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Information on EC 1.13.11.34 - arachidonate 5-lipoxygenase and Organism(s) Rattus norvegicus and UniProt Accession P12527

for references in articles please use BRENDA:EC1.13.11.34

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The taxonomic range for the selected organisms is: Rattus norvegicus
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
hide(Overall reactions are displayed. Show all >>)
arachidonate
+
O2
=
leukotriene A4
+
H2O
+
=
+

Synonyms
5-lipoxygenase, 5-lox, arachidonate 5-lipoxygenase, lox-5, leukotriene a4 synthase, lta synthase, arachidonic acid 5-lipoxygenase, lipoxygenase 5, 5-lo1, lox-15, more

SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5-lipoxygenase
-
5DELTA-lipoxygenase
-
-
-
-
arachidonic 5-lipoxygenase
-
-
-
-
arachidonic acid 5-lipoxygenase
-
-
-
-
C-5-lipoxygenase
-
-
-
-
DELTA5-lipoxygenase
-
-
-
-
leukotriene A4 synthase
-
-
-
-
leukotriene-A4 synthase
-
-
-
-
LTA synthase
-
-
-
-
LTA4 synthase
-
-
oxygenase, arachidonate, 5-lip-
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
dioxygenation
-
-
-
-
PATHWAY SOURCE
PATHWAYS
MetaCyc
15-epi-lipoxin biosynthesis, anandamide lipoxygenation, arachidonate metabolites biosynthesis, aspirin triggered resolvin D biosynthesis, aspirin triggered resolvin E biosynthesis, docosahexaenoate metabolites biosynthesis, icosapentaenoate metabolites biosynthesis, leukotriene biosynthesis, lipoxin biosynthesis, peptido-conjugates in tissue regeneration biosynthesis, resolvin D biosynthesis
SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 5-oxidoreductase
-
CAS REGISTRY NUMBER
COMMENTARY hide
80619-02-9
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY hide
Reversibility
r=reversible
ir=irreversible
?=not specified
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Substrates: -
Products: -
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate + O2
leukotriene A4
show the reaction diagram
-
Substrates: -
Products: -
?
11,14,17-eicosatrienoic acid + O2
?
show the reaction diagram
-
Substrates: -
Products: -
?
5,8,11,14,17-eicosapentaenoic acid + O2
?
show the reaction diagram
-
Substrates: -
Products: -
?
5,8,11-eicosatrienoic acid + O2
?
show the reaction diagram
-
Substrates: almost as active as arachidonic acid
Products: -
?
8,11,14-eicosatrienoic acid + O2
?
show the reaction diagram
-
Substrates: -
Products: -
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
Substrates: -
Products: -
?
docosahexaenoic acid + O2
?
show the reaction diagram
-
Substrates: -
Products: -
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY hide
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
Substrates: -
Products: is unstable and metabolized to leukotriene B4
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Substrates: -
Products: -
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
Substrates: -
Products: -
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1-oleoyl-2-acetyl-sn-glycerol
-
both Ca2+ and glyceride, e.g. 1-oleoyl-2-acetyl-sn-glycerol, might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
Ba2+
-
45% of the activation with Ca2+
Fe3+
-
because catalysis by 5-LO requires oxidation of Fe2+ to the active Fe3+ state by lipid hydroperoxides, the redox tone is an important parameter of cellular 5-LO activity
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-(3,4-dichlorobenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
82% inhibition at 0.005 mM
1-(3,4-dichlorobenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
38.5% inhibition at 0.005 mM
1-(4-chlorophenoxy)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
22% inhibition at 0.005 mM
1-(4-chlorophenoxy)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
26% inhibition at 0.005 mM
1-(4-chlorophenoxy)-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
70% inhibition at 0.005 mM
1-(4-methylbenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
