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Enzyme Nomenclature
Information on EC 1.13.11.34 - arachidonate 5-lipoxygenase
for references in articles please use BRENDA:EC1.13.11.34
Word Map on EC 1.13.11.34
- 1.13.11.34
-
cyclooxygenase
- inflammation
- prostaglandin
- leukocyte
- neutrophil
-
eicosanoids
-
ionophore
- asthma
- indomethacin
- macrophage
-
polymorphonuclear
-
thromboxane
- platelet
-
5-hete
- zileuton
-
proinflammatory
-
flap
- airway
-
eosinophil
-
allergic
-
mast
- peritoneal
-
cysteinyl
-
12-lipoxygenase
- edema
- histamine
- lta4
-
nordihydroguaiaretic
- lipoxygenases
-
bronchoconstriction
-
5-hydroxyeicosatetraenoic
- paf
-
asthmatic
-
basophil
-
platelet-activating
- ndga
-
antigen-induced
- anaphylaxis
-
lipoxins
-
zymosan
-
hetes
-
carrageenan-induced
- montelukast
- mpges-1
-
a23187-stimulated
- pharmacology
-
bronchoconstrictors
- synthesis
- bronchospasm
-
paf-induced
-
antiallergic
- drug development
- medicine
-
14carachidonic
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.13.11.34
-
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RECOMMENDED NAME
GeneOntology No.
arachidonate 5-lipoxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate = leukotriene A4 + H2O
(1b)
-
-
-
arachidonate + O2 = leukotriene A4 + H2O
overall reaction
-
-
-
arachidonate + O2 = (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(1a)
-
-
-
arachidonate + O2 = (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
kinetic mechainsm, overview
-
arachidonate + O2 = (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
a non-classical reaction mechanism
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dioxygenation
-
-
-
-
oxidation
redox reaction
-
-
-
-
reduction
-
-
-
-
oxidation
-
-
-
-
oxidation
-
the enzyme catalyzes the formation of 5(S)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid, 5(S)-hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid, and 5(S)-trans-5,6-oxido-7,9-trans-11,14-cis eicosatetraenoic acid
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 5-oxidoreductase
-
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CAS REGISTRY NUMBER
COMMENTARY
80619-02-9
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
-
439437, 439438, 439441, 439447, 439448, 439451, 439459, 439464, 439465, 439467, 439468, 439469, 439471, 439472, 439474, 439475, 439476, 439478, 439479, 657765, 658043, 659654, 660111, 672591, 672680, 673996, 675270, 675744, 675773, 676811, 676924, 677139, 684399, 684672, 685926, 686278, 687035, 687058, 688104, 688246, 688512, 688751, 689841, 689844, 689872, 693577, 702043, 702543, 702553, 702629, 702895, 704492, 704997, 705037, 705045, 705797, 711045, 711100, 711134, 711301, 711633, 711661, 711711, 712666, 727422, 728092
-
-
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690170, 741862, 741871, 741898, 741918, 741961, 741975, 742001, 742067, 742078, 742135, 742210, 742444, 742447, 742571, 743129, 743326, 743563, 743582, 743614
UniProt
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
additional information
malfunction
-
5-LO-/- infected with Trypanosoma cruzi, are more susceptible than C57BL/6 and wild-type 129Sv, showing higher parasitemia and mortality
malfunction
-
blockade of 5-LOX signaling results in downregulation of cyclin D1, matrix metalloproteinase (MMP-7, -9), urokinase plasminogen activator and its receptor, and pro-apoptotic proteins
malfunction
-
Trypanosoma cruzi infection in mice deficient in 5-lipoxygenase (5-LO) results in transiently increased parasitemia, and improved survival rate compared with wild type mice. Myocardia from 5-LO-deficient mice exhibit reduced inflammation, collagen deposition, and migration of CD4+, CD8+, and interferon-gamma-producer cells compared with wild type littermates. Moreover, decreased amounts of tumor necrosis factor-alpha, interferon-gamma, and nitric oxide synthase are found in the hearts of 5-LO-deficient mice
malfunction
-
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
malfunction
-
the naturally occuring mutant 5-LO catalytically inactive isoforms 5-LODELTA13, 5-LODELTA4 and 5-LOp12, lacking the exons 13, 4 or a part of exon 12, respectively, are identified in B and T cell lines as well as in primary B and T cells and monocytes. Wild-type 5-LO is localized in the nucleus whereas all natural mutant isoforms are located in the cytosol. 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. Detection of alternatively spliced 5-LO transcripts in primary monocytes of patients with rheumatoid arthritis and sepsis
malfunction
-
catalytically inactive mutant 5-LODELTA13, lacking exon 13, inhibits 5-LO product biosynthesis when co-expressed with active wild-type 5-LO1. Mutant 5-LODELTA13 inhibits leukotriene but not 5-hydroxyeicosatetraenoic acid (5-HETE) biosynthesis. This inhibition is independent of 5-LODELTA13-FLAP interactions since it occurs in cells expressing FLAP or not. Mutant 5-LODELTA13 is hyperphosphorylated on S523 and S273 compared to wild-type 5-LO1
malfunction
-
a protein isoform of human 5-LO that lacks exon 4, termed 5-LODELTA4, lacks canonical enzymatic activity as it misses the non-heme iron but it still retains ATP-binding affinity. The enzyme mutant 5-LODELTA4 stimulates wild-type 5-LO activity and product formation at low protein concentrations
metabolism
-
5-lipoxygenase is involved in the production of matrix metalloproteinase-9
physiological function
-
5-lipoxygenase/5-lipoxygenase activating protein interaction, which may serve as a feed-back control point for leukotriene C4 biosynthesis
physiological function
-
role of the 5-lipoxygenase pathway in B cells before the cells finally differentiate to plasma cells
physiological function
-
5-lipoxygenase products may not only play a major role in controlling heart tissue parasitism, i.e., host resistance to acute infection with Trypanosoma cruzi in vivo, but in the event of an infection also play an important part in erythrocyte oxidative stress, an NO-dependent effect. 5-lipoxygenase metabolites increase lipid peroxidation levels in erythrocytes during the early phase of murine Trypanosoma cruzi infection, but do not participate in the development of anemia, thrombocytopenia or leukopenia in Trypanosoma cruzi-infected mice
physiological function
-
5-lipoxygenase-derived lipid hydroperoxide is responsible for endogenous DNA-adduct formation. 5-lipoxygenase is responsible for the generation of the heptanone-etheno-2'-deoxyguanosine DNA-adduct in CESS cells
physiological function
-
catalyzes two steps in biosynthesis of leukotrienes, a group of lipid mediators of inflammation derived from arachidonic acid, which are used as antagonists in treatment of asthma. A potential role also in atherosclerosis
