Information on EC 1.14.13.194 - phylloquinone omega-hydroxylase

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The enzyme appears in viruses and cellular organisms

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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].
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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
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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
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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
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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-
-
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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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-
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?
gamma-tocopherol + NADPH + H+ + O2
?
show the reaction diagram
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-
-
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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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-
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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
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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contains Fe2+
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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 37°C
0.0235 - 0.08
arachidonic acid
0.125
erythromycin
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at pH 7.4 and 37°C
0.085
oleic acid
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at pH 7.4 and 37°C
0.047
palmitic acid
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at pH 7.4 and 37°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.458
3-hydroxypalmitate
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at pH 7.4 and 37°C
0.009
arachidonic acid
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at pH 7.4 and 37°C
0.02
oleic acid
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at pH 7.4 and 37°C
0.03
palmitic acid
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at pH 7.4 and 37°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.17
3-hydroxypalmitate
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at pH 7.4 and 37°C
0.12
arachidonic acid
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at pH 7.4 and 37°C
0.2
oleic acid
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at pH 7.4 and 37°C
0.63
palmitic acid
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at pH 7.4 and 37°C
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
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x * 50000, SDS-PAGE
58000
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x * 58000, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.194)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)