesky et al. 1998; Turesky et al. 2002; Turesky et al. 2001; Yamazaki et al. 2004; Zhou et al. 2004) |
| PhIP | 1B1 | Heterocyclic amine | Hydroxylation, N2- (activation) | 8961944, 11502724, 9855011, 10964100, 11377247, 11473383, 9328177 | (Crofts et al. 1997; Crofts et al. 1998; Josephy et al. 2001; Oda et al. 2001; Shimada et al. 2001a; Shou et al. 1996a; Williams et al. 2000) |
| PhIP | 1B1 | Heterocyclic amine | Hydroxylation, N2- and deamination (activation) | 9855011, 9328177, 27123158 | (Chun and Kim 2016; Crofts et al. 1997; Crofts et al. 1998) |
| Aniline reaction with norharman | 1A1 | Arylamine | Aminophenylnorharman formation (activation), high activity | 15279827 | (Nishigaki et al. 2004) |
| Aniline reaction with norharman | 1A2 | Arylamine | Aminophenylnorharman formation, activation, major enzyme | 15279827 | (Nishigaki et al. 2004) |
| Aniline reaction with norharman | 1B1 | Arylamine | Aminophenylnorharman formation, activation, very low activity | 15279827 | (Nishigaki et al. 2004) |
| Aniline reaction with norharman | 2B6 | Arylamine | Aminophenylnorharman formation, activation, very low activity | 15279827 | (Nishigaki et al. 2004) |
| Aniline reaction with norharman | 2D6 | Arylamine | Aminophenylnorharman formation, activation | 15279827 | (Nishigaki et al. 2004) |
| Aniline reaction with norharman | 2E1 | Arylamine | Aminophenylnorharman formation, activation, very low activity | 15279827 | (Nishigaki et al. 2004) |
| Aniline reaction with norharman | 3A4 | Arylamine | Aminophenylnorharman formation, activation, major enzyme | 15279827 | (Nishigaki et al. 2004) |
| Azinphos-methyl | 2C19 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, medium Km, high activity | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Azinphos-methyl | 1A1 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, medium Km, medium activity | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Azinphos-methyl | 1A2 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, medium Km, medium activity | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Azinphos-methyl | 2B6 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, medium Km, medium activity | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Azinphos-methyl | 2C19 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, medium Km, high activity | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Azinphos-methyl | 2C8 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, very low activity | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Azinphos-methyl | 2C9 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, very low activity | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Azinphos-methyl | 3A4 | Insecticide, organophosphate, benzotriazine organothiophosphate | Desulfuration (oxon formation), activation, very low activity, at higher concentrations | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Benzo[a]anthracene-3,4-diol | 1A1 | Polycyclic aromatic hydrocarbon (PAH) metabolite | Activation (weaker) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Benzo[a]anthracene-3,4-diol | 1A2 | PAH metabolite | Activation (weaker) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| trans-Benz[a]anthracene-3,4-diol | 2W1 | PAH metabolite | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| Benzo[g]chrysene-11,12-diol | 1A1 | PAH metabolite | Activation | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Benzo[g]chrysene-11,12-diol | 1B1 | PAH metabolite | Activation | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Benzo[g]chrysene-11,12-diol | 1A2 | PAH metabolite | Activation (weaker) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Benzo[b]fluoranthene-9,10-diol | 1A2 | PAH metabolite | Oxidation (activation) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Benzo[b]fluoranthene-9,10-diol | 2B6 | PAH metabolite | Oxidation (activation) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Benzo[b]fluoranthene-9,10-diol | 2C19 | PAH metabolite | Oxidation (activation) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Benzo[c]phenanthrene (B[c]P) | 2A13 | PAH | Activation (weaker) | 23432465 | (Shimada et al. 2013) |