physiological function
-
5-lipoxygenase plays a pivotal role in atherogenesis and is involved in plaque stability
physiological function
-
5-LO products significantly contribute to tumour cell proliferation
physiological function
-
activation of 5-LOX modulates the G1/S phase transition regulatory proteins and causes cell proliferation
physiological function
-
several arachidonic acid metabolites formed via the 5-LO pathway (5-HETE, 5-oxo-ETE, leukotriene B4, leukotriene D4) can promote proliferationof cancer cells
physiological function
-
5-lipoxygenase is a key determinant of acute myocardial inflammation and mortality during Trypanosoma cruzi infection
physiological function
-
5-lipoxygenase is implicated in the pathogenesis of inflammatory and immune diseases
physiological function
-
changes in 5-LOX activator ATP concentration in the cell can affect the production of 5-LOX products, such as leukotrienes and lipoxins, and thus have wide implications for the regulation of cellular inflammation. The enzyme is involved in the synthesis of leukotrienes B4 and A4, important metabolites of the regulation of inflammation. 5-LOX catalytic activity is regulated through several mechanisms by the cell. 5-LOX is recruited to the nuclear membrane upon cellular Ca2+ influx. Calcium binds to allosteric sites in the 5-LOX N-terminal polycystin-1/lipoxygenase/alpha-toxin (PLAT) domain, promoting attachment to the membrane via conserved tryptophan residues that embed into the lipid bilayer
physiological function
-
the enzyme initiates the synthesis of pro-inflammatory leukotrienes and catalyze the peroxidation of polyunsaturated fatty acids
physiological function
-
5-lipoxygenase (5-LOX) is the key player of pro-inflammatory leukotriene biosynthesis. Its regulatory or socalled PLAT (polycystin-1, lipoxygenase, alpha-toxin) domain binds allosteric modulators like calcium, membranes, coactosin-like protein and Dicer, thereby influencing 5-LOX activity at the nuclearmembrane by mediating translocation. The PLAT domain may also regulate cytosolic 5-LOX activity and possibly influence microRNA metabolism
physiological function
-
being a mobile enzyme, 5-LO migrates from the cytosol to the nuclear envelope where it is believed to interact with 5-lipoxygenase-activating protein (FLAP) and receives the substrate arachidonic acid. Enzyme 5-LO is prone to redox regulation in the cell, e.g. 5-LO inhibition by glutathione peroxidase (GPX) 1 and 4
physiological function
-
human 5-lipoxygenase (5-LOX) is responsible for the formation of leukotriene (LT)A4, a pivotal intermediate in the biosynthesis of the leukotrienes, a family of proinflammatory lipid mediator. Role of active site residues F421, Q363 and L368 in regulating the donor-acceptor distances, thus affecting H-transfer as well as regiospecificity of the enzyme reaction, the H-abstraction is the rate limiting step for 5-LOX and the observed KIE of 5-LOX is masked by a change in regioselectivity
physiological function
-
leukotrienes biosynthesis is initiated by the action of 5-LOX at the level of nuclear membrane and the mechanism of enzyme-membrane interaction is thought to involve structural flexibility and conformational changes at the level of the protein tertiary structure. The conformational change between the apo- and holo-5-LOX might contribute in vivo to the 5-LOX trafficking among different compartments of the cell, thus leading to a modulation of its signaling
physiological function
-
5-lipoxygenase enzyme catalyzes the initial steps in the biosynthesis of pro-inflammatory leukotrienes
physiological function
-
the 5-LO-derived leukotriene A4, LTA4, can be converted by the action of platelet 12-lipoxygenase (12-LO) to lipoxin A4 (LXA4), which exerts potent anti-inflammatory activities and vascular bed-dependent vasodilatory actions. Dietary plant sterols, beta-sitosterol, campesterol, and stigmasterol, in the combination used, can alleviate lipid peroxidation and inflammatory events in vivo. These effects are possibly exerted via the modulation of myeloperoxidase, 5-lipoxygenase, and 12-lipoxygenase activities
physiological function
-
leukotrienes are inflammatory mediators that play a pivotal role in many diseases like asthma bronchiale, atherosclerosis and in various types of cancer. The key enzyme for generation of leukotrienes is the 5-lipoxygenase, 5-LO, that catalyzes the initial steps in the conversion of arachidonate to the instable epoxide leukotriene A4 (LTA4) via the intermediate 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid (5-HpETE). LTA4 can then be metabolized by the LTA4 hydrolase to the potent chemoattractant and leukocyte activator LTB4 or conjugated with glutathione to the cysteinyl leukotriene LTC4 by LTC4 synthase
additional information
-
the active site of 5-LOX contains a nonheme Fe2+ ion coordinated by three polar histidines H372, H550, and H367, the carbonyl group of N554, the carboxylic group of the C-terminal I673, and a water molecule, modeling of the active site of 5-LOX. A hydrophobic cleft formed by nonpolar amino acids L414, I415, L368, L607, L420, F421, F177, A424, A410, A603, V604, and P569 can also play an important role in orientation of ligands in the active site of 5-LOX
additional information
-
structure-function analysis, overview. 5-LOX reveals a fully encapsulated active site, amino acid residue Phe177 plays a critical role in providing a fully functional active site, it shields the active site in the absence of substrate serving as the active site portal. Role for His600, deep in the elongated cavity, in positioning the substrate for catalysis
additional information
-
the ability of the isolated PLAT domain to bind Dicer C-terminus whereas the interaction with coactosin-like protein requires the interplay of the catalytic and the PLAT domain
additional information
-
modeling of the active conformation of human 5-LOX, overview
additional information
-
molecular dynamics simulations the conformational changes induced by iron removal in 5-LOX, overview. The degree of enzyme flexibility is related to the presence of iron into the active site that is able to stabilize the protein increasing its rigidity, structure modeling based on the crystal structure at 2.4 A resolution, overview
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(12S)hydroperoxy-5,8-cis-10-trans-13-cis-eicosatetraenoic acid + O2
(5S,12S)-dihydroperoxy-5,8-cis-10-trans-13-cis-eicosatetraenoic acid
-
22% of the activity with arachidonic acid
-
?
