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
1.14.13.93
-
RECOMMENDED NAME
GeneOntology No.
(+)-abscisic acid 8'-hydroxylase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(+)-abscisate + NADPH + H+ + O2 = 8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
PATHWAY
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).
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
(+)-abscisic acid 8'-hydroxylase
-
-
(+)-abscisic acid 8'-hydroxylase
O81077, Q949P1, Q9FH76, Q9LJK2
-
(+)ABA 8'-hydroxylase
A9QNE7
-
ABA 8'-hydroxylase
O81077
-
ABA 8'-hydroxylase
-
-
ABA 8'-hydroxylase
-
-
ABA 8'-hydroxylase
-
-
ABA 8'-hydroxylase
-
-
ABA 8'-hydroxylase
Q05JG2, Q0J185, Q6ZDE3
-
ABA 8'-hydroxylase
E3TB04, E3TB05, E3TB06, E3TB07
-
ABA 8'-hydroxylase
Prunus avium Hongdeng
E3TB04, E3TB05, E3TB06, E3TB07
-
-
ABA 8-hydroxylase
-
-
ABA8'OH-1
-
-
ABAQ 8-hydroxylase
-
-
abscisic acid 8'-hydroxylase
-
-
abscisic acid 8'-hydroxylase
O81077
-
abscisic acid 8'-hydroxylase
-
-
CYP707A
Q05JG2, Q0J185, Q6ZDE3
-
CYP707A1
Q949P1
-
CYP707A1
E3TB04
-
CYP707A1
Prunus avium Hongdeng
E3TB04
-
-
CYP707A1
A9QNE7
-
CYP707A2
O81077
-
CYP707A2
E3TB05
-
CYP707A2
Prunus avium Hongdeng
E3TB05
-
-
CYP707A3
Q9FH76
-
CYP707A3
E3TB07
-
CYP707A3
Prunus avium Hongdeng
E3TB07
-
-
CYP707A4
Q9LJK2
-
CYP707A4
E3TB06
-
CYP707A4
Prunus avium Hongdeng
E3TB06
-
-
CAS REGISTRY NUMBER
COMMENTARY
153190-37-5
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
4 isoforms, all induced by drought stress
-
-
Manually annotated by BRENDA team
; enzyme from recombinant Escherichia coli
-
-
Manually annotated by BRENDA team
about 3fold induction by (+)- or (-)-abscisate and about 15fold induction by 8,8,8-trifluoro-abscisate
-
-
Manually annotated by BRENDA team
expression in baculovirus system, isoforms CYP707A1, CYP707A3, CYP707A4
-
-
Manually annotated by BRENDA team
apple variant domestica, 90 days old seedlings
-
-
Manually annotated by BRENDA team
cv. Nipponbare, three genes OsABA8ox-2
UniProt
Manually annotated by BRENDA team
cv. Nipponbare, three genes OsABA8ox-3
UniProt
Manually annotated by BRENDA team
cv. Nipponbare, three genes OsABA8ox1
UniProt
Manually annotated by BRENDA team
rice cultivar Nipponbare, length of second leaf sheath of 7 days old seedlings grown in test solution
-
-
Manually annotated by BRENDA team
CYP707A1; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
CYP707A2; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
CYP707A3; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
CYP707A4; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
Prunus avium Hongdeng
CYP707A1; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
Prunus avium Hongdeng
CYP707A2; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
Prunus avium Hongdeng
CYP707A3; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
Prunus avium Hongdeng
CYP707A4; four cDNAs CYP707A1-CYP707A4 encoding ABA 8'-hydroxylase
UniProt
Manually annotated by BRENDA team
-
A9QNE7
UniProt
Manually annotated by BRENDA team
about 7fold induction by (+)- or (-)-abscisate
-
-
Manually annotated by BRENDA team
induction by abscisate
-
-
Manually annotated by BRENDA team
induction by abscisate, suppression by water stress
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
metabolism
-
ABA 8'-hydroxylase is the major and key P450 enzyme in the abscisic acid catabolism
metabolism
-
key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events)
metabolism
E3TB04, E3TB05, E3TB06, E3TB07, -
ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview; ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview; ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview; ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview. Application of abscisic acid induces the expression of CYP707A1-CYP707A3 as well as PacNCED1, encoding 9-cis-epoxycarotenoid dioxygenase, but downregulates the CYP707A4 transcript level. Expressions of CYP707A1 and CYP707A3 are strongly increased by water stress, while no significant differences in CYP707A2 and CYP707A4 expression are observed between dehydrated and control fruits
metabolism
Prunus avium Hongdeng
-
ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview; ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview; ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview; ABA 8'-hydroxylase is a key enzyme in the oxidative catabolism of abscisic acid. Endogenous abscisic acid content is modulated by a dynamic balance between biosynthesis and catabolism, which are regulated by NCED1 and CYP707As transcripts, respectively, during fruit maturation and under stress conditions, overview. Application of abscisic acid induces the expression of CYP707A1-CYP707A3 as well as PacNCED1, encoding 9-cis-epoxycarotenoid dioxygenase, but downregulates the CYP707A4 transcript level. Expressions of CYP707A1 and CYP707A3 are strongly increased by water stress, while no significant differences in CYP707A2 and CYP707A4 expression are observed between dehydrated and control fruits
