1.13.11.34: arachidonate 5-lipoxygenase
This is an abbreviated version!
For detailed information about arachidonate 5-lipoxygenase, go to the full flat file.
Word Map on EC 1.13.11.34
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1.13.11.34
-
cyclooxygenase
-
prostaglandin
-
leukocyte
-
neutrophil
-
eicosanoids
-
cox-2
-
asthma
-
indomethacin
-
ionophore
-
phospholipase
-
zileuton
-
polymorphonuclear
-
thromboxane
-
flap
-
airway
-
peritoneal
-
5-hete
-
platelet
-
eosinophil
-
mast
-
cysteinyl
-
allergic
-
edema
-
12-lipoxygenase
-
histamine
-
lta4
-
nordihydroguaiaretic
-
lipoxygenases
-
paf
-
ndga
-
bronchoconstriction
-
5-hydroxyeicosatetraenoic
-
asthmatic
-
basophil
-
platelet-activating
-
anaphylaxis
-
zymosan
-
antigen-induced
-
lipoxins
-
montelukast
-
hetes
-
mpges-1
-
carrageenan-induced
-
a23187-stimulated
-
paf-induced
-
pro-resolving
-
synthesis
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bronchospasm
-
medicine
-
drug development
-
14carachidonic
-
pharmacology
-
bronchoconstrictors
-
ulcerogenic
- 1.13.11.34
-
cyclooxygenase
- prostaglandin
- leukocyte
- neutrophil
-
eicosanoids
- cox-2
- asthma
- indomethacin
-
ionophore
- phospholipase
- zileuton
-
polymorphonuclear
-
thromboxane
- flap
- airway
- peritoneal
-
5-hete
- platelet
-
eosinophil
-
mast
-
cysteinyl
-
allergic
- edema
-
12-lipoxygenase
- histamine
- lta4
-
nordihydroguaiaretic
- lipoxygenases
- paf
- ndga
-
bronchoconstriction
-
5-hydroxyeicosatetraenoic
-
asthmatic
-
basophil
-
platelet-activating
- anaphylaxis
- zymosan
-
antigen-induced
-
lipoxins
- montelukast
-
hetes
- mpges-1
-
carrageenan-induced
-
a23187-stimulated
-
paf-induced
-
pro-resolving
- synthesis
- bronchospasm
- medicine
- drug development
-
14carachidonic
- pharmacology
-
bronchoconstrictors
-
ulcerogenic
Reaction
Synonyms
5-lipoxygenase, 5-LO, 5-LO1, 5-LOX, 5DELTA-lipoxygenase, 5LO, 5LOX-1, ALOX5, arachidonate 5-LO, arachidonate:oxygen oxidoreductase, arachidonic 5-lipoxygenase, arachidonic acid 5-lipoxygenase, C-5-lipoxygenase, DELTA5-lipoxygenase, H5-LO, leukotriene A4 synthase, leukotriene-A4 synthase, lipoxygenase 15, lipoxygenase 5, lipoxygenase-1, LO-1, LOX-15, LOX-5, LTA synthase, LTA4 synthase, oxygenase, arachidonate, 5-lip-, PMNL 5-lipoxygenase
ECTree
1.13.11.34 arachidonate 5-lipoxygenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.13.11.34 - arachidonate 5-lipoxygenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(12S)hydroperoxy-5,8-cis-10-trans-13-cis-eicosatetraenoic acid + O2
(5S,12S)-dihydroperoxy-5,8-cis-10-trans-13-cis-eicosatetraenoic acid
-
22% of the activity with arachidonic acid
-
?
(15S)-hydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid + O2
(5S,15S)-dihydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid
-
30% of the activity with arachidonic acid
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
1-linoleoyl lysophosphatidic acid + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidic acid
-
i.e. linoleoyl-lysoPA
major product
-
?
1-linoleoyl lysophosphatidylcholine + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidylcholine
-
i.e. linoleoyl-lysoPC
major product
-
?
2',7'-dichlorodihydrofluorescein diacetate + O2
2',7'-dichlorofluorescein
-
-
-
-
?
2',7'-dichlorodihydrofluorescein diacetate + O2
?
-
development of a fluorescence assay for 5-LOX, overview
-
-
?
5,8,11-eicosatrienoic acid + O2
?
-
almost as active as arachidonic acid
-
-
?
