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Information on EC 1.13.11.34 - arachidonate 5-lipoxygenase and Organism(s) Homo sapiens

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The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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
5-LOX
5DELTA-lipoxygenase
-
-
-
-
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 5
-
-
LOX-5
-
-
LTA synthase
-
-
-
-
LTA4 synthase
oxygenase, arachidonate, 5-lip-
-
-
-
-
PMNL 5-lipoxygenase
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
arachidonate + O2 = (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dioxygenation
-
-
-
-
oxidation
redox reaction
-
-
-
-
reduction
-
-
-
-
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
(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
show the reaction diagram
(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
15S-hydroperoxyeicosatetraenoic acid + O2
lipoxin A4
show the reaction diagram
-
-
-
?
2',7'-dichlorodihydrofluorescein diacetate + O2
?
show the reaction diagram
-
development of a fluorescence assay for 5-LOX, overview
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
5-hydroperoxyeicosatetraenoic acid
leukotriene A4 + H2O
show the reaction diagram
-
-
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
show the reaction diagram
analysis of the product distribution reveals that 5-LOX displays a reversal of selectivity to bypass abstracting the deuterium atom from C7
-
-
?
8,11,14-eicosatrienoic acid + O2
?
show the reaction diagram
-
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
show the reaction diagram
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
show the reaction diagram
arachidonate + O2
(5Z,8Z,11Z,13E)-(5S)-5-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
arachidonic acid + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyeicosa-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
arachidonic acid + O2
5-hydroperoxyeicosatetraenoic acid
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
(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
show the reaction diagram
(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
5-hydroperoxyeicosatetraenoic acid
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
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
arachidonic acid + O2
5-hydroperoxyeicosatetraenoic acid
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
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
Iron
-
wild-type enzyme contains 0.65 mol of iron per mol of enzyme, H372 and H550 constitute two of the iron ligands
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(-)-epicatechin
-
-
(1-[2-[4-(trifluoromethyl)phenyl]ethyl]-1H-1,2,3-triazol-4-yl)methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
compound forms pi-pi interactions with residues Phe177, His367 and coordinates iron
-
(1E)-1-(2,5-dihydroxyphenyl)-5-phenylpent-1-en-3-one
inhibits leukotriene biosynthesis in isolated human neutrophils and in whole blood
-
(1E)-1-(3,4-dihydroxyphenyl)-6-phenylhex-1-en-3-one
inhibits leukotriene biosynthesis in isolated human neutrophils and in whole blood
-
(1E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-5-phenylpent-1-en-3-one
inhibits leukotriene biosynthesis in isolated human neutrophils and in whole blood, retains 50% of inhibitory activity after up to one hour of incubation
-
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl]methanone
-
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl]methanone
-
(2E)-3-[4-[(1E)-3-[[(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoyl]oxy]prop-1-en-1-yl]phenyl]prop-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
caffeic acid phenylethyl ester analogue, IC50 value for inhibition of 5-Lox product synthesis in transfected HEK-293 cells is 0.00061 mM. Compound is a good radical scavenger
-
(2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
potent inhibition by 92%
(2E,2'E)-(1,1'-(2,2-bis((4-(cinnamoyloxymethyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-phenylacrylate)
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
(2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
potent inhibition by 91%
(2E,2'E)-(1,1'-(2-((4-(cinnamoyloxymethyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-phenylacrylate)
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
(2E,2'E)-2,2'-(4,4'-(2,2-bis(((1-(2-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)propane-1,3-diyl)bis(oxy)bis(methylene)bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
-
(2E,2'E)-2,2'-(4,4'-(2,2-bis(((1-(2-(cinnamoyloxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)propane-1,3-diyl)bis(oxy)bis(methylene)bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl) bis(3-phenylacrylate)
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
(2E,5E)-5-[(2E)-3-(furan-2-yl)prop-2-en-1-ylidene]-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one
-
-
(2E,6E,10E)-13-((R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)-N-(4-methoxybenzyl)-2,6,10-trimethyltrideca-2,6,10-trienamide
significant inhibitory activity in both cell-free and cell-based assays, inhibits leukotriene biosynthesis by human primary polymorphonuclear leukocytes, IC50 value 250 nM
-
(2E,6E,10E)-13-((R)-6-hydroxy-2,8-dimethylchroman-2-yl)-N-(4-methoxybenzyl)-2,6,10-trimethyltrideca-2,6,10-trienamide
significant inhibitory activity in both cell-free and cell-based assays, inhibits leukotriene biosynthesis by human primary polymorphonuclear leukocytes, IC50 value 184 nM
-
(2E,6E,10E)-13-(6-hydroxy-2,8-dimethylchroman-2-yl)-2,6,10-trimethyl-N-(pyridin-3-ylmethyl)trideca-2,6,10-trienamide
inhibits leukotriene biosynthesis by human primary polymorphonuclear leukocytes, IC50 value 415 nM
-
(2E,6E,10E)-N-benzyl-13-((R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienamide
significant inhibitory activity in both cell-free and cell-based assays, inhibits leukotriene biosynthesis by human primary polymorphonuclear leukocytes, IC50 value 173 nM
-
(2E,6E,10E)-N-benzyl-13-((R)-6-hydroxy-2,8-dimethylchroman-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienamide
inhibits leukotriene biosynthesis by human primary polymorphonuclear leukocytes, IC50 value 303 nM
-
(5E)-2-(3-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-aminophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-chlorophenyl)-5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-chlorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-hydroxyphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-methylphenyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(2,4-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3,5-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chlorobenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-methoxybenzylidene)-2-(4-methoxyphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-tert-butylbenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-[(methylperoxy)acetyl]benzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(anthracen-9-ylmethylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-4-[(methylperoxy)acetyl]benzylidene
-
-
(5E)-5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-[4-(dimethylamino)benzylidene]-2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one
-
-
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate
product inhibition
(5Z)-2-(cyclohexylamino)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5Z)-5-(4-methoxybenzylidene)-2-(pyrrolidin-1-yl)-1,3-thiazol-4(5H)-one
-
-
(5Z)-5-(4-methylbenzylidene)-2-(naphthalen-2-ylamino)-1,3-thiazol-4(5H)-one
-
-
(5Z)-5-benzylidene-2-(phenylamino)-1,3-thiazol-4(5H)-one
-
-
(E)-N-hydroxy-N-(3-(3-phenoxyphenyl)-allyl)acetamide
-
BWA4C
(R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl) methyl)-N-hydroxyheptanamide
-
-
(R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl) methyl)-N-hydroxyoctanamide
-
-
(R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)-N-hydroxypentanamide
-
-
(R)-N-(2-(diphenylamino)ethyl)-3-(3-(1-hydroxyureido)but-1-yn-1-yl)benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor
-
(R)-N-(3,3-bis(4-fluorophenyl)propyl)-3-(3-(1-hydroxyureido)but-1-yn-1-yl)benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor
-
([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)(naphthalen-1-yl)acetic acid
-
-
1-(2,4-difluorophenyl)-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
-
1-(2,4-dihydroxyphenyl)-2-(naphthalen-2-yl)ethanone
-
-
1-(3-[5-(hydroxyureido)methyl-2-methoxyphenoxy]propyl)-3-[4-(trifluoromethoxy)phenyl]urea
KM55, a multitarget ligand and dual 5-lipoxygenase (5-LO)/soluble epoxide hydrolase (sEH) inhibitor. KM55 potently inhibits both enzymes in vitro and attenuates the formation of leukotrienes in human whole blood. It significantly inhibits the LPS-induced adhesion of leukocytes to endothelial cells by blocking leukocyte activation. Compound synthesis and evaluation, overview. KM55 inhibits the formation of leukotriene B4 and 5-hydroxyeicosatrienoic acid, while the formation of 12-hydroperoxyicosatetraenoate and 15-hydroperoxyicosatetraenoate are unaffected. KM55 blocks leukocyte-endothelial cell interaction by impairing leukocyte activation, whereas endothelial cells are not affected
1-benzyl-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
-
1-O-dodecyl 2,3-O-isopropylidene-5,6-dideoxy-5-N-[4-(2-hydroxy-2-oxoethyl) phenylaminocarbonyl] amino-beta-L-gulofuranoside sodium salt
-
competitive inhibitor, IC50: 0.0035 mM with recombinant enzyme, IC50: 0.005 mM with native enzyme
1-[3-(methylsulfanyl)phenyl]-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
-
10,17(S)-dihydroxydocosahexaenoic acid
-
IC50: 0.017 mM
10-nitro-oleic acid
inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.0015 mM
-
11alpha,13-dihydrohelenalin acetate
-
enzyme from polymorphonuclear leukocyte
15-hydroperoxy-6,8,11,13-eicosatetraenoic acid
-
IC50: 0.0048 mM
2,3-dichlorophenyl 3,5-dinitrobenzoate
-
2,5-dimethoxy-3-tridecylbenzene-1,4-diol
-
2-(2,2-dimethyl-6-(4-nitrophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(2,2-dimethyl-7-phenyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(2-methoxyphenyl)-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)acetamide
-
-
2-(3-acetylphenyl)propanoic acid
-
2-(3-benzoylphenyl)propanoic acid
-
2-(3-phenoxyphenyl)propanoic acid
-
2-(4-(biphenyl-4-ylamino)-6-chloropyrimidine-2-ylthio)octanoic acid
-
-
2-(4-(biphenyl-4-ylmethylamino)-6-chloropyrimidin-2-ylthio)octanoic acid
-
-
2-(4-chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylthio)acetic acid
-
-
2-(4-chloro-6-(4'-cyanobiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
-
2-(4-chloro-6-(5-methoxy-2-methylbiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
-
2-(4-methylphenyl)-5-(2-phenylethenylidene)-1,3-thiazol-4(5H)-one
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(5-methyl-1,3-thiazol-2-yl)propanamide
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-1,3-thiazol-2-ylpropanamide
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-thiophen-3-ylpropanamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(methylsulfonyl)acetamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(phenylsulfonyl)acetamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-tosylacetamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1Hpyrrolizin-5-yl)-N-tosylpropanamide
-
-
2-(6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(6-(4-tert-butylphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(thiophen-2-ylmethyl)propanamide
-
-
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-1,3-thiazol-2-ylpropanamide
-
-
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
-
2-(dibenzo[b,d]furan-3-yl)-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2-([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)octanoic acid
-
-
2-benzyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2-hexyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2-hydroxy-5-(3-nitrophenyl)cyclohexa-2,5-diene-1,4-dione
-
-
2-hydroxy-5-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
-
-
2-hydroxy-5-methoxy-3-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
-
-
2-methoxy-5-(naphthalen-2-yloxy)cyclohexa-2,5-diene-1,4-dione
-
-
2-methyl-3-[(morpholine-4-carbonyl)amino]-3-oxopropanoic acid
-
2-phenylethyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate
-
2-phenylethyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
inhibits leukotriene biosynthesis in isolated human neutrophils and in whole blood
-
2-[(4-[[3,5-bis(2,2,2-trifluoroethoxy)phenyl]amino]-6-chloropyrimidin-2-yl)sulfanyl]octanoic acid
-
-
2-[2-[(2-methyl-1H-benzimidazol-1-yl)methyl]phenoxy]acetamide
a BRP-7 derivative
2-[2-[(2-[1-[4-(2-methylpropyl)phenyl]ethyl]-1H-benzimidazol-1-yl)methyl]phenoxy]acetamide
a BRP-7 derivative
2-[3-(2-methylpropanoyl)phenyl]propanoic acid
-
2-[3-(morpholine-4-carbonyl)phenyl]propanoic acid
-
2-[3-[(4-hydroxyphenyl)carbamoyl]phenyl]propanoic acid
-
2-[3-[hydroxy(phenyl)amino]phenyl]propanoic acid
-
2-[4'-(iso-propylphenyl)-amino]-5,6-dimethyl-1,4-benzoquinone
-
potent inhibitor, IC50: 0.006 mM
2-[4'-[(morpholin-4-yl)sulfanyl][1,1'-biphenyl]-3-yl]propanoic acid
-
2-[4-(morpholine-4-carbonyl)phenyl]propanoic acid
-
2-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
-
2-[5,8-dimethyl-7-(2-morpholin-4-ylethoxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-N-1,3-thiazol-2-ylpropanamide
