Information on EC 1.13.11.51 - 9-cis-epoxycarotenoid dioxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.13.11.51
-
RECOMMENDED NAME
GeneOntology No.
9-cis-epoxycarotenoid dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
9'-cis-neoxanthin + O2 = 2-cis,4-trans-xanthoxin + (3S,5R,6R)-5,6-dihydroxy-6,7-didehydro-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
-
-
-
-
9-cis-violaxanthin + O2 = 2-cis,4-trans-xanthoxin + (3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
-
-
-
-
a 9-cis-epoxycarotenoid + O2 = 2-cis,4-trans-xanthoxin + a 12'-apo-carotenal
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C-C-bond cleavage
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
abscisic acid biosynthesis
-
-
Carotenoid biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
-
SYSTEMATIC NAME
IUBMB Comments
9-cis-epoxycarotenoid 11,12-dioxygenase
Requires iron(II). Acts on 9-cis-violaxanthin and 9'-cis-neoxanthin but not on the all-trans isomers [2,3]. In vitro, it will cleave 9-cis-zeaxanthin. Catalyses the first step of abscisic-acid biosynthesis from carotenoids in chloroplasts, in response to water stress. The 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 1.14.13.93 [(+)-abscisic acid 8'-hydroxylase].
CAS REGISTRY NUMBER
COMMENTARY hide
199877-10-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene NCED6
-
-
Manually annotated by BRENDA team
gene AhNCED1
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
Clemenules mandarin
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
a cultivar showing thermoinhibition, gene NCED4
-
-
Manually annotated by BRENDA team
strain PCC 7120
-
-
Manually annotated by BRENDA team
Anabaena sp. PCC 7120
UniProt
Manually annotated by BRENDA team
-
TrEMBL
Manually annotated by BRENDA team
gene SoNCED
UniProt
Manually annotated by BRENDA team
gene SoNCED
UniProt
Manually annotated by BRENDA team
cv. Shiraz
-
-
Manually annotated by BRENDA team
Vitis vinifera x Vitis vinifera
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-hydroxy alpha-apo-10'-carotenoid acid + O2
cyclohexenone + mycorradicin
show the reaction diagram
-
-
-
-
?
3-OH-beta-apo-10'-carotenal + O2
apo-10',10-apocarotene-dial
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
3-OH-beta-apo-8'-carotenal + O2
apo-8',10-apocarotene-dial
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
4-hydroxymyxol 2'-fucoside + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
4-ketomyxol 2'-fucoside + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
9'-cis neoxanthin + O2
xanthoxin + ?
show the reaction diagram
-
-
-
-
?
9'-cis-neoxanthin + O2
2-cis,4-trans-xanthoxin + (3S,5R,6R)-5,6-dihydroxy-6,7-didehydro-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
9'-cis-neoxanthin + O2
5,6-epoxy-3-hydroxy-12'-apo-beta-caroten-12'-al + 3,5-dihydroxy-6,7-didehydro-12'-apo-beta-caroten-12'-al + ?
show the reaction diagram
-
-
-
-
?
9'-cis-neoxanthin + O2
?
show the reaction diagram
-
-
-
-
?
9-cis violaxanthin + O2
2-cis,4-trans-xanthoxin + ?
show the reaction diagram
-
-
-
-
?
9-cis-8'R-luteoxanthin + O2
?
show the reaction diagram
-
-
-
-
?
9-cis-8'S-luteoxanthin + O2
?
show the reaction diagram
-
-
-
-
?
9-cis-antheraxanthin + O2
?
show the reaction diagram
-
-
-
-
?
9-cis-neoxanthin + O2
xanthoxin + ?
show the reaction diagram
-
assay at pH 6.7, 22C, 20 min, reaction stopped by adding 50 microl of 25% Triton X-100
-
-
?
9-cis-violaxanthin + O2
2-cis,4-trans-xanthoxin + (3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
9-cis-violaxanthin + O2
5,6-epoxy-3-hydroxy-12'-apo-beta-caroten-12'-al + 5,6-epoxy-3-hydroxy-9-apo-beta-caroten-9-one + ?
show the reaction diagram
-
-
-
-
?
9-cis-violaxanthin + O2
?
show the reaction diagram
-
-
-
-
?
all-trans-violaxanthin + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + ?
show the reaction diagram
astaxanthin + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
beta,beta-carotene + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + 3-hydroxy-9-apo-beta-caroten-9-one + ?
show the reaction diagram
-
-
-
-
?
beta,beta-carotene + O2
all-trans retinal + ?
show the reaction diagram
-
-
-
-
?
beta-apo-10'-carotenal + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
beta-apo-8'-carotenal + O2
?
show the reaction diagram
beta-apo-8'-carotenal + O2
beta-ionone + ?
show the reaction diagram
-
-
-
-
?
beta-carotene + O2
?
show the reaction diagram
-
-
-
-
?
beta-carotene + O2
strigolactone + ?