5-hydroperoxyeicosatetraenoic acid
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
7,7-d2-arachidonate + O2
7-d-(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
analysis of the product distribution reveals that 5-LOX displays a reversal of selectivity to bypass abstracting the deuterium atom from C7
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(5S)-5-hydroperoxyicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonic acid + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
homo-gamma-linolenic acid + O2
8-L-hydroxy-9,11,14-eicosatrienoic acid
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
epoxidation
-
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
epoxidation
-
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
epoxidation
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
684399, 684672, 685926, 687035, 688246, 688512, 688751, 689841, 689844, 689872, 711134, 711633, 711661, 712666
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 via stereospecific hydration by LTA4 hydrolase, LTA4 induces VEGF transcription in malignant mesothelial cells, the enzyme is upregulated in cancer cells and is pro-angiogenic
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4, has no effect on on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
stereospecific removal of the pro-R hydrogen at C10 resulting in epoxide formation
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
efficient LTA4 formation of 5LO requires both phosphatidyl choline and coactosin-like protein
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate + O2
leukotriene A4
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate + O2
leukotriene A4
-
-
-
?
8,11,14-eicosatrienoic acid + O2
?
-
4% of the activity with 5,8,11,14,17-eicosapentaenoic acid
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
hydroperoxidation
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
hydroperoxidation
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
hydroperoxidation
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
overall reaction
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
product generation is both regiospecific and stereospecific, the S-isomer is produced
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
higher affinity of arachidonate than linoleic acid for the ferrous form of lipoxygenase-1. Hydrogen abstraction step displays high kinetic isotope effects on kcat due to tunneling contributions. Lack of solvent-dependent rate-limiting steps at lower temperatures with arachidonate as substrate
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
72% of the activity with 5,8,11,14,17-eicosapentaenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ minor amounts of the double oxygenation products
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
5(S)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid + 6-trans-leukotriene B4 + 12-epi-6-trans-leukotriene B4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
formation of leukotriene A4 without release of the intermediate (6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
5-hydroperoxyeicosatetraenoic acid + 11(S)-hydroperoxyeicosatetraenoic acid + 15-hydroperoxyeicosatetraenoic acid + 5(S),12(S)-dihydroperoxy-6,8,10,14-eicosatetraenoic acid + 6-trans-leukotriene B4 + 12-epi-6-trans-leukotiene B4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
5(S)-hydroperoxyeicosatetraenoic acid is the most abundant primary oxygenation product, representing 60% of the total hydroperoxyeicosatetraenoic acids, followed by 8(S)-hydroperoxyeicosatetraenoic acid, 9-hydroperoxyeicosatetraenoic acid, 11(S)-hydroperoxyeicosatetraenoic acid, 12-hydroperoxyeicosatetraenoic acid, and 15-hydroperoxyeicosatetraenoic acid in decreasing order of abundance, all possible diH(P)ETEs are detected
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
(5S,6R)-dihydroperoxy-7,9,11,14-eicosatetraenoic acid is produced as major product especially when the incubation is performed on ice rather than at room temperature, 6R-oxygenase activity
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ minor products: 5-hydroxy-6,8,11,14-eicosatetraenoic acid, 6-trans-leukotriene B4 and 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ leukotriene A4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
the enzyme is rather specific for the insertion of O2 at the fifth carbon on arachidonic acid
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
first committed step in the synthesis of leukotrienes
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
stereospecific abstraction of the pro-S hydrogen at C7, followed by insertion of molecular O2 at C5
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
linoleic acid + O2
?
-
lower affinity of linoleic acid than arachidonic acid for the ferrous form of lipoxygenase-1. Hydrogen abstraction step displays high kinetic isotope effects on kcat due to tunneling contributions
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
additional information
?
-
-
the purified protein expresses both 5-oxygenase and leukotriene A4 synthase activities in the ratio of 6:1
-
-
?
additional information
?
-
-
key enzyme in leukotriene metabolism, in human mast cells glucocorticoids effectively and selectively upregulate the expression
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
?
additional information
?
-
-
5-lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells, overview
-
-
?
additional information
?
-
-
ALOX5-derived lipid mediators leukotrienes and lipoxins have regulatory functions in inflammation by modulating activities of immune cells and cytokine production, host control of Mycobacterium tuberculosis is regulated by 5-lipoxygenase
-
-
?
additional information
?
-
-
inhibition of COX pathways does not increase the transformation of arachidonic acid by the 5-LOX pathway
-
-
?
additional information
?
-
-
key enzyme in biosynthesis of leukotrienes, overview. Upon cell activation, cytosolic and nuclear enzyme translocates the nuclear envelope, where it interacts with phospholipase A2, making free arachidonate available for 5-LO, and with 5-LO activating protein, i.e. FLAP. 5-LO regulates cancer cell survival and interferes with the mechanismtumor suppression, and increases cancer cell chemoresistance, overview
-
-
?
additional information
?
-
key enzyme in the leukotriene biosynthesis, pathway overview, the 5-LO pathway is linked to the development of cardiovascular disease and other diseases, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
?
additional information
?
