Application | Comment | Organism |
---|---|---|
agriculture | introduction of drought tolerance in apple seedlings, the 3R-isomer of the abscisic acid 8'-hydroxylase inhibitor abscinazole-F1 (3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol) has no growth-retardant effect on apple seedlings but induces stomatal closure and drought tolerance during dehydration at concentrations of 10, 50, and 100 microM (spray treatment) | Malus sylvestris |
Cloned (Comment) | Organism |
---|---|
recombinant truncated Arabidopsis enzyme (707A3d28, lack of putative membrane spanning segment at N-terminus), expressed in Escherichia coli BL21 | Arabidopsis thaliana |
truncated CYP707A3 (707A3d28), which lacks the putative membrane-spanning segment of the N-terminus, residues 3-28, coexpressed in Escherichia coli BL21 with Arabidopsis P450 reductase | Arabidopsis thaliana |
Inhibitors | Comment | Organism | Structure |
---|---|---|---|
(1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | 27% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
(1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | 27% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | 10% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | 10% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | 14% inhibition of recombinant enzyme with 10 microM inhibitor; inhibitory activity is much weaker than that of S-UNI | Arabidopsis thaliana | |
(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | 14% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8(6H)-one | 35% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8(6H)-one | 35% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[5,1-c][1,4]oxazin-8(6H)-one | 52% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[5,1-c][1,4]oxazin-8(6H)-one | 52% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[2,1-c][1,4]oxazin-8(6H)-one | - |
Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[5,1-c][1,4]oxazin-8(6H)-one | - |
Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 91% inhibition of recombinant enzyme with 10 microM inhibitor; abscinazole-F1, more than 50% inhibition at 0.01 mM, competitive inhibitor, is the most specific inhibitor against ABA 8'-hydroxylase, although it is not the strongest | Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 91% inhibition of recombinant enzyme with 10 microM inhibitor | Malus sylvestris | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 91% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine | 13% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine | 13% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | 100% inhibition of recombinant enzyme with 10 microM inhibitor; competitive inhibitor | Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol | 69% inhibition of recombinant enzyme with 10 microM inhibitor; more than 50% inhibition at 0.01 mM | Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol | 69% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine | 31% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine | 31% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 95% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 95% inhibition of recombinant enzyme with 10 microM inhibitor | Malus sylvestris | |
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 95% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 96% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 96% inhibition of recombinant enzyme with 10 microM inhibitor | Malus sylvestris | |
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | abscinazole-F1, 96% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | R-(+)-uniconazole, 79% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | R-(+)-uniconazole, 79% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | 87% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | 87% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | S-(+)-uniconazole, 100% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | S-(+)-uniconazole, 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Malus sylvestris | |
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | S-(+)-uniconazole, 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | 100% inhibition of recombinant enzyme with 10 microM inhibitor | Arabidopsis thaliana | |
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor | Oryza sativa | |
uniconazole | - |
Arabidopsis thaliana |
KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
0.0034 | - |
(+)-abscisic acid | 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C | Arabidopsis thaliana |
Localization | Comment | Organism | GeneOntology No. | Textmining |
---|---|---|---|---|
microsome | - |
Arabidopsis thaliana | - |
- |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 | Arabidopsis thaliana | - |
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 | Oryza sativa | - |
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 | Malus sylvestris | - |
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Arabidopsis thaliana | - |
- |
- |
Arabidopsis thaliana | - |
enzyme from recombinant Escherichia coli | - |
Malus sylvestris | - |
apple variant domestica, 90 days old seedlings | - |
Oryza sativa | - |
rice cultivar Nipponbare, length of second leaf sheath of 7 days old seedlings grown in test solution | - |
Purification (Comment) | Organism |
---|---|
recombinant enzyme production is induced, cells centrifuged, pellets resuspended in buffer A (50 mM potassium phosphate buffer, pH 7.25, 20% glycerol, 1 mM EDTA, 0.1 mM dithiothreitol), sonicated, centrifuged, supernatants collected | Arabidopsis thaliana |
Source Tissue | Comment | Organism | Textmining |
---|
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
(+)-S-abscisate + [reduced NADPH-hemoprotein reductase] + O2 | - |
Arabidopsis thaliana | 8'-hydroxyabscisate + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Arabidopsis thaliana | 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Oryza sativa | 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Malus sylvestris | 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 | - |
Arabidopsis thaliana | 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O | for inhibitor studies the decrease in production of phaseic acid is measured | ? |
Synonyms | Comment | Organism |
---|---|---|
ABA 8'-hydroxylase | - |
Arabidopsis thaliana |
ABA 8'-hydroxylase | - |
Oryza sativa |
ABA 8'-hydroxylase | - |
Malus sylvestris |
abscisic acid 8'-hydroxylase | - |
Arabidopsis thaliana |
abscisic acid 8'-hydroxylase | - |
Oryza sativa |
abscisic acid 8'-hydroxylase | - |
Malus sylvestris |
CYP707A | - |
Arabidopsis thaliana |
CYP707A3 | - |
Arabidopsis thaliana |
Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
---|---|---|---|---|---|
0.00001 | - |
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme | Arabidopsis thaliana | |
0.00016 | - |
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme | Arabidopsis thaliana | |
0.00042 | - |
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme | Arabidopsis thaliana | |
0.00042 | - |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | 3R-enantiomer, pH 7.25, 30°C | Arabidopsis thaliana | |
0.00052 | - |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[5,1-c][1,4]oxazin-8(6H)-one | 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme | Arabidopsis thaliana | |
0.00097 | - |
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme | Arabidopsis thaliana | |
0.00097 | - |
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | 3S-enantiomer, pH 7.25, 30°C | Arabidopsis thaliana | |
0.00145 | - |
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C | Arabidopsis thaliana |
IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
---|---|---|---|---|---|
additional information | - |
3R-isomer abscinazole-F1 (3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol) has no growth-retardant effect on apple seedlings but induces stomatal closure and drought tolerance during dehydration at concentrations of 10, 50, and 100 microM (spray treatment) in contrast to uniconazole (S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol) which has growth-retardant effects | Malus sylvestris | additional information | |
additional information | - |
no inhibition of rice seedling growth (second leaf sheath length) with (E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[2,1-c][1,4]oxazin-8(6H)-one, (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol, 3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol, 3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol | Oryza sativa | additional information | |
0.00018 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | |
0.0013 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | |
0.0023 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | |
0.0032 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol | |
0.0078 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol | |
0.0082 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | |
0.009 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | |
0.012 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine | |
0.028 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine | |
0.046 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol | |
0.058 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine | |
0.078 | - |
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium | Oryza sativa | (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine |
General Information | Comment | Organism |
---|---|---|
metabolism | key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events) | Arabidopsis thaliana |
metabolism | key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events) | Oryza sativa |
metabolism | key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events) | Malus sylvestris |