35% inhibition at 0.005 mM
1-(4-methylbenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
55% inhibition at 0.005 mM
1-benzyl-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
41% inhibition at 0.005 mM
1-benzyl-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
64% inhibition at 0.005 mM
1-benzyl-3-(4-morpholin-4-ylbutyl)-1H-indole
42% inhibition at 0.005 mM
1-benzyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
95% inhibition at 0.005 mM
1-benzyl-3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
32% inhibition at 0.005 mM
1-benzyl-3-[3-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]propyl]-5-methoxy-2-methyl-1H-indole
46.5% inhibition at 0.005 mM
1-benzyl-5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
80% inhibition at 0.005 mM
1-benzyl-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
54% inhibition at 0.005 mM
1-benzyl-5-methoxy-2-methyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
65% inhibition at 0.005 mM
3-(2-morpholin-4-yl-2-oxoethyl)-1-phenoxy-1H-indole
21% inhibition at 0.005 mM
3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
16% inhibition at 0.005 mM
3-(3-morpholin-4-yl-3-oxopropyl)-1-phenoxy-1H-indole
23% inhibition at 0.005 mM
3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
33% inhibition at 0.005 mM
3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
62% inhibition at 0.005 mM
3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
64% inhibition at 0.005 mM
4-((3,4-dichlorobenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
27% inhibition at 0.005 mM
4-((4-chlorobenzoyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
32% inhibition at 0.005 mM
4-(1-(4-methylbenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
34% inhibition at 0.005 mM
4-(1-benzoyl-1H-indol-3-yl)-1-morpholinobutan-1-one
58% inhibition at 0.005 mM
4-(1-benzyl-1H-indol-3-yl)-1-morpholinobutan-1-one
26% inhibition at 0.005 mM
5-chloro-1-(4-chlorophenoxy)-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
38% inhibition at 0.005 mM
5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
71% inhibition at 0.005 mM
5-methoxy-2-methyl-1-(4-methylbenzyl)-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
26% inhibition at 0.005 mM
5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
73% inhibition at 0.005 mM
tert-butyl 4-[4-(1-benzyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
38% inhibition at 0.005 mM
tert-butyl 4-[4-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
51.5% inhibition at 0.005 mM
tert-butyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
84% inhibition at 0.005 mM
tert-butyl 4-[4-(5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
71% inhibition at 0.005 mM
zileuton
87% inhibition at 0.005 mM
(10E,12E)-octadeca-10,12-dien-8-ynoic acid
-
-
(11E)-octadec-11-en-9-ynoic acid
-
-
(1E)-1-((1-[(1Z)-prop-1-en-1-yldisulfanyl]propyl)sulfinyl)prop-1-ene
-
-
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
-
-
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
inhibits reaction with arachidonate
([3-chloro-5-(2,3-dihydro-1H-inden-4-ylamino)phenyl]sulfanyl)acetic acid
-
-
1,10-phenanthroline
-
0.01 mM, 34% inhibition
1,4a-dimethyl-7-(propan-2-yl)-1-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene (non-preferred name)
-
-
1-(3,4-difluorophenyl)-1,2,4-triazinan-3-one
-
-
1-(3-bromophenyl)-1,2,4-triazinan-3-one
-
-
1-(3-chlorophenyl)-1,2,4-triazinan-3-one
-
-
1-(3-ethylphenyl)-1,2,4-triazinan-3-one
-
-
1-(3-hydroxyphenyl)-3-[4-(methylsulfonyl)phenyl]prop-2-yn-1-one
-
-
1-(6-methylpyridin-2-yl)-1,2,4-triazinan-3-one
-
-
1-hydroxy-1-[1-(5-methoxy-1-methyl-1H-indol-2-yl)ethyl]urea
-
-
1-phenyl-5-(propan-2-yl)-1,2,4-triazinan-3-one
-
-
1-[1-(6-tert-butyl-1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
-
-
1-[3-(benzyloxy)phenyl]-1,2,4-triazinan-3-one
-
-
1-[4-([3-fluoro-5-[4-(methylsulfinyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
-