-
-
2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
-
-
2-[7-[2-(dimethylamino)ethoxy]-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-1,3-thiazol-2-ylpropanamide
-
-
2-[7-[2-(dimethylamino)ethoxy]-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-pyridin-2-ylpropanamide
-
-
3'-nitrobiphenyl-2,4-diol
-
-
3,4,5-trimethoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
-
3,4,6-trimethoxy-5-undecylcyclohexa-2,4-dien-1-one
-
3-((naphthalene-1-yloxy)carbonyl)benzoic acid
-
3-(1,10-dihydroxydecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
-
3-(1-acetoxy-10-hydroxydecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
-
3-(1-carboxyethyl)benzoic acid
-
3-(10-hydroxydecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
-
3-(10-hydroxydecyl)-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
-
3-(11-hydroxyundecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
-
3-(11-hydroxyundecyl)-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
-
3-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(2-(trifluoromethyl)-benzyl)benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor
-
3-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(3-phenyl-3-(4-(trifluoromethoxy)phenyl)propyl)benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor
-
3-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(4-methoxy-2-(trifluoromethyl)benzyl)-benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor
-
3-(3-(1-hydroxyureido)hex-1-yn-1-yl)-N-(2-(trifluoromethyl)-benzyl)benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor
-
3-(6-(4-chlorphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)propionic acid
-
-
3-(8-hydroxyoctyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
-
3-(8-hydroxyoctyl)-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
-
3-(benzyloxycarbonyl)benzoic acid
-
3-(cyclohexylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
-
3-(decahydronaphthalen-2-ylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
-
3-(naphhthalen-1-ylcarbmoyl)benzoic acid
-
3-(phenylcarbamoyl)benzoic acid
-
3-acetyl-11-keto-beta-boswellic acid
allosteric inhibitor from frankincense, wedges between the membrane-binding and catalytic domains of 5-LOX, some 30 A from the catalytic iron. Binding promotes a shift in the regiospecificity, i.e. a significant increase in the formation of 12-hydroxyeicosatetraenoic acid with the most prominent effect at 10 microM
3-benzyl-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
-
-
3-dodecyl-4,5-dimethoxybenzene-1,2-diol
-
3-dodecyl-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
-
3-n-pentadecylcatechol
-
-
3-propylphenyl 3,5-dinitrobenzoate
-
3-tolyl 3,5-dinitrobenzoate
-
3-tridecyl-4,5-dimethoxybenzene-1,2-diol
shows anti-inflammatory effectiveness
3-undecyl-4,5-dimethoxybenzene-1,2-diol
-
3-[(10E)-pentadec-10'-en-1-yl]-catechol
-
-
3-[(10Z)-pentadec-10'-en-1-yl]-catechol
-
-
3-[4-(3-[[(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoyl]oxy]prop-1-yn-1-yl)phenyl]prop-2-yn-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
caffeic acid phenylethyl ester analogue, IC50 value for inhibition of 5-Lox product synthesis in transfected HEK-293 cells is 0.00036 mM. Compound is a good radical scavenger
-
4,5-dimethoxy-3-tridecylcyclohexa-3,5-diene-1,2-dione
shows anti-inflammatory effectiveness
4,5-dimethoxy-3-undecylcyclohexa-3,5-diene-1,2-dione
-
4-(1-benzothiophen-3-yl)benzene-1,3-diol
-
-
4-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(2-(trifluoromethyl)-benzyl)benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor, displays cellular activity in human polymorphonuclear leukocytes, oral bioavailability, and target engagement in vivo and demonstrates anti-inflammatory and anti-fibrotic efficiency in a kidney injury model caused by unilateral ureteral obstruction in mice
-
4-(4-(4-chlorophenyl)thiazol-2-ylimino)cyclohexa-2,5-dienone
ST-1905
4-(4-chlorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
-
IC50: 180 nM
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenoxy]methyl)-2H-chromen-2-one
-
IC50: 55 nM
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
-
IC50: 27 nM
4-(dibenzo[b,d]furan-3-yl)benzene-1,3-diol
-
-
4-(naphthalen-2-ylmethyl)benzene-1,3-diol
-
-
4-(thianthren-2-yl)benzene-1,3-diol
-
-
4-benzylbenzene-1,3-diol
-
-
4-chloro-N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00042 mM
4-chloro-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00083 mM
4-hexylbenzene-1,3-diol
-
-
4-methoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
-
4-methyl-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,2,3-thiadiazole-5-carboxamide
-
-
4-methyl-N-([4-[(2E)-3-(2,3,4-trimethylphenyl)prop-2 enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00045 mM
4-methyl-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00089 mM
4-[(1E)-3-(3-phenylpropoxy)prop-1-en-1-yl]benzene-1,2-diol
caffeic acid phenylethyl ester analogue, IC50 value for inhibition of 5-Lox product synthesis in transfected HEK-293 cells is 0.00018 mM. Compound is a good radical scavenger
-
4-[(1E)-3-(benzyloxy)prop-1-en-1-yl]benzene-1,2-diol
caffeic acid phenylethyl ester analogue, IC50 value for inhibition of 5-Lox product synthesis in transfected HEK-293 cells is 0.00043 mM. Compound is a good radical scavenger
-
4-[(4-cyclohexyl-5-methyl-1,3-thiazol-2-yl)amino]-2,6-dimethylphenol
lead compound, in vitro pharmacokinetic profile, shows no cytotoxicity, overview
4-[(hydroxy[1-[3'-(morpholin-4-yl)[1,1'-biphenyl]-3-yl]ethyl]amino)methyl]phenol
-
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-5 by 41%
4-[5-(6-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-5 by 51%
4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-5 by 94%
4-[[4-(2,4-dichlorophenyl)-5-methyl-1,3-thiazol-2-yl]amino]-2,6-dimethylphenol
lead compound, in vitro pharmacokinetic profile, shows no cytotoxicity, overview
4-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]phenol
-
4-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]imino]cyclohexa-2,5-dien-1-one
-
4-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]phenol
-
5-methoxy-3-tridecylbenzene-1,2,4-triol
-
5-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]benzene-1,2,3-triol
-
6-hydroxy-3,4-dimethoxy-5-undecylcyclohexa-2,4-dien-1-one
-
6-[(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]naphthalene-2-carboxylic acid
-
-
7,17(S)-dihydroxydocosahexaenoic acid
-
IC50: 0.007 mM
7-([3-fluoro-5-[(1R)-1-hydroxy-1-pyridin-2-ylpropyl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 175 nM
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-(4-fluorophenyl)-2H-chromen-2-one
-
-
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 200 nM
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-phenyl-2H-chromen-2-one
-
IC50: 300 nM
7-([3-fluoro-5-[(1S)-1-hydroxy-1-(1,3-thiazol-2-yl)propyl]phenoxy]methyl)-4-(4-fluorophenyl)-2H-chromen-2-one
-
IC50: 175 nM
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 9 nM
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-phenyl-2H-chromen-2-one
-
IC50: 26 nM
7-[[3-(1-ethyl-1-hydroxypropyl)-5-fluorophenoxy]methyl]-4-furan-3-yl-2H-chromen-2-one
-
IC50: 15 nM
AA-861
AA861
-
specific inhibition
ABT-761
-
-
arachidonate
substrate inhibition
baicalein
inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.0014 mM
benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
beta-hydroxyacteoside
-
enzyme from polymorphonuclear leukocyte
biphenyl-2,4-diol
-
-
biphenyl-3-yl 3,5-dinitrobenzoate
-
biphenyl-4-yl 3,5-dinitrobenzoate
-
BRP-7
benzimidazole derivative BRP-7 inhibits leukotriene biosynthesis in vitro and in vivo by targeting 5-lipoxygenase-activating protein (FLAP). BRP-7 blocks 5-LOX co-localization with FLAP at the nuclear envelope in neutrophils. No complete inhibition up to 0.01 mM
BW755C
-
CAS: 66000-40-6; i.e. 3-amino-1-[3-(trifluoromethyl)phenyl]-2-pyrazoline, IC50: 0.013 mM
BWA4C
caffeic acid
-
-
caffeic acid phenethyl ester
cannabidiol
-
-
capsaicin
-
enzyme from polymorphonuclear leukocyte
celecoxib
CGP28238
-
-
chalcone
inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.006 mM
cholesterol
-
addition to a membrane preperation in vitro reduces 5-lipoxygenase activity by half. Cholesterol sulfate can inhibit 5-lipoxygenase in intact cells
CJ-13,610
-
-
CJ-13610
-
-
Cox-189
-
-
curcumin
inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.0016 mM
cyrhetrenyl carboxylic acid
the compound is a good ROS generator
-
daidzein
-
noncompetitive
delphinidin 3-O-galactoside
-
from Vaccinium myrtillus berries, strong inhibitor, in a concentration-dependent manner
delphinidin 3-O-glucoside
-
from Vaccinium myrtillus berries, strong inhibitor, in a concentration-dependent manner
delta-garcinoic acid
i.e. an omega-oxidized tocotrienol, inhibits leukotriene biosynthesis by human primary polymorphonuclear leukocytes, IC50 value 345 nM
-
delta-tocopherol-13'-carboxychromanol
competitive, compound decreases leukotriene B4 from stimulated neutrophil-like cells without affecting translocation of 5-Lox from cytosol to the nucleus. Compound additionally inhibits cyclooxygenases Cox-1 and Cox-2
-
delta-tocotrienol
competitive, compound decreases leukotriene B4 from stimulated neutrophil-like cells without affecting translocation of 5-Lox from cytosol to the nucleus. Compound additionally inhibits cyclooxygenases Cox-1 and Cox-2
delta-tocotrienol-13'-carboxychromanol
competitive, compound decreases leukotriene B4 from stimulated neutrophil-like cells without affecting translocation of 5-Lox from cytosol to the nucleus. Compound additionally inhibits cyclooxygenases Cox-1 and Cox-2
-
Diamide
in 5-LO/FLAP-transfected HeLa cells, treatment with the thiol-oxidizing agent diamide which promotes glutathionylation at surface Cys residues leads to a decreased leukotriene synthesis by wild-type 5-LO
diclofenac
-
-
eltenac
-
-
embelin
ER-34122
-
-
ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-((2,4-difluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
ethyl 2-((2,6-dichlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
ethyl 2-((2,6-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
ethyl 2-((3,5-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
ethyl 2-((3-chlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
ethyl 2-((4-fluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
-
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-phenyl-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-[[4-chloro-6-(quinolin-6-ylamino)pyrimidin-2-yl]sulfanyl]octanoate
-
-
ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 5-hydroxy-1-methyl-2-((2-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
-
ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethoxy)phenylthio)methyl)-1H-indole-3-carboxylate
-
ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
-
ethyl 5-hydroxy-1-methyl-2-(phenylthiomethyl)-1H-indole-3-carboxylate
-
ethyl 5-hydroxy-2-((2-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
-
ethyl 5-hydroxy-2-((4-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
-
ethyl 5-hydroxy-2-(mesitylthiomethyl)-1-methyl-1H-indole-3-carboxylate
-
ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
-
-
ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl [2-[(2-[1-[4-(2-methylpropyl)phenyl]ethyl]-1H-benzimidazol-1-yl)methyl]phenoxy]acetate
a BRP-7 derivative
etoricoxib
-
-
eugenol
-
non-competitive, reversible inhibitor, IC50: 0.026 mM
ferrocenyl carboxylic acid
mixed type inhibitor. The compound shows better antioxidant activity than the antioxidant Trolox
-
forsythiaside
-
enzyme from polymorphonuclear leukocyte
genistein
-
noncompetitive
gingerdione
-
enzyme from polymorphonuclear leukocyte
glutathione
helenalin
-
enzyme from polymorphonuclear leukocyte
hyperforin
-
-
idebenone
-
L-656,224
-
i.e. 7-chloro-2-[(4-methoxyphenyl)-methyl]-3-methyl-5-propyl-4-benzofuranol, IC50: 0.0008 mM
L-670,630
-
IC50: 0.0004 mM
L-689,065
-
IC50: 0.0003 mM
L-697,198
-
IC50: 0.00002 mM
L-702,590
-
-
L-702,701
-
IC50: 0.0015 mM
L-739,010
-
-
L-746,530
-
IC50: 27 nM
L705,302
-
IC50: 0.00002 mM
licofelone
luteolin
inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.0006 mM
meloxicam
-
-
methanol
-
complete inhibition at 50% v/v
methyl (4-[(5E)-5-(4-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]phenoxy)acetate
-
-
methyl 2-(allylamino)-1H-indole-3-carboxylate
-
-
methyl 2-(benzylamino)-1H-indole-3-carboxylate
-
-
methyl 2-(diallylamino)-1H-indole-3-carboxylate
-
-
methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
-
-
methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
-
-
miogadial
-
potent inhibitor, IC50: 0.004 mM
miogatrial
-
potent inhibitor, IC50: 0.0075 mM
mithramycin
-
reduces endogenous 5-lipoxygenase in Mono Mac 6 cell, which blocks GC-boxes in the proximal part of the 5-lipoxygenase gene promoter
MK 886
-
i.e. CAS: 118414-82-7, inhibition of 5-lipoxygenase in prostate cancer cells blocks production of 5-hydroxyeicosatetraenoic acid and induces massive apoptosisin both hormone-responsive and hormone-nonresponsive prostate cancer cells
MK-886
MK886
ML-3000
-
i.e. licofelone, ML-3000 has no effect on 5-LOX product synthesis in whole-blood assay, inhibition of COX pathways does not increase the transformation of arachidonic acid by the 5-LOX pathway
myxochelin A