(15S)-hydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid + O2
(5S,15S)-dihydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid
-
30% of the activity with arachidonic acid
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
1-linoleoyl lysophosphatidic acid + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidic acid
-
i.e. linoleoyl-lysoPA
major product
-
?
1-linoleoyl lysophosphatidylcholine + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidylcholine
-
i.e. linoleoyl-lysoPC
major product
-
?
2',7'-dichlorodihydrofluorescein diacetate + O2
2',7'-dichlorofluorescein
-
-
-
-
?
2',7'-dichlorodihydrofluorescein diacetate + O2
?
-
development of a fluorescence assay for 5-LOX, overview
-
-
?
5,8,11-eicosatrienoic acid + O2
?
-
almost as active as arachidonic acid
-
-
?
5-hydroperoxyeicosatetraenoic acid
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
7,7-d2-arachidonate + O2
7,7-d2-(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
analysis of the product distribution reveals that 5-LOX displays a reversal of selectivity to bypass abstracting the deuterium atom from C7
-
-
?
arachidonic acid + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
homo-gamma-linolenic acid + O2
8-L-hydroxy-9,11,14-eicosatrienoic acid
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
epoxidation
-
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
epoxidation
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
684399, 684672, 685926, 687035, 688246, 688512, 688751, 689841, 689844, 689872, 711134, 711633, 711661, 712666
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 via stereospecific hydration by LTA4 hydrolase, LTA4 induces VEGF transcription in malignant mesothelial cells, the enzyme is upregulated in cancer cells and is pro-angiogenic
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4, has no effect on on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
stereospecific removal of the pro-R hydrogen at C10 resulting in epoxide formation
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
efficient LTA4 formation of 5LO requires both phosphatidyl choline and coactosin-like protein
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate + O2
leukotriene A4
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate + O2
leukotriene A4
-
-
-
?
8,11,14-eicosatrienoic acid + O2
?
-
4% of the activity with 5,8,11,14,17-eicosapentaenoic acid
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
hydroperoxidation
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
hydroperoxidation
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
741862, 741871, 741918, 741961, 741975, 742001, 742067, 742078, 742210, 742444, 742571, 743326, 743582, 743614
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
overall reaction
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
product generation is both regiospecific and stereospecific, the S-isomer is produced
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
higher affinity of arachidonate than linoleic acid for the ferrous form of lipoxygenase-1. Hydrogen abstraction step displays high kinetic isotope effects on kcat due to tunneling contributions. Lack of solvent-dependent rate-limiting steps at lower temperatures with arachidonate as substrate
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
72% of the activity with 5,8,11,14,17-eicosapentaenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ minor amounts of the double oxygenation products
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
5(S)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid + 6-trans-leukotriene B4 + 12-epi-6-trans-leukotriene B4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
formation of leukotriene A4 without release of the intermediate (6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
5-hydroperoxyeicosatetraenoic acid + 11(S)-hydroperoxyeicosatetraenoic acid + 15-hydroperoxyeicosatetraenoic acid + 5(S),12(S)-dihydroperoxy-6,8,10,14-eicosatetraenoic acid + 6-trans-leukotriene B4 + 12-epi-6-trans-leukotiene B4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
5(S)-hydroperoxyeicosatetraenoic acid is the most abundant primary oxygenation product, representing 60% of the total hydroperoxyeicosatetraenoic acids, followed by 8(S)-hydroperoxyeicosatetraenoic acid, 9-hydroperoxyeicosatetraenoic acid, 11(S)-hydroperoxyeicosatetraenoic acid, 12-hydroperoxyeicosatetraenoic acid, and 15-hydroperoxyeicosatetraenoic acid in decreasing order of abundance, all possible diH(P)ETEs are detected
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
(5S,6R)-dihydroperoxy-7,9,11,14-eicosatetraenoic acid is produced as major product especially when the incubation is performed on ice rather than at room temperature, 6R-oxygenase activity
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ minor products: 5-hydroxy-6,8,11,14-eicosatetraenoic acid, 6-trans-leukotriene B4 and 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ leukotriene A4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
i.e. 5,8,11,14-eicosatetraenoic acid
the enzyme is rather specific for the insertion of O2 at the fifth carbon on arachidonic acid
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
first committed step in the synthesis of leukotrienes
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
stereospecific abstraction of the pro-S hydrogen at C7, followed by insertion of molecular O2 at C5
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
linoleic acid + O2
?
