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Information on EC 1.13.11.31 - arachidonate 12-lipoxygenase
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1.13.11.31 arachidonate 12-lipoxygenaseIUBMB Comments
The product is rapidly reduced to the corresponding 12S-hydroxy compound.
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Word Map
- 1.13.11.31
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arachidonic
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cyclooxygenase
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12-hete
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eicosanoids
- prostaglandin
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polyunsaturated
- atherosclerosis
- neutrophil
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linoleic
- artery
- cytokine
- endothelial
- phospholipase
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nordihydroguaiaretic
- asthma
- baicalein
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12-hydroxyeicosatetraenoic
- reticulocyte
- monocyte
- cox-2
-
hetes
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lipoxins
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thromboxane
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polymorphonuclear
- atherogenesis
- ndga
- indomethacin
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docosahexaenoic
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eicosapentaenoic
- hydroperoxide
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polyenoic
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hydroxyeicosatetraenoic
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5,8,11,14-eicosatetraynoic
- phenidone
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ichthyosiform
- drug development
- erythroderma
- lipoxygenase-1
- zileuton
- ichthyosis
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pro-resolving
- etya
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5-lipoxygenase-activating
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protectins
- esculetin
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14carachidonic
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hydroperoxy
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13-hode
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a23187-stimulated
- medicine
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resolvins
- oxylipins
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
(12R)-lipoxygenase, (12R)-LOX, 11R-lipoxygenase, 11R-LOX, 12(R)-lipoxygenase, 12(S)-lipoxygenase, 12-hLO, 12-lipoxygenase, 12-LO, 12-LOX, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
12(S)-lipoxygenase
12-lipoxygenase
12-LO
12-LOX
12/15 lipoxygenase
12/15-lipoxygenase
12/15-LO
12/15-LOX
12/15LO
12DELTA-lipoxygenase
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12R-lipoxygenase
12R-LOX
12S-lipoxygenase
2/15-lipoxygenase
ALOX12
Alox12b
Alox15
arachidonate 12/15-lipoxygenase
C-12 lipoxygenase
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cardiac 12/15-LOX
DELTA 12-lipoxygenase
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leukocyte-type 12-lipoxygenase
leukocyte-type 12-LOX
leukotriene A4 synthase M
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LTA4 synthase
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oxylipin-producing enzyme
oygenase, arachidonate 12-lip-
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platelet-type 12-lipoxygenase
Platelet-type lipoxygenase 12
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12-lipoxygenase
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12-LOX
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12/15-lipoxygenase
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12S-lipoxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
arachidonate + O2 = (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dehydration
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dioxygenation
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oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 12-oxidoreductase
The product is rapidly reduced to the corresponding 12S-hydroxy compound.
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CAS REGISTRY NUMBER
COMMENTARY
82391-43-3
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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
1-linoleoyl lysophosphatidic acid + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidic acid
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i.e. linoleoyl-lysoPA
major product
-
?
1-linoleoyl lysophosphatidylcholine + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidylcholine
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i.e. linoleoyl-lysoPC
major product
-
?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
20-hydroxyeicosatetraenoic acid methyl ester + O2
8,20-dihydroxyeicosatetraenoic acid + 12,20-dihydroxyeicosatetraenoic acid + 9,20-dihydroxyeicosatetraenoic acid
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-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
14-hydroxy-4,7,10,12,16,19-docosahexaenoic acid
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activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
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?
4,7,10,13,16,19-docosahexaenoic acid + O2
14-hydroxy-4,7,10,13,16,19-docosahexaenoic acid
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-
-
-
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
5,15-(5S,15S)-dihydroperoxyarachidonic acid + O2
5S,14R,15S-trihydroperoxy-6,10,12-trans-8-cis-eicosatetraenoic acid
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the product is reduced to 5S,14R,15S,-8-cis-lipoxin B due to 14R-oxygenase activity of the enzyme
?
5,8,11-eicosatrienoic acid + O2
12-hydroxy-5,8,10-eicosatrienoic acid
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activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
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?
6,9,12-octadecatrienoic acid + O2
13-hydroxy-6,9,12-octadecatrienoic acid
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-
-
?
alpha-linolenic acid + O2
13-hydroxy-(9Z,11E,15Z)-octadecatrienoic acid
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-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
arachidonic acid + O2
(12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
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the mutant enzyme G441A converts arachidonic acid to 8S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 12R-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid in a 1.4:1 ratio
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?
arachidonic acid methyl ester + O2
12-hydroxyeicosatetraenoic acid methyl ester
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activity with (12R)-lipoxygenase and epidermal-type-(12S)-lipoxygenase, no activity with platelet-type (12S)-lipoxygenase
epidermal-type (12S)-lipoxygenase produces only 12-hydroxyeicosatetraenoic acid methyl ester, (12R)-lipoxygenase produces (12R)-hydroxyeicosatetraenoic acid methyl ester and (4R)-hydroxyeicosatetraenoic acid methyl ester
?
gamma linolenic acid + O2
10-hydroxy-octadeca-(6Z,8E,12Z)-trienoic acid
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poor substrate
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-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-(6Z,8E,12Z)-trienoic acid
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-
-
?
