1.3.1.107	chelerythrine + NAD(P)H + H+	-	Eschscholzia californica	dihydrochelerythrine + NAD(P)+	-	?	430028	
1.3.1.107	dihydrochelirubine + NAD(P)+	key reaction of benzophenanthridine detoxification. Detoxifying the phytoalexin sanguinarine produced by Eschscholzia californica (California poppy) itself, when it binds to the cell wall of the poppy cell	Eschscholzia californica	chelirubine + NAD(P)H + H+	-	ir	427427	
1.3.1.107	dihydrochelirubine + NADP+	dihydrochelirubine i.e. 5-methoxy-13-methyl-13,14-dihydro-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium. At alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction	Eschscholzia californica	chelirubine + NADPH + H+	chelirubine i.e. 5-methoxy-13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium	ir	428573	
1.3.1.107	dihydrosanguinarine + NAD(P)+	key reaction of benzophenanthridine detoxification. Detoxifying the phytoalexin sanguinarine produced by Eschscholzia californica (California poppy) itself, when it binds to the cell wall of the poppy cell	Eschscholzia californica	sanguinarine + NAD(P)H + H+	-	ir	427429	
1.3.1.107	dihydrosanguinarine + NAD+	dihydrosanguinarine i.e. 13-methyl-13,14-dihydro-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine. At alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction	Eschscholzia californica	sanguinarine + NADH + H+	sanguinarine i.e. 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium	ir	428575	
1.3.1.107	dihydrosanguinarine + NADP+	dihydrosanguinarine i.e. 13-methyl-13,14-dihydro-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine. At alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction	Eschscholzia californica	sanguinarine + NADPH + H+	sanguinarine i.e. 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium	ir	428576	
1.3.1.107	additional information	catalytic mechanism is as follows: the alkanolamine form of sanguinarine is fixed in a binding pocket, mainly consisting of hydrophobic amino acids, by the conserved residue Ser153. Both dioxolane rings of the alkaloid are bound by a triad of H-bonds originating from Cys157 connected to Asp158 and His161 and by the side chain of Lys175. Electron transfer is initiated by attacking the C6 of sanguinarine with the hydride ion of NADPH and the OH group at C6 with a proton originating from Ser153. The anionic form of Ser is then stabilized by the NH3+ group of Lys175. Removal of OH- followed by water formation completes the reduction process	Eschscholzia californica	?	-	?	89	
1.3.1.107	sanguinarine + NADH + H+	sanguinarine is converted 1.3times faster than chelerythrine. The reduction cannot be reversed by increasing the product concentrations, i.e. even a hundredfold excess of NAD(P)+ does not cause a detectable oxidation of added dihydrosanguinarine	Eschscholzia californica	dihydrosanguinarine + NAD+	-	ir	430706	
1.3.1.107	sanguinarine + NADPH + H+	-	Eschscholzia californica	dihydrosanguinarine + NADP+	-	?	430707