-
physiological function
-
ABA 8'-hydroxylase is the major and key P450 enzyme in the abscisic acid catabolism
physiological function
Q949P1, Q9FH76, Q9LJK2
CYP707A1 mutant shows similar phenotype to wild-type in freshly harvested or after-ripen seeds. Seeds of CYP707A1 mutant has its dormancy entirely broken 18 d after ripening. NO enhances the tolerance to abscisic acid in CYP707A1 mutant during germination. Abscisic acid concentrations decrease rapidly during the first 12 h in CYP707A1 mutant. NO enhances the tolerance to abscisic acid in CYP707A1 mutant; CYP707A2 plays a major role in abscisic acid catabolism during the first stage of imbibition. CYP707A2 is involved in NO-induced dormancy break. CYP707A2 mutant shows a strong dormancy in freshly harvested seeds. CYP707A2 mutant still maintains strong dormancy until 30 d. NO does not enhance the tolerance to abscisic acid in CYP707A2 mutant during germination; CYP707A3 mutant shows similar phenotype to wild-type in freshly harvested or after-ripen seeds, with the seeds of CYP707A3 mutant having a slightly higher germination rate than the wild-type. Seeds of CYP707A3 mutant has its dormancy entirely broken 18 d after ripening. NO enhances the tolerance to abscisic acid in CYP707A3 mutant during germination
physiological function
-
CYP707A1 and CYP707A3 are involved in stomatal opening in response to high humidity. Cyp707a1 and cyp707a3 mutants display lower stomatal conductance under turgid conditions (relative humidity 60%) than the wild-type. Cyp707a3 mutant exhibits high abscisic acid levels even after transferring to high-humidity conditions, whereas, under similar conditions, the cyp707a1 mutant exhibits low abscisic acid levels comparable to the wild-type. Stomatal closure of the cyp707a1 mutant, but not cyp707a3 mutant, is abscisic acid hypersensitive when epidermal peel ias treated with exogenous abscisic acid. CYP707A3 reduces the amount of mobile abscisic acid in vascular tissues in response to high humidity, whereas CYP707A1 inactivates local abscisic acid pools inside the guard cells
physiological function
-
important role for ABA8'OH-1 during early germination and in controlling dormancy in the coleorhiza
physiological function
-
CYP707A2 plays a major role in abscisic acid catabolism during the first stage of imbibition and regulates seeds dormancy. NO can break the dormancy of wild-type seeds, but it cannot break cyp707a2 mutant seed dormancy
physiological function
A9QNE7, -
CYP707A1 is most important for abscisic acid catabolism in pollinated ovaries. Transgenic plants, overexpressing CYP707A1, have reduced abscisic acid levels and exhibit abscisic acid-deficient phenotypes. Initiation of adventitious root growth on the stem of the CYP707A1 overexpression plants
physiological function
E3TB04, E3TB05, E3TB06, E3TB07, -
all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development; all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development; all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development; all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development
physiological function
Prunus avium Hongdeng
-
all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development; all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development; all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development; all four CYP707As are expressed at varying intensities throughout fruit development and appear to play overlapping roles in abscisic acid catabolism throughout sweet cherry fruit development
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
Q949P1, Q9FH76, Q9LJK2
-
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
A9QNE7, -
-
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
E3TB04, E3TB05, E3TB06, E3TB07, -
-
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
key enzyme in abscisic acid catabolism
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
Prunus avium Hongdeng
E3TB04, E3TB05, E3TB06, E3TB07
-
-
-
?
(+)-S-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(+)-S-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(+)-S-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
isoform CYP707A3 is specific for (+)-isomer
isoform CYP707A3, no hydroxylation at 7 position
-
?
(+-)-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
-
-
?
S-(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
S-(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisic acid + NADP+ + H2O
show the reaction diagram
-
-
for inhibitor studies the decrease in production of phaseic acid is measured
-
?
S-abscisate + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
9'-methyl-(+)-S-abscisate + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
3% of the activity with (+)-S-abscisate
-
-
?
additional information
?
