Information on EC 1.14.13.93 - (+)-abscisic acid 8'-hydroxylase

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The expected taxonomic range for this enzyme is: Magnoliophyta

EC NUMBER
COMMENTARY hide
1.14.13.93
-
RECOMMENDED NAME
GeneOntology No.
(+)-abscisic acid 8'-hydroxylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(+)-abscisate + NADPH + H+ + O2 = 8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Carotenoid biosynthesis
-
-
phaseic acid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
abscisate,NADPH:oxygen oxidoreductase (8'-hydroxylating)
A heme-thiolate protein (P-450). Catalyses the first step in the oxidative degradation of abscisic acid and is considered to be the pivotal enzyme in controlling the rate of degradation of this plant hormone [1]. CO inhibits the reaction, but its effects can be reversed by the presence of blue light [1]. The 8'-hydroxyabscisate formed can be converted into (-)-phaseic acid, most probably spontaneously. Other enzymes involved in the abscisic-acid biosynthesis pathway are EC 1.1.1.288 (xanthoxin dehydrogenase), EC 1.2.3.14 (abscisic-aldehyde oxidase) and EC 1.13.11.51 (9-cis-epoxycarotenoid dioxygenase).
CAS REGISTRY NUMBER
COMMENTARY hide
153190-37-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
apple variant domestica, 90 days old seedlings
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
(+)-abscisic acid + NADPH + H+ + O2
phaseic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(+)-S-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
(+-)-3'-methyl-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
32% of the activity with (+)-S-abscisate
-
-
?
(+-)-abscisic acid-3'-thio-n-butyl thiol + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
2% of the activity with (+)-S-abscisate
-
-
?
(1'S)-(+)-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
the enzyme is active with the naturally occuring (1'S)-(+)-enantiomer, but not with the naturally not occuring enantiomer (1'R)-(-)-abscisic acid. The C4'-oxo moiety coupled to the C2'-C3'-double bond in the key functional group for the enzyme to distinguish (1'S)-(+)-abscisic acid from (1'R)-(-)-abscisic acid
-
-
?
(2Z,4E)-5-[(1R,6R)-1-hydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
a structural analogue of abscisic acid lacking the C6 methyl group and the alpha,beta-unsaturated carbonyl in the six-membered ring, synthesis, overview. Both enantiomers of this analogue bind to the enzyme
-
-
?
(2Z,4E)-5-[(1S,6S)-1-hydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
a structural analogue of abscisic acid lacking the C6 methyl group and the alpha,beta-unsaturated carbonyl in the six-membered ring, synthesis, overview. Both enantiomers of this analogue bind to the enzyme
-
-
?
1'-deoxy-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
99% of the activity with (+)-S-abscisate
-
-
?
1'-deoxy-1'-fluoro-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
94% of the activity with (+)-S-abscisate
-
-
?
2'alpha,3'alpha-dihydro-2'alpha,3'alpha-epoxy-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
19% of the activity with (+)-S-abscisate
-
-
?
3'-bromo-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
5% of the activity with (+)-S-abscisate
-
-
?
3'-chloro-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
19% of the activity with (+)-S-abscisate
-
-
?
3'-fluoro-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
68% of the activity with (+)-S-abscisate
-
-
?
6-nor-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
60% of the activity with (+)-S-abscisate
-
-
?
7'-methyl-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
15% of the activity with (+)-S-abscisate
-
-
?
7'-nor-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
15% of the activity with (+)-S-abscisate
-
-
?
8'-fluoro-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
11% of the activity with (+)-S-abscisate
-
-
?
8'-methylene-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
4% of the activity with (+)-S-abscisate
-
-
?
9',9'-difluoro-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
3% of the activity with (+)-S-abscisate
-
-
?
9'-fluoro-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
33% of the activity with (+)-S-abscisate
-
-
?
9'-methyl-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
3% of the activity with (+)-S-abscisate
-
-
?