leukotriene A4 + O2
lipoxin A4
LTA4 can be converted by the action of platelet 12-lipoxygenase (12-LO) to lipoxin A4 (LXA4)
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-
?
linoleic acid + O2
13(S)-hydroxy-(9Z,11E)-octadecadienoic acid
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-
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?
linoleic acid methyl ester + O2
(9R)-hydroxyoctadecadienoic acid methyl ester
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-
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?
linoleic acid methyl ester + O2
13(S)-hydro(pero)xyoctadecadienoic acid methyl ester
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activity with epidermal-type (12S)-lipoxygenase, no activity with platelet-type (12S)-lipoxygenase and (12R)-lipoxygenase
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?
methyl arachidonate + O2
(15S,5Z,8Z,11Z,13E)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester
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?
11,14,17-eicosatrienoic acid + O2
?
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leukocyte enzyme: 28% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
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-
?
11,14,17-eicosatrienoic acid + O2
?
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no activity with enzyme from platelet
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?
11,14-eicosadienoic acid + O2
?
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leukocyte enzyme: 15% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
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?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
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(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but less by 15(S)-hydroxyeicosatetranoic acid, and 12(S)-HETE activates NADPH oxidase, overview, i.e. 12(S)-HPETE and 12(S)-HETE, the first is the predominant product
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?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
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(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but less by 15(S)-hydroxyeicosatetranoic acid, and 12(S)-HETE activates NADPH oxidase, overview, i.e. 12(S)-HPETE and 12(S)-HETE, the first is the predominant product
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?
4,7,10,13,16,19-docosahexaenoic acid + O2
?
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leukocyte enzyme: 92% of the activity with arachidonic acid, platelet enzyme: 7% of the activity with arachidonic acid
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?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
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enzyme from leukocyte, no activity with enzyme from platelet
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?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
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leukocyte enzyme: 15% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
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?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
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weak activity
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid and 5S,15S-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid are produced in a ratio of about 8:2
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
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?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
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40% of the activity with arachidonic acid
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-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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leukocyte enzyme: 73% of the activity with arachidonic acid, platelet enzyme: less than 94% of the activity with arachidonic acid
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?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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-
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?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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12-hydroxyeicosapentaenoic acid
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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-
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?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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-
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?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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14% of the activity with arachidonic acid
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-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
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leukocyte enzyme: 78% of the activity with arachidonic acid, platelet enzyme: 7% of the activity with arachidonic acid
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?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
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dihomo-gamma-linolenic acid
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-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
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activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
12-hydroxy-8,10,14-eicosatrienoic acid
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
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95% of the activity with arachidonic acid
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-
?
alpha-linolenic acid + O2
?
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leukocyte enzyme: 17% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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-
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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-
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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further metabolized to (12S)-hydroxyeicosatetraenoate, which inhibits apoptosis in gastric cancer and activates ERK phosphorylation and the ERK1/2 signalling pathway, 12-LOX activates protein kinase C in AGS cells, overview
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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-
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate, 12-HETE, has no effect on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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further metabolized to 12(S)-hydroxyeicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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i.e. 12(S)-HETE
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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12/15-LO protein levels and activity are increased in pathologically affected regions of Alzheimer’s disease brains, enzyme inhibition causes a decrease in amyloid-beta protein, 12/15-LO influences amyloid-beta protein precursor protein metabolism, overview
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-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
arachidonic acid metabolization by lipoxygenases, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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the platelet-type 12S-lipoxygenase isozyme is involved in angiotensin-II induced signaling in vascular smooth muscle cells
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-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
regioselective oxidation is achieved through control over the position of hydrogen atom abstraction by the geometry and size of the enzyme active site and through control by the protein over the interaction of molecular oxygen with the generated delocalized substrate radical, analysis of catalytic mechanisms of lipoxygenases using 10,10-dideuterated arachidonic acid, 13,13-dideuterated arachidonic acid, and 0,10,13,13-d4-AA, overview
i.e. 12-HPETE, 12-hLO also forms small amounts of 11-HPETE, 8-HPETE, and 15-HPETE, overview
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