| B[c]P | 2A6 | PAH | Activation (weaker) | 23432465 | (Shimada et al. 2013) |
| B[c]P | 1A1 | PAH | 3,4-Dihydrodiol-1,2-epoxide formation (weaker activation) | 9168260, 21781864, 11409939 | (Baum et al. 2001; Einolf et al. 1997; Seidel et al. 1998) |
| B[c]P | 1A2 | PAH | 3,4-Dihydrodiol-1,2-epoxide formation (major enzyme, activation) | 9168260, 21781864, 11409939 | (Baum et al. 2001; Einolf et al. 1997; Seidel et al. 1998) |
| B[c]P | 1B1 | PAH | 3,4-Dihydrodiol-1,2-epoxide formation (major enzyme, activation) | 9168260, 21781864, 11409939, 23432465 | (Baum et al. 2001; Einolf et al. 1997; Seidel et al. 1998; Shimada et al. 2013) |
| Benzo[c]phenanthrene 3,4-dihydrodiol (B[c]P-3,4-diol) | 1A2 | PAH metabolite | Activation (weak) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| B[c]P-3,4-diol | 1A1 | PAH metabolite | Activation (weaker) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| B[c]P-3,4-diol | 1B1 | PAH metabolite | Activation (weaker) | 14720319, 23432465, 27123158 | (Chun and Kim 2016; Shimada and Fujii-Kuriyama 2004; Shimada et al. 2013) |
| B[c]P-3,4-diol | 2A13 | PAH metabolite | Activation (weak) | 23432465 | (Shimada et al. 2013) |
| B[c]P-3,4-diol | 2A6 | PAH metabolite | Activation (weak) | 23432465 | (Shimada et al. 2013) |
| Benzo[a]pyrene (B[a]P) | 1A1 | PAH | trans-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation (activation) | 17640999, 14720319, 19330882 | (Kabler et al. 2009; Kim et al. 2007; Shimada and Fujii-Kuriyama 2004) |
| B[a]P | 1B1 | PAH | trans-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation. (medium Km, high activity, high efficiency, activation) | 8674051, 9721189, 11502724, 12584184, 9806168, 12628515, 23432465, 14720319, 27123158 | (Buters et al. 2003; Chun and Kim 2016; Guengerich et al. 2003; Kim et al. 1998; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1996; Shimada et al. 2013; Shimada et al. 2001a; Shimada et al. 1998) |
| (±)-Benzo[a]pyrene (B[a]P)-7,8-dihydrodiol | 2W1 | PAH metabolite | Oxidation (activation) | 16551781 | (Wu et al. 2006) |
| (±)-B[a]P-7,8-dihydrodiol | 1A1 | PAH metabolite | Oxidation, diol-epoxide formation (high activation) | 11952781, 21028851, 11502724, 14720319, 29219051, 18402469, 15720144, 16411658, 17295519 | (Gelhaus et al. 2011; Jiang et al. 2005; Jiang et al. 2006; Kisselev et al. 2002; Quinn and Penning 2008; Rendic and Guengerich 2018; Ruan et al. 2007; Shimada and Fujii-Kuriyama 2004; Shimada et al. 2001a) |
| (±)-B[a]P-7,8-dihydrodiol | 1B1 | PAH metabolite | Oxidation, diol-epoxide formation (high activation) | 16551781, 21028851, 11502724, 14720319, 29219051, 18402469, 15720144, 16411658, 17295519 | (Gelhaus et al. 2011; Jiang et al. 2005; Jiang et al. 2006; Quinn and Penning 2008; Rendic and Guengerich 2018; Ruan et al. 2007; Shimada and Fujii-Kuriyama 2004; Shimada et al. 2001a; Wu et al. 2006) |
| cis-(−)-B[a]P-7,8-dihydrodiol | 1A1 | PAH metabolite | cis-(syn)-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation (trans-diol epoxide formation), high activation | 14720319, 29219051 | (Rendic and Guengerich 2018; Shimada and Fujii-Kuriyama 2004) |
| cis-(−)-B[a]P-7,8-dihydrodiol | 1B1 | PAH metabolite | cis-(syn)-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation (trans-diol epoxide formation), high activation | 14720319, 29219051 | (Rendic and Guengerich 2018; Shimada and Fujii-Kuriyama 2004) |