1-[4-([3-fluoro-5-[4-(methylsulfonyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
-
11,14,17-Eicosatrienoic acid
2,3,4',5-tetrahydroxystilbene-2-O-D-glucoside
-
polymorphonuclear leukocyte
2-(2,4-dihydroxyphenyl)-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
-
-
2-(2-[ethyl(hydroxy)amino]ethyl)dibenzo[b,e]oxepin-11(6H)-one
-
-
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
-
-
2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
-
-
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
-
-
2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c]chromene-3,6,9-triol
-
-
2-(3-[hydroxy(methyl)amino]propyl)dibenzo[b,e]oxepin-11(6H)-one
-
-
3-(2-(2-[(4-chlorophenyl)sulfanyl]ethoxy)-3-methoxy-5-[5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-2-yl]benzyl)-1-hydroxy-1-methylurea
-
-
3-(4,5-dihydroxy-2-methyl-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl)-2-hydroxy-4,6-dimethoxybenzoic acid
-
-
3-ethoxy-11-oxours-12-en-23-oic acid
-
-
3-[4-(methylsulfonyl)phenyl]-1-[4-(propan-2-yl)phenyl]prop-2-yn-1-one
-
-
3-[5-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
-
-
4,4'-(2,3-dimethyl)-1,4-butanediylbis-1,2-benzenediol
-
-
4,7,10,13,16,19-docosahexaenoic acid
-
IC50: 0.0013 mM
4,9-dimethoxy-3-methyl-9,10-dihydrophenanthrene-2,7-diol
-
-
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)-N-methyltetrahydro-2H-pyran-4-carboxamide
-
-
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-ol
-
-
4-(3-fluoro-5[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-carboxylic acid
-
-
4-(6-methoxynaphthalen-2-yl)butan-2-one
-
-
4-(acetyloxy)-2-[4-(acetyloxy)-6-methylhept-5-en-2-yl]cyclohexyl (2Z)-2-methylbut-2-enoate
-
-
4-(furan-3-yl)-7-[[2-(tetrahydro-2H-pyran-4-yl)pyridin-4-yl]methoxy]naphthalene-2-carbonitrile
-
-
4-(furan-3-yl)-7-[[7-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydroquinolin-2-yl]oxy]naphthalene-2-carbonitrile
-
-
4-methylesculetin
-
polymorphonuclear leukocyte
4-[4-(4-fluoro-phenyl)-thiazol-2-ylamino]-2,6-dimethylphenol
-
KR-33749, the compound exhibits a more than 1000fold selectivity for 5-LO against 12-LO and 15-LO
5,5'-di(prop-2-en-1-yl)biphenyl-2,2'-diol
-
-
5,5-dimethyl-1-phenyl-1,2,4-triazinan-3-one
-
-
5,6-Dehydroarachidonate
-
irreversible
5,8,11,13-eicosatetraynoic acid
-
IC50: 0.028 mM
5-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole
-
-
5-butyl-1-phenyl-1,2,4-triazinan-3-one
-
-
5-ethyl-1-phenyl-1,2,4-triazinan-3-one
-
-
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
-
-
6-(trideca-1,4,7-triene-1-sulfinyl)-hex-5-enoic acid
-
-
6-ethenesulfinyl-hex-5-enoic acid
-
-
6-ethenesulfinyl-hex-5-enoic acid amide
-
-
6-hept-1-ene-1-sulfinyl-hex-5-enoic acid
-
-
6-hept-1-enylsulfanyl-hex-5-enoic acid
-
-
6-vinylsulfanyl-hex-5-enoic acid
-
-
6-vinylsulfanyl-hex-5-enoic acid amide
-
-
7,8-dihydroxy-2H-chromen-2-one
-
-
7-thiaarachidonic acid
-
-
8,11,14-eicosatrienoic acid
8-hydroxyquinoline
-
0.01 mM, 59% inhibition
AA861
-
IC50: 0.0026 mM
ABT 761
-
CAS: 154355-76-7
arachidonic acid
baicalein
-
IC50: 0.0012 mM
BW755C
caffeic acid
-
IC50: 0.046 mM
catechol
-
IC50: 0.062 mM
Cirsiliol
-
IC50: 0.098 mM
daphnetin
-
polymorphonuclear leukocyte
docosahexaenoic acid
-
substrate inhibition
eicosapentaenoic acid
epinephrine
-
IC50: 0.98 mM
esculetin
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
prevents leukotriene B4 production in pleural exudates of carrageenan-treated rats, associated with reduced severity of pleurisy. Significantly reduces the inflammatory reaction measured as exudate volume (77%), inflammatory cell numbers (40%), and leukotriene B4 levels (49%) in the pleural exudates
eupatilin
-
IC50: 0.098 mM
forsythiaside
-
polymorphonuclear leukocyte
fraxetin
-
polymorphonuclear leukocyte
glutathione
-
efficiency of non-redox-type 5-LO inhibitors depends on the presence of glutathione peroxidase activity leading to low hydroperoxide concentration
indomethacin
-
IC50: 0.36 mM
iodoacetamide