two molecules of arachidonic acid bind to one molecule of the enzyme, role of the PLAT domain in activity and membrane binding, overview
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-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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high oxygen affinity is important for effective catalysis, L367 is involved in oxygen access, channel structure, overview, arachidonic acid closes the substrate-binding pocket for oxygen diffusion but opens a fourth oxygen access channel
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
arachidonate induces cellular membrane disturbance and alters the mitochondrial membrane potential. 12-LOX is involved in covalent binding of alpha-naphthol to arachidonic acid in intact platelets, peroxidase-mediated co-oxidation with arachidonic acid, and peroxidase-mediated xenobiotic activation of alpha-naphthol cytotoxicity, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
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arachidonic acid promotes the glutamate-induced cell death, reduces caspase-3 activity, and diminishes internucleosomal DNA fragmentation, it also reduces intracellular NAD, ATP and membrane potentials due to mitochondrila membrane dysfunction, and reduces the inhibitory effect of N-alpha-tosyl-L-phenylalanine chloromethyl ketone and 3,4-dichloroisocumarin on the glutamate-induced cell death, overview
is further metabolized to 12(S)-hydroxyeicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
poly(ADP-ribose) polymerase activation of 12-LOX, but not NADPH oxidase, following zinc release, might play an important role in reactive oxygen species generation and decrease of viability in glucose-reload-treated neurons, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
the enzyme is involved in production of biologically active lipid mediators, (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate, 13-HODE, and 13-HOTE, in the intestine of iron-deficient rats, the lipids are almoste absent in wild-type rats, overview
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate
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?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
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i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
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i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
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i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
15-H(p)ETE is the major reaction product independent of the pH
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
12-H(p)ETE is the major reaction product of 12/15-LOX independent of the pH
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
platelet-type (12S)-lipoxygenase produces (12S)-hydroxyeicosatetraenoic acid and (8R)-hydroxyeicosatetraenoic acid, epidermal-type (12S)-lipoxygenase produces only 12-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
leukocyte-type enzyme produces 12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid, platelet-type enzyme produces only 12-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
platelet-type (12S)-lipoxygenase produces (12S)-hydroxyeicosatetraenoic acid and (8R)-hydroxyeicosatetraenoic acid, epidermal-type (12S)-lipoxygenase produces only 12-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid in the ratio of 6:1
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
H2QBX9
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
12-monohydroxy derivatives + 14-monohydroxy derivatives + a mixture of the 8,11,12- and 10,11,12-trihydroxy products of arachidonic acid and 10,13,14- and 12,13,14-trihydroxy derivatives of docosahexaenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
12/15LO eicosanoid products reduce cholesterol efflux to high density lipoproteins, regulate ATP-binding cassette transporter G1 expression and enhance ATP-binding cassette transporter G1 degradation and ATP-binding cassette transporter G1 serine phosphorylation
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
selective oxygenation at carbon 14 yields only the S-isomer
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
the 12-(S)-enantiomer is the predominant product
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE, and to 12(R)-HETE methyl ester
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE, and to 12(R)-HETE methyl ester
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE
-
-
?
arachidonic acid + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
eicosapentaenoic acid + O2
12-hydroxyeicosapentaenoic acid
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
leukocyte enzyme: 32% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
enzyme from leukocyte, no activity with enzyme from platelet
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
i.e. 6,9,12-octadecatrienoic acid
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
weak activity
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
101% of the activity with arachidonic acid
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
-
-
?
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
no activity with enzyme from platelet
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
enzyme from leukocyte
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
leukocyte enzyme: 11% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
i.e. 9,12-octadecadienoic acid
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
-
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
no activity with enzyme from platelet
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
35% of the activity with arachidonic acid
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
enzyme from leukocyte
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
-
19% of the activity with arachidonic acid
-
-
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
-
-
-
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
leukocyte enzyme: 18% of the activity with arachidonic acid, platelet enzyme: 6% of the activity with arachidonic acid
-
-
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
enzyme possesses 14,15-leukotriene A4 synthase activity, 8-oxygenase activity and 14-oxygenase activity
14R,15S-dihydroxy-5Z,8Z,10E,12E-eicosatetraenoic acid + 14S,15S-dihydroxy-5Z,8Z,10E,12E-eicosatetraenoic acid + 8S,15S-dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid + 8R,15S-dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid + 8R,15S-dihydroxy-5Z,9E,11E,13E-eicosatetraenoic acid + 8S,15S-dihydroxy-5Z,9E,11E,13E-eicosatetraenoic acid
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
-
-
-
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
-
14R,15S-dihydroxy-5Z,8Z,10E,12E-eicosatetraenoic acid + 14R,15S-epoxy-5Z,8Z,10E,12E-eicosatetraenoic acid
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
-
(8S,15S)-dihydroperoxy-5Z,9E,11Z,13E-eicosatetraenoic acid + (14R,15S)-erythro-dihydroperoxy-5Z,8Z,10E,12E-eicosatetraenoic acid
?
additional information
?
-
-
no reaction with mead acid and methyl esters of linolenic acid and arachidonate
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
-
endogenous phospholipid hydroperoxide glutathione peroxidase plays a pivotal role in the regulation of 12(S)-lipoxygenase and cyclooxygenase 1 activities by reducing the level of intracellular lipid hydroperoxides in arachidonate metabolism in A431 cells
-
-
?
additional information
?
-
-
interaction between c-Jun and Sp1 may account for the functional regulation of 12(S)-lipoxygenase gene regulation. The direct and cooperative interaction between c-Jun and Sp1 induced by EGF or PMA activates the expression of the human 12(S)-lipoxygenase gene. Sp1 may serve at least in part as a carrier to bring c-Jun to the promoter, thus transactivating the transcriptional activity of the human 12(S)-lipoxygenase gene
-
-
?
additional information
?
-
-
the 12/15-LOX metabolic pathway is increased and correlates with an oxidative imbalance in the Alzheimer‘s disease brain, implying that this enzyme might contribute to the pathogenesis of this neurodegenerative disorder
-
-
?
additional information
?