| trans-(−)-B[a]P-7,8-dihydrodiol | 3A7 | PAH metabolite | Oxidation (activation) | 9328287 | (Gillam et al. 1997) |
| trans-(−)-B[a]P-7,8-dihydrodiol | 1A1 | PAH metabolite | trans-(anti)-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation (trans-diol epoxide formation), medium Km, high activity | 7955101, 9152602, 8961944, 11502724, 15720144, 17295519, 9014198, 8043197, 1551116, 11238186, 7581497, 11952781, 12670496, 14633740, 19330882 | (Doehmer et al. 1995; Gautier et al. 1996; Jiang et al. 2005; Kabler et al. 2009; Kisselev et al. 2002; Ruan et al. 2007; Schwarz et al. 2001; Schwarz et al. 2003; Schwarz and Roots 2003; Shimada et al. 1994; Shimada et al. 1997b; Shimada et al. 2001a; Shou et al. 1996a; Shou et al. 1994; Yun et al. 1992) |
| trans-(−)-B[a]P-7,8-dihydrodiol | 1B1 | PAH metabolite | trans-(anti)-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation (trans-diol epoxide formation), low Km, high activity | 9152602, 10426814, 12807732, 15720144, 15861043, 16411658, 17295519 | (Jiang et al. 2005; Jiang et al. 2006; Mammen et al. 2005; Mammen et al. 2003; Ruan et al. 2007; Shimada et al. 1997b; Shimada et al. 1999) |
| trans-(+)-B[a]P-7,8-dihydrodiol | 3A7 | PAH metabolite | Oxidation (activation) | 9328287 | (Gillam et al. 1997) |
| trans-(+)-B[a]P-7,8-dihydrodiol | 2A13 | PAH metabolite | Oxidation (activation) | 23432465 | (Shimada et al. 2013) |
| trans-(+)-B[a]P-7,8-dihydrodiol | 2A6 | PAH metabolite | Oxidation (weak activation) | 23432465 | (Shimada et al. 2013) |
| trans-(+)-B[a]P-7,8-dihydrodiol | 1B1 | PAH metabolite | Oxidation, trans-(anti)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation (trans-diol epoxide formation), high efficiency activation | 23432465, 14720319, 29219051 | (Rendic and Guengerich 2018; Shimada and Fujii-Kuriyama 2004; Shimada et al. 2013) |
| trans-(+)-B[a]P-7,8-dihydrodiol | 1A1 | PAH metabolite | trans-(anti)-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro formation (trans-diol epoxide formation), medium Km, high activity, high efficiency activation | 7955101, 9152602, 8961944, 11502724, 15720144, 17295519, 9014198, 8043197, 1551116, 11238186, 7581497, 11952781, 12670496, 14633740, 14720319, 29219051, 19330882 | (Doehmer et al. 1995; Gautier et al. 1996; Jiang et al. 2005; Kabler et al. 2009; Kisselev et al. 2002; Rendic and Guengerich 2018; Ruan et al. 2007; Schwarz et al. 2001; Schwarz et al. 2003; Schwarz and Roots 2003; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1994; Shimada et al. 1997b; Shimada et al. 2001a; Shou et al. 1996a; Shou et al. 1994; Yun et al. 1992) |
| 1,3-Butadiene | 2A6 | Olefin | Butadiene monoxide (epoxybutene) formation (high activity, activation) | 8203896, 9016811, 8901879, 11397415, | (Bond and Medinsky 2001; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997) |
| 1,3-Butadiene | 1A2 | Olefin | Butadiene monoxide (epoxybutene) formation (activation) | 8203896, 9016811, 8901879, 11397415, 7586124 | (Bond and Medinsky 2001; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997; Seaton et al. 1995) |
| 1,3-Butadiene | 2B6 | Olefin | Butadiene monoxide (epoxybutene) formation (activation) | 8203896, 9016811, 8901879, 11397415, 7586124 | (Bond and Medinsky 2001; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997; Seaton et al. 1995) |
| 1,3-Butadiene | 2D6 | Olefin | Butadiene monoxide (epoxybutene) formation (activation) | 8203896, 9016811, 8901879, 11397415, 7586124 | (Bond and Medinsky 2001; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997; Seaton et al. 1995) |
