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Information on EC 1.14.14.94 - leukotriene-B4 20-monooxygenase
for references in articles please use BRENDA:EC1.14.14.94
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
1.14.14.94 leukotriene-B4 20-monooxygenase
IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein found in mammals.
The enzyme appears in viruses and cellular organisms
- 1.14.14.94
- warfarin
- vkorc1
- cyp2c9
-
anticoagulant
-
arachidonic
-
dosing
-
pharmacogenetic
- 20-hete
-
20-hydroxyeicosatetraenoic
- cyp4fs
- cyp4a11
-
omega-hydroxylation
- epoxide
-
eicosanoids
- cyp3a5
-
interindividual
-
acenocoumarol
-
pharmacogenomics
-
thromboembolic
-
non-genetic
- cyp1b1
-
omega-oxidation
-
17-octadecynoic
-
epoxyeicosatrienoic
-
pharmacogenes
-
genotype-guided
-
lipoxins
Synonyms
cyp4f2, cyp4f3, cyp4f12, cyp4f11, cyp4f8, cyp4f3b, cytochrome p450 4f2, ltb4 omega-hydroxylase, cyp4f3a, cyp4f4, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP4F13
CYP4F14
CYP4F15
CYP4F18
CYP4F2
CYP4F3
CYPIVF2
-
-
-
-
CYPIVF3
-
-
-
-
Cytochrome P450-LTB-omega
-
-
-
-
EC 1.14.13.30
-
-
formerly
-
leukotriene B4 20-hydroxylase
-
-
-
-
leukotriene B4 omega-hydroxylase
Leukotriene-B4 20-monooxygenase
-
-
-
-
leukotriene-B4 omega-hydroxylase
-
-
-
-
LTB4 20-hydroxylase
-
-
-
-
LTB4 hydroxylase
LTB4 omega-hydroxylase
oxygenase, leukotriene B4 20-mono-
-
-
-
-
CYP4F3
CYP4F3 undergoes tissue-specific alternative splicing to CYP4F3A and CYP4F3B
LTB4 omega-hydroxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2 = (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2 = (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
a heme-thiolate protein P450
-
-
-
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2 = (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
not identical with EC 1.14.13.34
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
omega-oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
alpha-tocopherol degradation, arachidonate metabolites biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (20-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein found in mammals.
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CAS REGISTRY NUMBER
COMMENTARY
90119-11-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
(E,Z,Z,Z)-8-hydroxy-5,9,11,14-eicosatetraenoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F2
Products: -
Products: -
?
(Z12(13))-epoxyoctadec-(Z9)-enoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
(Z12(13))-epoxyoctadec-Z9-enoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
(Z9(10))-epoxyoctadec-(Z12)-enoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
(Z9(10))-epoxyoctadec-Z12-enoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
(Z9(10))-epoxyoctadecanoic acid + NADPH + O2
?
-
Substrates: omega-hydroxylation activity and weak (omega-1)-hydroxylation activity
Products: -
Products: -
?
12-hydroxyeicosatetraenoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3A
Products: -
Products: -
?
12-hydroxystearate + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
20-hydroxy-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3
Products: -
Products: -
?
20-hydroxy-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
5-deoxy-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
5-deoxy-20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
5-epi-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
5-epi-20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
5-hydroxy-6,8,11,14-eicosatetraenoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3
Products: -
Products: -
?
6-trans-12-epi-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
6-trans-12-epi-20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
9,11-diazo-15-deoxy-prostaglandin H2 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F8
Products: -
Products: -
?
9,11-epoxymethano-prostaglandin H2 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F8
Products: -
Products: -
?
alpha-tocopherol + [reduced NADPH-hemoprotein reductase] + O2
alpha-13'-hydroxy-tocopherol + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
alpha-tocotrienol + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
arachidonate + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-5,8,11,14-eicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
18(R)-hydroxyarachidonate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
Substrates: -
Products: -
Products: -
?
delta-tocopherol + [reduced NADPH-hemoprotein reductase] + O2
delta-13'-hydroxy-tocopherol + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
delta-tocotrienol + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
gamma-tocopherol + [reduced NADPH-hemoprotein reductase] + O2
13'-hydroxy-gamma-tocopherol + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
gamma-tocotrienol + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: induction of in all-trans-retinoic acid-treated HL60 cells
Products: -
Products: -
?
prostaglandin A1 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin A1 + [oxidized NADPH-hemoprotein reductase] + H2O
prostaglandin H1 + [reduced NADPH-hemoprotein reductase] + O2
19-hydroxy-prostaglandin H1 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: CYP4F8
Products: -
Products: -
?
prostaglandin H2 + [reduced NADPH-hemoprotein reductase] + O2
19-hydroxy-prostaglandin H2 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: CYP4F8
Products: -
Products: -
?