-
-
12-lipoxygenase induces apoptosis of human gastric cancer AGS cells via the ERK1/2 signal pathway, overview
-
-
?
additional information
?
-
-
exogenously added arachidonic acid and 12(S)-hydroxyeicosatetraenoate, but not 12(R)-hydroxyeicosatetraenoate, as well as 2-arachidonoylglycerol increase invasion by PC-3 cancer cells, overview
-
-
?
additional information
?
-
-
a bifunctional enzyme exhibiting 12-lipoxygenase and 15-lipoxygenase, EC 1.13.11.33, activities
-
-
?
additional information
?
-
-
a bifunctional enzyme exhibiting 12-LO and 15-LO activity
-
-
?
additional information
?
-
product distributions of lipoxygenases under various conditions, overview
-
-
?
additional information
?
-
-
product distributions of lipoxygenases under various conditions, overview
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type subject produces 21% 12-hydroperoxyicosatetraenoate and 79% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
-
12-lipoxygenase metabolites of arachidonic acid mediate metabotropic glutamate receptor-dependent long-term depression at hippocampal CA3-CA1 synapses
-
-
?
additional information
?
-
-
increased expression of 12-LO has deleterius effects in beta cells
-
-
?
additional information
?
-
-
lipoxin A4 and docosahexaenoic acid-derived neuroprotectin D1 are lipid autacoids formed by 12/15-lipoxygenase pathway that exhibit anti-inflammatory and neuroprotective properties. The enzyme also shows action in wound healing that is distinct from the anti-inflammatory properties
-
-
?
additional information
?
-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
-
-
?
additional information
?
-
-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
-
-
?
additional information
?
-
-
a bifunctional enzyme exhibiting 12-LO and 15-LO activity, the enzyme is also able to catalyze stereoselective oxidation of linoleic acid at position 13 over 9 to preferentially form 13(S)-hydroperoxyoctadienoic acid, which enhances MCP-1 expression, overview
-
-
?
additional information
?
-
-
reactive oxygen species formation catalyzed by 12-LOX
-
-
?
additional information
?
-
12/15-LOX generates (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, when arachidonic acid is the substrate, the enzyme produces small amounts of 15S-HETE and primarily 12S-HETE (ratio of 1:3). In case of linolenic acid as a substrate, 13S-hydroxyoctadecadienoic acid (13S-HODE) is generated via the interstage product 13S-hydroperoxyoctadecadienoic acid (13SHPODE). Inflammatory eicosanoids are produced by eosinophils in a 12/15-LOX dependent manner. Another family of 12/15-LOX products are hepoxilins. They are enzymatic products of the conversion of 12S-HPETE, but can also be produced by non-enzymatic modification of 12S-HPETE or 12RHPETE. In the latter case, hemine or haemoglobin may act as a non-specific catalyst
-
-
?
additional information
?
-
the enzymatic peroxidation reaction consists of four consecutive steps: At first a hydrogen atom is stereoselectively abstracted from one of the bisallylic methylene-groups forming an enzyme-bound radical. Secondly one of the two associated cis-double bonds is rearranged and forms a conjugated cis-trans-diene. Consecutively a peroxy radical is produced by inserting molecular oxygen. Finally the radical is reduced by antarafacial re-inserting of a hydrogen atom. The resulting product of this peroxidation reaction depends on the respective fatty acid, which is used as a substrate
-
-
?
additional information
?
-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
-
-
?
additional information
?
-
-
a bifunctional enzyme exhibiting 12-LO and 15-LO activity, the enzyme is also able to catalyze stereoselective oxidation of linoleic acid at position 13 over 9 to preferentially form 13(S)-hydroperoxyoctadienoic acid, which enhances MCP-1 expression, overview
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 54% 12-hydroperoxyicosatetraenoate and 46% 15-hydroperoxyicosatetraenoate with 76% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
the bifunctional enzyme also forms (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate, the product of 15-LO activity, EC 1.13.11.33, in a ratio of 9:1 15(S)-HPETE to 12(S)-HPETE
-
-
?
additional information
?
-
-
binding of allosteric effector [13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid] shifts the monomer-dimer equilibrium toward dimer formation
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 3% 12-hydroperoxyicosatetraenoate and 97% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 3% 12-hydroperoxyicosatetraenoate and 97% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
H2QBX9
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 20% 12-hydroperoxyicosatetraenoate and 80% 15-hydroperoxyicosatetraenoate with 135% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 20% 12-hydroperoxyicosatetraenoate and 80% 15-hydroperoxyicosatetraenoate with 135% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
H2QBX9
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 78% 12-hydroperoxyicosatetraenoate and 22% 15-hydroperoxyicosatetraenoate with 37% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
the enzyme might, in a fast and effective way, be involved in the formation of signal and/or defense molecules thus contributing to the breoad resistance of mosses against pathogens
-
-
?
additional information
?