-
0.01 mM, 20% inhibition
leucocyanidol
-
polymorphonuclear leukocyte
myrtol
-
enzyme from RBL-1 cell
-
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
-
N-hydroxy-N-[1-(1-methyl-1H-indol-2-yl)ethyl]acetamide
-
-
NEM
-
0.01 mM, 75% inhibition
nordihydroguiaraetic acid
-
IC50: 0.00021 mM
norepinephrine
-
IC50: 0.49 mM
oroxindin
-
polymorphonuclear leukocyte
piceid
-
polymorphonuclear leukocyte
quercetagetin-7-O-beta-D-glucoside
-
polymorphonuclear leukocyte
quercetin
-
IC50: 0.0021 mM
resveratrol
-
polymorphonuclear leukocyte
rutin
-
IC50: 0.033 mM
sideritoflavone
-
polymorphonuclear leukocyte
suspensaside
-
polymorphonuclear leukocyte
tambuletin
-
polymorphonuclear leukocyte
verbascoside
-
polymorphonuclear leukocyte
zileuton
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5-lipoxygenase-activating protein
-
a 18000 Da integral membrane protein required, in peripheral cells, for the activation of 5-lipoxygenase
-
5-LO-activating protein
-
i.e. FLAP, a small permanently membrane-bound protein that is essential for the biosynthesis of leukotrienes from endogenous arachidonic acid. FLAP binds arachidonic acid and is thought to assist in the provision of substrate to 5-LO
-
7-thiaarachidonic acid
-
-
adenosine
-
stimulates at 0.01 mM or lower
Adenosine 5'-O-(2-thiodiphosphate)
-
stimulates at 0.01 mM or lower
ADP
-
about half as active as ATP
AMP
-
about half as active as ATP
CTP
-
about half as active as ATP
Guanosine 5'-O-(2-thiodiphosphate)
-
stimulates at 0.01 mM or lower
guanosine 5'-O-(3-thiotriphosphate)
-
10fold stimulation of arachidonic acid oxidation at 0.0005-0.001 mM
additional information
-
coactosin-like protein, i.e. CLP, can bind to 5-LO and supports Ca2+-induced 5-LO enzyme activity. CLP seems to function as a chaperone or scaffold for 5-LO, upregulation of 5-LO through the C2-like domain
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.024
5,8,11,14,17-eicosapentaenoic acid
-
-
0.032
5,8,11-eicosatrienoic acid
-
-
0.017 - 0.182
arachidonic acid
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0137
arachidonic acid
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00087
1-(3,4-dichlorobenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
Rattus norvegicus
-
0.00225
1-(4-chlorophenoxy)-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
Rattus norvegicus
-
0.00317
1-benzyl-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
Rattus norvegicus
-
0.00085
1-benzyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
Rattus norvegicus
-
0.00095
1-benzyl-5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
Rattus norvegicus
-
0.00206
3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
Rattus norvegicus
-
0.00238
3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
Rattus norvegicus
-
0.074
4-(1-benzyl-1H-indol-3-yl)-1-morpholinobutan-1-one
Rattus norvegicus
-
0.00133
5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
Rattus norvegicus
-
0.00316
5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
Rattus norvegicus
-
0.00074
tert-butyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
Rattus norvegicus
-
0.00083
zileuton
Rattus norvegicus
-
0.005
(10E,12E)-octadeca-10,12-dien-8-ynoic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.06
(11E)-octadec-11-en-9-ynoic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0005
(1E)-1-((1-[(1Z)-prop-1-en-1-yldisulfanyl]propyl)sulfinyl)prop-1-ene
Rattus norvegicus
-
pH and temperature not specified in the publication
0.003
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0039
([3-chloro-5-(2,3-dihydro-1H-inden-4-ylamino)phenyl]sulfanyl)acetic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.029
1,4a-dimethyl-7-(propan-2-yl)-1-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene (non-preferred name)
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0028
1-(3,4-difluorophenyl)-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0021