-
lower affinity of linoleic acid than arachidonic acid for the ferrous form of lipoxygenase-1. Hydrogen abstraction step displays high kinetic isotope effects on kcat due to tunneling contributions
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
the purified protein expresses both 5-oxygenase and leukotriene A4 synthase activities in the ratio of 6:1
-
-
-
additional information
?
-
-
key enzyme in leukotriene metabolism, in human mast cells glucocorticoids effectively and selectively upregulate the expression
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
-
additional information
?
-
-
5-lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells, overview
-
-
-
additional information
?
-
-
ALOX5-derived lipid mediators leukotrienes and lipoxins have regulatory functions in inflammation by modulating activities of immune cells and cytokine production, host control of Mycobacterium tuberculosis is regulated by 5-lipoxygenase
-
-
-
additional information
?
-
-
inhibition of COX pathways does not increase the transformation of arachidonic acid by the 5-LOX pathway
-
-
-
additional information
?
-
-
key enzyme in biosynthesis of leukotrienes, overview. Upon cell activation, cytosolic and nuclear enzyme translocates the nuclear envelope, where it interacts with phospholipase A2, making free arachidonate available for 5-LO, and with 5-LO activating protein, i.e. FLAP. 5-LO regulates cancer cell survival and interferes with the mechanismtumor suppression, and increases cancer cell chemoresistance, overview
-
-
-
additional information
?
-
key enzyme in the leukotriene biosynthesis, pathway overview, the 5-LO pathway is linked to the development of cardiovascular disease and other diseases, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
-
no significant effect of LTB4, 12-hydroperoxyeicosatetraenoic acid or 15-hydroperoxyeicosatetraenoic acid on leukemic blast growth and on their apoptose rate, overview
-
-
-
additional information
?
-
-
the enzyme is involved in survival of Epstein-Barr virus-converted B lymphoma cells via function of 5-hydroperoxyeicosatetraenoic acid, overview
-
-
-
additional information
?
-
-
the enzyme is the key enzyme in biosynthesis of biologically active leukotrienes
-
-
-
additional information
?
-
-
the enzyme, catalyzing the key step in leukotriene biosynthesis, interacts with methyl jasmonate, which is probably involved in the anticarcinogenic activity of methyl jasmonate inducing apoptosis, overview
-
-
-
additional information
?
-
-
the enzyme catalyzes the dioxygenation of polyunsaturated fatty acids
-
-
-
additional information
?
-
-
5-LOX catalyzes a 2-step reaction where arachidonic acid (AA) is oxygenated, resulting in formation of 5(S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid (5-HPETE), with subsequent formation of leukotriene A4 (LTA4). Active site structure and binding of substrate arachidonate involving residues F421, F177, Q363, L414 and L368 during the reaction, model, overview
-
-
-
additional information
?
-
-
detectable 5-LO products derived from conversion of arachidonate are quantified by HPLC and comprise 5-H(p)ETE (a mixture of 5-HETE (5S-hydroxy-6,8,11,14(E,Z,Z,Z)-eicosatetraenoic acid) and 5-HpETE (5S-hydroperoxy-6,8,11,14(E,Z,Z,Z)-eicosatetraenoic acid)) and the non-enzymatic hydrolysis products of leukotriene A4, 6-trans-leukotriene B4 (5S,12R-dihydroxy-6,8,10,14(E,E,E,Z)-eicosatetraenoic acid) and 6-trans-12-epi-LTB4 (5S,12S-dihydroxy-6,8,10,14-(E,E,E,Z)-eicosatetraenoic acid)
-
-
-
additional information
?
-
-
arachidonate 5-lipoxygenase and leukotriene A5 synthase are identical
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
additional information
?
-
inhibition of 5-lipoxygenase does not affect cardiac ischemia-reperfusion injury but the post-ischemic inflammatory response, overview
-
-
-
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
-
additional information
?
-
5-LOX is the key enzyme in the biosynthesis of leukotrienes through catalyzing the initial two steps in conversion of arachidonic acid to leukotrienes
-
-
-
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
-
stereo-selectivity in LOX-catalyzed oxygenation of lysophospholipids, overview
-
-
-
additional information
?
-
-
5-lipoxygenase has a two-domain structure, the small N-terminal beta-barrel domain and a larger catalytic domain containing a single atom of non-heme iron coordinating with His525, His530, His716 and Ile864
-
-
-
additional information
?
-
-
the enzyme exhibits 6R-oxygenase activity with (5S)-hydroxy and (5S)-hydroperoxy acids as substrates
-
-
-
additional information
?
-
-
the enzyme is involved in lipoxin synthesis from 5,15-dihydroxyperoxyeicosatetraenoic acid via 5,6-epoxide
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(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
5-hydroperoxyeicosatetraenoic acid
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
epoxidation
-
-
?
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
A0A075C1I3
epoxidation
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
P09917
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 via stereospecific hydration by LTA4 hydrolase, LTA4 induces VEGF transcription in malignant mesothelial cells, the enzyme is upregulated in cancer cells and is pro-angiogenic
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4, has no effect on on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
efficient LTA4 formation of 5LO requires both phosphatidyl choline and coactosin-like protein
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
P12527
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
-
-
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
hydroperoxidation
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
A0A075C1I3
hydroperoxidation
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
-
741862, 741871, 741918, 741961, 741975, 742001, 742067, 742078, 742210, 742444, 742571, 743326, 743582, 743614
-
-
?
arachidonate + O2
(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H2O
-
overall reaction
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
P09917
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
first committed step in the synthesis of leukotrienes
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
P48999
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
P48999
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
P48999
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
P12527
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
-
-
-
?
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in leukotriene metabolism, in human mast cells glucocorticoids effectively and selectively upregulate the expression
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
-
additional information
?
-
-
5-lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells, overview
-
-
-
additional information
?