-
-
the enzyme might, in a fast and effective way, be involved in the formation of signal and/or defense molecules thus contributing to the breoad resistance of mosses against pathogens
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 14% 12-hydroperoxyicosatetraenoate and 86% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 14% 12-hydroperoxyicosatetraenoate and 86% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
intestinal leukocyte-type isozyme Alox15 shows poor or no 15-lipoxygenase activity, EC 1.13.11.33
-
-
?
additional information
?
-
in the brain, the principal 12/15-LOX metabolites of arachidonate are (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, cf. EC 1.13.11.33
-
-
?
additional information
?
-
in the brain, the principal 12/15-LOX metabolites of arachidonate are (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, cf. EC 1.13.11.33
-
-
?
additional information
?
-
-
enzyme shows 14R-oxygenase activity and 14,15-leukotriene A synthase activity
-
-
?
additional information
?
-
-
stereo-selectivity in LOX-catalyzed oxygenation of lysophospholipids, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL 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
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
leukotriene A4 + O2
lipoxin A4
LTA4 can be converted by the action of platelet 12-lipoxygenase (12-LO) to lipoxin A4 (LXA4)
-
-
?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
-
-
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but less by 15(S)-hydroxyeicosatetranoic acid, and 12(S)-HETE activates NADPH oxidase, overview
-
?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
-
-
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but less by 15(S)-hydroxyeicosatetranoic acid, and 12(S)-HETE activates NADPH oxidase, overview
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
further metabolized to (12S)-hydroxyeicosatetraenoate, which inhibits apoptosis in gastric cancer and activates ERK phosphorylation and the ERK1/2 signalling pathway, 12-LOX activates protein kinase C in AGS cells, overview
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate, 12-HETE, has no effect on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
further metabolized to 12(S)-hydroxyeicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
12/15-LO protein levels and activity are increased in pathologically affected regions of Alzheimer’s disease brains, enzyme inhibition causes a decrease in amyloid-beta protein, 12/15-LO influences amyloid-beta protein precursor protein metabolism, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
arachidonic acid metabolization by lipoxygenases, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
the platelet-type 12S-lipoxygenase isozyme is involved in angiotensin-II induced signaling in vascular smooth muscle cells
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
arachidonate induces cellular membrane disturbance and alters the mitochondrial membrane potential. 12-LOX is involved in covalent binding of alpha-naphthol to arachidonic acid in intact platelets, peroxidase-mediated co-oxidation with arachidonic acid, and peroxidase-mediated xenobiotic activation of alpha-naphthol cytotoxicity, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
arachidonic acid promotes the glutamate-induced cell death, reduces caspase-3 activity, and diminishes internucleosomal DNA fragmentation, it also reduces intracellular NAD, ATP and membrane potentials due to mitochondrila membrane dysfunction, and reduces the inhibitory effect of N-alpha-tosyl-L-phenylalanine chloromethyl ketone and 3,4-dichloroisocumarin on the glutamate-induced cell death, overview
is further metabolized to 12(S)-hydroxyeicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
poly(ADP-ribose) polymerase activation of 12-LOX, but not NADPH oxidase, following zinc release, might play an important role in reactive oxygen species generation and decrease of viability in glucose-reload-treated neurons, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
the enzyme is involved in production of biologically active lipid mediators, (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate, 13-HODE, and 13-HOTE, in the intestine of iron-deficient rats, the lipids are almoste absent in wild-type rats, overview
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
H2QBX9
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE, and to 12(R)-HETE methyl ester
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE, and to 12(R)-HETE methyl ester
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
-
endogenous phospholipid hydroperoxide glutathione peroxidase plays a pivotal role in the regulation of 12(S)-lipoxygenase and cyclooxygenase 1 activities by reducing the level of intracellular lipid hydroperoxides in arachidonate metabolism in A431 cells
-
-
?
additional information
?
-
-
interaction between c-Jun and Sp1 may account for the functional regulation of 12(S)-lipoxygenase gene regulation. The direct and cooperative interaction between c-Jun and Sp1 induced by EGF or PMA activates the expression of the human 12(S)-lipoxygenase gene. Sp1 may serve at least in part as a carrier to bring c-Jun to the promoter, thus transactivating the transcriptional activity of the human 12(S)-lipoxygenase gene
-
-
?
additional information
?
-
-
the 12/15-LOX metabolic pathway is increased and correlates with an oxidative imbalance in the Alzheimer‘s disease brain, implying that this enzyme might contribute to the pathogenesis of this neurodegenerative disorder
-
-
?
additional information
?
-
-
12-lipoxygenase induces apoptosis of human gastric cancer AGS cells via the ERK1/2 signal pathway, overview
-
-
?
additional information
?
-
-
exogenously added arachidonic acid and 12(S)-hydroxyeicosatetraenoate, but not 12(R)-hydroxyeicosatetraenoate, as well as 2-arachidonoylglycerol increase invasion by PC-3 cancer cells, overview
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type subject produces 21% 12-hydroperoxyicosatetraenoate and 79% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
-
12-lipoxygenase metabolites of arachidonic acid mediate metabotropic glutamate receptor-dependent long-term depression at hippocampal CA3-CA1 synapses
-
-
?
additional information
?