show the reaction diagram
-
two cleavage steps by CCD7 and CCD8
-
-
?
beta-cryptoxanthin + O2
?
show the reaction diagram
canthaxanthin + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
diapocarotenedial + O2
?
show the reaction diagram
-
-
-
-
?
echinenone + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
gamma-carotene + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
lutein + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + ?
show the reaction diagram
-
-
-
-
?
lycopene + O2
?
show the reaction diagram
-
-
-
-
?
myxol + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
myxol 2'-fucoside + O2
?
show the reaction diagram
assay at pH 7.8, 28C, incubation stopped by adding one volume of acetone
-
-
?
torulene + O2
?
show the reaction diagram
-
-
-
-
?
zeaxanthin + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + ?
show the reaction diagram
zeaxanthin + O2
?
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
9'-cis-neoxanthin + O2
2-cis,4-trans-xanthoxin + (3S,5R,6R)-5,6-dihydroxy-6,7-didehydro-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
Q9M6E8
drought-induced biosynthesis of abscisic acid is regulated by the 9-cis-epoxy-carotenoid cleavage reaction
-
-
?
9-cis-violaxanthin + O2
2-cis,4-trans-xanthoxin + (3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
Q9M6E8
drought-induced biosynthesis of abscisic acid is regulated by the 9-cis-epoxy-carotenoid cleavage reaction
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-
?
additional information
?
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,3S,6R)-(3'Z)-1,5,5-trimethyl-6-(3'-methyl-5'-(phenylamino)-pent-3'-en-1'-ynyl)-7-oxabicyclo[4.1.0]heptan-3-ol
-
1 mM, complete inhibition of enzyme activity
(1R,3S,6R)-(3'Z)-1,5,5-trimethyl-6-(3'-methyl-5'-(phenylthio)-pent-3'-en-1'-ynyl)-7-oxa-bicyclo[4.1.0]heptan-3-ol
-
1 mM, complete inhibition of enzyme activity
(1R,4R,6R)-(3'Z)-1-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-2,2,6-trimethylcyclohexane-1,4-diol
-
1 mM, about 25% inhibition of enzyme activity
(1S,4R,6R)-(3'Z)-1-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-2,2,6-trimethylcyclohexane-1,4-diol
-
1 mM, about 65% inhibition of enzyme activity
(2Z,4E)-5-(1'-hydroxy-2',2',6'-trimethyl-4'-oxocyclohexyl)-3-methylpenta-2,4-dienyl 2-(thiophen-2''-yl)acetate
-
1 mM, about 70% inhibition of enzyme activity
(3,4-dimethoxybenzyl)[2-(4-methoxy-phenyl)-ethyl]methylamine
-
IC50: 0.087 mM
(4R,5S)-(3'Z)-4-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexanone
-
1 mM, complete inhibition of enzyme activity
(4S,5R)-(3'Z)-4-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexanone
-
1 mM, about 55% inhibition of enzyme activity
(4S,5R/4R,5S)-(3'Z)-4-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexanone
-
1 mM, 75% inhibition of enzyme activity
1-aminocyclopropane-1-carboxylic acid
1-methylcyclopropene
2-([[2-(4-hydroxyphenyl)ethyl]amino]methyl)phenol
-
IC50: 0.16 mM
abamine
-
1 mM, about 70% inhibition of enzyme activity
abamine SG
-
1 mM, about 80% inhibition of enzyme activity
abscisic acid
fluridone
N-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl]-4-methoxyaniline
-
IC50: 0.145 mM
nordihydroguaiaretic acid
[[(E)-3-(3,4-dimethoxy-phenyl)-allyl]-(4-fluoro-benzyl)-amino]-acetic acid methyl ester
-
IC50: 0.055 mM. Inhibitor of abscisic acid biosynthesis inhibits abscisic acid accumulation and stomatal closing
[[3-(3,4-dimethoxyphenyl)allyl]-(4-fluorobenzyl)amino]acetic acid methyl ester
-
competitive
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
abscisic acid
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.027 - 0.049
9'-cis-neoxanthin
0.008
9-cis-8'R-luteoxanthin
-
-
0.015
9-cis-8'S-luteoxanthin
-
-
0.02
9-cis-antheraxanthin
-
-
0.024
9-cis-neoxanthin
-
-
0.058
9-cis-violaxanthin
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0388
[[3-(3,4-dimethoxyphenyl)allyl]-(4-fluorobenzyl)amino]acetic acid methyl ester
-
pH 7.0, 20C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.087
(3,4-dimethoxybenzyl)[2-(4-methoxy-phenyl)-ethyl]methylamine
Vigna unguiculata
-
IC50: 0.087 mM
0.16
2-([[2-(4-hydroxyphenyl)ethyl]amino]methyl)phenol
Vigna unguiculata
-
IC50: 0.16 mM
0.145
N-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl]-4-methoxyaniline
Vigna unguiculata
-
IC50: 0.145 mM
0.183
nordihydroguaiaretic acid
Vigna unguiculata
-
IC50: 0.183 mM
0.055
[[(E)-3-(3,4-dimethoxy-phenyl)-allyl]-(4-fluoro-benzyl)-amino]-acetic acid methyl ester
Vigna unguiculata
-
IC50: 0.055 mM. Inhibitor of abscisic acid biosynthesis inhibits abscisic acid accumulation and stomatal closing
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7
-
assay at
7.2
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28
at 20C decreased enzyme acitivity
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.04
sequence calculation
8.39
-
calculated from amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
CsNCED1 and CsNCED2
Manually annotated by BRENDA team
-
in developing ovary
Manually annotated by BRENDA team
-
drought-induced expression of AtNCED3 is restricted to the vascular parenchyma cells
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
CCDI, CCD7
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55000
value about, Western blot
66860
-