| 1,3-Butadiene | 2E1 | Olefin | Butadiene monoxide (epoxybutene), (S)- and (R)- formation (high activity, activation, major enzyme) | 8203896, 9635416, 17298833 | (Boysen et al. 2007; Duescher and Elfarra 1994; Nieusma et al. 1998) |
| Butadiene monoxide (1,2-epoxy-3-butene) | 3A4 | Olefin, butadiene metabolite | Diepoxybutane (at high concentrations, activation) | 8203896, 9016811, 8901879, 11397415, 7586124 | (Bond and Medinsky 2001; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997; Seaton et al. 1995) |
| Butadiene monoxide (1,2-epoxy-3-butene) | 2A6 | Olefin, butadiene metabolite | Diepoxybutane, meso- (major) and (±)- formation (activation) | 8203896, 9016811, 8901879, 11397415, 7586124 | (Bond and Medinsky 2001; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997; Seaton et al. 1995) |
| Butadiene monoxide (1,2-epoxy-3-butene) | 2C9 | Olefin, butadiene metabolite | Diepoxybutane, meso- (major) and (±)- formation (activation) | 8203896, 9016811, 8901879, 11397415, 7586124 | (Bond and Medinsky 2001; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997; Seaton et al. 1995) |
| Butadiene monoxide (1,2-epoxy-3-butene) | 2E1 | Olefin, butadiene metabolite | Diepoxybutane, meso- (major) and (±)- formation (activation) | 8203896, 9016811, 8901879, 11397415, 7586124, 17298833 | (Bond and Medinsky 2001; Boysen et al. 2007; Duescher and Elfarra 1994; Elfarra et al. 1996; Krause and Elfarra 1997; Seaton et al. 1995) |
| Chloromethylindolines | 2W1 | Indoline | Oxidation (activation) | 27257736, 23589180 | (Guo et al. 2016; Travica et al. 2013) |
| Chlorpyrifos | 2C9 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, low activity | 11502728, 15764407 | (Sams et al. 2004; Tang et al. 2001) |
| Chlorpyrifos | 3A4 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, medium Km, major at high concentration (100 μM) | 11502728, 21782601, 12620367, 11714865, 15764407, 16757081, 17079358, 17110060, 10996483, 20709133 | (Buratti et al. 2006; Buratti et al. 2002; Buratti et al. 2003; Croom et al. 2010; Dai et al. 2001; Foxenberg et al. 2007; Mutch and Williams 2006; Sams et al. 2004; Sams et al. 2000; Tang et al. 2001) |
| Chlorpyrifos | 1A2 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation, major enzyme), activation, low Km, medium activity | 11502728, 21782601, 12620367, 16757081, 17079358 | (Buratti et al. 2002; Buratti et al. 2003; Foxenberg et al. 2007; Mutch and Williams 2006; Tang et al. 2001) |
| Chlorpyrifos | 2B6 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), major enzyme, activation, medium activity, low Km, high activity and major reaction at low concentrations | 11502728, 21782601, 12620367, 15764407, 16757081, 17079358, 29463407, 20709133, 22281205 | (Buratti et al. 2002; Buratti et al. 2003; Foxenberg et al. 2007; Mutch and Williams 2006; Tang et al. 2001) |
| Chlorpyrifos | 2C19 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, medium Km, medium to low activity | 11502728, 21782601, 15764407, 16757081, 17079358, 20709133 | (Buratti et al. 2002; Croom et al. 2010; Dai et al. 2001; Mutch and Williams 2006; Sams et al. 2004; Tang et al. 2001) |
| Chlorpyrifos | 2D6 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, low activity | 15764407, 16757081, 10996483 | (Buratti et al. 2002; Croom et al. 2010; Dai et al. 2001; Mutch and Williams 2006; Sams et al. 2004; Tang et al. 2001) |
| Chlorpyrifos | 3A5 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, medium Km, medium activity | 16757081, 17079358, 17110060, 17079358 | (Buratti et al. 2006; Foxenberg et al. 2007; Mutch and Williams 2006; Sams et al. 2004) |
| Chlorpyrifos | 2C8 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation | 16757081, 21782601 | (Buratti et al. 2002; Sams et al. 2004) |