S-(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisic acid + NADP+ + H2O
show the reaction diagram
S-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
(+)-abscisic acid + NADPH + H+ + O2
phaseic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(1'S)-(+)-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
the enzyme is active with the naturally occuring (1'S)-(+)-enantiomer, but not with the naturally not occuring enantiomer (1'R)-(-)-abscisic acid. The C4'-oxo moiety coupled to the C2'-C3'-double bond in the key functional group for the enzyme to distinguish (1'S)-(+)-abscisic acid from (1'R)-(-)-abscisic acid
-
-
?
S-(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisic acid + NADP+ + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
-
-
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-1'-methoxy-abscisate
-
competitive
(+)-8',8'-difluoroabscisate
-
competitive
(+)-8'-acetylene-abscisate
(+)-8'-cyano-abscisic acid
-
competitive
(+)-8'-ethyl-abscisic acid
-
competitive
(+)-8'-methylacetylene-abscisic acid
-
competitive
(+)-8'-methylene-abscisate
-
competitive
(+)-8'-propargyl-abscisate
-
competitive
(+)-9'-allyl-abscisate
-
suicide inhibitor
(+)-9'-propargyl-abscisate
-
suicide inhibitor
(+-)-3'-methyl-abscisate
-
competitive, 64% inhibition at 0.05 mM
(+-)-abscisic acid-3'-thio-n-butyl thiol
-
competitive, 51% inhibition at 0.05 mM
-
(-)-8'-propargyl-abscisate
-
competitive
(-)-9'-propargyl-abscisate
-
suicide inhibitor
(-)-AHI1
-
competitive inhibition
(1'R)-(-)-4'-deoxo-abscisic acid
-
competitive inhibition
(1'R)-(-)-6-nor-abscisic acid
-
competitive inhibition
(1'R,2'R)-(-)-2',3'-dihydro-4'-deoxo-abscisic acid
-
competitive inhibition
(1'S*,2'S*,6'S*)-(+-)-6-nor-2',3'-dihydro-4'-deoxo-8',8'-difluoro-abscisate
-
50% inhibition at 0.00063 mM
(1'S*,2'S*,6'S*)-(+-)-6-nor-2',3'-dihydro-4'-deoxo-abscisate
-
50% inhibition at 0.00091 mM
(1E)-1-(4-chlorophenyl)-2-[2-(hydroxymethyl)-1H-imidazol-1-yl]-4,4-dimethylpent-1-en-3-ol
-
31% inhibition at 0.01 mM
(1E)-1-(4-chlorophenyl)-2-[5-(hydroxymethyl)-1H-imidazol-1-yl]-4,4-dimethylpent-1-en-3-ol
-
95% inhibition at 0.01 mM
(1E)-1-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
(1E)-1-[4-(4-heptyl-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
0.01 mM, inhibits by 96%
(1E)-1-[4-[4-(1-hydroxybutyl)-1H-1,2,3-triazol-1-yl]phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
0.01 mM, inhibits by 92%
(1E)-1-[4-[4-(1-hydroxyethyl)-1H-1,2,3-triazol-1-yl]phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
0.01 mM, inhibits by 77%
(1E)-1-[4-[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
0.01 mM, inhibits by 83%
(1E)-4,4-dimethyl-1-[4-(4-nonyl-1H-1,2,3-triazol-1-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
0.01 mM, inhibits by 100%
(1E)-4,4-dimethyl-1-[4-(4-pentadecyl-1H-1,2,3-triazol-1-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
0.01 mM, inhibits by 54%
(1E)-4,4-dimethyl-1-[4-(4-propyl-1H-1,2,3-triazol-1-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
0.01 mM, inhibits by 92%
(1E)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-1-[4-(4-tridecyl-1H-1,2,3-triazol-1-yl)phenyl]pent-1-en-3-ol
-
0.01 mM, inhibits by 95%
(1E)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-1-[4-(4-undecyl-1H-1,2,3-triazol-1-yl)phenyl]pent-1-en-3-ol
-
0.01 mM, inhibits by 100%
(1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
(E)-1-(1-(4-chlorophenyl)-3-fluoro-4,4-dimethylpent-1-en-2-yl)-1H-1,2,4-triazole
-
i.e. UNI-F
(E)-1-(1-(4-chlorophenyl)-4,4-dimethylpent-1-en-2-yl)-1H-imidazole
-
i.e. IMI-H
(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