isolated from extracts of the predatory myxobacterium Pyxidicoccus fallax HKI 727, IC50 values for inhibition of proliferative cells K-562 and HeLa are 0.3052 mM and 0.0039 mM, respectively
myxochelin C
isolated from extracts of the predatory myxobacterium Pyxidicoccus fallax HKI 727, IC50 values for inhibition of proliferative cells K-562 and HeLa are 0.424 mM and 0.0535 mM, respectively
myxochelin D
isolated from extracts of the predatory myxobacterium Pyxidicoccus fallax HKI 727, IC50 values for inhibition of proliferative cells K-562 and HeLa are above 0.5 mM
N-(3,4-dimethoxyphenyl)-3,5-dinitrobenzamide
-
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,3-benzodioxole-5-carboxamide
-
-
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)cyclopentanecarboxamide
-
-
N-(3-(4-chlorophenyl)-3-phenylpropyl)-3-(3-(1-hydroxyureido)-but-1-yn-1-yl)benzamide
dual 5-LOX/soluble epoxide hydrolase inhibitor
-
N-(3-bromobenzyl)-3,5-dinitrobenzamide
-
N-(3-bromophenyl)-3,5-dinitrobenzamide
-
N-(3-chlorophenyl)-3,5-dinitrobenzamide
-
N-(3-phenoxycinnamyl)-acetohydroxamic acid
-
-
N-(4-chlorophenyl)-N-hydroxy-N'-(3-chlorophenyl)urea
-
IC50: 0.0001 mM
N-(4-methoxyphenyl)-3,5-dinitrobenzamide
-
N-(biphenyl-3-yl)-3,5-dinitrobenzamide
-
N-(furan-2-ylmethyl)-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
-
N-(naphthalene-1-yl)-3,5-dinitrobenzamide
-
N-([(5R)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)-N-hydroxy-2-methylpropanamide
-
-
N-([(5R)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)-N-hydroxycyclopropanecarboxamide
-
-
N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)-4-methylbenzenesulfonamide
-
IC50: 0.00045 mM
N-3-tolyl-3,5-dinitrobenzamide
-
N-cyclopentyl-2-[7-(2-methoxyethoxy)-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide
-
-
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
-
N-phenyl-3,5-dinitrobenzamide
-
N-tert-butyl-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
-
naphthalen-1-yl 3,5-dinitrobenzoate
JMC-4, identified from virtual inhibitor screening
naphthalene-1-yl 3-nitrobenzoate
-
NAPQI
compound reacts with catalytically relevant cysteine residues 416 and 418
-
nimesulide
-
-
nordihydroguaiaretic acid
parecoxib
-
-
phenyl 3,5-dinitrobenzoate
-
Plumbagin
inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.007 mM
polygodial
-
strong inhibitory activity, IC50: 0.0086 mM
primin
compound reacts with catalytically relevant cysteine residues 416 and 418, inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.0028 mM
-
Rev-5901
-
competitive 5-LO inhibitor
rofecoxib
RWJ-63556
-
-
S-2474
-
-
SC-560
-
-
SC-756
-
-
shikonin
inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.0015 mM
shogaol
sulindac sulfide
suspensaside
-
enzyme from polymorphonuclear leukocyte
tepoxalin
-
-
thymoquinone
compound reacts with catalytically relevant cysteine residues 416 and 418, inhibition of the 5-LO product formation of intact human polymorphonuclear leukocytes, IC50 value 0.0015 mM
U73122
valdecoxib
-
-
verbascoside
-
enzyme from polymorphonuclear leukocyte
YS121
-
-
ZD 2138
ZD-2138
-
-
Zileutin
-
-
zileuton
ZM 230,486
-
IC50: 0.00009 mM
ZM230487
-
-
[1-(2-cyclohexylethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
compound is equipotent to zileuton. It forms pi-pi interactions with residues His367, Phe421 and coordinates iron
-
[1-(2-[[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
-
[1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
-
[1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-phenylprop-2-enoate
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
[1-(3-[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2-[(3-[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2,2-bis[[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propoxy)methyl]-2-[[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
incorporation of additional caffeoyl units in hexamer results in less potent inhibition
[1-(3-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2-[(3-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2,2-bis[[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propoxy)methyl]-2-[[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-phenylprop-2-enoate
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
[2-[(2-methyl-1H-benzimidazol-1-yl)methyl]phenoxy]acetyl chloride
a BRP-7 derivative
[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone
-
[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone
-
[3-(bromocarbonyl)phenyl](morpholin-4-yl)acetic acid
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,25(OH)2D3
-
gives a strong (100fold) upregulation of 5-lipoxygenase protein in differentiating Mono Mac 6 cells
5-lipoxygenase activating protein
-
5-lipoxygenase activating protein is crucial for conversion of endogenous substrate by 5LO 5-lipoxygenase activating protein also stimulates the utilization of exogenous arachidonic acid, and greatly (190fold) stimulates utilization of (5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
-
5-lipoxygenase-activating protein
-
functional 5-LOX requires binding to 5-lipoxygenase-activating protein which helps 5-LOX binding to arachidonic acid at the nuclear membrane and enhances the efficiency of leukotriene synthesis
-
5-LO activating protein
-
i.e. FLAP, Ca2+ induces the translocation of 5-LO from a soluble compartment to nuclear structures, where 5-LO co-localizes with 5-LO activating protein
-
5-LOX activating protein
-
-
-
adenosine
-
58% of the activation with ATP
ADP
-
74% of the activation with ATP
ADP-beta-S
-
82% of the activation with ATP
AMP
-
68% of the activation with ATP
AMP-4-nitrophenylphosphate
-
77% of the activation with ATP
ATP-alphaS
-
118% of the activation with ATP
ATP-gammaS
-
80% of the activation with ATP
CLP
-
can upregulate and modulate the 5-lipoxygenase pathway in vitro
-
coactosin-like protein
-
FLAP
-
Nicotine
-
treatment with 0.01 mM nicotine activates 5-lipoxygenase gastric cancer cell lines from 36-72 h
phosphatidylcholine
phosphocholine
phosphocholine in combination with Ca2+ markedly stimulate the formation of leukotrienes by wild-type 5-LO and mutant C159S/C300S/C416S/C418S, whereas their effect on the 5-LO W13A/W75A/W102A mutant is small
protein factors from human leukocyte
-
transforming growth factor beta
-
gives a strong (100fold) upregulation of 5-lipoxygenase protein in differentiating Mono Mac 6 cells
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.014 - 0.019
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
0.0093 - 0.01144
7,7-d2-arachidonate
0.0033 - 0.053
arachidonate
0.012
arachidonic acid
-
-
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.01
7,7-d2-arachidonate
0.004 - 1.2
arachidonate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.108 - 0.87
7,7-d2-arachidonate
0.14 - 350
arachidonate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00071
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl]methanone
pH and temperature not specified in the publication
0.0009
(2,4-dihydroxyphenyl)[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl]methanone
pH and temperature not specified in the publication
0.016
2-(3-acetylphenyl)propanoic acid
pH and temperature not specified in the publication
0.00136
2-(3-benzoylphenyl)propanoic acid
pH and temperature not specified in the publication
0.00267
2-(3-phenoxyphenyl)propanoic acid
pH and temperature not specified in the publication
0.0455
2-methyl-3-[(morpholine-4-carbonyl)amino]-3-oxopropanoic acid
pH and temperature not specified in the publication
0.00734
2-[3-(2-methylpropanoyl)phenyl]propanoic acid
pH and temperature not specified in the publication
0.00734
2-[3-(morpholine-4-carbonyl)phenyl]propanoic acid
pH and temperature not specified in the publication
0.00042
2-[3-[(4-hydroxyphenyl)carbamoyl]phenyl]propanoic acid
pH and temperature not specified in the publication
0.0057
2-[3-[hydroxy(phenyl)amino]phenyl]propanoic acid
pH and temperature not specified in the publication
0.00013
2-[4'-[(morpholin-4-yl)sulfanyl][1,1'-biphenyl]-3-yl]propanoic acid
pH and temperature not specified in the publication
0.0112
2-[4-(morpholine-4-carbonyl)phenyl]propanoic acid
pH and temperature not specified in the publication
0.17
3-(1-carboxyethyl)benzoic acid
pH and temperature not specified in the publication
0.00515
4-[(hydroxy[1-[3'-(morpholin-4-yl)[1,1'-biphenyl]-3-yl]ethyl]amino)methyl]phenol
pH and temperature not specified in the publication
0.00011
4-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]phenol
pH and temperature not specified in the publication
0.00032
5-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]benzene-1,2,3-triol
pH and temperature not specified in the publication
0.0398
arachidonate
pH and temperature not specified in the publication
0.0016
delta-tocopherol-13'-carboxychromanol
pH not specified in the publication, temperature not specified in the publication
-
0.0022
delta-tocotrienol
pH not specified in the publication, temperature not specified in the publication
0.0008
delta-tocotrienol-13'-carboxychromanol
pH not specified in the publication, temperature not specified in the publication
-
0.001
ferrocenyl carboxylic acid
pH 7.5, 23°C
-
0.00059
[3-(1-[hydroxy[(3,4,5-trihydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone
pH and temperature not specified in the publication
0.00018
[3-(1-[hydroxy[(4-hydroxyphenyl)methyl]amino]ethyl)phenyl](morpholin-4-yl)methanone
pH and temperature not specified in the publication
0.0398
[3-(bromocarbonyl)phenyl](morpholin-4-yl)acetic acid
pH and temperature not specified in the publication
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00051
(1E)-1-(2,5-dihydroxyphenyl)-5-phenylpent-1-en-3-one
Homo sapiens
inhibition of 5-Lox product biosynthesis in polymorphonuclear leukocyte, 37°C, pH not specified in the publication
-
0.00052
(1E)-1-(3,4-dihydroxyphenyl)-6-phenylhex-1-en-3-one
Homo sapiens
inhibition of 5-Lox product biosynthesis in polymorphonuclear leukocyte, 37°C, pH not specified in the publication
-
0.00041
(1E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-5-phenylpent-1-en-3-one
Homo sapiens
inhibition of 5-Lox product biosynthesis in polymorphonuclear leukocyte, 37°C, pH not specified in the publication
-
0.00066 - 0.00246
(2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
0.00079 - 0.00237
(2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
0.03
(2E,5E)-5-[(2E)-3-(furan-2-yl)prop-2-en-1-ylidene]-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one
0.000572
(2E,6E,10E)-13-((R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)-N-(4-methoxybenzyl)-2,6,10-trimethyltrideca-2,6,10-trienamide
Homo sapiens
pH 7.4, 37°C
-
0.000094
(2E,6E,10E)-13-((R)-6-hydroxy-2,8-dimethylchroman-2-yl)-N-(4-methoxybenzyl)-2,6,10-trimethyltrideca-2,6,10-trienamide
Homo sapiens
pH 7.4, 37°C
-
0.000077
(2E,6E,10E)-13-(6-hydroxy-2,8-dimethylchroman-2-yl)-2,6,10-trimethyl-N-(pyridin-3-ylmethyl)trideca-2,6,10-trienamide
Homo sapiens
pH 7.4, 37°C
-
0.000595
(2E,6E,10E)-N-benzyl-13-((R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienamide
Homo sapiens
pH 7.4, 37°C
-
0.00005
(2E,6E,10E)-N-benzyl-13-((R)-6-hydroxy-2,8-dimethylchroman-2-yl)-2,6,10-trimethyltrideca-2,6,10-trienamide
Homo sapiens
pH 7.4, 37°C
-
0.00013 - 0.00038
(5E)-2-(3-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
0.00012 - 0.00024
(5E)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
0.00011 - 0.00055
(5E)-2-(4-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
0.00063 - 0.00193
(5E)-2-(4-aminophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
0.00011 - 0.0004
(5E)-2-(4-chlorophenyl)-5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one
0.00009 - 0.00028
(5E)-2-(4-chlorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
0.00065 - 0.00169
(5E)-2-(4-hydroxyphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
0.0004 - 0.00245
(5E)-2-(4-methylphenyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazol-4(5H)-one
0.00098 - 0.00202
(5E)-5-(2,4-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.0008 - 0.0013
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.00048 - 0.00054
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
0.00013 - 0.00035
(5E)-5-(3,5-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.0027 - 0.01
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.003 - 0.0095
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
0.00125 - 0.0029
(5E)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.0003 - 0.00058
(5E)-5-(3-chlorobenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.003 - 0.0044
(5E)-5-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
0.00032 - 0.004
(5E)-5-(4-methoxybenzylidene)-2-(4-methoxyphenyl)-1,3-thiazol-4(5H)-one
0.0003 - 0.00066
(5E)-5-(4-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.00015 - 0.002
(5E)-5-(4-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
0.0003 - 0.00091
(5E)-5-(4-tert-butylbenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
0.00019 - 0.00211
(5E)-5-(4-[(methylperoxy)acetyl]benzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.0003 - 0.00065
(5E)-5-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
0.0003 - 0.004
(5E)-5-(anthracen-9-ylmethylidene)-2-phenyl-1,3-thiazol-4(5H)-one
0.00035 - 0.00073
(5E)-5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
0.02 - 0.03
(5E)-5-[4-(dimethylamino)benzylidene]-2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one
0.012 - 0.014
(5Z)-2-(cyclohexylamino)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one