-
-
ALOX5-derived lipid mediators leukotrienes and lipoxins have regulatory functions in inflammation by modulating activities of immune cells and cytokine production, host control of Mycobacterium tuberculosis is regulated by 5-lipoxygenase
-
-
-
additional information
?
-
-
inhibition of COX pathways does not increase the transformation of arachidonic acid by the 5-LOX pathway
-
-
-
additional information
?
-
-
key enzyme in biosynthesis of leukotrienes, overview. Upon cell activation, cytosolic and nuclear enzyme translocates the nuclear envelope, where it interacts with phospholipase A2, making free arachidonate available for 5-LO, and with 5-LO activating protein, i.e. FLAP. 5-LO regulates cancer cell survival and interferes with the mechanismtumor suppression, and increases cancer cell chemoresistance, overview
-
-
-
additional information
?
-
P09917
key enzyme in the leukotriene biosynthesis, pathway overview, the 5-LO pathway is linked to the development of cardiovascular disease and other diseases, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
-
no significant effect of LTB4, 12-hydroperoxyeicosatetraenoic acid or 15-hydroperoxyeicosatetraenoic acid on leukemic blast growth and on their apoptose rate, overview
-
-
-
additional information
?
-
-
the enzyme is involved in survival of Epstein-Barr virus-converted B lymphoma cells via function of 5-hydroperoxyeicosatetraenoic acid, overview
-
-
-
additional information
?
-
-
the enzyme is the key enzyme in biosynthesis of biologically active leukotrienes
-
-
-
additional information
?
-
-
the enzyme, catalyzing the key step in leukotriene biosynthesis, interacts with methyl jasmonate, which is probably involved in the anticarcinogenic activity of methyl jasmonate inducing apoptosis, overview
-
-
-
additional information
?
-
-
the enzyme catalyzes the dioxygenation of polyunsaturated fatty acids
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
P48999
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
additional information
?
-
P48999
inhibition of 5-lipoxygenase does not affect cardiac ischemia-reperfusion injury but the post-ischemic inflammatory response, overview
-
-
-
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
P48999
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
-
additional information
?
-
P12527
5-LOX is the key enzyme in the biosynthesis of leukotrienes through catalyzing the initial two steps in conversion of arachidonic acid to leukotrienes
-
-
-
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
-
the enzyme is involved in lipoxin synthesis from 5,15-dihydroxyperoxyeicosatetraenoic acid via 5,6-epoxide
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
1-Oleoyl-2-acetyl-sn-glycerol
Ca2+
Fe
Fe2+
Fe3+
Iron
Mg2+
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
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
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
Ca2+
-
5-lipoxygenase product formation in arachidonic acid-stimulated polymorphonuclear leukocytes is independent of Ca2+. Ca2+ and 5-lipoxygenase phosphorylation seem to be required for arachidonic acid-induced 5-lipoxygenase product formation
Ca2+
-
activates, Ca2+ induces the translocation of 5-LO from a soluble compartment to nuclear structures, where 5-LO co-localizes with 5-LO activating protein, FLAP
Ca2+
-
binds at the C2-like domain, stimulates and induces enzyme translocation from the nuclear soluble to the envelope fraction, both Ca2+ and glyceride might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
Ca2+
-
upon stimulation with calcium ionophore, GFP-5-lipoxygenase translocates to the nuclear envelope allowing it to interact with 5-lipoxygenase activating protein (FLAP) and leukotriene C4 synthase
Ca2+
-
Ca2+ is required for 5LO activity, the enzyme contains two Ca2+, full activation is reached at 0.004-0.01 mM Ca2+
Ca2+
-
5-LOX is recruited to the nuclear membrane upon cellular Ca2+ influx. Calcium binds to allosteric sites in the 5-LOX N-terminal polycystin-1/lipoxygenase/alpha-toxin (PLAT) domain, promoting attachment to the membrane via conserved tryptophan residues that embed into the lipid bilayer
Ca2+
-
phosphocholine in combination with Ca2+ markedly stimulate the formation of leukotrienes by wild-type 5-LO and C159S/C300S/C416S/C418S mutant, whereas their effect on the 5-LO 3W mutant is small
Ca2+
-
whilst the catalytic domain of wild-type 5-LO is destabilized by calcium, addition of calcium has no influence on the catalytic domain of 5-LODELTA4
Ca2+
-
binds at the C2-like domain, stimulates and induces enzyme translocation from the nuclear soluble to the envelope fraction, both Ca2+ and glyceride might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
Ca2+
-
5-lipoxygenase product formation in arachidonic acid-stimulated polymorphonuclear leukocytes is independent of Ca2+
Ca2+
-
binds at the C2-like domain, stimulates and induces enzyme translocation from the nuclear soluble to the envelope fraction, both Ca2+ and glyceride might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
Fe
-
the iron acts as electron acceptor and donor, during hydrogen abstraction and peroxide formation
Fe2+
-
isoflavones reduce active state iron to ferrous state and prevent the activation of the resting enzyme
Fe2+
-
a nonheme Fe2+ ion coordinated by three polar histidines H372, H550, and H367, the carbonyl group of N554, the carboxylic group of the C-terminal I673, and a water moleculein the active site, overview. On interaction with the active site, the ligands replaces the H2O molecule
Fe2+
-
a non-heme iron-containing enzyme. LOX catalytic activity depends on the presence of iron in the active site. Iron removal is able to affect the membrane binding properties of the enzyme, molecular dynamics simulations, overview
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
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
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
Iron
-
contains one iron atom per molecule, the native enzyme is in a pseudo-axial high-spin ferric state
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(17S)-hydroperoxy-4,7,10,13,15,19-docosahexaenoyl lysophosphatidylcholine
-
-