-
-
isomerisation of 8-hydroxy-abscisic acid to phaseic acid is not catalyzed by enzyme
-
-
-
additional information
?
-
-
specific for (+)-isomer of abscisate
-
-
-
additional information
?
-
-
substrate recognition strictly requires the 6'-methyl groups
-
-
-
additional information
?
-
-, Q05JG2, Q0J185, Q6ZDE3
a rapid decrease of the plant hormone abscisic acid to its oxidized derivative phaseic acid under submergence is a prerequisite for the enhanced elongation of submerged shoots of rice, ethylene has a regulatory role, overview
-
-
-
additional information
?
-
O81077
different mutants: mutations in genes involved in the ethylene signal transduction pathway and a mutation at the start of exon 2
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
E3TB04, E3TB05, E3TB06, E3TB07, -
-
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
-
key enzyme in abscisic acid catabolism
-
-
?
(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisate + NADP+ + H2O
show the reaction diagram
Prunus avium Hongdeng
E3TB04, E3TB05, E3TB06, E3TB07
-
-
-
?
S-(+)-abscisic acid + NADPH + H+ + O2
8'-hydroxyabscisic 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
-
-
?
additional information
?
-
-, Q05JG2, Q0J185, Q6ZDE3
a rapid decrease of the plant hormone abscisic acid to its oxidized derivative phaseic acid under submergence is a prerequisite for the enhanced elongation of submerged shoots of rice, ethylene has a regulatory role, overview
-
-
-
additional information
?
-
O81077
different mutants: mutations in genes involved in the ethylene signal transduction pathway and a mutation at the start of exon 2
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
NADPH
E3TB04, E3TB05, E3TB06, E3TB07, -
-
cytochrome P450
-
-
-
additional information
-
NADH may not substitute for NADPH
-
additional information
-
NADH may not substitute for NADPH
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
(+)-1'-methoxy-abscisate
-
competitive
(+)-8',8'-difluoroabscisate
-
competitive
(+)-8'-acetylene-abscisate
-
suicide inhibitor
(+)-8'-acetylene-abscisate
-
about 60% inactivation
(+)-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'-oxo-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
-
0.01 mM, inhibits by 100%
(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
-
27% inhibition of recombinant enzyme with 10 microM inhibitor
(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
(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
(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
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
i.e. uniconazole
(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
-
14% inhibition of recombinant enzyme with 10 microM inhibitor; inhibitory activity is much weaker than that of S-UNI
(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
(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
-
35% inhibition of recombinant enzyme with 10 microM inhibitor
(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
(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
(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
(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
-
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
(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
(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
(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
(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
(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
(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
(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
(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
(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
(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
(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
-
abscinazole-F1, 95% inhibition of recombinant enzyme with 10 microM inhibitor
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
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
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
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
-
oxidized form
cytochrome c
-
0.1 mM, complete inhibition
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
-
98% inhibition at 0.01 mM
methyl (2E)-3-[1-[(1E)-1-(4-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl]-1H-imidazol-5-yl]prop-2-enoate
-
-
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
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
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
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
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
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
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
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
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
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
additional information
-
not inactivating: (+)-8-methylene-abscisate, (+)-8-methylacetylene-abscisate
-
additional information
-
inhibition of reaction at O2 concentrations less than 10% v/v
-
additional information
-
inhibitor synthesis, overview. Conformational energy profiles of ligands by computational molecular dynamics simulation, inhibition kinetics, overview. No inhibition by (1'R,2'R)-(-)-2',3'-dihydro-abscisic acid
-
additional information
-
pH-dependent partition coefficient of the inhibitors at different pH values, overview, no inhibition by 7'-hydroxy abscisic acid, four-step synthesis of 7'-hydroxy-abscisic acid from alpha-ionone, overview
-
additional information
-
about 4.8fold reduced expression in Arabidopsis thaliana mutant aba2 with a mutation at the start of exon 2; about 5.6fold reduced expression in Arabidopsis thaliana mutant etr1 with altered gene expression of the ethylene signal transduction pathway
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
4-chloroindole-3-acetic acid
A9QNE7, -
auxin, stimulates
abscisic acid
A9QNE7, -
stimulates
additional information
-, Q05JG2, Q0J185, Q6ZDE3
the mRNA level of OsABA8ox-2 does not increase under submergence culture conditions; the mRNA level of OsABA8ox-3 does not increase under submergence culture conditions; treatment of aerobic seedlings with ethylene and its precursor 1-aminocyclopropane-1-carboxylate rapidly induces the expression of OsABA8ox1, which is suppressed by 1-methylcyclopropene, an inhibitor of ethylene action. the mRNA level of OsABA8ox1 increases dramatically within 1 h under submergence culture conditions
-
additional information
-
high humidity reduces the abscisic acid levels by the activation of CYP707A1 and CYP707A3