0.03
(5Z)-5-(4-methoxybenzylidene)-2-(pyrrolidin-1-yl)-1,3-thiazol-4(5H)-one
0.03
(5Z)-5-(4-methylbenzylidene)-2-(naphthalen-2-ylamino)-1,3-thiazol-4(5H)-one
0.03
(5Z)-5-benzylidene-2-(phenylamino)-1,3-thiazol-4(5H)-one
0.0019
(R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl) methyl)-N-hydroxyheptanamide
Homo sapiens
pH 7.5, 25°C
-
0.0016
(R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl) methyl)-N-hydroxyoctanamide
Homo sapiens
pH 7.5, 25°C
-
0.0033
(R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)-N-hydroxypentanamide
Homo sapiens
pH 7.5, 25°C
-
0.00011
(R)-N-(2-(diphenylamino)ethyl)-3-(3-(1-hydroxyureido)but-1-yn-1-yl)benzamide, (R)-N-(3,3-bis(4-fluorophenyl)propyl)-3-(3-(1-hydroxyureido)but-1-yn-1-yl)benzamide
Homo sapiens
pH 7.4, 37°C
-
0.00011
(R)-N-(3,3-bis(4-fluorophenyl)propyl)-3-(3-(1-hydroxyureido)but-1-yn-1-yl)benzamide
Homo sapiens
-
pH 7.4, 37°C
-
0.005
([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)(naphthalen-1-yl)acetic acid
Homo sapiens
-
in intact polymorphonuclear leukocytes
0.0006 - 0.007
1-(2,4-difluorophenyl)-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
0.0068 - 0.01
1-(2,4-dihydroxyphenyl)-2-(naphthalen-2-yl)ethanone
0.0013
1-(3-[5-(hydroxyureido)methyl-2-methoxyphenoxy]propyl)-3-[4-(trifluoromethoxy)phenyl]urea
Homo sapiens
pH 7.4, 37°C
0.003 - 0.01
1-benzyl-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
0.005
1-O-dodecyl 2,3-O-isopropylidene-5,6-dideoxy-5-N-[4-(2-hydroxy-2-oxoethyl) phenylaminocarbonyl] amino-beta-L-gulofuranoside sodium salt
Homo sapiens
-
competitive inhibitor, IC50: 0.0035 mM with recombinant enzyme, IC50: 0.005 mM with native enzyme
0.001 - 0.004
1-[3-(methylsulfanyl)phenyl]-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
0.017
10,17(S)-dihydroxydocosahexaenoic acid
Homo sapiens
-
IC50: 0.017 mM
0.0006
10-nitro-oleic acid
Homo sapiens
pH 7.4, 37°C
-
0.0048
15-hydroperoxy-6,8,11,13-eicosatetraenoic acid
Homo sapiens
-
IC50: 0.0048 mM
0.05
2,3-dichlorophenyl 3,5-dinitrobenzoate
Homo sapiens
pH 7.4, 37°C
0.00026
2,5-dimethoxy-3-tridecylbenzene-1,4-diol
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0015
2-(2,2-dimethyl-6-(4-nitrophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
Homo sapiens
-
-
0.00031
2-(2,2-dimethyl-7-phenyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
Homo sapiens
-
-
0.004 - 0.01
2-(2-methoxyphenyl)-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)acetamide
0.0007 - 0.0015
2-(4-(biphenyl-4-ylamino)-6-chloropyrimidine-2-ylthio)octanoic acid
0.001 - 0.002
2-(4-(biphenyl-4-ylmethylamino)-6-chloropyrimidin-2-ylthio)octanoic acid
0.0004 - 0.0015
2-(4-chloro-6-(4'-cyanobiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
0.0005 - 0.002
2-(4-chloro-6-(5-methoxy-2-methylbiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
0.00023 - 0.0004
2-(4-methylphenyl)-5-(2-phenylethenylidene)-1,3-thiazol-4(5H)-one
0.0008 - 0.001
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(5-methyl-1,3-thiazol-2-yl)propanamide
0.0008 - 0.001
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-1,3-thiazol-2-ylpropanamide
0.0009 - 0.006
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
0.003 - 0.008
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-thiophen-3-ylpropanamide
0.00023
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(methylsulfonyl)acetamide
Homo sapiens
-
-
0.00025
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(phenylsulfonyl)acetamide
Homo sapiens
-
-
0.00026
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-tosylacetamide
Homo sapiens
-
-
0.0016
2-(6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
Homo sapiens
-
-
0.00018
2-(6-(4-tert-butylphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
Homo sapiens
-
-
0.008 - 0.01
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(thiophen-2-ylmethyl)propanamide
0.0008 - 0.005
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
0.0008 - 0.01
2-(dibenzo[b,d]furan-3-yl)-5-hydroxycyclohexa-2,5-diene-1,4-dione
0.0041 - 0.0065
2-([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)octanoic acid
0.01
2-benzyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
0.0014 - 0.003
2-hexyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
0.0046 - 0.01
2-hydroxy-5-(3-nitrophenyl)cyclohexa-2,5-diene-1,4-dione
0.00078 - 0.0023
2-hydroxy-5-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
0.01
2-hydroxy-5-methoxy-3-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
0.00028 - 0.0067
2-methoxy-5-(naphthalen-2-yloxy)cyclohexa-2,5-diene-1,4-dione
0.00032 - 0.00033
2-phenylethyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate
-
0.00029
2-phenylethyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Homo sapiens
inhibition of 5-Lox product biosynthesis in polymorphonuclear leukocyte, 37°C, pH not specified in the publication
-
0.0015 - 0.003
2-[(4-[[3,5-bis(2,2,2-trifluoroethoxy)phenyl]amino]-6-chloropyrimidin-2-yl)sulfanyl]octanoic acid
0.006
2-[4'-(iso-propylphenyl)-amino]-5,6-dimethyl-1,4-benzoquinone
Homo sapiens
-
potent inhibitor, IC50: 0.006 mM
0.00068
2-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
0.00018
2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
Homo sapiens
-
-
0.001 - 0.01
2-[7-[2-(dimethylamino)ethoxy]-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-1,3-thiazol-2-ylpropanamide
0.01
3'-nitrobiphenyl-2,4-diol
0.0009 - 0.01
3,4,5-trimethoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
0.00031
3,4,6-trimethoxy-5-undecylcyclohexa-2,4-dien-1-one
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.05
3-((naphthalene-1-yloxy)carbonyl)benzoic acid
Homo sapiens
pH 7.4, 37°C
0.00146
3-(1,10-dihydroxydecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00049
3-(1-acetoxy-10-hydroxydecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00175
3-(10-hydroxydecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00108
3-(10-hydroxydecyl)-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00151
3-(11-hydroxyundecyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00196
3-(11-hydroxyundecyl)-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0007
3-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(2-(trifluoromethyl)-benzyl)benzamide
Homo sapiens
pH 7.4, 37°C
-
0.00011
3-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(3-phenyl-3-(4-(trifluoromethoxy)phenyl)propyl)benzamide
Homo sapiens
pH 7.4, 37°C
-
0.0017
3-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(4-methoxy-2-(trifluoromethyl)benzyl)-benzamide
Homo sapiens
pH 7.4, 37°C
-
0.0003
3-(3-(1-hydroxyureido)hex-1-yn-1-yl)-N-(2-(trifluoromethyl)-benzyl)benzamide
Homo sapiens
pH 7.4, 37°C
-
0.00184
3-(8-hydroxyoctyl)-2,5-dimethoxycyclohexa-2,5-diene-1,4-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00022
3-(8-hydroxyoctyl)-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.05
3-(benzyloxycarbonyl)benzoic acid
Homo sapiens
pH 7.4, 37°C
0.01
3-(cyclohexylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
0.00058 - 0.011
3-(decahydronaphthalen-2-ylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
0.05
3-(naphhthalen-1-ylcarbmoyl)benzoic acid
Homo sapiens
pH 7.4, 37°C
0.05
3-(phenylcarbamoyl)benzoic acid
Homo sapiens
pH 7.4, 37°C
0.01
3-benzyl-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
0.00024
3-dodecyl-4,5-dimethoxybenzene-1,2-diol
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00013
3-dodecyl-4,5-dimethoxycyclohexa-3,5-diene-1,2-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00274
3-n-pentadecylcatechol
Homo sapiens
pH 7.5, temperature not specified in the publication
-
0.0065
3-propylphenyl 3,5-dinitrobenzoate
Homo sapiens
pH 7.4, 37°C
0.0005
3-tolyl 3,5-dinitrobenzoate
Homo sapiens
pH 7.4, 37°C
0.00006
3-tridecyl-4,5-dimethoxybenzene-1,2-diol
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0001
3-undecyl-4,5-dimethoxybenzene-1,2-diol
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00116
3-[(10E)-pentadec-10'-en-1-yl]-catechol
Homo sapiens
i.e. a catechol mixture from Lithrea caustica containing 65% of the compound, pH 7.5, temperature not specified in the publication
-
0.00209
3-[(10Z)-pentadec-10'-en-1-yl]-catechol
Homo sapiens
pH 7.5, temperature not specified in the publication
-
0.00008
4,5-dimethoxy-3-tridecylcyclohexa-3,5-diene-1,2-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00009
4,5-dimethoxy-3-undecylcyclohexa-3,5-diene-1,2-dione
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.01
4-(1-benzothiophen-3-yl)benzene-1,3-diol
0.001
4-(3-(1-hydroxyureido)but-1-yn-1-yl)-N-(2-(trifluoromethyl)-benzyl)benzamide
Homo sapiens
pH 7.4, 37°C
-
0.00004
4-(4-(4-chlorophenyl)thiazol-2-ylimino)cyclohexa-2,5-dienone
Homo sapiens
pH 7.4, 37°C, recombinant enzyme
0.00018
4-(4-chlorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
Homo sapiens
-
IC50: 180 nM
0.000055
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenoxy]methyl)-2H-chromen-2-one
Homo sapiens
-
IC50: 55 nM
0.000027
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
Homo sapiens
-
IC50: 27 nM
0.0063 - 0.01
4-(dibenzo[b,d]furan-3-yl)benzene-1,3-diol
0.0023 - 0.0074
4-(naphthalen-2-ylmethyl)benzene-1,3-diol
0.0021 - 0.0032
4-(thianthren-2-yl)benzene-1,3-diol
0.009 - 0.01
4-benzylbenzene-1,3-diol
0.00042
4-chloro-N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
Homo sapiens
-
IC50: 0.00042 mM
0.00083
4-chloro-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
Homo sapiens
-
IC50: 0.00083 mM
0.0028 - 0.0046
4-hexylbenzene-1,3-diol
0.006 - 0.01
4-methoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
0.01
4-methyl-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,2,3-thiadiazole-5-carboxamide
0.00045
4-methyl-N-([4-[(2E)-3-(2,3,4-trimethylphenyl)prop-2 enoyl]phenyl]carbamoyl)benzenesulfonamide
Homo sapiens
-
IC50: 0.00045 mM
0.00089
4-methyl-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
Homo sapiens
-
IC50: 0.00089 mM
0.00003
4-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]phenol
Homo sapiens
pH 7.4, 37°C, recombinant enzyme
0.00029
5-methoxy-3-tridecylbenzene-1,2,4-triol
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.00092
6-hydroxy-3,4-dimethoxy-5-undecylcyclohexa-2,4-dien-1-one
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.009 - 0.01
6-[(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]naphthalene-2-carboxylic acid
0.007
7,17(S)-dihydroxydocosahexaenoic acid
Homo sapiens
-
IC50: 0.007 mM
0.000175
7-([3-fluoro-5-[(1R)-1-hydroxy-1-pyridin-2-ylpropyl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
Homo sapiens
-
IC50: 175 nM
0.0002
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
Homo sapiens
-
IC50: 200 nM
0.0003
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-phenyl-2H-chromen-2-one
Homo sapiens
-
IC50: 300 nM
0.000175
7-([3-fluoro-5-[(1S)-1-hydroxy-1-(1,3-thiazol-2-yl)propyl]phenoxy]methyl)-4-(4-fluorophenyl)-2H-chromen-2-one
Homo sapiens
-
IC50: 175 nM
0.000009
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-furan-3-yl-2H-chromen-2-one
Homo sapiens
-
IC50: 9 nM
0.000026
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-phenyl-2H-chromen-2-one
Homo sapiens
-
IC50: 26 nM
0.000015
7-[[3-(1-ethyl-1-hydroxypropyl)-5-fluorophenoxy]methyl]-4-furan-3-yl-2H-chromen-2-one
Homo sapiens
-
IC50: 15 nM
0.0038
AA-861
Homo sapiens
pH 7.4, 37°C
0.00029
baicalein
Homo sapiens
pH 7.4, 37°C
0.00013 - 0.00035
benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00017 - 0.00048
benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0028 - 0.0042
biphenyl-2,4-diol
0.038
biphenyl-3-yl 3,5-dinitrobenzoate
Homo sapiens
pH 7.4, 37°C
0.05
biphenyl-4-yl 3,5-dinitrobenzoate
Homo sapiens
pH 7.4, 37°C
0.0048
BRP-7
Homo sapiens
pH 7.4, 37°C
0.013
BW755C
Homo sapiens
-
i.e. 3-amino-1-[3-(trifluoromethyl)phenyl]-2-pyrazoline, IC50: 0.013 mM
0.0002
BWA4C
Homo sapiens
pH 7.4, 37°C
0.025
caffeic acid
Homo sapiens
-
-
0.00097
caffeic acid phenethyl ester
Homo sapiens
inhibition of 5-Lox product biosynthesis in polymorphonuclear leukocyte, 37°C, pH not specified in the publication
0.0195
celecoxib
Homo sapiens
-
37°C, whole blood assay
0.0007
chalcone
Homo sapiens
pH 7.4, 37°C
0.00115 - 0.00155
CJ-13610
Homo sapiens
-
pH 7.5, 37°C, dependent on assay method via fluorescence or UV measurement, kinetics, overview
0.0014
curcumin
Homo sapiens
pH 7.4, 37°C
0.05
cyrhetrenyl carboxylic acid
Homo sapiens
above 0.050 mM, pH 7.5, 23°C
-
0.157
daidzein
Homo sapiens
-
pH 7.4, 27°C
0.0069
delphinidin 3-O-galactoside
Homo sapiens
-
-
0.00215
delphinidin 3-O-glucoside
Homo sapiens
-
-
0.000057
delta-garcinoic acid
Homo sapiens
pH 7.4, 37°C
-
0.00023
embelin
Homo sapiens
pH 7.4, 37°C
0.00065 - 0.0018
ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0032
ethyl 2-((2,4-difluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0008
ethyl 2-((2,6-dichlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0008
ethyl 2-((2,6-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0018
ethyl 2-((3,5-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0038
ethyl 2-((3-chlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.005
ethyl 2-((4-fluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.000097 - 0.0012
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0016 - 0.0017
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.00015 - 0.00045
ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000086 - 0.00023
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0017 - 0.002