| Chlorpyrifos | 3A7 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, medium Km, low activity | 17079358, 17110060 | (Buratti et al. 2006; Mutch and Williams 2006) |
| trans-Chrysene-1,2-diol | 1A2 | PAH, chrysene metabolite | Oxidation (weaker activation) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| trans-Chrysene-1,2-diol | 2W1 | PAH, chrysene metabolite | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| trans-Chrysene-1,2-diol | 1A1 | PAH, chrysene metabolite | Oxidation (activation) | 11502724, 8961944, 9152602, 14720319 | (Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997; Shimada et al. 2001a; Shou et al. 1996a) |
| trans-Chrysene-1,2-diol | 1B1 | PAH, chrysene metabolite | Oxidation (activation) | 8674051, 9721189, 11502724, 12584184, 9152602, 10426814, 9685642, 14720319 | (Buters et al. 2003; Guengerich and Shimada 1998; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997b; Shimada et al. 1996; Shimada et al. 2001a; Shimada et al. 1999; Shimada et al. 1998) |
| Diazinon | 3A5 | Insecticide, organophosphate, phosphorothioate | Desulfuration (oxon formation), activation, high activity | 16757081 | (Mutch and Williams 2006) |
| Diazinon | 1A1 | Insecticide, organophosphate, phosphorothioate | Desulfuration (oxon formation), activation, medium Km, medium activity | 21969518 | (Ellison et al. 2012) |
| Diazinon | 2E1 | Insecticide, organophosphate, phosphorothioate | Desulfuration (oxon formation), activation, low Km, medium activity, at lower concentration | 21782601, 12620367 | (Buratti et al. 2002; Buratti et al. 2003) |
| Diazinon | 2B6 | Insecticide, organophosphate, phosphorothioate | Desulfuration (oxon formation), activation, medium Km, medium to high activity | 21782601, 12620367, 11708902, 15764407, 16757081, 21969518 | (Buratti et al. 2002; Buratti et al. 2003; Dai et al. 2001a; Ellison et al. 2012; Kappers et al. 2001; Sams et al. 2004) |
| Diazinon | 2C19 | Insecticide, organophosphate, phosphorothioate | Desulfuration (oxon formation), activation, medium to high Km, medium to high activity, major enzyme | 21782601, 12620367, 16757081, 11708902, 21969518 | (Buratti et al. 2002; Buratti et al. 2003; Ellison et al. 2012; Kappers et al. 2001; Sams et al. 2004) |
| Diazinon | 1A2 | Insecticide, organophosphate, phosphorothioate | Desulfuration (oxon formation), activation, high Km, medium activity | 21782601, 12620367, 21969518 | (Buratti et al. 2002; Buratti et al. 2003; Ellison et al. 2012) |
| Diazinon | 3A4 | Insecticide, organophosphate, phosphorothioate | Desulfuration (oxon formation), activation, medium to high Km, high activity | 21782601, 12620367, 21969518 | (Buratti et al. 2002; Buratti et al. 2003; Ellison et al. 2012) |
| Dibenzo[b,k]fluoranthene | 1A1 | PAH | Oxidation (activation) | 10613181 | (Durant et al. 1999) |
| Dibenzo[a,l]pyrene (DB[a,l]P) (11R,12R)-dihydrodiol | 1A2 | PAH metabolite | Activation (weaker) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| Dibenzo[a,l]pyrene (DB[a,l]P) | 1A2 | PAH | (−)-syn- and (−)-anti-11,12-dihydrodiol-13,14-epoxide form. (medium Km, high activity, high efficiency, activation) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| DB[a,l]P | 2W1 | PAH | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| DB[a,l]P | 1B1 | PAH | (−)-syn- and (−)-anti-11,12-dihydrodiol-13,14-epoxide formation (medium Km, high activity, high efficiency, activation) | 8674051, 9721189, 11502724, 12584184, 9152602, 9625737, 10506751, 8968059, 9354437, 17623886, 12628515, 14720319, 27123158 | (Buters et al. 2003; Chun and Kim 2016; Guengerich et al. 2003; King et al. 1999; Luch et al. 1998; Mahadevan et al. 2007; Shimada et al. 1997a; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997b; Shimada et al. 1996; Shimada et al. 2001a; Shimada et al. 1998; Shou et al. 1996c) |
