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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
- endothelial
- phospholipase
- neutrophil
- atherosclerosis
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polyunsaturated
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linoleic
- artery
- baicalein
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lipoxins
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hetes
- monocyte
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12-hydroxyeicosatetraenoic
- cox-2
- reticulocyte
- asthma
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nordihydroguaiaretic
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thromboxane
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eicosapentaenoic
- hydroperoxide
- ndga
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polymorphonuclear
- atherogenesis
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docosahexaenoic
- indomethacin
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5,8,11,14-eicosatetraynoic
- etya
- zileuton
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13-hode
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hydroperoxy
- lipoxygenase-1
- erythroderma
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hydroxyeicosatetraenoic
- medicine
- esculetin
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protectins
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ichthyosiform
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resolvins
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polyenoic
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pro-resolving
- drug development
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14carachidonic
- ichthyosis
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ferroptosis
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5-lipoxygenase-activating
- phenidone
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a23187-stimulated
- oxylipins
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
12-lipoxygenase, 15-lipoxygenase, 12-lox, alox5, 15-lox-1, alox15, 12-lo, 15-lo, 12/15-lipoxygenase, 12/15-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
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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
(14S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + ?
(13S,14S)-epoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid
-
-
-
?
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
(14S)-14-hydroxy-4,7,10,13,16,19-docosahexaenoic acid
-
-
-
-
?
4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + O2
(11S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + (14S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + (17S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-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
?
5,8,11,14,17-eicosapentaenoic acid + O2
(12S)-12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
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-
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?
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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?
5S-hydroperoxy-6E,8Z,10E,14Z-eicosatetraenoic acid + O2
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5S,15S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
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-
-
?
5S-hydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + O2
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
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-
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?
5S-hydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + O2
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5S,15S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
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-
-
?
6,9,12-octadecatrienoic acid + O2
13-hydroxy-6,9,12-octadecatrienoic acid
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?
arachidonate + O2
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
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-
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?
arachidonate + O2
(5Z,8Z,11Z,13E)-(12S)-12-hydroperoxyicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
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-
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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)-hydroperoxy-(9Z,11E)-octadecadienoic acid
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?
linoleic acid methyl ester + O2
(9R)-hydroperoxy-(10E,12Z)-octadecadienoic acid methyl ester
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?
linoleic acid methyl ester + O2
13(S)-hydroperoxyoctadecadienoic 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
14-hydroxy-4,7,10,12,16,19-docosahexaenoic acid
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-
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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
?
-
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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-
-
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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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-
-
-
?
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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-
-
?
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
-
-
?
alpha-linolenic acid + O2
13-hydroxy-(9Z,11E,15Z)-octadecatrienoic acid
-
-
-
-
?
alpha-linolenic acid + O2
13-hydroxy-(9Z,11E,15Z)-octadecatrienoic 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
-
-
?
arachidonate +