1-(3-bromophenyl)-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0035
1-(3-chlorophenyl)-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0066
1-(3-ethylphenyl)-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.3
1-(3-hydroxyphenyl)-3-[4-(methylsulfonyl)phenyl]prop-2-yn-1-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0039
1-(6-methylpyridin-2-yl)-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0038
1-hydroxy-1-[1-(5-methoxy-1-methyl-1H-indol-2-yl)ethyl]urea
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0039
1-phenyl-5-(propan-2-yl)-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0056
1-[1-(6-tert-butyl-1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0049
1-[3-(benzyloxy)phenyl]-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00034
1-[4-([3-fluoro-5-[4-(methylsulfinyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
Rattus norvegicus
-
pH and temperature not specified in the publication
0.000195
1-[4-([3-fluoro-5-[4-(methylsulfonyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
Rattus norvegicus
-
pH and temperature not specified in the publication
0.015
11,14,17-Eicosatrienoic acid
Rattus norvegicus
-
IC50: 0.015 mM
0.1
2-(2,4-dihydroxyphenyl)-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0055
2-(2-[ethyl(hydroxy)amino]ethyl)dibenzo[b,e]oxepin-11(6H)-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.03
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Rattus norvegicus
-
pH and temperature not specified in the publication
0.02 - 2
2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0032
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0036
2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c]chromene-3,6,9-triol
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0049
2-(3-[hydroxy(methyl)amino]propyl)dibenzo[b,e]oxepin-11(6H)-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.01
3-(2-(2-[(4-chlorophenyl)sulfanyl]ethoxy)-3-methoxy-5-[5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-2-yl]benzyl)-1-hydroxy-1-methylurea
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0042
3-(4,5-dihydroxy-2-methyl-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl)-2-hydroxy-4,6-dimethoxybenzoic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0015
3-ethoxy-11-oxours-12-en-23-oic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.32
3-[4-(methylsulfonyl)phenyl]-1-[4-(propan-2-yl)phenyl]prop-2-yn-1-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0005
3-[5-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0013
4,7,10,13,16,19-docosahexaenoic acid
Rattus norvegicus
-
IC50: 0.0013 mM
0.0085
4,9-dimethoxy-3-methyl-9,10-dihydrophenanthrene-2,7-diol
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0068
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)-N-methyltetrahydro-2H-pyran-4-carboxamide
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0006
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-ol
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00054
4-(3-fluoro-5[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-carboxylic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.003
4-(6-methoxynaphthalen-2-yl)butan-2-one
Rattus norvegicus
-
value above, pH and temperature not specified in the publication
0.0077
4-(acetyloxy)-2-[4-(acetyloxy)-6-methylhept-5-en-2-yl]cyclohexyl (2Z)-2-methylbut-2-enoate
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0055
4-(furan-3-yl)-7-[[2-(tetrahydro-2H-pyran-4-yl)pyridin-4-yl]methoxy]naphthalene-2-carbonitrile
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0038
4-(furan-3-yl)-7-[[7-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydroquinolin-2-yl]oxy]naphthalene-2-carbonitrile
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00007
4-[4-(4-fluoro-phenyl)-thiazol-2-ylamino]-2,6-dimethylphenol
Rattus norvegicus
-
in 50 mM Tris-HCl buffer (pH 7.4) containing 0.4 mM CaCl2+ , 0.024 mg/ml alpha-phosphatidylcholine and 0.02 mM ATP, at 22°C