(E)-2-(2-((1-(4-(3-hydroxy-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)ethoxy)ethyl 4-methylbenzenesulfonate
-
i.e. abscinazole-E1, or UT1-E2Ts, or Abz-E1, a specific potent inhibitor of ABA 8'-hydroxylase, that is a weak inhibitor of ent-kaurene oxidase, CYP701A, EC 1.14.13.78, both in vitro and in vivo
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8(6H)-one
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[5,1-c][1,4]oxazin-8(6H)-one
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[2,1-c][1,4]oxazin-8(6H)-one
-
-
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[5,1-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
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine
(S,E)-1-(1-(4-chlorophenyl)-3-fluoro-4,4-dimethylpent-1-en-2-yl)-1H-imidazole
-
i.e. IMI-F
(S,E)-1-(1-(4-chlorophenyl)-3-methoxy-4,4-dimethylpent-1-en-2-yl)-1H-imidazole
-
i.e. IMI-OMe
(Z)-1-(1-(4-chlorophenyl)-4,4-dimethylpent-1-en-2-yl)-1H-imidazole
-
-
-
1'-deoxy-(+)-S-abscisate
-
competitive, 73% inhibition at 0.05 mM
1'-deoxy-1'-fluoro-(+)-S-abscisate
-
competitive, 100% inhibition at 0.05 mM
1'-deoxy-7'-hydroxy abscisic acid
-
63% inhibition of the enzyme at 0.05 mM
1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-4,4-dimethylpentan-1-ol
-
-
1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-4,4-dimethylpentan-1-one
-
-
1-[(1E)-1-(4-chlorophenyl)-3-ethoxy-4,4-dimethylpent-1-en-2-yl]-5-(ethoxymethyl)-1H-imidazole
-
62% inhibition at 0.01 mM
1-[(1E)-1-(4-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl]-1H-imidazole-5-carbaldehyde
-
91% inhibition at 0.01 mM
1-[(1E)-1-(4-chlorophenyl)-3-methoxy-4,4-dimethylpent-1-en-2-yl]-5-(methoxymethyl)-1H-imidazole
-
95% inhibition at 0.01 mM
2'alpha,3'alpha-dihydro-2'alpha,3'alpha-epoxy-(+)-S-abscisate
-
competitive, 56% inhibition at 0.05 mM
3'-azido-(+)-S-abscisate
-
competitive, 38% inhibition at 0.05 mM
3'-bromo-(+)-S-abscisate
-
competitive, 65% inhibition at 0.05 mM
3'-chloro-(+)-S-abscisate
-
competitive, 70% inhibition at 0.05 mM
3'-fluoro-(+)-S-abscisate
-
competitive, 84% inhibition at 0.05 mM
3'-iodo-(+)-S-abscisate
-
competitive, 54% inhibition at 0.05 mM
3R-(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
4-(1-[4-[(1E)-3-hydroxy-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-1-yl]phenyl]-1H-1,2,3-triazol-4-yl)butanoic acid
-
0.01 mM, inhibits by 63%
5'alpha,8'-cyclo-(+)-S-abscisate
-
competitive, 28% inhibition at 0.05 mM
6-nor-(+)-S-abscisate
-
competitive, 88% inhibition at 0.05 mM
7'-methyl-(+)-S-abscisate
-
competitive, 83% inhibition at 0.05 mM
7'-nor-(+)-S-abscisate
-
competitive, 28% inhibition at 0.05 mM
7'-oxo abscisic acid
-
24% inhibition of the enzyme at 0.05 mM
8',8',8'-trifluoro-(+)-S-abscisate
-
competitive, 38% inhibition at 0.05 mM
8',8'-difluoro-(+)-S-abscisate
-
competitive, 83% inhibition at 0.05 mM
8'-fluoro-(+)-S-abscisate
-
competitive, 83% inhibition at 0.05 mM
8'-methyl-(+)-S-abscisate
-
competitive, 35% inhibition at 0.05 mM
8'-methylene-(+)-S-abscisate
-
competitive, 33% inhibition at 0.05 mM
9',9',9'-trifluoro-(+)-S-abscisate
-
competitive, 55% inhibition at 0.05 mM
9',9'-difluoro-(+)-S-abscisate
-
competitive, 76% inhibition at 0.05 mM
9'-fluoro-(+)-S-abscisate
-
competitive, 83% inhibition at 0.05 mM
9'-methyl-(+)-S-abscisate
-
competitive, 26% inhibition at 0.05 mM
abscinazole-F1
-
-
abscisic aldehyde
-
competitive, 31% inhibition at 0.05 mM
CO
-
inhibition is reversible by blue and amber light
cytochrome c
diniconazole
-
potent competitive inhibitor, decreases seed germination rate by 65.6% at 36 h of imbibition