calculated from sequence of cDNA
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
-
VP14 is imported into chloroplast with cleavage of a short stroma-targeting domain. Mature VP14 exists in two forms, one of which is soluble in stroma and the other bound to thylakoid
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
glutathione sepharose 4 fast flow resin
-
recombinant
-
Talon resin immobilized metal affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
creation of transgenic tobacco plants in which expression of the LeNCED1 coding region is under tetracycline-inducible control. Transgenic tomato plants are also produced containing the leNCED1 coding region under the control of one of two strong constitutive promoters, either the doubly enhanced CaMV 35S promoter or the chimaeric/super-promoter
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enzyme produced in transgenic Nicotiana plumbaginifolia. Constitutive expression of PvNCED1 results in an increase in abscisic acid and its catabolite, phaseic acid. When the PcNCED1 gene is driven by dexamethasone-inducible promoter, a transient induction of PvNCED1 message and accumulation of
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expressed in Arabidopsis thaliana
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expressed in Escherichia coli JM109 cells
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expressed in Escherichia coli strain JM109 and strain BL21
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expressed in Nicotiana tabacum
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expression as a glutathion-S-transferase fusion protein in Escherichia coli BL21
expression in Escherichia coli
-
expression in Escherichia coli as a fusion to glutathione S-transferase
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expression in Escherichia coli BL21
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expression in Escherichia coli strain DH5alpha
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expression in Escherichia coli strain DH5alpha; expression in Escherichia coli strain DH5alpha
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expression in Escherichia coli. Import of PvNCED1 into pea chloroplasts
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expression in transgenic Arabidopsis
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functional expression in, using CaMV35S promoter, and complementation of seeds of the Arabidopsis thaliana nced6-1 nced9-1 double mutant restoring germination thermosensitivity
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gene AhNCED1, expression analysis
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gene NCED6, transgenic expression in Arabidopsis thaliana by Agrobacterium tumefaciens transfection method, expression analysis
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gene SlNCED1, real-time quantitative reverse transcription, phylogenetic tree
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gene SoNCED, DNA and amino acid sequence determination and analysis, phylogenetic tree, quantitative real-time PCR expression analysis
NCED3 quantitative RT-PCR expression analysis; quantitative RT-PCR expression analysis of wild-type enzyme and lenc1 mutant, overview
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
elevated transient expression of AhNCED1, increased AhNCED1 mRNA and protein levels, and increased abscisic acid content are detected in the vascular cambium of a drought-tolerant peanut cultivar (Yueyou 7) under a water stress treatment. Synthesis of abscisic acid and AhNCED1 in the leaves of cultivar Yueyou 7 takes place more quickly than in the control cultivar Shanyou 523; elevated transient expression of AhNCED1, increased AhNCED1 mRNA and protein levels, and increased abscisic acid content are detected in the vascular cambium of a drought-tolerant peanut cultivar Yueyou 7 under a water stress treatment. Synthesis of abscisic acid and AhNCED1 in the leaves of cultivar Yueyou 7 takes place more quickly than in the control cultivar Shanyou 523
heat but not water stress elevates NCED4 expression in leaves, while NCED2 and NCED3 exhibited the opposite responses. NCED2 and NCED3 expression increases markedly in response to water stress; water stress elevates expression of gene NCED4 in leaves in cultivar UC96US23
identification of the lenc1, i.e. low expression of NCED3 1, mutation, the mutant shows lower AtNCED3 promoter activity after dehydration treatment compared to the wild-type. The lenc1 mutant is hypersensitive to methyl viologen, LiCl, NaCl, and high light
significant increase in SoNCEDmRNA level and its correlation with superoxide production rate and abscisic acid accumulation in leaves and roots of sugarcane variety GT21 when exposed to water stress
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H173A
-
inactive enzyme
H221A
-
inactive enzyme
H285A
-
inactive enzyme
H68A
-
inactive enzyme
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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it is possible to manipulate abscisic acid levels in plants by overexpressing the key regulatory gene in abscisic acid biosynthesis. Stress tolerance can be improved by increasing abscisic acid level