0.002
5,5'-di(prop-2-en-1-yl)biphenyl-2,2'-diol
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0048
5,5-dimethyl-1-phenyl-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.028
5,8,11,13-eicosatetraynoic acid
Rattus norvegicus
-
IC50: 0.028 mM
0.003
5-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole
Rattus norvegicus
-
value above, pH and temperature not specified in the publication
0.0084
5-butyl-1-phenyl-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.006
5-ethyl-1-phenyl-1,2,4-triazinan-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00137
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0069
7,8-dihydroxy-2H-chromen-2-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00219
8,11,14-eicosatrienoic acid
Rattus norvegicus
-
IC50: 0.00219 mM
0.0026
AA861
Rattus norvegicus
-
IC50: 0.0026 mM
0.00023
arachidonic acid
Rattus norvegicus
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00023 mM
0.0012
baicalein
Rattus norvegicus
-
IC50: 0.0012 mM
0.53
BW755C
Rattus norvegicus
-
IC50: 0.53 mM
0.046
caffeic acid
Rattus norvegicus
-
IC50: 0.046 mM
0.062
catechol
Rattus norvegicus
-
IC50: 0.062 mM
0.098
Cirsiliol
Rattus norvegicus
-
IC50: 0.098 mM
0.00065
eicosapentaenoic acid
Rattus norvegicus
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00065 mM
0.98
epinephrine
Rattus norvegicus
-
IC50: 0.98 mM
0.0045
esculetin
Rattus norvegicus
-
IC50: 0.0045 mM
0.098
eupatilin
Rattus norvegicus
-
IC50: 0.098 mM
0.36
indomethacin
Rattus norvegicus
-
IC50: 0.36 mM
0.15
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00119
N-hydroxy-N-[1-(1-methyl-1H-indol-2-yl)ethyl]acetamide
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00021
nordihydroguiaraetic acid
Rattus norvegicus
-
IC50: 0.00021 mM
0.49
norepinephrine
Rattus norvegicus
-
IC50: 0.49 mM
0.0021
quercetin
Rattus norvegicus
-
IC50: 0.0021 mM
0.033
rutin
Rattus norvegicus
-
IC50: 0.033 mM
0.00028
zileuton
Rattus norvegicus
-
in 50 mM Tris-HCl buffer (pH 7.4) containing 0.4 mM CaCl2+ , 0.024 mg/ml alpha-phosphatidylcholine and 0.02 mM ATP, at 22°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9
-
pH 7.0: 66% of maximal activity, pH 9.0: about 60% of maximal activity
top print hide Go to Organism Search
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
top print hide Go to Source Tissue Search
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
expression is not significantly different between diabetic and control rats. Activation of the 5-lipoxygenase previously reported in streptozotocin-induced diabetic rats can be explained by an augmented sensitivity to cysteinyl leukotrienes in the diabetic aorta
Manually annotated by BRENDA team
-
high level of expression
Manually annotated by BRENDA team
-
high level of expression, colocalization of 5-lipoxygenase and 5-lipoxygenase-activating protein in CA1 pyramidal neurons
Manually annotated by BRENDA team
top print hide Go to Localization Search
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
-
localization of enzyme and reactions, and activation in the cell, overview
-
Manually annotated by BRENDA team
Highest Expressing Human Cell Lines
Cell Line Links Gene Links
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
LOX5_RAT
673
0
78087
Swiss-Prot
-
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
73000
-
x * 73000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystal structure analysis
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
half-life: 30 s
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 48 h, no appreciable loss of activity
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Sf-21 insect cells
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
due to their high potency against 5-lipoxygenase and the marked efficacy in biological systems, benzo[g]indole-3-carboxylates may have potential as anti-inflammatory therapeutics
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
DeWolf, W.E.