methyl (2E)-3-[1-[(1E)-1-(4-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl]-1H-imidazol-5-yl]prop-2-enoate
methyl (2Z)-3-[1-[(1E)-1-(4-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl]-1H-imidazol-5-yl]prop-2-enoate
-
100% inhibition at 0.01 mM
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol
R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
S-UNI
-
inhibits by 100%
S-uniconazole
-
i.e. S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol or UNI-OH, an azole-containing P450 inhibitor and a plant growth retardant, is a strong inhibitor of the enzyme, structure-activity relationship, the main site of action of UNI-OH is suggested to be ent-kaurene oxidase, EC 1.14.13.78, UNI-OH also inhibits brassinosteroid biosynthesis, and alters the level of other plant hormones, such as auxins, cytokinins, ethylene, and abscisic acid, overview
Tetcyclacis
-
50% inhibition at 0.001 mM
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-chloroindole-3-acetic acid
auxin, stimulates
abscisic acid
NADH
-
-
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0034
(+)-abscisic acid
0.0013 - 0.016
(+)-S-abscisate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0111
(+)-1'-methoxy-abscisate
-
pH 7.6, 30C
0.00017
(+)-8',8'-difluoroabscisate
-
pH 7.25, 30C
0.019
(+)-8'-acetylene-abscisate
-
pH 7.6, 30C
0.187
(+)-8'-cyano-abscisic acid
-
pH 7.6, 30C
0.0129
(+)-8'-ethyl-abscisic acid
-
pH 7.6, 30C
0.284
(+)-8'-methylacetylene-abscisic acid
-
pH 7.6, 30C
0.122
(+)-8'-methylene-abscisate
-
pH 7.6, 30C
0.0011
(+)-8'-propargyl-abscisate
-
pH 7.6, 30C
0.0055
(+)-9'-allyl-abscisate
-
pH 7.6, 30C
0.00027
(+)-9'-propargyl-abscisate
-
pH 7.6, 30C
0.056
(-)-8'-propargyl-abscisate
-
pH 7.6, 30C
0.0135
(-)-9'-propargyl-abscisate
-
pH 7.6, 30C
0.027
(1'R)-(-)-4'-deoxo-abscisic acid
-
pH 7.2-7.3, 30C
0.00045
(1'R,2'R)-(-)-2',3'-dihydro-4'-deoxo-abscisic acid
-
pH 7.2-7.3, 30C
0.00041
(1'S*,2'S*,6'S*)-(+-)-6-nor-2',3'-dihydro-4'-deoxo-8',8'-difluoro-abscisate
-
pH 7.25, 30C
0.0004
(1'S*,2'S*,6'S*)-(+-)-6-nor-2',3'-dihydro-4'-deoxo-abscisate
-
pH 7.25, 30C
0.00016
(1E)-1-(4-chlorophenyl)-2-[5-(hydroxymethyl)-1H-imidazol-1-yl]-4,4-dimethylpent-1-en-3-ol
-
-
0.034
(E)-1-(1-(4-chlorophenyl)-3-fluoro-4,4-dimethylpent-1-en-2-yl)-1H-1,2,4-triazole
-
pH 7.2-7.3, 30C, recombinant enzyme
0.000027
(E)-2-(2-((1-(4-(3-hydroxy-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)ethoxy)ethyl 4-methylbenzenesulfonate
-
pH 7.25, 30C, recombinant enzyme
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
0.00042 - 0.00097
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol
0.0012
(S,E)-1-(1-(4-chlorophenyl)-3-methoxy-4,4-dimethylpent-1-en-2-yl)-1H-imidazole
-
pH 7.2-7.3, 30C, recombinant enzyme
0.00024
1-[(1E)-1-(4-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl]-1H-imidazole-5-carbaldehyde
-
-
0.00019
1-[(1E)-1-(4-chlorophenyl)-3-methoxy-4,4-dimethylpent-1-en-2-yl]-5-(methoxymethyl)-1H-imidazole
-
-
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
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
0.000195
4-(1-[4-[(1E)-3-hydroxy-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-1-yl]phenyl]-1H-1,2,3-triazol-4-yl)butanoic acid
-
-
0.00016
6-nor-(+)-S-abscisate
-
pH 7.25, 30C
0.00071
8',8',8'-trifluoro-(+)-S-abscisate
-
pH 7.25, 30C
0.00017
8',8'-difluoro-(+)-S-abscisate
-
pH 7.25, 30C
0.00027
8'-fluoro-(+)-S-abscisate
-
pH 7.25, 30C
0.00094
8'-methyl-(+)-S-abscisate
-
pH 7.25, 30C
0.00543
8'-methylene-(+)-S-abscisate
-
pH 7.25, 30C
0.00106
9',9',9'-trifluoro-(+)-S-abscisate
-
pH 7.25, 30C
0.00025
9',9'-difluoro-(+)-S-abscisate
-
pH 7.25, 30C
0.00078
9'-fluoro-(+)-S-abscisate
-
pH 7.25, 30C