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: inactivation of leukotriene B4, a mediator of inflammation
Products: -
Products: -
?
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: LTB4 inactivation, in vivo inhibition of CYP4F18 results in a marked increase in calcium flux and a 220% increases in the chemotactic response of mouse polymorphonuclear leukocytes to LTB4
Products: -
Products: -
?
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: inactivation of leukotriene B4, a mediator of inflammation
Products: -
Products: -
?
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: inactivation of leukotriene B4, a mediator of inflammation
Products: -
Products: -
?
12-hydroxy-5,8,10,14-eicosatetraenoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
12-hydroxy-5,8,10,14-eicosatetraenoic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F2
Products: -
Products: -
?
6-trans-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
6-trans-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F2
Products: -
Products: -
?
6-trans-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3
Products: -
Products: -
?
6-trans-leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3A
Products: -
Products: -
?
arachidonate + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-5,8,11,14-eicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonate + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-5,8,11,14-eicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: very poor substrate
Products: -
Products: -
?
arachidonate + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-5,8,11,14-eicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: the enzyme is the principal arachidonate omega-hydroxylase in liver, CYP4F2
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: CYP4F3A is expressed in human leukocytes and catalyzes the omega-hydroxylation of LTB4
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: CYP4F3A catalyzes the omega-hydroxylation of LTB4
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: leukotriene B4 is identical with (6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: the enzyme plays a critical role in regulating the biological effect of leukotriene B4, CYP4F3
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: yielding omega-COOH-leukotriene B4 via omega-hydroxy-leukotriene B4 and omega-CHO-leukotriene B4, CYP4F3
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: all recombinant proteins generate product I from leukotriene B4, which in all cases is indistinguishable from the 20-hydroxy-leukotriene B4 reference compound assayed under similar conditions. CYP4F3A is the most efficient leukotriene B4 20-hydroxylase. CYP4F3A and 4F3B generate a secondary product, which is 20-COOH leukotriene B4 derived from 20-hydroxy-leukotriene B4. CYP4F12 is least efficient, generating several additional products. Product I derived from CYP4F3A and that from epidermal keratinocytes are identical to the 20-hydroxy-leukotriene B4 reference compound
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: leukotriene B4 is identical with (6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: leukotriene B4 is identical with (6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate
Products: -
Products: -
?
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: leukotriene B4 is identical with (6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate
Products: -
Products: -
?
lipoxin A4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
lipoxin A4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3 preferentially omega-jydroxylates lipoxin B4 over lipoxin A4
Products: -
Products: -
?
lipoxin A4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: no omega-hydroxylation of LXB4, CYP4F2
Products: -
Products: -
?
lipoxin A4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3A
Products: -
Products: -
?
lipoxin B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
lipoxin B4 + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: CYP4F3 preferentially omega-jydroxylates lipoxin B4 over lipoxin A4
Products: -
Products: -
?
prostaglandin A1 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin A1 + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: recombinant CYP4F14
Products: -
Products: -
?
prostaglandin A1 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin A1 + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: overview, stereochemical requirement for substrate specificity
Products: -
Products: -
?
additional information
?
-
-
Substrates: recombinant protein CYP4F2
Products: -
Products: -
?
additional information
?
-
-
Substrates: recombinant protein CYP4F3, wide substrate specificity
Products: -
Products: -
?
additional information
?
-
-
Substrates: CYP4F3B and CYP4F2 may function collaboratively as 20-HETE synthetase as well as omega-hydroxylases for leukotiene b4 and other lipoxygenase-dependent eicosanoids in human liver and other tissues
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with 20-hydroxy-leukotriene B4 and lipoxin B4
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Products: -
?
additional information
?
-
Substrates: cytochrome P450 4F2 gene encodes for the major CYP enzyme responsible for the synthesis of 20-hydroxyeicosatetraenoic acid in the human kidney
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Products: -
?
additional information
?
-
-
Substrates: cytochrome P450 4F2 gene encodes for the major CYP enzyme responsible for the synthesis of 20-hydroxyeicosatetraenoic acid in the human kidney
Products: -
Products: -
?
additional information
?
-
-
Substrates: leukotriene B4 and arachidonate omega-hydroxylase activities are both CYP4F2-catalyzed in the liver, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: CYP4F3A also catalyzes the omega-hydroxylation of epoxyeicosatrieonic acids
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Products: -
?
additional information
?
-
Substrates: recombinant protein CYP4F14
Products: -
Products: -
?
additional information
?
-
-
Substrates: recombinant protein CYP4F14
Products: -
Products: -
?
additional information
?