Enzymatic studies on purified 5-lipoxygenase
Lipoxygenases and Their Products (Crooke, S. T. ed. ) Academic Press
105-135
1991
Rattus norvegicus, Cavia porcellus, Homo sapiens, Sus scrofa
-
Manually annotated by BRENDA team
McMillan, R.M.; Masters, D.J.; Vickers, V.C.; Dicken, M.P.; Jacobs, V.N.
Metabolism of unsaturated fatty acids by RBL-1 5-lipoxygenase: influence of substrate solubility and product inactivation
Biochim. Biophys. Acta
1005
170-176
1989
Rattus norvegicus
Manually annotated by BRENDA team
Denis, D.; Choo, L.Y.; Riendeau, D.
Activation of 5-lipoxygenase by guanosine 5-O-(3-thiotriphosphate) and other nucleoside phosphorothioates: redox properties of thionucleotide analogs
Arch. Biochem. Biophys.
273
592-596
1989
Rattus norvegicus
Manually annotated by BRENDA team
Haurand, M.; Flohe, L.
Kinetic studies on arachidonate 5-lipoxygenase from rat basophilic leukemia cells
Biol. Chem. Hoppe-Seyler
369
133-142
1988
Rattus norvegicus
Manually annotated by BRENDA team
Masters, D.J.; Jacobs, V.N.; Carr, V.J.; McMillan, R.M.
Kinetics of 5-lipoxygenase: influence of substrate solubility and product inactivation
Biochem. Soc. Trans.
16
38-39
1988
Rattus norvegicus
-
Manually annotated by BRENDA team
Skoog, M.T.; Nichols, J.S.; Wiseman, J.S.
5-Lipoxygenase from rat PMN lysate
Prostaglandins
31
561-576
1986
Rattus norvegicus
Manually annotated by BRENDA team
Wiseman, J.S.; Skoog, M.T.; Nichols, J.S.; Harrison, B.L.
Kinetics of leukotriene A4 synthesis by 5-lipoxygenase from rat polymorphonuclear leukocytes
Biochemistry
26
5684-5689
1987
Rattus norvegicus
Manually annotated by BRENDA team
Corey, E.J.; Casman, J.R.; Eckrich, T.M.; Corey, D.R.
A new class of irreversible inhibitors of leukotriene biosynthesis
J. Am. Chem. Soc.
107
713-715
1985
Rattus norvegicus
-
Manually annotated by BRENDA team
Furukawa, M.; Yoshimoto, T.; Ochi, K.; Yamamoto, S.
Studies on arachidonate 5-lipoxygenase of rat basophilic leukemia cells
Biochim. Biophys. Acta
795
458-465
1984
Rattus norvegicus
Manually annotated by BRENDA team
Corey, E.J.; Lansbury, P.T.; Cashman, J.R.; Kanter, S.S.
Mechanism of the irreversible deactivation of arachidonate 5-lipoxygenase by 5,6-dehydroarachidonate
J. Am. Chem. Soc.
106
1501-1503
1984
Rattus norvegicus
-
Manually annotated by BRENDA team
Brock, T.G.; McNish, R.W.; Peters-Golden, M.
Translocation and leukotriene synthetic capacity of nuclear 5-lipoxygenase in rat basophilic leukemia cells and alveolar macrophages
J. Biol. Chem.
270
21652-21658
1995
Rattus norvegicus, Homo sapiens
Manually annotated by BRENDA team
Brock, T.G.; Paine, R.; Peters-Golden, M.
Localization of 5-lipoxygenase to the nucleus of unstimulated rat basophilic leukemia cells
J. Biol. Chem.
269
22059-22066
1994
Rattus norvegicus
Manually annotated by BRENDA team
Bell, R.L.; Harris, R.R.