(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)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[3-methoxy-4-(3-phenoxypropoxy)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(morpholin-4-ylcarbonyl)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(piperidin-1-ylcarbonyl)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(pyrrolidin-1-ylcarbonyl)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-[(4-methylpiperazin-1-yl)carbonyl]phenyl]prop-2-en-1-one
-
-
(2E)-3-[3-(2-ethoxyethoxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(2-ethoxyethoxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(3-ethoxypropoxy)-3-methoxyphenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(benzyloxy)-3-bromo-5-methoxyphenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(benzyloxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(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
-
-
(2Z)-2-[4-(acetylamino)phenyl]-3-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
-
(5E)-2-(4-methylphenyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-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-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-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-[4-(dimethylamino)benzylidene]-2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one
-
-
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
inhibits reaction with arachidonate
([3-chloro-5-(2,3-dihydro-1H-inden-4-ylamino)phenyl]sulfanyl)acetic acid
-
-
([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)(naphthalen-1-yl)acetic acid
-
-
1,4a-dimethyl-7-(propan-2-yl)-1-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene (non-preferred name)
-
-
1-(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-(3,4-dichlorobenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
82% inhibition at 0.005 mM
1-(3,4-dichlorobenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
38.5% inhibition at 0.005 mM
1-(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-(4-aminosulfonylphenyl)-5-(2-chloropyridin-4-yl)-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-chlorobenzyl)-2-[2,2-dimethyl-3-(1H-tetrazol-5-yl)propyl]-4-methyl-6-[2-(5-phenylpyridin-2-yl)ethyl]-2,2a,4,5-tetrahydro-1H-thiopyrano[2,3,4-cd]indole
-
-
1-(4-chlorophenoxy)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
22% inhibition at 0.005 mM
1-(4-chlorophenoxy)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
26% inhibition at 0.005 mM
1-(4-chlorophenoxy)-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
70% inhibition at 0.005 mM
1-(4-methanesulfonylphenyl)-5-(2-chloropyridin-4-yl)-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-methanesulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-methylbenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
35% inhibition at 0.005 mM
1-(4-methylbenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
55% inhibition at 0.005 mM
1-(8-tert-butyl-4,4-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-cyclopropylbutan-1-one
-
-
1-(benzyloxy)hept-2-yn-4-ol
-
forms three hydrogen bonds with 5-lipoxygenase
1-(difluoromethyl)-5-[[2-(methylsulfonyl)phenyl]ethynyl]pyridin-2(1H)-one
-
-
1-benzyl-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
41% inhibition at 0.005 mM
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-benzyl-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
64% inhibition at 0.005 mM
1-benzyl-3-(4-morpholin-4-ylbutyl)-1H-indole
42% inhibition at 0.005 mM
1-benzyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
95% inhibition at 0.005 mM
1-benzyl-3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
32% inhibition at 0.005 mM
1-benzyl-3-[3-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]propyl]-5-methoxy-2-methyl-1H-indole
46.5% inhibition at 0.005 mM
1-benzyl-5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
80% inhibition at 0.005 mM
1-benzyl-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
54% inhibition at 0.005 mM
1-benzyl-5-methoxy-2-methyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
65% inhibition at 0.005 mM
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 inhibitior, IC50: 0.0035 mM with recombinant enzyme, IC50: 0.005 mM with native enzyme
1-[(4methylbenzyl)oxy]hept-2-yn-4-ol
-
is more potent than 1-(benzyloxy)hept-2-yn-4-ol to 5-lipoxygenase
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
-
-
1-[4-([3-fluoro-5-[4-(methylsulfinyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
-
1-[4-([3-fluoro-5-[4-(methylsulfonyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
-
2,3,4',5-tetrahydroxystilbene-2-O-D-glucoside
-
polymorphonuclear leukocyte
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
micromolar 5-LOX inhibitory activity
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-(2,4-dihydroxyphenyl)-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
-
-
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-(4-chloro-6-(5-methoxy-2-methylbiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
-
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-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-([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)octanoic acid
-
-
2-[(4-[[3,5-bis(2,2,2-trifluoroethoxy)phenyl]amino]-6-chloropyrimidin-2-yl)sulfanyl]octanoic acid
-
-
2-[2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
micromolar 5-LOX inhibitory activity
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-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
micromolar 5-LOX inhibitory activity
2-[4'-(iso-propylphenyl)-amino]-5,6-dimethyl-1,4-benzoquinone
-
potent inhibitor, IC50: 0.006 mM
2-[4-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
micromolar 5-LOX inhibitory activity
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
-
-
3,4,5-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-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
micromolar 5-LOX inhibitory activity
3-(2-(2-[(4-chlorophenyl)sulfanyl]ethoxy)-3-methoxy-5-[5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-2-yl]benzyl)-1-hydroxy-1-methylurea
-
-
3-(2-morpholin-4-yl-2-oxoethyl)-1-phenoxy-1H-indole
21% inhibition at 0.005 mM
3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
16% inhibition at 0.005 mM
3-(3-morpholin-4-yl-3-oxopropyl)-1-phenoxy-1H-indole
23% inhibition at 0.005 mM
3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
33% inhibition at 0.005 mM
3-(4,5-dihydroxy-2-methyl-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl)-2-hydroxy-4,6-dimethoxybenzoic acid
-
-
3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