-
-
no significant effect of LTB4, 12-hydroperoxyeicosatetraenoic acid or 15-hydroperoxyeicosatetraenoic acid on leukemic blast growth and on their apoptose rate, overview
-
-
?
additional information
?
-
-
the enzyme is involved in survival of Epstein-Barr virus-converted B lymphoma cells via function of 5-hydroperoxyeicosatetraenoic acid, overview
-
-
?
additional information
?
-
-
the enzyme is the key enzyme in biosynthesis of biologically active leukotrienes
-
-
?
additional information
?
-
-
the enzyme, catalyzing the key step in leukotriene biosynthesis, interacts with methyl jasmonate, which is probably involved in the anticarcinogenic activity of methyl jasmonate inducing apoptosis, overview
-
-
?
additional information
?
-
the enzyme catalyzes the dioxygenation of polyunsaturated fatty acids
-
-
?
additional information
?
-
5-LOX catalyzes a 2-step reaction where arachidonic acid (AA) is oxygenated, resulting in formation of 5(S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid (5-HPETE), with subsequent formation of leukotriene A4 (LTA4). Active site structure and binding of substrate arachidonate involving residues F421, F177, Q363, L414 and L368 during the reaction, model, overview
-
-
?
additional information
?
-
-
5-LOX catalyzes a 2-step reaction where arachidonic acid (AA) is oxygenated, resulting in formation of 5(S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid (5-HPETE), with subsequent formation of leukotriene A4 (LTA4). Active site structure and binding of substrate arachidonate involving residues F421, F177, Q363, L414 and L368 during the reaction, model, overview
-
-
?
additional information
?
-
detectable 5-LO products derived from conversion of arachidonate are quantified by HPLC and comprise 5-H(p)ETE (a mixture of 5-HETE (5S-hydroxy-6,8,11,14(E,Z,Z,Z)-eicosatetraenoic acid) and 5-HpETE (5S-hydroperoxy-6,8,11,14(E,Z,Z,Z)-eicosatetraenoic acid)) and the non-enzymatic hydrolysis products of leukotriene A4, 6-trans-leukotriene B4 (5S,12R-dihydroxy-6,8,10,14(E,E,E,Z)-eicosatetraenoic acid) and 6-trans-12-epi-LTB4 (5S,12S-dihydroxy-6,8,10,14-(E,E,E,Z)-eicosatetraenoic acid)
-
-
?
additional information
?
-
-
detectable 5-LO products derived from conversion of arachidonate are quantified by HPLC and comprise 5-H(p)ETE (a mixture of 5-HETE (5S-hydroxy-6,8,11,14(E,Z,Z,Z)-eicosatetraenoic acid) and 5-HpETE (5S-hydroperoxy-6,8,11,14(E,Z,Z,Z)-eicosatetraenoic acid)) and the non-enzymatic hydrolysis products of leukotriene A4, 6-trans-leukotriene B4 (5S,12R-dihydroxy-6,8,10,14(E,E,E,Z)-eicosatetraenoic acid) and 6-trans-12-epi-LTB4 (5S,12S-dihydroxy-6,8,10,14-(E,E,E,Z)-eicosatetraenoic acid)
-
-
?
additional information
?
-
no substrate: 5S,15S-dihydroperoxyeicosatetraenoic acid
-
-
-
additional information
?
-
-
no substrate: 5S,15S-dihydroperoxyeicosatetraenoic acid
-
-
-
additional information
?
-
-
arachidonate 5-lipoxygenase and leukotriene A5 synthase are identical
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
additional information
?
-
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
?
additional information
?
-
-
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
?
additional information
?
-
inhibition of 5-lipoxygenase does not affect cardiac ischemia-reperfusion injury but the post-ischemic inflammatory response, overview
-
-
?
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
?
additional information
?
-
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
?
additional information
?
-
5-LOX is the key enzyme in the biosynthesis of leukotrienes through catalyzing the initial two steps in conversion of arachidonic acid to leukotrienes
-
-
?
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
?
additional information
?
-
-
stereo-selectivity in LOX-catalyzed oxygenation of lysophospholipids, overview
-
-
?
additional information
?
-
-
5-lipoxygenase has a two-domain structure, the small N-terminal beta-barrel domain and a larger catalytic domain containing a single atom of non-heme iron coordinating with His525, His530, His716 and Ile864
-
-
?
additional information
?
-
-
the enzyme exhibits 6R-oxygenase activity with (5S)-hydroxy and (5S)-hydroperoxy acids as substrates
-
-
?
additional information
?
-
-
the enzyme is involved in lipoxin synthesis from 5,15-dihydroxyperoxyeicosatetraenoic acid via 5,6-epoxide
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
?
