Information on EC 1.14.13.194 - phylloquinone omega-hydroxylase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.194
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RECOMMENDED NAME
GeneOntology No.
phylloquinone omega-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
phylloquinone + NADPH + H+ + O2 = omega-hydroxyphylloquinone + NADP+ + H2O
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
phylloquinone,NADPH:oxygen oxidoreductase (omega-hydroxyphylloquinone forming)
A heme-thiolate protein (cytochrome P-450). Isolated from human tissue. The enzyme will also act on menaquinone-4. Prolonged action of CYP4F2, but not CYP4F11, on the omega hydroxyl group oxidizes it to the corresponding carboxylic acid. CYP4F2 also oxidizes leukotriene B4; see EC 1.14.13.30, leukotriene-B4 20-monooxygenase [1].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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disruption of the CYP4F14 gene causes severe perturbations in vitamin E metabolism
metabolism
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CYP4F14 is the major but not the only vitamin E-omega-hydroxylase in mice
physiological function
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CYP4F2 is the principle leukotriene B4 omega-hydroxylating enzyme expressed in human liver and plays an important role in regulating circulating as well as hepatic levels of this powerful proinflammatory eicosanoid
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-hydroxypalmitate + NADPH + H+ + O2
3,16-dihydroxypalmitate + NADP+ + H2O
show the reaction diagram
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?
3-hydroxypalmitate + NADPH + H+ + O2
?
show the reaction diagram
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?
3-hydroxystearate + NADPH + H+ + O2
3,18-dihydroxystearate + NADP+ + H2O
show the reaction diagram
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?
amitriptyline + NADPH + H+ + O2
?
show the reaction diagram
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-
-
?
arachidonic acid + NADPH + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxy-eicosatetraenoic acid + NADP+ + H2O
show the reaction diagram
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?
arachidonic acid + NADPH + H+ + O2
?
show the reaction diagram
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?
arachidonic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
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?
benzphetamine + NADPH + H+ + O2
?
show the reaction diagram
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?
chlorpromazine + NADPH + H+ + O2
?
show the reaction diagram
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?
erythromycin + NADPH + H+ + O2
?
show the reaction diagram
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most efficient substrate
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?
ethylmorphine + NADPH + H+ + O2
?
show the reaction diagram
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?
gamma-tocopherol + NADPH + H+ + O2
?
show the reaction diagram
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?
imipramine + NADPH + H+ + O2
?
show the reaction diagram
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?
leukotriene B4 + NADPH + H+ + O2
20-hydroxyleukotriene B4 + NADP+ + H2O
show the reaction diagram
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?
leukotriene B4 + NADPH + H+ + O2
?
show the reaction diagram
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?
lipoxin A4 + NADPH + H+ + O2
?
show the reaction diagram
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?
menaquinone-4 + NADPH + H+ + O2
?
show the reaction diagram
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?
oleic acid + NADPH + H+ + O2
?
show the reaction diagram
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?
palmitic acid + NADPH + H+ + O2
?
show the reaction diagram
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?
phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
show the reaction diagram
pirenzepine + NADPH + H+ + O2
?
show the reaction diagram
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?
theophylline + NADPH + H+ + O2
?
show the reaction diagram
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?
verapamil + NADPH + H+ + O2
?
show the reaction diagram
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?
additional information
?
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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
menaquinone-4 + NADPH + H+ + O2
?
show the reaction diagram
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?
phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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contains Fe2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
prostaglandin A1
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additional information
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unaffected by lauric acid, palmitic acid, and prostaglandin F2alpha
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0564 - 0.074
3-hydroxypalmitate
0.055
3-hydroxystearate
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in 100 mM potassium phosphate buffer (pH 7.4), at 37C
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0.0235 - 0.08
arachidonic acid
0.125
erythromycin
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at pH 7.4 and 37C
0.085
oleic acid
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at pH 7.4 and 37C
0.047
palmitic acid
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at pH 7.4 and 37C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.458
3-hydroxypalmitate
Homo sapiens
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at pH 7.4 and 37C
0.009
arachidonic acid
Homo sapiens
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at pH 7.4 and 37C
0.02
oleic acid
Homo sapiens
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at pH 7.4 and 37C
0.03
palmitic acid
Homo sapiens
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at pH 7.4 and 37C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.17
3-hydroxypalmitate
Homo sapiens
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at pH 7.4 and 37C
55681
0.12
arachidonic acid
Homo sapiens
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at pH 7.4 and 37C
290
0.2
oleic acid
Homo sapiens
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at pH 7.4 and 37C
380
0.63
palmitic acid
Homo sapiens
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at pH 7.4 and 37C
535
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni2+-NTA agarose column chromatography, Biogel HTP hydroxylapatite column chromatography, and aminopropyl SPE column chromatography
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tryptamine CH-Sepharose column chromatography, DE-53 cellulose column chromatography, and Hypatite C column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expressed in Escherichia coli BL21 cells
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expressed in Saccharomyces cerevisiae AH22 cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
retinoic acid can regulate CYP4F2 gene activity with RXRalpha heterodimers stimulating while RARalpha functioning to repress CYP4F2 gene expression
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