| DB[a,l]P | 1A1 | PAH | (−)-syn- and (−)-anti-11,12-dihydrodiol-13,14-epoxide formation (medium Km, high activity, high efficiency, activation) | 8961944, 9152602, 10207125, 10493514, 10506751, 8968059, 10613181, 14720319, 19330882 | (Durant et al. 1999; Kabler et al. 2009; King et al. 1999; Luch et al. 1999a; Luch et al. 1999b; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997b; Shou et al. 1996a; Shou et al. 1996c) |
| trans-DB[a,l]P-11,12-diol | 2W1 | PAH metabolite | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| trans-(−)-DB[a,l]P-(11R,12R)-diol | 1A1 | PAH metabolite | (−)-anti- and (+)-syn-11,12-dihydrodiol-13,14-epoxide formation (medium Km, high activity, activation) | 7955101, 8961944, 11502724, 10207125, 10493514, 14720319 | (Luch et al. 1999a; Luch et al. 1999b; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1994; Shimada et al. 2001a; Shou et al. 1996a) |
| trans-(−)-DB[a,l]P-(11R,12R)-diol | 1B1 | PAH metabolite | (−)-anti-11,12-Dihydrodiol-13,14-epoxide formation (medium Km, high activity, high efficiency, activation) | 8674051, 9721189, 11502724, 12584184, 9625737, 10207125, 10493514, 10506751, 10739169, 11465393, 9354437, 10426814, 12628515, 14720319 | (Buters et al. 2003; Guengerich et al. 2003; King et al. 1999; Luch et al. 1998; Luch et al. 1999a; Luch et al. 1999b; Shimada et al. 1997a; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1996; Shimada et al. 2001a; Shimada et al. 2001b; Shimada et al. 1999; Shimada et al. 1998; Watanabe et al. 2000) |
| trans-2,3-Dihydroxy-2,3-dihydrofluoranthene | 1B1 | PAH metabolite | Oxidation (activation) | 8674051, 9721189, 11502724, 12584184, 9685642 | (Buters et al. 2003; Guengerich and Shimada 1998; Shimada et al. 1996; Shimada et al. 2001a; Shimada et al. 1998) |
| 7,12-Dimethylbenz[a]anthracene (7,12-DMBA) | 2W1 | PAH | Oxidation (activation) | 16551781 | (Wu et al. 2006) |
| 7,12-DMBA | 1B1 | PAH | Oxidation (low Km, high activity and efficiency, activation) | 11502724, 8674051, 9152602, 27123158 | (Chun and Kim 2016; Shimada et al. 1997b; Shimada et al. 1996; Shimada et al. 2001a) |
| 7,12-DMBA | 1B1 | PAH | Oxidation (activation) | 23432465, 27123158 | (Chun and Kim 2016; Shimada et al. 2013) |
| 7,12-DMBA | 1A1 | PAH | Oxidation (low Km, high activity and efficiency, activation) | 7955101, 8961944, 11502724, 10575002 | (Ciolino and Yeh 1999; Shimada et al. 1994; Shimada et al. 2001a; Shou et al. 1996a) |
| 7,12-DMBA | 1A1 | PAH | Oxidation (low Km, high activity and efficiency, activation) | 7955101, 8961944, 11502724, 9152602, 23432465 | (Shimada et al. 1994; Shimada et al. 1997b; Shimada et al. 2013; Shimada et al. 2001a; Shou et al. 1996a) |
| 7,12-DMBA | 1B1 | PAH | Oxidation (activation) | 8674051, 11502724 | (Shimada et al. 1996; Shimada et al. 2001a) |
| trans-7,12-DMBA-3,4-diol | 1A2 | PAH metabolite | Oxidation (weaker activation) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| trans-7,12-DMBA-3,4-diol | 2W1 | PAH metabolite | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| trans-7,12-DMBA-3,4-diol | 2A13 | PAH metabolite | Activation | 23432465 | (Shimada et al. 2013) |
| trans-7,12-DMBA-3,4-diol | 1A1 | PAH metabolite | 3,4-Dihydrodiol-1,2-epoxide formation (medium Km, high activity, high efficiency activation) | 11502724, 9152602, 11360624, 8989918, 9685642, 14720319 | (Guengerich and Shimada 1998; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997b; Shimada et al. 2001a; Shou et al. 1996b; Wu et al. 1997) |
| trans-7,12-DMBA-3,4-diol | 1B1 | PAH metabolite | 3,4-Dihydrodiol-1,2-epoxide formation (medium Km, high activity, high efficiency activation) | 8674051, 9721189, 11502724, 12584184, 9152602, 10426814, 23432465, 14720319 | (Buters et al. 2003; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997b; Shimada et al. 1996; Shimada et al. 2013; Shimada et al. 2001a; Shimada et al. 1999; Shimada et al. 1998) |