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.00058 - 0.0043
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
0.0012 - 0.0057
ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
0.01 - 0.03
ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
0.03
ethyl 2-(3-chlorobenzyl)-5-phenyl-1H-benzo[g]indole-3-carboxylate
0.007 - 0.01
ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000045 - 0.00052
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0033 - 0.0048
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
0.00014 - 0.00034
ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00013 - 0.00052
ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000095 - 0.0006
ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000084 - 0.0012
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0007 - 0.0012
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.000067 - 0.00032
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.002 - 0.0021
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
0.000096 - 0.0005
ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00015 - 0.00065
ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00025 - 0.0017
ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0003 - 0.0024
ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
0.000031 - 0.00049
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0017 - 0.0028
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
0.000049 - 0.0028
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0007 - 0.0039
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
0.0006 - 0.019
ethyl 2-[[4-chloro-6-(quinolin-6-ylamino)pyrimidin-2-yl]sulfanyl]octanoate
0.0034 - 0.01
ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
0.0008
ethyl 5-hydroxy-1-methyl-2-((2-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0009
ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethoxy)phenylthio)methyl)-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0042
ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0057
ethyl 5-hydroxy-1-methyl-2-(phenylthiomethyl)-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0029
ethyl 5-hydroxy-2-((2-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0023
ethyl 5-hydroxy-2-((4-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0007
ethyl 5-hydroxy-2-(mesitylthiomethyl)-1-methyl-1H-indole-3-carboxylate
Homo sapiens
pH 7.4, 37°C, cell-free enzyme extract
0.0055 - 0.0073
ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
0.00013 - 0.00044
ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
0.00033 - 0.0028
ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.026
eugenol
Homo sapiens
-
non-competitive, reversible inhibitor, IC50: 0.026 mM
0.0025
ferrocenyl carboxylic acid
Homo sapiens
pH 7.5, 23°C
-
0.125
genistein
Homo sapiens
-
pH 7.4, 27°C
0.0008
L-656,224
Homo sapiens
-
i.e. 7-chloro-2-[(4-methoxyphenyl)-methyl]-3-methyl-5-propyl-4-benzofuranol, IC50: 0.0008 mM
0.0004
L-670,630
Homo sapiens
-
IC50: 0.0004 mM
0.0003
L-689,065
Homo sapiens
-
IC50: 0.0003 mM
0.00002
L-697,198
Homo sapiens
-
IC50: 0.00002 mM
0.0015
L-702,701
Homo sapiens
-
IC50: 0.0015 mM
0.000027
L-746,530
Homo sapiens
-
IC50: 27 nM
0.00002
L705,302
Homo sapiens
-
IC50: 0.00002 mM
0.00006
luteolin
Homo sapiens
pH 7.4, 37°C
0.00058 - 0.00086
methyl (4-[(5E)-5-(4-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]phenoxy)acetate
0.03
methyl 2-(allylamino)-1H-indole-3-carboxylate
0.0034 - 0.004
methyl 2-(benzylamino)-1H-indole-3-carboxylate
0.0069 - 0.0125
methyl 2-(diallylamino)-1H-indole-3-carboxylate
0.0098 - 0.0102
methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
0.0035 - 0.0083
methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
0.0065 - 0.0081
methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
0.0035 - 0.0055
methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
0.0079 - 0.0134
methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
0.0072 - 0.0098
methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
0.004
miogadial
Homo sapiens
-
potent inhibitor, IC50: 0.004 mM
0.0075
miogatrial
Homo sapiens
-
potent inhibitor, IC50: 0.0075 mM
0.0032
MK-886
Homo sapiens
-
37°C, whole blood assay
0.0011
MK886
Homo sapiens
pH 7.4, 37°C
0.1
ML-3000
Homo sapiens
-
above, 37°C, whole blood assay
0.05
N-(3,4-dimethoxyphenyl)-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.002 - 0.01
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,3-benzodioxole-5-carboxamide
0.008 - 0.01
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)cyclopentanecarboxamide
0.00012
N-(3-(4-chlorophenyl)-3-phenylpropyl)-3-(3-(1-hydroxyureido)-but-1-yn-1-yl)benzamide
Homo sapiens
pH 7.4, 37°C
-
0.0144
N-(3-bromobenzyl)-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.05
N-(3-bromophenyl)-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.05
N-(3-chlorophenyl)-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.000038 - 0.00016
N-(3-phenoxycinnamyl)-acetohydroxamic acid
0.0001
N-(4-chlorophenyl)-N-hydroxy-N'-(3-chlorophenyl)urea
Homo sapiens
-
IC50: 0.0001 mM
0.0027
N-(4-methoxyphenyl)-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.05
N-(biphenyl-3-yl)-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.0009 - 0.01
N-(furan-2-ylmethyl)-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
0.05
N-(naphthalene-1-yl)-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.0039
N-([(5R)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)-N-hydroxy-2-methylpropanamide
Homo sapiens
pH 7.5, 25°C
-
0.0035
N-([(5R)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)-N-hydroxycyclopropanecarboxamide
Homo sapiens
pH 7.5, 25°C
-
0.00045
N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)-4-methylbenzenesulfonamide
Homo sapiens
-
IC50: 0.00045 mM
0.05
N-3-tolyl-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.01
N-cyclopentyl-2-[7-(2-methoxyethoxy)-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide
0.00005 - 0.00016
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
0.0152
N-phenyl-3,5-dinitrobenzamide
Homo sapiens
pH 7.4, 37°C
0.004 - 0.01
N-tert-butyl-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
0.0246
naphthalene-1-yl 3-nitrobenzoate
Homo sapiens
pH 7.4, 37°C
0.003
NAPQI
Homo sapiens
pH 7.4, 37°C
-
0.00009
nordihydroguaiaretic acid
Homo sapiens
-
pH 7.5, 37°C, assay method via fluorescence measurement
0.0158
phenyl 3,5-dinitrobenzoate
Homo sapiens
pH 7.4, 37°C
0.00143
Plumbagin
Homo sapiens
pH 7.4, 37°C
0.0086
polygodial
Homo sapiens
-
strong inhibitory activity, IC50: 0.0086 mM
0.0006
primin
Homo sapiens
pH 7.4, 37°C
-
0.00013
SC-756
Homo sapiens
-
pH 7.5, 37°C, assay method via fluorescence measurement
0.0005
shikonin
Homo sapiens
pH 7.4, 37°C
0.0006
shogaol
Homo sapiens
pH 7.4, 37°C
0.02
sulindac sulfide
Homo sapiens
-
pH and temperature not specified in the publication
0.00017
U73122
Homo sapiens
pH 7.4, 37°C
0.0003
ZD 2138
Homo sapiens
-
i.e. CAS: 140841-32-3, IC50: 0.0003 mM
0.00011 - 0.00012
ZD-2138
Homo sapiens
-
pH 7.5, 37°C, dependent on assay method via fluorescence or UV measurement
0.00012 - 0.01
zileuton
0.00009
ZM 230,486
Homo sapiens
-
IC50: 0.00009 mM
0.00074 - 0.00148
[1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
additional information
additional information
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.006
-
-
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
21
assay at
22
assay at
27
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
induced by a Ca2+ ionophore, from acute myeloid leukemic and acute lymphoid leukemic patients, upregulation of the enzyme, quantitative expression analysis
Manually annotated by BRENDA team
-
osteoarthritic chondrocyte
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
normal skin keratinocytes and a cell line of human keratinocytes, HaCaT
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
from peripheral venous blood
Manually annotated by BRENDA team
-
high expression of 5-lipoxygenase in mantle zone B cells from tonsils, weak expression in germinal centre cells and no expression in plasma cells from tonsils. High expression in mantle B cell lymphoma and weak or no expression in follicular lymphoma. Primary leukemized mantle B cell lymphoma (B-prolymphocytic leukaemia cells) and mantle B cell lymphoma cell lines also expressed 5-lipoxygenase
Manually annotated by BRENDA team
-
5-lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells, overview
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
mainly
Manually annotated by BRENDA team
-
when leukocytes are activated to produce leukotrienes, 5-LO moves from the cytosol to the perinuclear membrane
Manually annotated by BRENDA team
iron removal is able to affect the membrane binding properties of the enzyme, molecular dynamics simulations, overview
Manually annotated by BRENDA team
additional information
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
LOX5_HUMAN
674
0
77983
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
13800
isolated enzyme PLAT domain, gel filtration
78000
-
SDS-PAGE
80000
-
x * 80000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
structure modeling, overview
additional information
-
residues 1-128 of the enzyme form the regulatory C2-like domain
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystal structure analysis
in complex with inhibitor nordihydroguaiaretic acid, at 2.71 A resolution. The presence of the inhibitor is incompatible with the closed structure of the enzyme. Structure in complex with inhibitor 3-acetyl-11-keto-beta-boswellic acid at 3.0 A resolution. 3-Acetyl-11-keto-beta-boswellic acid lies lengthwise in a deep groove between the amino-terminal and catalytic domains
molecular docking of inhibitor delta-garcinoic acid. Trp102 within the allosteric binding site is important for binding. There is an intermolecular hydrogen bond between the ligand's phenolic oxygen and the NH of the indole of Trp102 and one links the amide function of Val110's backbone and the ligand's carbonyl group. The phytyl-like side chain and both methyl substituents of the chromanol form hydrophobic interactions with Val110, His130, Lys133, Tyr383, and Arg401
molecular docking of inhibitor ferrocenyl carboxylic acid. The carboxylate group of the ferrocenyl complex may be oriented towards the catalytic site of the enzyme or may be located at the cavity entrance of the active site
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A603L
site-directed mutagenesis, almost inactive mutant
A603L/Y181A
site-directed mutagenesis, the mutant shows activity similar to the wild-type enzyme
C159S
site-directed mutagenesis, the mutant shows altered susceptibillity to 2-aminothiazole inhibitors compared to the wild-type enzyme
C159S/C300S/C416S/C418S
site-directed mutagenesis, the mutant shows unaltered product synthesis
C240A
site-directed mutagenesis, the mutation renders the enzyme less susceptible to product inactivation
C300S
site-directed mutagenesis, the mutant shows altered susceptibillity to 2-aminothiazole inhibitors compared to the wild-type enzyme
C416S
site-directed mutagenesis, the mutant shows altered susceptibillity to 2-aminothiazole inhibitors compared to the wild-type enzyme
C418S
site-directed mutagenesis, the mutant shows altered susceptibillity to 2-aminothiazole inhibitors compared to the wild-type enzyme
C561A
site-directed mutagenesis, the mutation renders the enzyme less susceptible to product inactivation
D170S/G174N
site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme
E254K
-
naturally occuring non-synonymous exonic variant g.760G/A is associated with tuberculosis, genotyping of 1916 sputum-positive patients with pulmonary tuberculosis from Ghana and in 2269 exposed, apparently healthy control individuals, polymorphisms of a variable number of tandem repeats of the ALOX5 promoter and of the exonic non-synonymous variant g.760G>A are analyzed by fragment length determination and fluorescence resonance energy transfer, respectively, and DNA sequencing. The association of the exonic variant is stronger in infections caused by the mycobacterial lineage Mycobacterium africanum West-African 2, overview, distribution of haplotypes, overview
F177A
site-directed mutagenesis, the mutant shows activity similar to the wild-type enzyme
F177A/Y181A
site-directed mutagenesis, the mutant shows activity similar to the wild-type enzyme
F177A/Y181A/H600V
site-directed mutagenesis, the mutant shows about 50% reduced activity compared to the wild-type enzyme
F359W/A4241
-
8-lipoxygenating mutant
F359W/A424I/N425M/A603I
G174N
site-directed mutagenesis, inactive mutant
H362Q
-
reduced enzyme activity, similar amounts of iron as non-mutated enzyme
H367N
-
inactive, contains 0.2 mol of iron per mol of protein, compared to 0.86 mol of iron per mol of protein for the wild-type enzyme
H367Q
-
inactive, contains 0.5 mol of iron per mol of protein, compared to 0.86 mol of iron per mol of protein for the wild-type enzyme
H367S
-
inactive, contains 0.5 mol of iron per mol of protein, compared to 0.86 mol of iron per mol of protein for the wild-type enzyme
H372Q
-
no detectable enzyme activity, practically devoid of iron
H390Q
-
reduced enzyme activity, similar amounts of iron as non-mutated enzyme
H399Q
-
reduced enzyme activity, similar amounts of iron as non-mutated enzyme
H550Q
-
no detectable enzyme activity, practically devoid of iron
H600A