-
-
increased expression of 12-LO has deleterius effects in beta cells
-
-
?
additional information
?
-
-
lipoxin A4 and docosahexaenoic acid-derived neuroprotectin D1 are lipid autacoids formed by 12/15-lipoxygenase pathway that exhibit anti-inflammatory and neuroprotective properties. The enzyme also shows action in wound healing that is distinct from the anti-inflammatory properties
-
-
?
additional information
?
-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
-
-
?
additional information
?
-
-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
-
-
?
additional information
?
-
12/15-LOX generates (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, when arachidonic acid is the substrate, the enzyme produces small amounts of 15S-HETE and primarily 12S-HETE (ratio of 1:3). In case of linolenic acid as a substrate, 13S-hydroxyoctadecadienoic acid (13S-HODE) is generated via the interstage product 13S-hydroperoxyoctadecadienoic acid (13SHPODE). Inflammatory eicosanoids are produced by eosinophils in a 12/15-LOX dependent manner. Another family of 12/15-LOX products are hepoxilins. They are enzymatic products of the conversion of 12S-HPETE, but can also be produced by non-enzymatic modification of 12S-HPETE or 12RHPETE. In the latter case, hemine or haemoglobin may act as a non-specific catalyst
-
-
?
additional information
?
-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 54% 12-hydroperoxyicosatetraenoate and 46% 15-hydroperoxyicosatetraenoate with 76% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 3% 12-hydroperoxyicosatetraenoate and 97% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 3% 12-hydroperoxyicosatetraenoate and 97% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
H2QBX9
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 20% 12-hydroperoxyicosatetraenoate and 80% 15-hydroperoxyicosatetraenoate with 135% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 20% 12-hydroperoxyicosatetraenoate and 80% 15-hydroperoxyicosatetraenoate with 135% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 78% 12-hydroperoxyicosatetraenoate and 22% 15-hydroperoxyicosatetraenoate with 37% overall activity compared to the human enzyme activity
-
-
?
additional information
?
-
the enzyme might, in a fast and effective way, be involved in the formation of signal and/or defense molecules thus contributing to the breoad resistance of mosses against pathogens
-
-
?
additional information
?
-
-
the enzyme might, in a fast and effective way, be involved in the formation of signal and/or defense molecules thus contributing to the breoad resistance of mosses against pathogens
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 14% 12-hydroperoxyicosatetraenoate and 86% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 14% 12-hydroperoxyicosatetraenoate and 86% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
in the brain, the principal 12/15-LOX metabolites of arachidonate are (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, cf. EC 1.13.11.33
-
-
?
additional information
?
-
in the brain, the principal 12/15-LOX metabolites of arachidonate are (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, cf. EC 1.13.11.33
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
Fe2+
Iron
Ca2+
the specific activity of recombinant soluble zf12-LOX mutant is increased by nearly 75% (25 nmol/min/mg) in the presence of calcium as compared to that in its absence (7 nmol/min/mg), while for the site-2 mutant, it is 5 nmol/min/mg irrespective of the presence of calcium. Ca2+ decreases the aggregation temperature of soluble zf12-LOX mutant, while secondary structure is maintained. Presence of Ca2+ induces increase in molecular dimensions of soluble zf12-LOX mutant
Ca2+
-
not essential for activity, partially purified enzyme is stimulated approximately 2fold in the presence of 0.1-5.0 mM Ca2+
Fe2+
required for the catalytic cycle of fatty acid oxidation by lipoxygenase, overview
Fe2+
0.94 atoms of iron per molecule. Loss of the mass of an iron atom from the protein as the pH is lowered from 5 to 4. The iron goes through acid-induced unfolding accompanied by the appearance of an iron-free intermediate that retains a native conformation
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-cis-p-coumaroyl)-beta-D-glucopyranoside
liguroside B, NMR spectral analysis
(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-trans-p-coumaroyl)-beta-D-glucopyranoside
liguroside A, NMR spectral analysis
11-thialinoleic acid
-
is a competitive inhibitor of 12-lipoxygenase with arachidonate as substrate. Presence of inhibitor does not alter the product distribution for 12-lipoxygenase. It does not change the regioselectivity of 12-lipoxygenase
2,2'-dipyridyl
-
1 mM, 87% inactivation, no reactivation by addition of excess Fe2+ or Fe3+
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
-
IC50: 0.007 mM
3-[3-bromo-5-(2,6-dibromo-4-{2-[2-(3-bromo-4-hydroxy-phenyl)-ethylcarbamoyl]-2-[(E)-hydroxyimino]-ethyl}-phenoxy)-4-methyl-phenyl]-N-[(E)-2-(3,5-dibromo-4-hydroxy-phenyl)-vinyl]-2-[(E)-hydroxyimino]-propionamide
-
IC50: 0.0004 mM
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-12 by 5%
4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-12 by 3%
alpha-mangostin
NSC30552, a natural product, caspase-3 pathway inhibitor, performs selective inhibition of 12-LO
baicalien
the 12LO inhibitor induces a 2-2.5fold increase in cell death, which appears to result from apoptosis, as indicated by DNA fragmentation, activation of procaspase 3 to caspase 3 and cytochrome c release from the mitochondria to the cytosol. This apoptosis can be prevented by treatment with the 12LO product, 12 hydroxyeicosatetraenoic acid (12HETE)
-
esculetine
-
inhibits the enzyme and its binding to cytoplasmic muscle fibrills, overview
GT-E