| 5,6-Dimethylchrysene-1,2-diol | 1A1 | PAH metabolite | Oxidation (activation) | 7955101, 8961944, 11502724, 9152602, 16946553, 14720319 | (Shimada 2006; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1994; Shimada et al. 1997b; Shimada et al. 2001a; Shou et al. 1996a) |
| trans-5,6-Dimethylchrysene-1,2-diol | 2W1 | PAH metabolite | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| trans-5,6-Dimethylchrysene-1,2-diol | 1A2 | PAH metabolite | Oxidation (activation) | 7955101, 8961944, 16946553, 14720319 | (Shimada 2006; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1994; Shou et al. 1996a) |
| trans-5,6-Dimethylchrysene-1,2-diol | 1B1 | PAH metabolite | Oxidation (activation) | 8674051, 9721189, 11502724, 12584184, 9152602, 10426814, 9685642, 14720319 | (Buters et al. 2003; Guengerich and Shimada 1998; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997b; Shimada et al. 1996; Shimada et al. 2001a; Shimada et al. 1999; Shimada et al. 1998) |
| N,N-Dimethylformamide (DMF) | 2E1 | Organic solvent | N-Demethylation (high activity, activation) | 1538706, 8477011, 11684354 | (Amato et al. 2001; Hyland et al. 1992; Mráz et al. 1993) |
| N-Hydroxymethyl, N-methylformamide, | 2E1 | Organic solvent, dimethylformamide metabolite | Demethylation, N- (high activity, activation) | 1538706, 8477011, 11684354 | (Amato et al. 2001; Hyland et al. 1992; Mráz et al. 1993) |
| 3-Methoxy-4-aminoazobenzene | 2W1 | Azoarylamine | Oxidation (activation) | 16379042 | (Turesky et al. 1998) |
| 3-Methylcholanthrene | 1A1 | PAH | Oxidation (activation) | 11360624, 14720319 | (Shimada and Fujii-Kuriyama 2004; Wu et al. 1997) |
| 5-Methylchrysene | 1A1 | PAH | Oxidation (medium Km, high activity, high efficiency, activation) | 7955101, 8961944, 11502724, 27123158 | (Chun and Kim 2016; Shimada et al. 1994; Shimada et al. 2001a; Shou et al. 1996a) |
| 3-Methylchrysene-1,2-diol | 1A1 | PAH metabolite | Activation | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| 3-Methylchrysene-1,2-diol | 1B1 | PAH metabolite | Activation | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| 3-Methylchrysene-1,2-diol | 1A2 | PAH metabolite | Activation (weaker) | 14720319 | (Shimada and Fujii-Kuriyama 2004) |
| trans-5-Methylchrysene-1,2-diol | 2W1 | PAH metabolite | Oxidation (activation) | 16379042 | (Brandon et al. 2006) |
| trans-5-Methylchrysene-1,2-diol | 2A6 | PAH metabolite | Oxidation (medium Km, high activity, high efficiency activation) | 23432465, 14720319 | (Shimada and Fujii-Kuriyama 2004; Shimada et al. 2013) |
| trans-5-Methylchrysene-1,2-diol | 2A13 | PAH metabolite | Oxidation (medium Km, high activity, high efficiency activation) | 23432465, 14720319 | (Shimada and Fujii-Kuriyama 2004; Shimada et al. 2013) |
| trans-5-Methylchrysene-1,2-diol | 1A1 | PAH metabolite | Oxidation (medium Km, high activity, high efficiency activation) | 7955101, 11502724, 9152602, 16485905, 16946553 | (Shimada 2006; Shimada et al. 1994; Shimada et al. 1997b; Shimada and Guengerich 2006; Shimada et al. 2001a) |
| trans-5-Methylchrysene-1,2-diol | 1B1 | PAH metabolite | Oxidation (medium Km, high activity, high efficiency activation) | 8674051, 9721189, 11502724, 12584184, 10426814, 9152602, 16485905, 9685642, 23432465, 14720319 | (Buters et al. 2003; Guengerich and Shimada 1998; Shimada and Fujii-Kuriyama 2004; Shimada et al. 1997b; Shimada and Guengerich 2006; Shimada et al. 1996; Shimada et al. 2013; Shimada et al. 2001a; Shimada et al. 1999; Shimada et al. 1998) |