62% inhibition at 0.005 mM
3-(6-(4-chlorphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)propionic acid
-
-
3-(decahydronaphthalen-2-ylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
-
3-tridecyl-4,5-dimethoxybenzene-1,2-diol
-
shows anti-inflammatory effectiveness
3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
64% inhibition at 0.005 mM
3-[5-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
-
-
3-[[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]methyl]-1-[4-(methylsulfonyl)phenyl]-5-phenyl-1H-pyrazole
-
-
4,5-dimethoxy-3-tridecylcyclohexa-3,5-diene-1,2-dione
-
shows anti-inflammatory effectiveness
4-((3,4-dichlorobenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
27% inhibition at 0.005 mM
4-((4-chlorobenzoyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
32% inhibition at 0.005 mM
4-(1-(4-methylbenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
34% inhibition at 0.005 mM
4-(1-benzoyl-1H-indol-3-yl)-1-morpholinobutan-1-one
58% inhibition at 0.005 mM
4-(1-benzyl-1H-indol-3-yl)-1-morpholinobutan-1-one
26% inhibition at 0.005 mM
4-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
micromolar 5-LOX inhibitory activity
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)-N-methyltetrahydro-2H-pyran-4-carboxamide
-
-
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-ol
-
-
4-(3-fluoro-5[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-carboxylic acid
-
-
4-(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)-5-(4-(methylsulfonyl)phenyl)-1,2-selenazole
-
60% inhibition at 0.01 mM
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-(acetyloxy)-2-[4-(acetyloxy)-6-methylhept-5-en-2-yl]cyclohexyl (2Z)-2-methylbut-2-enoate
-
-
4-(furan-3-yl)-7-[[2-(tetrahydro-2H-pyran-4-yl)pyridin-4-yl]methoxy]naphthalene-2-carbonitrile
-
-
4-(furan-3-yl)-7-[[6-(4-hydroxytetrahydro-2H-pyran-4-yl)pyridin-2-yl]methoxy]naphthalene-2-carbonitrile
-
-
4-(furan-3-yl)-7-[[7-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydroquinolin-2-yl]oxy]naphthalene-2-carbonitrile
-
-
4-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-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-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-hydroxy-5-nitrophenyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-hydroxyphenyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-methoxyphenyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-phenylethyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(propan-2-yl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-methyl-N-phenylbenzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-propylbenzamide
-
-
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-[1-(4-chlorobenzyl)-4-methyl-6-[(5-phenylpyridin-2-yl)methoxy]-2,2a,4,5-tetrahydro-1H-thiopyrano[2,3,4-cd]indol-2-yl]-3,3-dimethyl-N-(methylsulfonyl)butanamide
-
-
4-[4-(4-fluoro-phenyl)-thiazol-2-ylamino]-2,6-dimethylphenol
-
KR-33749, the compound exhibits a more than 1000fold selectivity for 5-LO against 12-LO and 15-LO
4-[5-(1H-indol-3-yl)-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide
-
-
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
-
-
4-[5-(6-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
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-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]phenol
-
-
5-(2-[[3-(trifluoromethyl)phenyl]amino]phenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
5-(3,5-di-tert-butyl-4-hydroxybenzylidene)thiazolidin-2,4-dione
-
effective inhibitor of 5-LOX in vivo
5-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole
-
-
5-(7-tert-butyl-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-5-oxopentanenitrile
-
-
5-chloro-1-(4-chlorophenoxy)-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
38% inhibition at 0.005 mM
5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
71% inhibition at 0.005 mM
5-methoxy-2-methyl-1-(4-methylbenzyl)-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
26% inhibition at 0.005 mM
5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
73% inhibition at 0.005 mM
5-[[hydroxy(2-methyl-1-[3-[(morpholin-4-yl)oxy]phenyl]propyl)amino]methyl]benzene-1,2,3-triol
-
-
6-[(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]naphthalene-2-carboxylic acid
-
-
6-[[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]methyl]-1-methylquinolin-2(1H)-one
-
-
7-(4-methylphenyl)-6-[4-(methylsulfonyl)phenyl]-2,3-dihydro-1H-pyrrolizine
-
-
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-tert-butyl-N-ethyl-N,3,3-trimethyl-2,3-dihydro-1-benzofuran-5-carboxamide
-
-
7-[[3-(1-ethyl-1-hydroxypropyl)-5-fluorophenoxy]methyl]-4-furan-3-yl-2H-chromen-2-one
-
IC50: 15 nM
7-[[3-(4-methoxytetrahydro-2H-pyran-4-yl)benzyl]oxy]-4-phenylnaphtho[2,3-c]furan-1(3H)-one
-
-
7-[[3-fluoro-5-(3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl)phenoxy]methyl]-4-(furan-3-yl)quinoline-2-carbonitrile
-
-
acetonylacetone bisphenylhydrazone
-
IC50 for reaction with linoleic acid: 0.015 mM, IC50 for reaction with arachidonic acid: 0.0039 mM
benzaldehyde phenylhydrazone
-
IC50 for reaction with linoleic acid: 0.0345 mM, IC50 for reaction with arachidonic acid: 0.0014 mM
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
-
cholesterol
-
addition to a membrane preperation in vitro reduces 5-lipoxygenase activity by half. Cholesterol sulfate can inhibit 5-lipoxygenase in intact cells
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
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
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-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-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-2-((2-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
-
-
ethyl 5-hydroxy-2-((4-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate
-
-
ethyl [2-[(2-[1-[4-(2-methylpropyl)phenyl]ethyl]-1H-benzimidazol-1-yl)methyl]phenoxy]acetate
-
a BRP-7 derivative
L-651,392
-
i.e. 4-bromo-2,7-dimethoxy-3H-phenothiazin-3-one, + 1 mM NADH, IV50: 0.0003-0.0005 mM
L-651,896
-
i.e. 2,3-dihydro-6-[3-(2-hydroxymethyl)-phenyl-2-propenyl]-5-benzofuranol, IC50: 0.0003-0.0004 mM
methyl (4-[(5E)-5-(4-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]phenoxy)acetate
-
-
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
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-(2,4-dimethylphenyl)-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
