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

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Rattus norvegicus
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The taxonomic range for the selected organisms is: Rattus norvegicus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
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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, pmnl 5-lipoxygenase, 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
-
-, -, -, -, -, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 5-oxidoreductase
-
CAS REGISTRY NUMBER
COMMENTARY hide
80619-02-9
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
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
-
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
-
-
-
?
(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
-
-
-
?
11,14,17-eicosatrienoic acid + O2
?
show the reaction diagram
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
5,8,11-eicosatrienoic acid + O2
?
show the reaction diagram
-
almost as active as arachidonic acid
-
-
?
8,11,14-eicosatrienoic acid + O2
?
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
docosahexaenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
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
-
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
-
-
-
?
(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
-
-
-
-
?
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