| N-Nitrosodi-n-propylamine | 3A4 | Nitrosamine | Depropylation, N- (medium Km, high activity, medium efficiency, activation) | 10910959 | (Teiber and Hollenberg 2000) |
| Parathion | 2C9 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, medium Km, medium activity | 17079358 | (Foxenberg et al. 2007) |
| Parathion | 1A1 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, medium Km, low activity | 10414794, 21969518 | (Ellison et al. 2012; Mutch et al. 1999) |
| Parathion | 2A6 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation | 10794390, 12669189 | (Eaton 2000; Mutch et al. 2003) |
| Parathion | 3A5 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, medium Km, medium activity | 10794390, 12669189, 10414794, 17079358, 17110060 | (Buratti et al. 2006; Eaton 2000; Foxenberg et al. 2007; Mutch et al. 1999; Mutch et al. 2003) |
| Parathion | 2B6 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, low Km, medium to high activity | 10794390, 12669189, 10414794, 21782601, 12620367, 16757081, 17079358, 21969518 | (Buratti et al. 2002; Buratti et al. 2003; Eaton 2000; Ellison et al. 2012; Foxenberg et al. 2007; Mutch et al. 1999; Mutch et al. 2003; Mutch and Williams 2006) |
| Parathion | 1A2 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, low or medium Km, high activity | 10794390, 12669189, 21782601, 12620367, 16757081, 17079358, 21969518 | (Buratti et al. 2002; Buratti et al. 2003; Eaton 2000; Ellison et al. 2012; Foxenberg et al. 2007; Mutch et al. 2003; Mutch and Williams 2006) |
| Parathion | 2C19 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, low Km, medium activity | 10794390, 12669189, 21782601, 16757081, 17079358, 21969518 | (Buratti et al. 2002; Eaton 2000; Ellison et al. 2012; Foxenberg et al. 2007; Mutch et al. 2003; Mutch and Williams 2006) |
| Parathion | 2E1 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, very low activity | 10794390, 12669189,16757081 | (Eaton 2000; Mutch et al. 2003) |
| Parathion | 2D6 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation and 4-nitrophenol (p-nitrophenol) formation | 10794390, 12669189, 16757081, 10996483 | (Eaton 2000; Mutch et al. 2003; Mutch and Williams 2006; Sams et al. 2000) |
| Parathion | 3A7 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation | 17110060, 17079358 | (Buratti et al. 2006; Foxenberg et al. 2007) |
| Parathion | 2C8 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation | 21782601, 10794390, 12669189, 10414794, 16757081 | (Buratti et al. 2002; Eaton 2000; Mutch et al. 1999; Mutch et al. 2003; Mutch and Williams 2006) |
| Parathion | 3A4 | Insecticide, organophosphate and acaricide, dicarboximide | Desulfuration (oxon formation), activation, major enzyme, high Km, high activity | 9023313, 10794390, 12669189, 10414794, 21782601, 12620367, 17079358, 17110060, 10996483 | (Buratti et al. 2006; Buratti et al. 2002; Buratti et al. 2003; Butler and Murray 1997; Eaton 2000; Foxenberg et al. 2007; Mutch et al. 1999; Mutch et al. 2003; Sams et al. 2000) |
| 3-(N-Phenylamino)propane-1,2-diol (PAP) | 2C18 | Toxic oil compound | Hydroxylation (aromatic), high Km, high activity, activation | 17672514 | (Martínez-Cabot et al. 2007) |
| PAP | 2C8 | Toxic oil compound | Hydroxylation (aromatic), high Km, high activity, activation | 17672514 | (Martínez-Cabot et al. 2007) |
| PAP | 2C9 | Toxic oil compound | Hydroxylation (aromatic), high Km, high activity, activation | 17672514 | (Martínez-Cabot et al. 2007) |
| PAP | 2D6 | Toxic oil compound | Hydroxylation (aromatic), high Km, high activity, activation | 17672514 | (Martínez-Cabot et al. 2007) |
| 2,4,3´,5´-Tetramethoxystilbene | 1B1 | Cancer chemopreventive, trans-hydroxystilbene derivative | Oxidation (major enzyme, activation) | 16120791, 11719446 | (Chun et al. 2001; Chun et al. 2005) |