0.00429
9'-methyl-(+)-S-abscisate
-
pH 7.25, 30C
0.00012
methyl (2E)-3-[1-[(1E)-1-(4-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl]-1H-imidazol-5-yl]prop-2-enoate
-
-
0.00022
methyl (2Z)-3-[1-[(1E)-1-(4-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl]-1H-imidazol-5-yl]prop-2-enoate
-
-
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
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
0.0027
S-(+)-uniconazole
-
pH 7.2-7.3, 30C, recombinant enzyme
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
0.00001
S-UNI
-
-
0.034
UNI-H
-
pH 7.2-7.3, 30C, recombinant enzyme
0.0086
UNI-OMe
-
pH 7.2-7.3, 30C, recombinant enzyme
additional information
additional information
-
inhibition kinetics, computational methods, overview
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.046
(1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.0013
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.0023
(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.028 - 0.058
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine
0.009
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.0032
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.078
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.0078
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.012
R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.00018
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.0082
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
Oryza sativa
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
additional information
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2 - 7.3
7.25
-
assay at
7.4 - 7.8
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
major site of CYP707A1 and CYP707A3 expression
Manually annotated by BRENDA team
-
major site of CYP707A1 and CYP707A3 expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 53000, isoform CYC707A1, x * 52000, isoform CYP707A3, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a truncated CYP707A3 (707A3d28), which lacks the putative membrane-spanning segment of the N-terminus (residues 328) coexpressed in Escherichia coli strain BL21 with Arabidopsis P450 reductase
-
cDNA CYP707A1, DNA and amino acid sequence determination and analysis, phylogenetic tree; cDNA CYP707A2, DNA and amino acid sequence determination and analysis, phylogenetic tree; cDNA CYP707A3, DNA and amino acid sequence determination and analysis, phylogenetic tree; cDNA CYP707A4, DNA and amino acid sequence determination and analysis, phylogenetic tree
coding region (base 6-1,478) amplified and cloned in the Gateway entry vector pENTR/D-TOPO. CYP707A1 coding region recombined between the Cauliflower Mosaic Virus 35S promoter in the pGD625 vector and the NOPALINE SYNTHASE terminator. Transgenic plants generated by Agrobacterium tumefaciens-mediated transformation
CYP707A3, coexpression with Arabidopsis thaliana P450 reductase ATR2 in Escherichia coli
-
expression in baculovirus system, isoforms CYP707A1, CYP707A3, CYP707A4
-
leaves from wild-type plants transfected with the expression plasmid NpABAH
-
promoter fragment of the translational start of each CYP707A amplified and cloned into pENTR/D-TOPO vector, cloned into the binary vector, pGWB3, with a recombination cassette for the expression of GUS-fused protein. Resulting plasmids electroporated into Agrobacterium strain GV3101, which is used to transform wild-type Arabidopsis accession Columbia plants
-
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
-