-
100 mM, dried radix of Glycine tomentella freeze-dried to a powder, IC50: 0.00072 mg/ml
-
michellamine B
NSC661755, potent but non-selective inhibitor, a natural anti-viral agent
N-([5-chloro-2-(dimethylamino)-8-hydroxyquinolin-7-yl](furan-2-yl)methyl)acetamide
-
-
N-([5-chloro-8-hydroxy-2-(piperidin-1-yl)quinolin-7-yl](furan-2-yl)methyl)acetamide
-
-
N-[(5-chloro-8-hydroxy-1,2,3,4,4a,8a-hexahydroquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(5-methylthiophen-2-yl)methyl]propanamide
-
-
neodysidenin
natural product from marine sponge Dysidea herbacea from Papua New Guinea, extraction and purification, overview, steady-state inhibition kinetics, competitive mode of inhibition, selective for 12-LO
siRNA
-
inhibition of p12-LOX in JB6 P+ cells by siRNA transfection, causes a significant suppression of 12-O-tetradecanoylphorbol-13-acetate-induced neoplastic transformation by 61% compared with that in control cells
-
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
-
mixed type inhibition towards the ferric form of 12-lipoxygenase
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
-
shows the oxidation of the inactive ferrous enzyme to the active ferric enzyme and competes with arachidonic acid for the ferric enzyme
AA861
-
prevents cell death, the 12/15-LOX inhibitor and the proteasome protect against exogenous glutamate, but not by preventing glutathione depletion. LOX inhibition, but not proteasome inhibition, reduces oxidative stress in glutamate-treated HT22 cells. The mitochondrial membrane potential is protected by coinhibition with baicalien
arachidonic acid
-
inhibits reaction with 5-hydroxy-6,8,11,14-eicodatetraenoic acid
baicalein
-
inhibits the enzyme and its binding to cytoplasmic muscle fibrills, overview
baicalein
-
inhibition of 12-LOX enzymatic activity using baicalein inhibits MMP9 expression in PC3 cells
baicalein
-
p12-LOX specific inhibitor, suppresses proliferation of JB6 P+ cells when cells are seeded at a low density in a culture plate by 81%
baicalein
-
prevents cell death, the 12/15-LOX inhibitor and the proteasome protect against exogenous glutamate, but not by preventing glutathione depletion. LOX inhibition, but not proteasome inhibition, reduces oxidative stress in glutamate-treated HT22 cells. The mitochondrial membrane potential is protected by coinhibition with AA861
ML355
a selective 12-LOX inhibitor, blocks both FcgammaRIIa-induced platelet aggregation and (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate production
-
ML355
-
a selective 12-LOX inhibitor, blocks both FcgammaRIIa-induced platelet aggregation and (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate production
-
PD146176
-
selective inhibitor of 12/15-LOX, macrophages treated with PD146176 elaborate reduced levels of interleukin-12 in response to Toxoplasma gondii antigen
additional information
development of an assay method for high throughput screening of libraries for platelet-type 12-hLO selective inhibitors, four organo-mercurial compounds with NCI library IDs NSC20410, NSC268879, NSC321237, and NSC321239, are also found to be selectively inhibitory, but not pursued further due to their potentially toxic side effects, overview
-
additional information
-
development of an assay method for high throughput screening of libraries for platelet-type 12-hLO selective inhibitors, four organo-mercurial compounds with NCI library IDs NSC20410, NSC268879, NSC321237, and NSC321239, are also found to be selectively inhibitory, but not pursued further due to their potentially toxic side effects, overview
-
additional information
-
comparison of structural requirements for flavonoid inhibitory potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2, the two latter belong to EC 1.13.11.33, overview, catechols are essential for high potency, isoflavones and isoflavanones tend to select against 12-hLO, isoflavans tend to select against isozyme 15-hLO-1, but few flavonoids target isozyme 15-hLO-2, molecular modeling analysis, overview
-
additional information
-
the histone deacetylase inhibitor trichostatin A inhibits EGF-induced 12(S)-lipoxygenase expression via downregulation of c-Jun and Sp1 expression, enhancement of Sp1 acetylation, and inhibition of Sp1, c-Jun, and p300 recruitment to the gene promoter of 12-LO, overview
-
additional information
-
enzyme inhibition causes a decrease in amyloid-beta protein
-
additional information
-
0.01 mM 4-[5-(6-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide or rofecoxib do not inhibit LOX-12
-
additional information
-
physico-chemical state of the substrate and the complex equilibrium between fatty acid monomers, acid soaps and micelles may impact the reaction specificity of LOX-isoforms
-
additional information
Chinese tea Qing Shan Lu Shui, which contains lower catechin levels than the other tested teas, inhibits the enzyme activity, 12-LOX inhibitory activity–guided fractionation of the aqueous ethanol extract are used to isolate twp components: monoterpene glycosides liguroside A and liguroside B, i.e. (2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-trans-p-coumaroyl)-beta-D-glucopyranoside and (2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-cis-p-coumaroyl)-beta-D-glucopyranoside, respectively. Inhibitory effect on leukocyte-type 12-LOX activity and catechin contents of 12 Chinese teas, overview
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
alpha-Naphthol
slight activation of enzyme activity at 0.25 mM, but not at 0.5 mM
additional information
-
the enzyme is induced by the epidermal growth factor, EGF
-
additional information
the potent vasoconstricting and pro-inflammatory hormone angiotensin II (Ang II) led to increases in leukocyte-type 12-LO mRNA and protein levels, as well as increased enzyme activity
-
additional information
