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Information on EC 1.14.13.194 - phylloquinone omega-hydroxylase Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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The enzyme appears in viruses and cellular organisms
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phylloquinone omega-hydroxylase
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phylloquinone + NADPH + H+ + O2 = omega-hydroxyphylloquinone + NADP+ + H2O
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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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leukotriene B4 omega-hydroxylase
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vitamin K1 omega-hydroxylase
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CYP4F11
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CYP4F2
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brenda
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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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3-hydroxypalmitate + NADPH + H+ + O2
3,16-dihydroxypalmitate + NADP+ + H2O
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3-hydroxypalmitate + NADPH + H+ + O2
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3-hydroxystearate + NADPH + H+ + O2
3,18-dihydroxystearate + NADP+ + H2O
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amitriptyline + NADPH + H+ + O2
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arachidonic acid + NADPH + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxy-eicosatetraenoic acid + NADP+ + H2O
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arachidonic acid + NADPH + H+ + O2
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arachidonic acid + NADPH + H+ + O2
? + NADP+ + H2O
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benzphetamine + NADPH + H+ + O2
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chlorpromazine + NADPH + H+ + O2
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erythromycin + NADPH + H+ + O2
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most efficient substrate
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ethylmorphine + NADPH + H+ + O2
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gamma-tocopherol + NADPH + H+ + O2
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imipramine + NADPH + H+ + O2
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leukotriene B4 + NADPH + H+ + O2
20-hydroxyleukotriene B4 + NADP+ + H2O
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leukotriene B4 + NADPH + H+ + O2
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lipoxin A4 + NADPH + H+ + O2
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menaquinone-4 + NADPH + H+ + O2
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oleic acid + NADPH + H+ + O2
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palmitic acid + NADPH + H+ + O2
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
pirenzepine + NADPH + H+ + O2
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theophylline + NADPH + H+ + O2
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verapamil + NADPH + H+ + O2
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additional information
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
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additional information
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the enzyme exhibits tocopherol-omega-hydroxylase activity
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additional information
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no activity with fluoxetine, lipoxin B4, prostaglandin A1, prostaglandin E1, 5-hete, and 12-hete
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additional information
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CYP4F2 discriminates between tocopherols and phylloquinone in vitro, but alpha-tocopherol does not apparently increase phylloquinone omega-hydroxylation by this mechanism
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menaquinone-4 + NADPH + H+ + O2
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
additional information
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
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phylloquinone + NADPH + H+ + O2
omega-hydroxyphylloquinone + NADP+ + H2O
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additional information
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the enzyme exhibits tocopherol-omega-hydroxylase activity
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additional information
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CYP4F2 discriminates between tocopherols and phylloquinone in vitro, but alpha-tocopherol does not apparently increase phylloquinone omega-hydroxylation by this mechanism
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NADPH
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additional information
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unaffected by lauric acid, palmitic acid, and prostaglandin F2alpha
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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
0.0564
3-hydroxypalmitate
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in 100 mM potassium phosphate buffer (pH 7.4), at 37°C
0.074
3-hydroxypalmitate
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at pH 7.4 and 37°C
0.0235
arachidonic acid
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pH and temperature not specified in the publication
0.08
arachidonic acid
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at pH 7.4 and 37°C
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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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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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50000
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x * 50000, SDS-PAGE
58000
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x * 58000, SDS-PAGE
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?
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x * 50000, SDS-PAGE
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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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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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retinoic acid can regulate CYP4F2 gene activity with RXRalpha heterodimers stimulating while RARalpha functioning to repress CYP4F2 gene expression
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CP4F2_HUMAN
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59853
Swiss-Prot
CP4FB_HUMAN
524
60146
Swiss-Prot
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Parker, R.S.; Sontag, T.J.; Swanson, J.E.; McCormick, C.C.
Discovery, characterization, and significance of the cytochrome P450 omega-hydroxylase pathway of vitamin E catabolism
Ann. N. Y. Acad. Sci.
1031
13-21
2004
Homo sapiens
brenda
Jin, R.; Koop, D.R.; Raucy, J.L.; Lasker, J.M.
Role of human CYP4F2 in hepatic catabolism of the proinflammatory agent leukotriene B4
Arch. Biochem. Biophys.
359
89-98
1998
Homo sapiens
brenda
Tang, Z.; Salamanca-Pinzon, S.; Wu, Z.; Xiao, Y.; Guengerich, F.
Human cytochrome P450 4F11: Heterologous expression in bacteria, purification, and characterization of catalytic function
Arch. Biochem. Biophys.
494
86-93
2010
Homo sapiens
brenda
Zhang, X.; Hardwick, J.P.
Regulation of CYP4F2 leukotriene B4 omega-hydroxylase by retinoic acids in HepG2 cells
Biochem. Biophys. Res. Commun.
279
864-871
2000
Homo sapiens
brenda
Edson, K.Z.; Prasad, B.; Unadkat, J.D.; Suhara, Y.; Okano, T.; Guengerich, F.P.; Rettie, A.E.
Cytochrome P450-dependent catabolism of vitamin K: omega-hydroxylation catalyzed by human CYP4F2 and CYP4F11
Biochemistry
52
8276-8285
2013
Homo sapiens
brenda
Bardowell, S.A.; Duan, F.; Manor, D.; Swanson, J.E.; Parker, R.S.
Disruption of mouse cytochrome P450 4F14 (Cyp4f14 gene) causes severe perturbations in vitamin E metabolism
J. Biol. Chem.
287
26077-26086
2012
Mus musculus
brenda
Dhar, M.; Sepkovic, D.W.; Hirani, V.; Magnusson, R.P.; Lasker, J.M.
Omega oxidation of 3-hydroxy fatty acids by the human CYP4F gene subfamily enzyme CYP4F11
J. Lipid Res.
49
612-624
2008
Homo sapiens
brenda
Powell, P.K.; Wolf, I.; Jin, R.; Lasker, J.M.
Metabolism of arachidonic acid to 20-hydroxy-5,8,11,14-eicosatetraenoic acid by P450 enzymes in human liver: involvement of CYP4F2 and CYP4A11
J. Pharmacol. Exp. Ther.
285
1327-1336
1998
Homo sapiens
brenda
Farley, S.M.; Leonard, S.W.; Taylor, A.W.; Birringer, M.; Edson, K.Z.; Rettie, A.E.; Traber, M.G.
omega-Hydroxylation of phylloquinone by CYP4F2 is not increased by alpha-tocopherol
Mol. Nutr. Food Res.
57
1785-1793
2013
Rattus norvegicus
brenda
Kalsotra, A.; Turman, C.M.; Kikuta, Y.; Strobel, H.W.
Expression and characterization of human cytochrome P450 4F11: Putative role in the metabolism of therapeutic drugs and eicosanoids
Toxicol. Appl. Pharmacol.
199
295-304
2004
Homo sapiens
brenda
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