The enzymology and pharmacology of 5-lipoxygenase and 5-lipoxygenase activating protein
Clin. Rev. Allergy Immunol.
17
91-109
1999
Rattus norvegicus, Cavia porcellus, Homo sapiens, Sus scrofa, Oryctolagus cuniculus
Manually annotated by BRENDA team
Lammers, C.H.; Schweitzer, P.; Facchinetti, P.; Arrang, J.M.; Madamba, S.G.; Siggins, G.R.; Piomelli, D.
Arachidonate 5-lipoxygenase and its activating protein: prominent hippocampal expression and role in somatostatin signaling
J. Neurochem.
66
147-152
1996
Rattus norvegicus
Manually annotated by BRENDA team
Radmark, O.
Arachidonate 5-lipoxygenase
Prostaglandins
68-69
211-234
2002
Rattus norvegicus, Homo sapiens, Sus scrofa, Solanum tuberosum, Mus musculus, Oryctolagus cuniculus
Manually annotated by BRENDA team
Brkert, E.; Szellas, D.; Radmark, O.; Steinhilber, D.; Werz, O.
Cell type-dependent activation of 5-lipoxygenase by arachidonic acid
J. Leukocyte Biol.
73
191-200
2003
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Schneider, I.; Bucar, F.
Lipoxygenase inhibitors from natural plant sources. Part 1: Medicinal plants with inhibitory activity on arachidonate 5-lipoxygenase and 5-lipoxygenase/cyclooxygenase
Phytother. Res.
19
81-102
2005
Glycine max, Helianthus tuberosus, Cavia porcellus, Bos taurus, Rattus norvegicus, Sus scrofa, Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Hardy, G.; Vergnaud, S.; Lunardi, J.; Peoc'h, M.; Bessard, G.; Stanke-Labesque, F.
5-Lipoxygenase expression and activity in aorta from streptozotocin-induced diabetic rats
Prostaglandins
75
91-103
2005
Rattus norvegicus
Manually annotated by BRENDA team
Zheng, M.; Zheng, M.; Ye, D.; Deng, Y.; Qiu, S.; Luo, X.; Chen, K.; Liu, H.; Jiang, H.
Indole derivatives as potent inhibitors of 5-lipoxygenase: design, synthesis, biological evaluation, and molecular modeling
Bioorg. Med. Chem. Lett.
17
2414-2420
2007
Rattus norvegicus (P12527)
Manually annotated by BRENDA team
Radmark, O.; Werz, O.; Steinhilber, D.; Samuelsson, B.
5-Lipoxygenase: regulation of expression and enzyme activity
Trends Biochem. Sci.
32
332-341
2007
Homo sapiens (P09917), Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Radmark, O.; Samuelsson, B.
5-Lipoxygenase: mechanisms of regulation
J. Lipid Res.
50 Suppl
S40-S45
2009
Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Karg, E.M.; Luderer, S.; Pergola, C.; Buehring, U.; Rossi, A.; Northoff, H.; Sautebin, L.; Troschuetz, R.; Werz, O.
Structural optimization and biological evaluation of 2-substituted 5-hydroxyindole-3-carboxylates as potent inhibitors of human 5-lipoxygenase
J. Med. Chem.
52
3474-3483
2009
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Cho, Y.S.; Kim, C.H.; Surh, J.H.; Kang, N.S.; Yoo, S.E.; Cheon, H.G.
Identification of 4-[4-(4-fluoro-phenyl)-thiazol-2-ylamino]-2,6-dimethyl-phenol (KR-33749) as an inhibitor of 5-lipoxygenase with potent antiinflammatory activity
Pharmacology
86
65-72
2010
Rattus norvegicus
Manually annotated by BRENDA team
Khairullina, V.; Taipov, I.; Gerchikov, A.; Zarudii, F.
Structure-activity relationship in a series of natural and synthetic inhibitors of 5-lipoxygenase catalytic activity
Pharm. Chem. J.
46
553-564
2012
Rattus norvegicus
-
Manually annotated by BRENDA team