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Information on EC 1.14.14.137 - (+)-abscisic acid 8'-hydroxylase and Organism(s) Oryza sativa and UniProt Accession Q05JG2

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IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein found in plants. 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 . CO inhibits the reaction, but its effects can be reversed by the presence of blue light . The 8'-hydroxyabscisate formed can be converted into (-)-phaseic acid, most probably spontaneously.
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Oryza sativa
UNIPROT: Q05JG2
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Word Map
  • 1.14.14.137
  • dormancy
  • 9-cis-epoxycarotenoid
  • imbibition
  • phaseic
  • 8'-hydroxylation
  • pre-harvest
  • after-ripening
  • +-abscisic
  • aba-responsive
  • diniconazole
  • epoxycarotenoids
  • agriculture
The taxonomic range for the selected organisms is: Oryza sativa
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
aba 8'-hydroxylase, cyp707a, cyp707a2, cyp707a3, cyp707a1, abscisic acid 8'-hydroxylase, ahcyp707a1, taaba8'oh1, aba-8'-hydroxylase, ahcyp707a2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ABA 8'-hydroxylase
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ABA 8'-hydroxylase
abscisic acid 8'-hydroxylase
-
-
SYSTEMATIC NAME
IUBMB Comments
abscisate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (8'-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein found in plants. 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.
CAS REGISTRY NUMBER
COMMENTARY hide
153190-37-5
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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 Arabidopsis enzyme with 10 microM inhibitor
(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
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14% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8(6H)-one
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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 Arabidopsis 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
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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 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
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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 Arabidopsis 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
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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
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abscinazole-F1, 96% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor
diniconazole
-
potent competitive inhibitor, decreases seed germination rate by 65.6% at 36 h of imbibition
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol
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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
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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
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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
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100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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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
Oryza sativa
-
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
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cv. Nipponbare, three genes OsABA8ox1
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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expression of ABA8ox3 is greatest among the three ABA8ox genes, while ABA8ox1 is hardly detected during germination
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
expression of ABA8ox genes, especially ABA8ox2 and ABA8ox3, is sensitively suppressed in the presence of exogenously supplied glucose, leading to delay of germination
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expression of ABA8ox3 encoding ABA 8'-hydroxylase is significantly increased during the first 6 h of imbibition
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Saika, H.; Okamoto, M.; Miyoshi, K.; Kushiro, T.; Shinoda, S.; Jikumaru, Y.; Fujimoto, M.; Arikawa, T.; Takahashi, H.; Ando, M.; Arimura, S.; Miyao, A.; Hirochika, H.; Kamiya, Y.; Tsutsumi, N.; Nambara, E.; Nakazono, M.
Ethylene promotes submergence-induced expression of OsABA8ox1, a gene that encodes ABA 8-hydroxylase in rice
Plant Cell Physiol.
48
287-298
2007
Oryza sativa (Q05JG2), Oryza sativa (Q0J185), Oryza sativa (Q6ZDE3), Oryza sativa
Manually annotated by BRENDA team
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.
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
Bioorg. Med. Chem.
17
6620-6630
2009
Arabidopsis thaliana, Malus sylvestris, Oryza sativa
Manually annotated by BRENDA team
Zhu, G.; Ye, N.; Zhang, J.
Glucose-induced delay of seed germination in rice is mediated by the suppression of ABA catabolism rather than an enhancement of ABA biosynthesis
Plant Cell Physiol.
50
644-651
2009
Oryza sativa
Manually annotated by BRENDA team