site-directed mutagenesis, inactive mutant
S271A
S663A
site-directed mutagenesis, mutation of the phosphorylation site results in impaired cellular 5-LO product formation when transfected cells are selectively activated by arachidonic acid
W102A
W13/75/102A
-
triple mutant shows higher total activity than the wild type enzyme
W13A
-
the mutation upregulates leukotriene production, the enzyme activity of the mutant 5-LO at low concentrations of phosphatidylcholine (0.005 mg/ml) and arachidonic acid (0.02 mM) is reduced compared to the wild type enzyme
W13A/W75A/W102A
site-directed mutagenesis, the mutant is not activated by Ca2+ and phosphocholine
W147L
site-directed mutagenesis, inactive mutant
W75A
-
the mutation upregulates leukotriene production, the enzyme activity of the mutant 5-LO at low concentrations of phosphatidylcholine (0.005 mg/ml) and arachidonic acid (0.02 mM) is reduced compared to the wild type enzyme
W75G
site-directed mutagenesis, the mutation causes reduced aggregation and substantially increased thermal stability of the mutant. The mutant still shows Ca2+ interactions. Mutation W75G thermally stabilises the isolated PLAT domain
Y181A
site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme
additional information
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
coactosin-like protein functions as a stabilizing chaperone for 5-lipoxygenase (preventing non-turnover inactivation)
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, stable for weeks
-
0-4°C, 30 min, 40-60% loss of activity
-
4°C, stable for days
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
MonoQ column chromatography
-
partially purified by sonication, centrifugation and gel filtration
-
recombinant enzyme
-
recombinant enzyme from Escherichia coli strain BL21 by ATP affinity chromatography
recombinant enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography, and anion exchange chromatography
recombinant enzyme partially from Escherichia coli strain MV1190 by ammonium sulfate fractionation and ATP affinity chromatography
-
recombinant His-tagged wild-type and mutant enzymes from Escherichia coli strain Rosetta2 by cobalt affinity chromatography and ultrafiltration
recombinant His-tagged wild-type enzyme and enzyme mutant from Escherichia coli strain BL21(DE3) by nickel affinity chromatography, tag cleavage by TEV protease, and gel filtration, isolated enzyme PLAT domain
recombinant soluble 5-LODELTA4 mutant and wild-type enzyme 5-LO from Escherichia coli strain BL21(DE3) by ATP affinity chromatography and anion exchange chromatography
recombinant soluble MBP-regulatory C2-like domain fusion protein from Escherichia coli strain BL21(DE3) by amylose affinity chromatography, fusion protein cleavage by TEV protease, and further purification of the C2-like domain by hydrophobic interaction chromatography
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
5-lipoxygenase cDNA cloned into EGFP fusion protein vector (pEGFP-h5-LO) and expressed in HEK293/T or COS-7 cells, or into a pUC13 vector, full length 5-lipoxygenase cDNA subcloned into pGEX and pcDNA3, expressed in Escherichia coli Y1090
-
detection of alternatively spliced 5-LO transcripts in B and T cell lines and in primary cells encoding naturally occuring mutant 5-LO catalytically inactive isoforms 5-LODELTA13, 5-LODELTA4 and 5-LOp12, that lack the exons 13, 4 or a part of exon 12, respectively, RT-PCR expression analysis of 5-LO-WT and isoform expression. Coexpression of the truncated natural isoforms with 5-LO-wild-type in transiently and stably transfected HEK-293T cells
DNA and amino acid sequence analysis
-
Escherichia coli MV1190 transformed with pT3-5LO plasmid
-
expressed in Escherichia coli
-
expressed in Escherichia coli BL21 and MV1190 cells
-
expression in Escherichia coli
expression in Escherichia coli strain MV1190
-
expression in HEK-293 cell
expression in HEK-293 cells
expression in human osteosarcoma cell line 143.98.2
-
expression of regulatory C2-like domain of the enzyme, residues 1-128, containing a tobacco etch virus protease-cleavage site, in Escherichia coli strain BL21(DE3) as soluble maltose-binding-protein fusion protein
-
from adipose tissue, expression of the enzyme in Spodoptera frugiperda Sf9 cells using the baculovirus transfection system, subcloning and propagation of the virus in Escherichia coli strain DH10
-
gene 5-LOX, recombinant expression of the enzyme in Escherichia coli strain BL21(DE3)
gene ALOX5, located on chromosome 10q11.21, it spans a region of 71.9 kbp and consists of 13 introns named A-M and 14 exons, semiquantitative PCR enzyme expression analysis. Recombinant expression of enzyme mutant 5-LODELTA4 in HEK-293T cells from expression plasmid, recombinant expression of soluble 5-LODELTA4 mutant and of wild-type enzyme 5-LO in Escherichia coli strain BL21(DE3)
gene alox5, recombinant expression in Escherichia coli strain BL21
gene ALOX5, recombinant expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain Rosetta2
gene ALOX5, recombinant expression of wild-type and mutant enzymes in HeLa cells, HEK-293 cells, and in Escherichia coli strain BL21 (DE3)
genotyping of 1916 sputum-positive patients with pulmonary tuberculosis from Ghana and in 2269 exposed, apparently healthy control individuals, polymorphisms of a variable number of tandem repeats of the ALOX5 promoter and of the exonic non-synonymous variant g.760G>A are analyzed by fragment length determination and fluorescence resonance energy transfer, respectively, and DNA sequencing. ALOX5 gene expression depends on the copy number of the Sp1-binding sequences in the promoter, whereby the 5 allele, compared with the 3, 4 and 6 alleles, is associated with the highest degree of expression
-
HEK 293 cells stably transfected with a pcDNA3.1 vector expressing 5-lipoxygenase
-
high expression baculovirus system
-
recombinant expression of enzyme in Escherichia coli strain BL21(DE3)
recombinant expression of His-tagged wild-type enzyme, enzyme mutant, and isolated enzyme PLAT domain in Escherichia coli strain BL21(DE3)
the gene contains 14 exons, DNA methylation is responsible for suppression of 5-LO expression, the 5-LO core promoter is completely methylated in the cell lines U-937 and HL-60TB, which do not express 5-LO protein, regulation mechanisms, overview, expression in HeLa cells, which lack endogenous enzyme, for promoter analysis, the basal promoter undergoes DNA looping to distant gene regions
wild-type and mutant enzyme F359W/A424I/N425M/A603I, expression in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
0.01 mM hydroxynonenal induces 5-LOX promoter activity significantly by 310% and 580% after 48 and 72 h of incubation, respectively. The addition of anti-transforming growth factor-beta1 antibody reduces hydroxynonenal-induced 5-LOX expression by 40%
-
aberrant methylation may lead to upregulated 5-lipoxygenase expression in tumor cells. The 5-lipoxygenase core promoter is completely methylated in cell lines U-937 and HL-60TB, which do not express 5-lipoxygenase. Treatment with the demethylating agent 5-aza-2'deoxycytidine restores 5-lipoxygenase expression
-
coexpression of the truncated natural isoforms inhibits or stimulates 5-LO-wild-type expression in transiently and stably transfected HEK-293T cells suggesting that the isoforms have other functions than canonical leukotriene biosynthesis
DNA methylation is responsible for suppression of 5-lipoxygenase expression in most cell types
-
methyl-DNA binding proteins MBD1, MBD2 and MeCP2 downregulate 5-LO mRNA expression in U-937 cells
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
medicine
pharmacology
human 5-lipoxygenase is a well-validated target for anti-inflammatory therapy. Development of 5-LOX inhibitors with higher activities is highly required
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
Cavia porcellus, Homo sapiens, Rattus norvegicus, Sus scrofa
-
Manually annotated by BRENDA team
Denis, D.; Falgueyret, J.P.; Riendeau, D.; Abramovitz, M.
Characterization of the activity of purified recombinant human 5-lipoxygenase in the absence and presence of leukocyte factors
J. Biol. Chem.
266
5072-5079
1991
Homo sapiens
Manually annotated by BRENDA team
Rouzer, C.A.; Samuelsson, B.
Leukocyte arachidonate 5-lipoxygenase: isolation and characterization
Methods Enzymol.
187
312-319
1990
Homo sapiens
Manually annotated by BRENDA team
Cashman, J.R.; Lambert, C.; Sigal, E.
Inhibition of human leukocyte 5-lipoxygenase by 15-HPETE and related eicosanoids
Biochem. Biophys. Res. Commun.
155
38-44
1988
Homo sapiens
Manually annotated by BRENDA team
Rouzer, C.A.; Rands, E.; Kargman, S.; Jones, R.E.; Register, R.B.; Dixon, R.A.F.
Characterization of cloned human leukocyte 5-lipoxygenase expressed in mammalian cells
J. Biol. Chem.
263
10135-10140
1988
Homo sapiens
Manually annotated by BRENDA team
Soberman, R.J.
5- and 15(omega-6)-lipoxygenases from human polymorphonuclear leukocytes
Methods Enzymol.
163
344-349
1988
Homo sapiens
Manually annotated by BRENDA team
Rouzer, C.A.; Shimizu, T.; Samuelsson, B.
On the nature of the 5-lipoxygenase reaction in human leukocytes: characterization of a membrane-associated stimulatory factor
Proc. Natl. Acad. Sci. USA
82
7505-7509
1985
Homo sapiens
Manually annotated by BRENDA team
Falgueyret, J.P.; Denis, D.; MacDonald, D.; Hutchinson, J.H.; Riendeau, D.
Characterization of the arachidonate and ATP binding sites of human 5-lipoxygenase using photoaffinity labeling and enzyme immobilization
Biochemistry
34
13603-13611
1995
Homo sapiens
Manually annotated by BRENDA team
Colamorea, T.; Di Paola, R.; Macchia, F.; Guerrese, M.C.; Tursi, A.; Butterfield, J.H.; Caiaffa, M.F.; Haeggstrom, J.Z.; Macchia, L.
5-Lipoxygenase Upregulation by Dexamethasone in Human Mast Cells
Biochem. Biophys. Res. Commun.
265
617-624
1999
Homo sapiens
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
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Ghosh, J.; Myers, C.E.
Inhibition of arachidonate 5-lipoxygenase triggers massive apoptosis in human prostate cancer cells
Proc. Natl. Acad. Sci. USA
95
13182-13187
1998
Homo sapiens
Manually annotated by BRENDA team
Janssen-Timmen, U.; Vickers, P.J.; Wittig, U.; Lehmann, W.D.; Stark, H.J.; Fusenig, N.E.; Rosenbach, T.; Raedmark, O.; Samuelsson, B.; Habenicht, A.J.R.
Expression of 5-lipoxygenase in differentiating human skin keratinocytes
Proc. Natl. Acad. Sci. USA
92
6966-6970
1995
Homo sapiens
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
Cavia porcellus, Oryctolagus cuniculus, Homo sapiens, Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Walther, M.; Ivanov, I.; Myagkova, G.; Kuhn, H.
Alterations of lipoxygenase specificity by targeted substrate modification and site-directed mutagenesis
Chem. Biol.
8
779-790
2001
Homo sapiens
Manually annotated by BRENDA team
Schwarz, K.; Gerth, C.; Anton, M.; Kuhn, H.
Alterations in Leukotriene Synthase Activity of the Human 5-Lipoxygenase by Site-Directed Mutagenesis Affecting Its Positional Specificity
Biochemistry
39
14515-14521
2000
Homo sapiens
Manually annotated by BRENDA team
Young, R.N.
Inhibitors of 5-lipoxygenase: a therapeutic potential yet to be fully realized?
Eur. J. Med. Chem.
34
671-685
1999
Homo sapiens
-
Manually annotated by BRENDA team
Wetterholm, A.; Macchia, L.; Haeggstrom, J.Z.
Zinc and other divalent cations inhibit purified leukotriene A4 hydrolase and leukotriene B4 biosynthesis in human polymorphonuclear leukocytes
Arch. Biochem. Biophys.
311
253-271
1994
Homo sapiens
-
Manually annotated by BRENDA team
Zhang, Y.Y.; Lind, B.; Raadmark, O.; Samuelsson, B.
Iron content of human 5-lipoxygenase. Effects of mutations regarding conserved histidine residues
J. Biol. Chem.
268
2535-2541
1993
Homo sapiens
Manually annotated by BRENDA team
Radmark, O.
Arachidonate 5-lipoxygenase
Prostaglandins
68-69
211-234
2002
Oryctolagus cuniculus, Homo sapiens, Mus musculus, Rattus norvegicus, Solanum tuberosum, Sus scrofa
Manually annotated by BRENDA team
Ghosh, J.
Rapid induction of apoptosis in prostate cancer cells by selenium: reversal by metabolites of arachidonate 5-lipoxygenase
Biochem. Biophys. Res. Commun.
315
624-635
2004
Homo sapiens
Manually annotated by BRENDA team
Pande, A.H.; Moe, D.; Nemec, K.N.; Qin, S.; Tan, S.; Tatulian, S.A.
Modulation of human 5-lipoxygenase activity by membrane lipids
Biochemistry
43
14653-14666
2004
Homo sapiens
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
Bos taurus, Cavia porcellus, Glycine max, Helianthus tuberosus, Homo sapiens, Mus musculus, Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Grimm, E.L.; Brideau, C.; Chauret, N.; Chan, C.C.; Delorme, D.; Ducharme, Y.; Ethier, D.; Falgueyret, J.P.; Friesen, R.W.; Guay, J.; Hamel, P.; Riendeau, D.; Soucy-Breau, C.; Tagari, P.; Girard, Y.
Substituted coumarins as potent 5-lipoxygenase inhibitors
Bioorg. Med. Chem. Lett.
16
2528-2531
2006
Homo sapiens
Manually annotated by BRENDA team
Abe, M.; Ozawa, Y.; Uda, Y.; Morimitsu, Y.; Nakamura, Y.; Osawa, T.
A novel labdane-type trialdehyde from myoga (Zingiber mioga Roscoe) that potently inhibits human platelet aggregation and human 5-lipoxygenase
Biosci. Biotechnol. Biochem.
70
2494-2500
2006
Homo sapiens
Manually annotated by BRENDA team
Shirumalla R. , S.R.; Naruganahalli K. , N.K.; Dastidar S. , D.S.; Sattigeri , S.V.; Kaur , K.G.; Deb , D.C.; Gupta J. , G.J.; Salman , S.M.; Ray , R.A.