-
-
Substrates: CYP4F18 is a critical protein in the regulation of LTB4 metabolism, the enzyme is active in down-regulation of responses to leukotriene B4, i.e. LTB4, leukotriene B4 is a potent chemoattractant for polymorphonuclear leukocytes and other cells, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: lipopolysaccharide treatament suppresses CYP4F4 and upregulates CYP4F5 mRNA expression in rat liver whereas renal CYP4Fs are essentially unchanged. BaSO4 treatment, in contrast, increases both hepatic and renal CYP4F expression levels
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
arachidonate + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-5,8,11,14-eicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: the enzyme is the principal arachidonate omega-hydroxylase in liver, CYP4F2
Products: -
Products: -
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leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-leukotriene B4 + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: the enzyme plays a critical role in regulating the biological effect of leukotriene B4, CYP4F3
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leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
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Substrates: induction of in all-trans-retinoic acid-treated HL60 cells
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(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
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(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: inactivation of leukotriene B4, a mediator of inflammation
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(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: LTB4 inactivation, in vivo inhibition of CYP4F18 results in a marked increase in calcium flux and a 220% increases in the chemotactic response of mouse polymorphonuclear leukocytes to LTB4
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(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: inactivation of leukotriene B4, a mediator of inflammation
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(6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: inactivation of leukotriene B4, a mediator of inflammation
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leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
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leukotriene B4 + [reduced NADPH-hemoprotein reductase] + O2
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: CYP4F3A is expressed in human leukocytes and catalyzes the omega-hydroxylation of LTB4
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additional information
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Substrates: CYP4F3B and CYP4F2 may function collaboratively as 20-HETE synthetase as well as omega-hydroxylases for leukotiene b4 and other lipoxygenase-dependent eicosanoids in human liver and other tissues
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additional information
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Substrates: cytochrome P450 4F2 gene encodes for the major CYP enzyme responsible for the synthesis of 20-hydroxyeicosatetraenoic acid in the human kidney
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additional information
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Substrates: cytochrome P450 4F2 gene encodes for the major CYP enzyme responsible for the synthesis of 20-hydroxyeicosatetraenoic acid in the human kidney
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additional information
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Substrates: leukotriene B4 and arachidonate omega-hydroxylase activities are both CYP4F2-catalyzed in the liver, overview
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additional information
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Substrates: CYP4F18 is a critical protein in the regulation of LTB4 metabolism, the enzyme is active in down-regulation of responses to leukotriene B4, i.e. LTB4, leukotriene B4 is a potent chemoattractant for polymorphonuclear leukocytes and other cells, overview
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additional information
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Substrates: lipopolysaccharide treatament suppresses CYP4F4 and upregulates CYP4F5 mRNA expression in rat liver whereas renal CYP4Fs are essentially unchanged. BaSO4 treatment, in contrast, increases both hepatic and renal CYP4F expression levels
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
all-trans-retinoic acid
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after 6 days of retinoid exposure, cutaneous transcripts arising from Cyp4f13, 4f14, and 4f37 are down-regulated. No changes in transcript abundance for the Cyp4f16, 4f17, and 4f18 genes
additional information
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in vivo inhibition of CYP4F18 results in a marked increase in calcium flux and a 220% increase in the chemotactic response of mouse PMN to LTB4
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
all-trans retinoic acid
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significantly induces expression of CYP4F3A at both mRNA and protein levels in cultured HL-60 cells
all-trans-retinoic acid
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after 6 days of retinoid exposure, cutaneous transcripts arising from Cyp4f39 are up-regulated. No changes in transcript abundance for the Cyp4f16, 4f17, and 4f18 genes
lipopolysaccharide
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upregulates expression and activity of LTB4OH in ex-smokers in a dose-dependent manner, but not in smokers. In vitro smoke exposure of ex-smokers' bronchoalveolar lavage cells abrogates the lipopolysaccharide-induced up-regulation of LTB4OH mRNA expression, thus tobacco smoke alters bronchoalveolar lavage cell LTB4OH mRNA expression in response to lipopolysaccharide exposure
phenol
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significantly induces expression of CYP4F3A at both mRNA and protein levels in cultured and differentiated HL-60 cells, in the proerythroid cell line K-562, and ex vivo in human neutrophils
additional information
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CYP4F18 expression is induced in bone marrow-derived dendritic cells by bacterial lipopolysaccharide, a ligand for TLR4, and by poly(I-C), a ligand for TLR3
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additional information
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hepatic enzyme is not induced by phenobarbital or 3-methylcholanthrene
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
7.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8 - 9.5
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pH 6.8: about 50% of activity maximum, pH 9.5: about 70% of activity maximum
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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