-
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-(furan-2-ylmethyl)-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
-
N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)-4-methylbenzenesulfonamide
-
IC50: 0.00045 mM
N-benzyl-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
-
N-cyclopentyl-2-[7-(2-methoxyethoxy)-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide
-
-
N-dodecyl-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
-
N-methyl-2[4-(2,4,6-trimethylphenyl)phenyl]-propenehydroxamic acid
-
IC50: 0.0005 mM
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
-
tert-butyl 4-[4-(1-benzyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
38% inhibition at 0.005 mM
tert-butyl 4-[4-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
51.5% inhibition at 0.005 mM
tert-butyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
84% inhibition at 0.005 mM
tert-butyl 4-[4-(5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
71% inhibition at 0.005 mM
[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-[(1S,8aR)-2-formyl-5,5,8a-trimethyldecahydronaphthalen-1-yl]ethylidene]propanedial
-
-
[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
-
-
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-5 by 41%
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-15 by 31%
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-(6-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-15 by 36%
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-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-15 by 36%
AA861
-
i.e. 2-(12-hydroxydodeca-5,10-diynyl)-3,5,6-trimethyl-1,4-benzoquinone, IC50: 0.004-0.01 mM
arachidonic acid
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00023 mM; substrate inhibition
BW755C
-
CAS: 66000-40-6; i.e. 3-amino-1-[3-(trifluoromethyl)phenyl]-2-pyrazoline, IC50: 0.013 mM
BWA4C
-
a direct inhibitor of 5-LO, treatment results not only in a suppression of leukotriene production, but in an almost complete inhibition of enzymatic
eicosapentaenoic acid
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00065 mM; substrate inhibition
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
prevents leukotriene B4 production in pleural exudates of carrageenan-treated rats, associated with reduced severity of pleurisy. Significantly reduces the inflammatory reaction measured as exudate volume (77%), inflammatory cell numbers (40%), and leukotriene B4 levels (49%) in the pleural exudates
glutathione
-
efficiency of non-redox-type 5-LO inhibitors depends on the presence of glutathione peroxidase activity leading to low hydroperoxide concentration
glutathione
-
efficiency of non-redox-type 5-LO inhibitors depends on the presence of glutathione peroxidase activity leading to low hydroperoxide concentration
glutathione
-
efficiency of non-redox-type 5-LO inhibitors depends on the presence of glutathione peroxidase activity leading to low hydroperoxide concentration
L-656,224
-
i.e. 7-chloro-2-[(4-methoxyphenyl)-methyl]-3-methyl-5-propyl-4-benzofuranol, IC50: 0.0008 mM
MK886
-
specific inhibitor of 5-hydroperoxyeicosatetraenoic acid synthesis by the enzyme
nordihydroguaiaretic acid
-
reduces oxidative damage of erythrocytes in C57BL/6 Trypanosoma cruzi-infected mice but not in C57BL/6 iNOS-/- infected mice
nordihydroguaiaretic acid
-
is more potent inhibitor of 5-lipoxygenase than 1-(benzyloxy)hept-2-yn-4-ol
nordihydroguiaraetic acid
-
IC50 for reaction with linoleic acid: 0.17 mM, IC50 for reaction with arachidonic acid: 0.0365 mM
zileuton
-
IC50: 0.0038 mM with recombinant enzyme, IC50: 0.0011 mM with native enzyme
zileuton
-
reduces exudate formation (77%), cell infiltration (41%), and leukotriene B4 exudate levels (66%)
additional information
-
plant extracts with inhibitory activity on arachidonate 5-lipoxygenase, inhibition of the 5-lipoxygenase pathway is considered to be interesting in the treatment of a variety of inflammatory diseases
-
additional information
-
classes of 5-lipoxygenase inhibitors: 1. compounds that inhibit the enzyme via antioxidant mechanism - NGDA, BW755c, AA-861, ICI-207968, and A-53612. High toxicity, unacceptable for clinical development. 2. compounds that interact with the non-heme iron moiety of the enzyme - BW-A4A, and ABT-761 both effective in asthma and zileuton. 3. nonredox competitive inhibitors - ZD-2138 and L-697198
-
additional information
-
plant extracts with inhibitory activity on arachidonate 5-lipoxygenase, inhibition of the 5-lipoxygenase pathway is considered to be interesting in the treatment of a variety of inflammatory diseases.
-
additional information
-
plant extracts with inhibitory activity on arachidonate 5-lipoxygenase, inhibition of the 5-lipoxygenase pathway is considered to be interesting in the treatment of a variety of inflammatory diseases.
-
additional information
-
plant extracts with inhibitory activity on arachidonate 5-lipoxygenase, inhibition of the 5-lipoxygenase pathway is considered to be interesting in the treatment of a variety of inflammatory diseases.
-
additional information
-
classes of 5-lipoxygenase inhibitors: 1. compounds that inhibit the enzyme via antioxidant mechanism - NGDA, BW755c, AA-861, ICI-207968, and A-53612. High toxicity, unacceptable for clinical development. 2. compounds that interact with the non-heme iron moiety of the enzyme - BW-A4A, and ABT-761 both effective in asthma and zileuton. 3. nonredox competitive inhibitors - ZD-2138 and L-697198
-
additional information
-
overview: inhibitors and perspectives for future drug development
-
additional information
-
zinc inhibits leukotriene B4 formation due to a direct or indirect inhibitory effect on 5-lipoxygenase
-
additional information
-
selenium-induced apoptosis in prostate cancer cells may be mediated through inhibition of the activity of arachidonate 5-lipoxygenase. The anti-cancer effects of selenium may be substantially compromised by consumption of high-fat diets rich in arachidonic acid or its precursor fatty acids
-
additional information
-
no inhibition by galanal A, galanal B and 8beta(17)-epoxy-15-hydroxy-12(E)-labden-16-al
-
additional information
-
enzyme activity is inhibited by essential oil from Ballota africana (IC50: 29.99 ppm), methanol extract from Croton sylvaticus (IC50: 25.64 ppm), aqueous extract from Croton sylvaticus (IC50: 60.9 ppm), methanol extract f