-
a significant increase of 12-lipoxygenase enzyme activity in presence of arachidonic acid under GSH depletion induced by glutamate in C6 glimoa cells, overview
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0072
arachidonic acid
cytosolic hp-12LOX, pH 7.4, recombinant wild-type enzyme
0.0087
arachidonic acid
membrane hp-12LOX, pH 7.4, recombinant wild-type enzyme
additional information
additional information
dependence of the recombinant His-tagged isozyme hp-12LOX enzymatic reaction rate on the concentration of arachidonic acid and pH, kinetics, overview
-
additional information
additional information
-
dependence of the recombinant His-tagged isozyme hp-12LOX enzymatic reaction rate on the concentration of arachidonic acid and pH, kinetics, overview
-
additional information
additional information
-
free-energy distribution for oxygen inside the substrate-free rabbit 12/15-LOX, containing four nested free-energy isosurfaces with different energy levels, overview
-
additional information
additional information
-
kinetics with lysophospholipid substrates
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.002
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
-
inhibition of the ferric form of 12-lipoxygenase, free enzyme
0.0045
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
-
inhibition of the ferric form of 12-lipoxygenase, substrate-bound form of enzyme
0.07
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
-
inhibition of the ferrous form of 12-lipoxygenase
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0007
(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-cis-p-coumaroyl)-beta-D-glucopyranoside
Sus scrofa
pH 7.4, 30°C, recombinant leukocyte-type enzyme
0.0017
(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-trans-p-coumaroyl)-beta-D-glucopyranoside
Sus scrofa
pH 7.4, 30°C, recombinant leukocyte-type enzyme
0.0041
2,3,4,5-tetrabromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.0041 mM
0.00041
2,3,5-tribromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.00041 mM
0.007
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
Homo sapiens
-
IC50: 0.007 mM
0.0004
3-[3-bromo-5-(2,6-dibromo-4-{2-[2-(3-bromo-4-hydroxy-phenyl)-ethylcarbamoyl]-2-[(E)-hydroxyimino]-ethyl}-phenoxy)-4-methyl-phenyl]-N-[(E)-2-(3,5-dibromo-4-hydroxy-phenyl)-vinyl]-2-[(E)-hydroxyimino]-propionamide
Homo sapiens
-
IC50: 0.0004 mM
0.075
N-([5-chloro-2-(dimethylamino)-8-hydroxyquinolin-7-yl](furan-2-yl)methyl)acetamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.075
N-([5-chloro-8-hydroxy-2-(piperidin-1-yl)quinolin-7-yl](furan-2-yl)methyl)acetamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.075
N-[(2,5-dichloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.075
N-[(4-chloro-1-hydroxynaphthalen-2-yl)(furan-2-yl)methyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.002
N-[(5-bromo-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.002
N-[(5-bromo-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.001
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.014
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.075
N-[(5-bromofuran-2-yl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.003
N-[(5-chloro-8-hydroxy-1,2,3,4,4a,8a-hexahydroquinolin-7-yl)(furan-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.05
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-fluorophenyl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.15
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.0035
N-[(5-chloro-8-hydroxyquinolin-7-yl)(5-methylthiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.003
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.0016
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.025
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]-4-methylbenzamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.003
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.025
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]benzamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.001
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.001
N-[(5-chloro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.001
N-[(5-chloro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.15
N-[(5-chloro-8-hydroxyquinolin-7-yl)methyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.075
N-[(5-chloro-8-methoxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.005
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.002
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.0008
N-[(8-hydroxy-5-nitroquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.0034
N-[(8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.025
N-[(R)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.025
N-[(R)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.00043
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.00038
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.0026
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]acetamide
Homo sapiens
-
pH 8.0, 23°C
0.0012
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
0.15
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.05
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.075
N-[1-(5-fluoro-8-hydroxyquinolin-7-yl)ethyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23°C
0.0012
N-[furan-2-yl(8-hydroxy-5-nitroquinolin-7-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.3
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
7.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.1 - 8.6
-
pH 6.1: 37% of maximal activity, pH 8.6: 44% of maximal activity
6.3 - 8.8
-
pH 6.3: about 70% of maximal activity, pH 8.8: about 40% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
22
25
30
37
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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