RBx 7796: A novel inhibitor of 5-lipoxygenase
Inflamm. Res.
55
517-527
2006
Homo sapiens
Manually annotated by BRENDA team
Butovich, I.A.; Lukyanova, S.M.; Bachmann, C.
Dihydroxydocosahexaenoic acids of the neuroprotectin D family: synthesis, structure, and inhibition of human 5-lipoxygenase
J. Lipid Res.
47
2462-2474
2006
Homo sapiens
Manually annotated by BRENDA team
Araico, A.; Terencio, M.C.; Alcaraz, M.J.; Dominguez, J.N.; Leon, C.; Ferrandiz, M.L.
Phenylsulphonyl urenyl chalcone derivatives as dual inhibitors of cyclo-oxygenase-2 and 5-lipoxygenase
Life Sci.
78
2911-2918
2006
Homo sapiens
Manually annotated by BRENDA team
Poeckel, D.; Niedermeyer, T.H.; Pham, H.T.; Mikolasch, A.; Mundt, S.; Lindequist, U.; Lalk, M.; Werz, O.
Inhibition of human 5-lipoxygenase and anti-neoplastic effects by 2-amino-1,4-benzoquinones
Med. Chem.
2
591-595
2006
Homo sapiens
Manually annotated by BRENDA team
Rakonjac, M.; Fischer, L.; Provost, P.; Werz, O.; Steinhilber, D.; Samuelsson, B.; Radmark, O.
Coactosin-like protein supports 5-lipoxygenase enzyme activity and up-regulates leukotriene A4 production
Proc. Natl. Acad. Sci. USA
103
13150-13155
2006
Homo sapiens
Manually annotated by BRENDA team
Raghavenra, H.; Diwakr, B.T.; Lokesh, B.R.; Naidu, K.A.
Eugenol--the active principle from cloves inhibits 5-lipoxygenase activity and leukotriene-C4 in human PMNL cells
Prostaglandins Leukot. Essent. Fatty Acids
74
23-27
2006
Homo sapiens
Manually annotated by BRENDA team
Frum, Y.; Viljoen, A.M.
In vitro 5-lipoxygenase and anti-oxidant activities of South African medicinal plants commonly used topically for skin diseases
Skin Pharmacol. Physiol.
19
329-335
2006
Homo sapiens
Manually annotated by BRENDA team
Pufahl, R.A.; Kasten, T.P.; Hills, R.; Gierse, J.K.; Reitz, B.A.; Weinberg, R.A.; Masferrer, J.L.
Development of a fluorescence-based enzyme assay of human 5-lipoxygenase
Anal. Biochem.
364
204-212
2007
Homo sapiens
Manually annotated by BRENDA team
Mahesha, H.G.; Singh, S.A.; Rao, A.G.
Inhibition of lipoxygenase by soy isoflavones: evidence of isoflavones as redox inhibitors
Arch. Biochem. Biophys.
461
176-185
2007
Homo sapiens
Manually annotated by BRENDA team
Belfiore, M.C.; Natoni, A.; Barzellotti, R.; Merendino, N.; Pessina, G.; Ghibelli, L.; Gualandi, G.
Involvement of 5-lipoxygenase in survival of Epstein-Barr virus (EBV)-converted B lymphoma cells
Cancer Lett.
254
236-243
2007
Homo sapiens
Manually annotated by BRENDA team
Gonzalez-Periz, A.; Claria, J.
New approaches to the modulation of the cyclooxygenase-2 and 5-lipoxygenase pathways
Curr. Top. Med. Chem.
7
297-309
2007
Homo sapiens
Manually annotated by BRENDA team
Herb, F.; Thye, T.; Niemann, S.; Browne, E.N.; Chinbuah, M.A.; Gyapong, J.; Osei, I.; Owusu-Dabo, E.; Werz, O.; Ruesch-Gerdes, S.; Horstmann, R.D.; Meyer, C.G.
ALOX5 variants associated with susceptibility to human pulmonary tuberculosis
Hum. Mol. Genet.
17
1052-1060
2008
Homo sapiens
Manually annotated by BRENDA team
Cook-Moreau, J.M.; El-Makhour Hojeij, Y.; Barriere, G.; Rabinovitch-Chable, H.C.; Faucher, K.S.; Sturtz, F.G.; Rigaud, M.A.
Expression of 5-lipoxygenase (5-LOX) in T lymphocytes
Immunology
122
157-166
2007
Homo sapiens
Manually annotated by BRENDA team
Ezekwudo, D.E.; Wang, R.C.; Elegbede, J.A.
Methyl jasmonate induced apoptosis in human prostate carcinoma cells via 5-lipoxygenase dependent pathway
J. Exp. Ther. Oncol.
6
267-277
2007
Homo sapiens
Manually annotated by BRENDA team
Franke, L.; Schwarz, O.; Mueller-Kuhrt, L.; Hoernig, C.; Fischer, L.; George, S.; Tanrikulu, Y.; Schneider, P.; Werz, O.; Steinhilber, D.; Schneider, G.
Identification of natural-product-derived inhibitors of 5-lipoxygenase activity by ligand-based virtual screening
J. Med. Chem.
50
2640-2646
2007
Homo sapiens
Manually annotated by BRENDA team
Massi, P.; Valenti, M.; Vaccani, A.; Gasperi, V.; Perletti, G.; Marras, E.; Fezza, F.; Maccarrone, M.; Parolaro, D.
5-Lipoxygenase and anandamide hydrolase (FAAH) mediate the antitumor activity of cannabidiol, a non-psychoactive cannabinoid
J. Neurochem.
104
1091-1100
2008
Homo sapiens, Hordeum vulgare
Manually annotated by BRENDA team
Vincent, C.; Fiancette, R.; Donnard, M.; Bordessoule, D.; Turlure, P.; Trimoreau, F.; Denizot, Y.
5-LOX, 12-LOX and 15-LOX in immature forms of human leukemic blasts
Leuk. Res.
32
1756-1762
2008
Homo sapiens
Manually annotated by BRENDA team
Sudina, G.F.; Pushkareva, M.A.; Shephard, P.; Klein, T.
Cyclooxygenase (COX) and 5-lipoxygenase (5-LOX) selectivity of COX inhibitors
Prostaglandins Leukot. Essent. Fatty Acids
78
99-108
2008
Homo sapiens
Manually annotated by BRENDA team
Loetzer, K.; Jahn, S.; Kramer, C.; Hildner, M.; Nuesing, R.; Funk, C.D.; Habenicht, A.J.
5-Lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells
Prostaglandins Other Lipid Mediat.
84
108-115
2007
Homo sapiens
Manually annotated by BRENDA team
Michel, A.A.; Steinhilber, D.; Werz, O.
Development of a method for expression and purification of the regulatory C2-like domain of human 5-lipoxygenase
Protein Expr. Purif.
59
110-116
2008
Homo sapiens
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
Mus musculus, Rattus norvegicus, Homo sapiens (P09917)
Manually annotated by BRENDA team
Koeberle, A.; Zettl, H.; Greiner, C.; Wurglics, M.; Schubert-Zsilavecz, M.; Werz, O.
Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase
J. Med. Chem.
51
8068-8076
2008
Homo sapiens
Manually annotated by BRENDA team
Strid, T.; Svartz, J.; Franck, N.; Hallin, E.; Ingelsson, B.; Soederstroem, M.; Hammarstroem, S.
Distinct parts of leukotriene C(4) synthase interact with 5-lipoxygenase and 5-lipoxygenase activating protein
Biochem. Biophys. Res. Commun.
381
518-522
2009
Homo sapiens
Manually annotated by BRENDA team
Macdonald, D.; Brideau, C.; Chan, C.C.; Falgueyret, J.P.; Frenette, R.; Guay, J.; Hutchinson, J.H.; Perrier, H.; Prasit, P.; Riendeau, D.; Tagari, P.; Therien, M.; Young, R.N.; Girard, Y.
Substituted 2,2-bisaryl-bicycloheptanes as novel and potent inhibitors of 5-lipoxygenase activating protein
Bioorg. Med. Chem. Lett.
18
2023-2027
2008
Homo sapiens
Manually annotated by BRENDA team
Doiron, J.; Boudreau, L.H.; Picot, N.; Villebonet, B.; Surette, M.E.; Touaibia, M.
Synthesis and 5-lipoxygenase inhibitory activity of new cinnamoyl and caffeoyl clusters
Bioorg. Med. Chem. Lett.
19
1118-1121
2009
Homo sapiens
Manually annotated by BRENDA team
Reddy, M.V.; Billa, V.K.; Pallela, V.R.; Mallireddigari, M.R.; Boominathan, R.; Gabriel, J.L.; Reddy, E.P.
Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors
Bioorg. Med. Chem.
16
3907-3916
2008
Oryctolagus cuniculus, Homo sapiens
Manually annotated by BRENDA team
Mahshid, Y.; Lisy, M.; Wang, X.; Spanbroek, R.; Flygare, J.; Christensson, B.; Bjoerkholm, M.; Sander, B.; Habenicht, A.; Claesson, H.
High expression of 5-lipoxygenase in normal and malignant mantle zone B lymphocytes
BMC Immunol.
10
2-2
2009
Homo sapiens
Manually annotated by BRENDA team
Jian, W.; Lee, S.H.; Williams, M.V.; Blair, I.A.
5-Lipoxygenase-mediated endogenous DNA damage
J. Biol. Chem.
284
16799-16807
2009
Homo sapiens
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
Liedtke, A.J.; Keck, P.R.; Lehmann, F.; Koeberle, A.; Werz, O.; Laufer, S.A.
Arylpyrrolizines as inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1) or as dual inhibitors of mPGES-1 and 5-lipoxygenase (5-LOX)
J. Med. Chem.
52
4968-4972
2009
Homo sapiens
Manually annotated by BRENDA team
Knaup, B.; Oehme, A.; Valotis, A.; Schreier, P.
Anthocyanins as lipoxygenase inhibitors
Mol. Nutr. Food Res.
53
617-624
2009
Homo sapiens
Manually annotated by BRENDA team
Chen, S.H.; Fahmi, H.; Shi, Q.; Benderdour, M.
Regulation of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase-activating protein/5-lipoxygenase by 4-hydroxynonenal in human osteoarthritic chondrocytes
Arthritis Res. Ther.
12
R21
2010
Homo sapiens
Manually annotated by BRENDA team
Radmark, O.; Samuelsson, B.
Regulation of the activity of 5-lipoxygenase, a key enzyme in leukotriene biosynthesis
Biochem. Biophys. Res. Commun.
396
105-110
2010
Homo sapiens
Manually annotated by BRENDA team
Esser, J.; Rakonjac, M.; Hofmann, B.; Fischer, L.; Provost, P.; Schneider, G.; Steinhilber, D.; Samuelsson, B.; Radmark, O.
Coactosin-like protein functions as a stabilizing chaperone for 5-lipoxygenase: Role of tryptophan 102
Biochem. J.
425
265-274
2010
Homo sapiens
Manually annotated by BRENDA team
Katryniok, C.; Schnur, N.; Gillis, A.; von Knethen, A.; Sorg, B.; Looijenga, L.; Radmark, O.; Steinhilber, D.
Role of DNA methylation and methyl-DNA binding proteins in the repression of 5-lipoxygenase promoter activity
Biochim. Biophys. Acta
1801
49-57
2010
Homo sapiens
Manually annotated by BRENDA team
Fischer, A.S.; Metzner, J.; Steinbrink, S.D.; Ulrich, S.; Angioni, C.; Geisslinger, G.; Steinhilber, D.; Maier, T.J.
5-Lipoxygenase inhibitors induce potent anti-proliferative and cytotoxic effects in human tumour cells independently of suppression of 5-lipoxygenase activity
Br. J. Pharmacol.
161
936-949
2010
Homo sapiens
Manually annotated by BRENDA team
Shin, V.Y.; Jin, H.C.; Ng, E.K.; Sung, J.J.; Chu, K.M.; Cho, C.H.
Activation of 5-lipoxygenase is required for nicotine mediated epithelial-mesenchymal transition and tumor cell growth
Cancer Lett.
292
237-245
2010
Homo sapiens
Manually annotated by BRENDA team
Steinbrink, S.D.; Pergola, C.; Buehring, U.; George, S.; Metzner, J.; Fischer, A.S.; Haefner, A.K.; Wisniewska, J.M.; Geisslinger, G.; Werz, O.; Steinhilber, D.; Maier, T.J.
Sulindac sulfide suppresses 5-lipoxygenase at clinically relevant concentrations
Cell. Mol. Life Sci.
67
797-806
2010
Homo sapiens
Manually annotated by BRENDA team
Radmark, O.; Samuelsson, B.
Microsomal prostaglandin E synthase-1 and 5-lipoxygenase: potential drug targets in cancer
J. Intern. Med.
268
5-14
2010
Homo sapiens
Manually annotated by BRENDA team
Filosa, R.; Peduto, A.; Aparoy, P.; Schaible, A.M.; Luderer, S.; Krauth, V.; Petronzi, C.; Massa, A.; de Rosa, M.; Reddanna, P.; Werz, O.
Discovery and biological evaluation of novel 1,4-benzoquinone and related resorcinol derivatives that inhibit 5-lipoxygenase
Eur. J. Med. Chem.
67
269-279
2013
Homo sapiens
Manually annotated by BRENDA team
Hofmann, B.; Barzen, S.; Roedl, C.B.; Kiehl, A.; Borig, J.; Zivkovic, A.; Stark, H.; Schneider, G.; Steinhilber, D.