three genes OsABA8ox1, -2 and -3, expression analysis, expression of gene OsABA8ox1 in Saccharomyces cerevisiae microsomes, expression of gene OsABA8ox1 as GFP-tagged protein in Allium cepa cells in the endoplasmic reticulum; three genes OsABA8ox1, -2 and -3, expression analysis, expression of gene OsABA8ox1 in Saccharomyces cerevisiae microsomes, expression of gene OsABA8ox1 as GFP-tagged protein in Allium cepa cells in the endoplasmic reticulum; three genes OsABA8ox1, -2 and -3, expression analysis, expression of gene OsABA8ox1 in Saccharomyces cerevisiae microsomes, expression of gene OsABA8ox1 as GFP-tagged protein in Allium cepa cells in the endoplasmic reticulum
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
3 h after tuber wounding, expression of isoforms CYP707A1 and CYP707A3 is increased more than 6fold and more than 69fold, respectively
-
ABA8'OH-1 is up-regulated in after-ripened tissues, highest expression in after-ripened coleorhiza
-
application of abscisic acid induces the expression of CYP707A1. Expression of CYP707A1 is strongly increased by water stress; application of abscisic acid induces the expression of CYP707A2. Expression of CYP707A2 is not significantly altered in dehydrated fruits compared to control fruits; application of abscisic acid induces the expression of CYP707A3. Expression of CYP707A3 is strongly increased by water stress
application of abscisic acid suppresses the expression of CYP707A2. Expression of CYP707A2 is not significantly altered in dehydrated fruits compared to control fruits
concomitant with the production of capsidiol is the induction of ABA 8'-hydroxylase in elicited plants. Expression of ABAH is induced in wild-type plants and in Npaba2 and Npaba1 mutants after cellulase treatment at time points corresponding to the expression of 5-epiaristolochene synthase and 5-epi-aristolochene hydroxylase and capsidiol synthesis
-
expression of ABA8ox genes, especially ABA8ox2 and ABA8ox3, is sensitively suppressed in the presence of exogenously supplied glucose, leading to delay of germination
-
expression of ABA8ox3 encoding ABA 8'-hydroxylase is significantly increased during the first 6 h of imbibition
-
mRNA concentration of CYP707A1 strongly increases after pollination in whole ovaries. CYP707A1 mRNA levels are several 100fold upregulated after pollination, specifically in ovules/placenta and not in pericarp. CYP707A1 overexpression line has approximately 45fold higher mRNA levels than wild-type
the enzyme is highly expressed during seed development; the enzyme is highly expressed during seed development; the enzyme is highly expressed during seed development
transcription decreases to a lower level after 12 h of imbibition; transcription decreases to a lower level after 12 h of imbibition; transcription decreases to a lower level after 12 h of imbibition; transcription decreases to a lower level after 12 h of imbibition
transcription increases during the first 6 h of imbibition; transcription increases during the first 6 h of imbibition; transcription increases during the first 6 h of imbibition; transcription increases during the first 6 h of imbibition
when wild-type plants are transferred to high-humidity conditions (relative humidity 90%), CYP707A1 and CYP707A3 transcript levels increase primarily in guard cells and vascular tissues, respectively
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
CYP707A2 knockout mutant, hyperdormancy in seeds, accumulates 6fold higher levels of abscisic acid than wild-type
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
inhibition by CO is reversible by blue and amber light
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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)