BRENDA - Enzyme Database show
show all sequences of 1.14.14.137

Abscinazole-F1, a conformationally restricted analogue of the plant growth retardant uniconazole and an inhibitor of ABA 8-hydroxylase CYP707A with no growth-retardant effect

Todoroki, Y.; Kobayashi, K.; Shirakura, M.; Aoyama, H.; Takatori, K.; Nimitkeatkai, H.; Jin, M.H.; Hiramatsu, S.; Ueno, K.; Kondo, S.; Mizutani, M.; Hirai, N.; Bioorg. Med. Chem. 17, 6620-6630 (2009)

Data extracted from this reference:

Application
Application
Commentary
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(Commentary)
Commentary
Organism
recombinant truncated Arabidopsis enzyme (707A3d28, lack of putative membrane spanning segment at N-terminus), expressed in Escherichia coli BL21; 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
Inhibitors
Commentary
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 [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0034
-
(+)-abscisic acid
50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30C
Arabidopsis thaliana
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Arabidopsis thaliana
-
-
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
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
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
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 (Commentary)
Commentary
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
Source Tissue
Commentary
Organism
Textmining
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(+)-S-abscisate + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Arabidopsis thaliana
8'-hydroxyabscisate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Arabidopsis thaliana
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Oryza sativa
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Malus sylvestris
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Arabidopsis thaliana
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
for inhibitor studies the decrease in production of phaseic acid is measured
-
-
?
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
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, 30C, 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, 30C, 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, 30C, 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, 30C
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, 30C, 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, 30C, 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, 30C
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, 30C
Arabidopsis thaliana
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
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
Application (protein specific)
Application
Commentary
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(Commentary) (protein specific)
Commentary
Organism
recombinant truncated Arabidopsis enzyme (707A3d28, lack of putative membrane spanning segment at N-terminus), expressed in Escherichia coli BL21; 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
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
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
Inhibitors (protein specific)
Inhibitors
Commentary
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
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
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, 30C, 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, 30C, 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, 30C, 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, 30C
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, 30C, 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, 30C, 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, 30C
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, 30C
Arabidopsis thaliana
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0034
-
(+)-abscisic acid
50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30C
Arabidopsis thaliana
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Arabidopsis thaliana
-
-
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
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
-
-
?
Purification (Commentary) (protein specific)
Commentary
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 (protein specific)
Source Tissue
Commentary
Organism
Textmining
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(+)-S-abscisate + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Arabidopsis thaliana
8'-hydroxyabscisate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Arabidopsis thaliana
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Oryza sativa
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Malus sylvestris
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
696761
Arabidopsis thaliana
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
for inhibitor studies the decrease in production of phaseic acid is measured
-
-
?
General Information
General Information
Commentary
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)
Malus sylvestris
metabolism
key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events)
Oryza sativa
General Information (protein specific)
General Information
Commentary
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)
Malus sylvestris
metabolism
key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events)
Oryza sativa
Other publictions for EC 1.14.14.137
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
745629
Sales
-
Salt tolerance in apple seedl ...
Malus domestica
J. Plant Growth Regul.
36
643-650
2017
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746096
Arbona
Depletion of abscisic acid le ...
Citrus sinensis x Citrus trifoliata
Plant Mol. Biol.
93
623-640
2017
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746066
Cai
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Characterization and expressi ...
Morus notabilis
Plant Cell Tissue Organ. Cult.
127
237-249
2016
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746158
Son
Abscisic acid metabolic genes ...
Triticum aestivum
Planta
244
429-447
2016
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746462
Takeuchi
Abscinazole-E3M, a practical ...
Arabidopsis thaliana
Sci. Rep.
6
37060
2016
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1
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12
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5
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746269
Liu
Cloning and expression analys ...
Arachis hypogaea
PLoS ONE
9
e97025
2014
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727261
Chono
Isolation of a wheat (Triticum ...
Triticum aestivum
Breed. Sci.
63
104-115
2013
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728206
Suttle
Wounding of potato tubers indu ...
Solanum tuberosum
J. Plant Physiol.
170
560-566
2013
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711477
Okazaki
Abscinazole-E1, a novel chemic ...
Arabidopsis thaliana
Bioorg. Med. Chem.
19
406-413
2011
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1
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5
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711425
Todoroki
Selectivity improvement of an ...
Arabidopsis thaliana
Bioorg. Med. Chem. Lett.
20
5506-5509
2010
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1
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8
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712862
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Cloning and expression analysi ...
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Induction of ABA 8'-hydroxylas ...
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