A class of 5-benzylidene-2-phenylthiazolinones with high potency as direct 5-lipoxygenase inhibitors
J. Med. Chem.
54
1943-1947
2011
Homo sapiens
Manually annotated by BRENDA team
Kretschmer, S.B.M; Woltersdorf, S.; Vogt, D.; Lillich, F.F.; Ruehl, M.; Karas, M.; Maucher, I.V.; Roos, J.; Haefner, A.-K.; Kaiser, A.; Wurglics, M.; Schubert-Zsilavecz, M.; Angioni, C.; Geisslinger, G.; Stark, H.; Steinhilber, D.; Hofmann, B.
Characterization of the molecular mechanism of 5-lipoxygenase inhibition by 2-aminothiazoles
Biochem. Pharmacol.
123
52-62
2017
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Khayrullina, V.R.; Taipov, I.A.; Veselovsky, A.V.; Shcherbinin, D.S.; Gerchikov, A.Y.
New inhibitors of 5-lipoxygenase catalytic activity based on 2-(3-methylphenyl)propanoic acid and 4-substituted morpholine derivatives
Biochemistry (Moscow)
79
376-384
2014
Homo sapiens (P09917)
Manually annotated by BRENDA team
Smyrniotis, C.J.; Barbour, S.R.; Xia, Z.; Hixon, M.S.; Holman, T.R.
ATP allosterically activates the human 5-lipoxygenase molecular mechanism of arachidonic acid and 5(S)-hydroperoxy-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid
Biochemistry
53
4407-4419
2014
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Mitra, S.; Bartlett, S.G.; Newcomer, M.E.
Identification of the substrate access portal of 5-lipoxygenase
Biochemistry
54
6333-6342
2015
Homo sapiens (P09917)
Manually annotated by BRENDA team
Schroeder, M.; Haefner, A.K.; Hofmann, B.; Radmark, O.; Tumulka, F.; Abele, R.; Doetsch, V.; Steinhilber, D.
Stabilisation and characterisation of the isolated regulatory domain of human 5-lipoxygenase
Biochim. Biophys. Acta
1842
1538-1547
2014
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Haefner, A.K.; Gerstmeier, J.; Hoernig, M.; George, S.; Ball, A.K.; Schroeder, M.; Garscha, U.; Werz, O.; Steinhilber, D.
Characterization of the interaction of human 5-lipoxygenase with its activating protein FLAP
Biochim. Biophys. Acta
1851
1465-1472
2015
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Ball, A.K.; Beilstein, K.; Wittmann, S.; Sueruen, D.; Saul, M.J.; Schnuetgen, F.; Flamand, N.; Capelo, R.; Kahnt, A.S.; Frey, H.; Schaefer, L.; Marschalek, R.; Haefner, A.K.; Steinhilber, D.
Characterization and cellular localization of human 5-lipoxygenase and its protein isoforms 5-LODELTA13, 5-LODELTA4 and 5-LOp12
Biochim. Biophys. Acta
1862
561-571
2017
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Shang, E.; Liu, Y.; Wu, Y.; Zhu, W
; He, C.; Lai, L. Development of 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors
Bioorg. Med. Chem.
22
2396-2402
2014
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Mittal, M.; Kumar, R.B.; Balagunaseelan, N.; Hamberg, M.; Jegerschoeld, C.; Radmark, O.; Haeggstroem, J.Z.; Rinaldo-Matthis, A.
Kinetic investigation of human 5-lipoxygenase with arachidonic acid
Bioorg. Med. Chem. Lett.
26
3547-3551
2016
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Torras, J.; Maccarrone, M.; Dainese, E.
Molecular dynamics study on the apo- and holo-forms of 5-lipoxygenase
Biotechnol. Appl. Biochem.
65
54-61
2017
Homo sapiens (P09917)
Manually annotated by BRENDA team
Pergola, C.; Gerstmeier, J.; Moench, B.; Caliskan, B.; Luderer, S.; Weinigel, C.; Barz, D.; Maczewsky, J.; Pace, S.; Rossi, A.; Sautebin, L.; Banoglu, E.; Werz, O.
The novel benzimidazole derivative BRP-7 inhibits leukotriene biosynthesis in vitro and in vivo by targeting 5-lipoxygenase-activating protein (FLAP)
Br. J. Pharmacol.
171
3051-3064
2014
Homo sapiens (P09917)
Manually annotated by BRENDA team
Peduto, A.; Scuotto, M.; Krauth, V.; Roviezzo, F.; Rossi, A.; Temml, V.; Esposito, V.; Stuppner, H.; Schuster, D.; D'Agostino, B.; Schiraldi, C.; de Rosa, M.; Werz, O.; Filosa, R.
Optimization of benzoquinone and hydroquinone derivatives as potent inhibitors of human 5-lipoxygenase
Eur. J. Med. Chem.
127
715-726
2017
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Peduto, A.; Bruno, F.; Dehm, F.; Krauth, V.; de Caprariis, P.; Weinigel, C.; Barz, D.; Massa, A.; De Rosa, M.; Werz, O.; Filosa, R.
Further studies on ethyl 5-hydroxy-indole-3-carboxylate scaffold design, synthesis and evaluation of 2-phenylthiomethyl-indole derivatives as efficient inhibitors of human 5-lipoxygenase
Eur. J. Med. Chem.
81
492-498
2014
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Ho, X.L.; Liu, J.J.; Loke, W.M.
Plant sterol-enriched soy milk consumption modulates 5-lipoxygenase, 12-lipoxygenase, and myeloperoxidase activities in healthy adults - a randomized-controlled trial
Free Radic. Res.
50
1396-1407
2016
Homo sapiens (P09917)
Manually annotated by BRENDA team
Schieferdecker, S.; Koenig, S.; Koeberle, A.; Dahse, H.-M.; Werz, O.; Nett, M.
Myxochelins target human 5-lipoxygenase
J. Nat. Prod.
78
335-338
2015
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Meirer, K.; Glatzel, D.; Kretschmer, S.; Wittmann, S.K.; Hartmann, M.; Bloecher, R.; Angioni, C.; Geisslinger, G.; Steinhilber, D.; Hofmann, B.; Fuerst, R.; Proschak, E.
Design, synthesis and cellular characterization of a dual inhibitor of 5-lipoxygenase and soluble epoxide hydrolase
Molecules
22
45
2016
Homo sapiens (P09917)
Manually annotated by BRENDA team
Chagas-Paula, D.A.; Oliveira, T.B.; Faleiro, D.P.V.; Oliveira, R.B.; Da Costa, F.B.
Outstanding anti-inflammatory potential of selected Asteraceae species through the potent dual inhibition of cyclooxygenase-1 and 5-lipoxygenase
Planta Med.
81
1296-1307
2015
Homo sapiens (P09917)
Manually annotated by BRENDA team
Allain, E.P.; Boudreau, L.H.; Flamand, N.; Surette, M.E.
The Intracellular localisation and phosphorylation profile of the human 5-lipoxygenase DELTA13 isoform differs from that of its full length counterpart
PLoS ONE
10
e0132607
2015
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Haefner, A.K.; Beilstein, K.; Graab, P.; Ball, A.K.; Saul, M.J.; Hofmann, B.; Steinhilber, D.
Identification and characterization of a new protein isoform of human 5-lipoxygenase
PLoS ONE
11
e0166591
2016
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Maucher, I.V.; Ruehl, M.; Kretschmer, S.B.; Hofmann, B.; Kuehn, B.; Fettel, J.; Vogel, A.; Fluegel, K.T.; Manolikakes, G.; Hellmuth, N.; Haefner, A.K.; Golghalyani, V.; Ball, A.K.; Piesche, M.; Matrone, C.; Geisslinger, G.; Parnham, M.J.; Karas, M.; Steinhilber, D.; Roos, J.; Maier, T.J.
Michael acceptor containing drugs are a novel class of 5-lipoxygenase inhibitor targeting the surface cysteines C416 and C418
Biochem. Pharmacol.
125
55-74
2017
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Green, A.R.; Freedman, C.; Tena, J.; Tourdot, B.E.; Liu, B.; Holinstat, M.; Holman, T.R.
5 S,15 S-Dihydroperoxyeicosatetraenoic Acid (5,15-diHpETE) as a lipoxin intermediate Reactivity and kinetics with human leukocyte 5-lipoxygenase, platelet 12-lipoxygenase, and reticulocyte 15-lipoxygenase-1
Biochemistry
57
6726-6734
2018
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Perry, S.C.; Horn, T.; Tourdot, B.E.; Yamaguchi, A.; Kalyanaraman, C.; Conrad, W.S.; Akinkugbe, O.; Holinstat, M.; Jacobson, M.P.; Holman, T.R.
Role of human 15-lipoxygenase-2 in the biosynthesis of the lipoxin intermediate, 5S,15S-diHpETE, implicated with the altered positional specificity of human 15-lipoxygenase-1
Biochemistry
59
4118-4130
2020
Homo sapiens (P09917)
Manually annotated by BRENDA team
Doiron, J.A.; Leblanc, L.M.; Hebert, M.J.; Levesque, N.A.; Pare, A.F.; Jean-Francois, J.; Cormier, M.; Surette, M.E.; Touaibia, M.
Structure-activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors
Chem. Biol. Drug Des.
89
514-528
2017
Homo sapiens (P09917)
Manually annotated by BRENDA team
Selka, A.; Doiron, J.A.; Lyons, P.; Dastous, S.; Chiasson, A.; Cormier, M.; Turcotte, S.; Surette, M.E.; Touaibia, M.
Discovery of a novel 2,5-dihydroxycinnamic acid-based 5-lipoxygenase inhibitor that induces apoptosis and may impair autophagic flux in RCC4 renal cancer cells
Eur. J. Med. Chem.
179
347-357
2019
Homo sapiens (P09917)
Manually annotated by BRENDA team
Dinh, C.P.; Ville, A.; Neukirch, K.; Viault, G.; Temml, V.; Koeberle, A.; Werz, O.; Schuster, D.; Stuppner, H.; Richomme, P.; Helesbeux, J.J.; Seraphin, D.
Structure-based design, semi-synthesis and anti-inflammatory activity of tocotrienolic amides as 5-lipoxygenase inhibitors
Eur. J. Med. Chem.
202
112518
2020
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Echeverria, J.; Urzua, A.
Inhibition of soybean 15-lipoxygenase and human 5-lipoxygenase by extracts of leaves, stem bark, phenols and catechols isolated from Lithraea caustica (Anacardiaceae)
Front. Pharmacol.
11
594257
2020
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Roy, P.; Faye, D.; Blanchard, S.; Cormier, M.; Doiron, J.; Surette, M.; Touaibia, M.
New caffeic acid phenylethyl ester analogs bearing substituted triazole Synthesis and structure-activity relationship study towards 5-lipoxygenase inhibition
J. Chem.
2017
2380531
2017
Homo sapiens (P09917)
-
Manually annotated by BRENDA team
Phillips, O.A.; Bosso, M.A.; Ezeamuzie, C.I.
Synthesis and structure-activity relationships of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives as 5-lipoxygenase inhibitors
J. Enzyme Inhib. Med. Chem.
35
1471-1482
2020
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Hiesinger, K.; Kramer, J.S.; Beyer, S.; Eckes, T.; Brunst, S.; Flauaus, C.; Wittmann, S.K.; Weizel, L.; Kaiser, A.; Kretschmer, S.B.M.; George, S.; Angioni, C.; Heering, J.; Geisslinger, G.; Schubert-Zsilavecz, M.; Schmidtko, A.; Pogoryelov, D.; Pfeilschifter, J.; Hofmann, B.; Steinhilber, D.; Sch, S.c.h.w.
Design, synthesis, and structure-activity relationship studies of dual inhibitors of soluble epoxide hydrolase and 5-lipoxygenase
J. Med. Chem.
63
11498-11521
2020
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Park, N.Y.; Im, S.; Jiang, Q.
Different forms of vitamin E and metabolite 13-carboxychromanols inhibit cyclooxygenase-1 and its catalyzed thromboxane in platelets, and tocotrienols and 13-carboxychromanols are competitive inhibitors of 5-lipoxygenase
J. Nutr. Biochem.
100
108884
2022
Homo sapiens (P09917)
Manually annotated by BRENDA team
Gilbert, N.C.; Gerstmeier, J.; Schexnaydre, E.E.; Boerner, F.; Garscha, U.; Neau, D.B.; Werz, O.; Newcomer, M.E.
Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products
Nat. Chem. Biol.
16
783-790
2020
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team
Munoz-Osses, M.; Quiroz, J.; Vasquez-Martixadnez, Y.; Flores, E.; Navarrete, E.; Godoy, F.; Torrent, C.; Cortez-San Martin, M.; Gomez, A.; Mascayano, C.
Evaluation of cyrhetrenyl and ferrocenyl precursors as 5-lipoxygenase inhibitors - biological and computational studies
New J. Chem.
45
13360-13368
2021
Homo sapiens (P09917)
-
Manually annotated by BRENDA team
Mbarik, M.; Poirier, S.; Doiron, J.; Selka, A.; Barnett, D.; Cormier, M.; Touaibia, M.; Surette, M.
Phenolic acid phenethylesters and their corresponding ketones Inhibition of 5-lipoxygenase and stability in human blood and HepaRG cells
Pharmacol. Res. Perspect.
7
e00524
2019
Homo sapiens (P09917), Homo sapiens
Manually annotated by BRENDA team