-
additional information
-
blue light does not affect ABA8'OH-1
-
additional information
-
NO regulates seed dormancy and germination and such action needs CYP707As family's participation
-
additional information
A9QNE7, -
CYP707A1 is not affected by gibberellin 3 treatment, in contrast to pollination, which has a stimulating effect
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0034
-
(+)-abscisic acid
-
50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30C
0.0034
-
(+)-abscisic acid
-
-
0.0013
-
(+)-S-abscisate
-
pH 7.25, 30C, isoform CYP707A3
0.016
-
(+)-S-abscisate
-
pH 7.6, 30C
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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'-oxo-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
2.7e-05
-
(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
-
(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
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
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
-
-
0.00145
-
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
1e-05
-
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
0.034
-
UNI-H
-
pH 7.2-7.3, 30C, recombinant enzyme
0.0086
-
UNI-OMe
-
pH 7.2-7.3, 30C, recombinant enzyme
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
-
-
additional information
-
additional information
-
inhibition kinetics, computational methods, overview
-
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
-
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
-
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
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.028
-
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.058
-
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
0.009
-
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
-
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
-
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
-
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
-
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
-
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
-
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
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium
additional information
-
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
-
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
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.2
7.3
-
assay at
7.25
-
-
assay at
7.4
7.8
-
-
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
E3TB04, E3TB05, E3TB06, E3TB07, -
all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A1, overview; all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A2, overview; all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A3, overview; all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A4, overview
Manually annotated by BRENDA team
Prunus avium Hongdeng
-
all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A1, overview; all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A2, overview; all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A3, overview; all four CYP707As are expressed at varying intensities throughout sweet cherry fruit development, expression pattern of CYP707A4, overview
-
Manually annotated by BRENDA team
-
major site of CYP707A1 and CYP707A3 expression
Manually annotated by BRENDA team
A9QNE7, -
low level
Manually annotated by BRENDA team
Q949P1, Q9FH76, Q9LJK2
CYP707A2 transcription is much higher than the other CYP707A genes; CYP707A4 transcription is the lowest of the CYP707A genes
Manually annotated by BRENDA team
-
expression of ABA8ox3 is greatest among the three ABA8ox genes, while ABA8ox1 is hardly detected during germination
Manually annotated by BRENDA team
-, Q05JG2, Q0J185, Q6ZDE3
-
Manually annotated by BRENDA team
-, Q05JG2, Q0J185, Q6ZDE3
-
Manually annotated by BRENDA team
-
CYP707A3 plays a major role in regulating abscisic acid levels, whereas CYP707A1 plays a minor role in regulating abscisic acid levels in shoots
Manually annotated by BRENDA team
-
major site of CYP707A1 and CYP707A3 expression
Manually annotated by BRENDA team
additional information
-
after-ripened coleorhiza
Manually annotated by BRENDA team
additional information
A9QNE7, -
high level in plant placenta
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
integral membrane protein
-
Manually annotated by BRENDA team
-, Q05JG2, Q0J185, Q6ZDE3
-
-
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
x * 53000, isoform CYC707A1, x * 52000, isoform CYP707A3, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
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
-
CYP707A3, coexpression with Arabidopsis thaliana P450 reductase ATR2 in Escherichia coli
-
expression in baculovirus system, isoforms CYP707A1, CYP707A3, CYP707A4
-
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
-
leaves from wild-type plants transfected with the expression plasmid NpABAH
-
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
-, Q05JG2, Q0J185, Q6ZDE3
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
E3TB04, E3TB05, E3TB06, E3TB07, -
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
A9QNE7, -
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
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
Q949P1, Q9FH76, Q9LJK2
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
Q949P1, Q9FH76, Q9LJK2
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
-
ABA8'OH-1 is up-regulated in after-ripened tissues, highest expression in after-ripened coleorhiza
-
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
-
application of abscisic acid suppresses the expression of CYP707A2. Expression of CYP707A2 is not significantly altered in dehydrated fruits compared to control fruits
E3TB04, E3TB05, E3TB06, E3TB07, -
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
E3TB04, E3TB05, E3TB06, E3TB07, -
application of abscisic acid suppresses the expression of CYP707A2. Expression of CYP707A2 is not significantly altered in dehydrated fruits compared to control fruits
Prunus avium Hongdeng
-
-
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
Prunus avium Hongdeng
-
-
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
A9QNE7, -
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
CYP707A2 knockout mutant, hyperdormancy in seeds, accumulates 6fold higher levels of abscisic acid than wild-type
Renatured/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
inhibition by CO is reversible by blue and amber light
-
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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)