Information on EC 1.14.13.199 - docosahexaenoic acid omega-hydroxylase

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The expected taxonomic range for this enzyme is: Homo sapiens

EC NUMBER
COMMENTARY hide
1.14.13.199
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RECOMMENDED NAME
GeneOntology No.
docosahexaenoic acid omega-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
docosahexaenoate + NADPH + H+ + O2 = 22-hydroxydocosahexaenoate + NADP+ + H2O
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
docosahexaenoate,NADPH:O2 oxidoreductase (22-hydroxydocosahexaenoate forming)
Isolated from human eye tissue. Defects in the enzyme are associated with Bietti crystalline corneoretinal dystrophy. The enzyme also produces some 21-hydroxydocosahexaenoate. Acts in a similar way on icosapentaenoic acid.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
defects in the enzyme are associated with Bietti crystalline corneoretinal dystrophy
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
9(10)-epoxystearic acid + NADPH + H+ + O2
18-hydroxy-9(10)-epoxystearic acid + NADP+ + H2O
show the reaction diagram
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-
?
arachidonic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + NADP+ + H2O
show the reaction diagram
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-
?
docosahexaenoate + NADPH + H+ + O2
22-hydroxydocosahexaenoate + NADP+ + H2O
show the reaction diagram
docosahexaenoic acid + NADPH + H+ + O2
22-hydroxydocosahexaenoic acid + NADP+ + H2O
show the reaction diagram
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-
-
?
docosapentaenoic acid + NADPH + H+ + O2
22-hydroxydocosapentaenoic acid + NADP+ + H2O
show the reaction diagram
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-
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-
?
eicosapentaenoic acid + NADPH + H+ + O2
20-hydroxyeicosapentaenoic acid + NADP+ + H2O
show the reaction diagram
eicosatrienoic acid + NADPH + H+ + O2
20-hydroxyeicosatrienoic acid + NADP+ + H2O
show the reaction diagram
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?
icosapentaenoic acid + NADPH + H+ + O2
22-hydroxyicosapentaenoic acid + NADP+ + H2O
show the reaction diagram
icosapentaenoate i.e. (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
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?
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
docosahexaenoate + NADPH + H+ + O2
22-hydroxydocosahexaenoate + NADP+ + H2O
show the reaction diagram
Q6ZWL3
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
CYP4V2 displays a typical reduced carbon monoxide-bound P450 spectrum
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
docosahexaenoic acid
eicosapentaenoic acid
eicosatrienoic acid
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10 microM, 32% inhibition of arachidonic acid metabolism
omega-3 docosapentaenoic acid
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inhibitory to reaction of arachidonic acid
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
a human cell line spontaneously generated from normal human retinal pigmented epithelium
Manually annotated by BRENDA team
endothelial cell
Manually annotated by BRENDA team
islet cells
Manually annotated by BRENDA team
glandular epithelial cells
Manually annotated by BRENDA team
additional information
negligible amount is found in human kidney. No expression in small intestine
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 60000, SDS-PAGE; x * 62163, liquid chromatography-mass spectrometry analysis
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
isolated through nickel affinity and hydroxyapatite chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in insect cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is associated with differentiation of HepaRG cels and unaffected by fatty acid overload
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H331P
the naturally occuring mutant protein CYP4V2 protein is expressed at high levels in ocular target tissues of patients with Bietti’s crystalline corneoretinal dystrophy. The enzyme is metabolically active toward polyunsaturated fatty acids. The functional deficit among patients with Bietti’s crystalline corneoretinal dystrophy who carry the H331P variant is most likely a consequence of the instability of the mutant protein