Page last updated: 2024-10-06

Arachidonic acid metabolism

Proteins (36)

ProteinSynonymsTaxonomy
Prostaglandin reductase 2PRG-2; EC 1.3.1.48; 15-oxoprostaglandin 13-reductase; Zinc-binding alcohol dehydrogenase domain-containing protein 1Homo sapiens (human)
Fatty-acid amide hydrolase 1EC 3.5.1.99; Anandamide amidohydrolase 1; Fatty acid ester hydrolase; 3.1.1.-; Oleamide hydrolase 1Homo sapiens (human)
Prostaglandin E synthaseEC 5.3.99.3; Glutathione peroxidase PTGES; 1.11.1.-; Glutathione transferase PTGES; 2.5.1.18; Microsomal glutathione S-transferase 1-like 1; MGST1-L1; Microsomal prostaglandin E synthase 1; MPGES-1; p53-induced gene 12 proteinHomo sapiens (human)
Polyunsaturated fatty acid 5-lipoxygenaseEC 1.13.11.-; Arachidonate 5-lipoxygenase; 5-LO; 5-lipoxygenase; 1.13.11.34Homo sapiens (human)
Arachidonate 5-lipoxygenase-activating proteinFLAP; MK-886-binding proteinHomo sapiens (human)
Prostaglandin G/H synthase 1EC 1.14.99.1; Cyclooxygenase-1; COX-1; Prostaglandin H2 synthase 1; PGH synthase 1; PGHS-1; PHS 1; Prostaglandin-endoperoxide synthase 1Homo sapiens (human)
Multidrug resistance-associated protein 1 EC 7.6.2.2; ATP-binding cassette sub-family C member 1; Glutathione-S-conjugate-translocating ATPase ABCC1; 7.6.2.3; Leukotriene C(4) transporter; LTC4 transporterHomo sapiens (human)
Prostaglandin G/H synthase 2EC 1.14.99.1; Cyclooxygenase-2; COX-2; PHS II; Prostaglandin H2 synthase 2; PGH synthase 2; PGHS-2; Prostaglandin-endoperoxide synthase 2Homo sapiens (human)
Aldo-keto reductase family 1 member C3EC 1.1.1.-; EC 1.1.1.210; EC 1.1.1.53; EC 1.1.1.62; 17-beta-hydroxysteroid dehydrogenase type 5; 17-beta-HSD 5; 3-alpha-HSD type II, brain; 3-alpha-hydroxysteroid dehydrogenase type 2; 3-alpha-HSD type 2; 1.1.1.357; Chlordecone reductase homolog HAKRb; DiHomo sapiens (human)
MAP kinase-activated protein kinase 2MAPK-activated protein kinase 2; MAPKAP kinase 2; MAPKAP-K2; MAPKAPK-2; MK-2; MK2; EC 2.7.11.1Homo sapiens (human)
Hematopoietic prostaglandin D synthaseH-PGDS; EC 5.3.99.2; GST class-sigma; Glutathione S-transferase; 2.5.1.18; Glutathione-dependent PGD synthase; Glutathione-requiring prostaglandin D synthase; Prostaglandin-H2 D-isomeraseHomo sapiens (human)
Leukotriene A-4 hydrolaseLTA-4 hydrolase; EC 3.3.2.6; Leukotriene A(4) hydrolase; Tripeptide aminopeptidase LTA4H; 3.4.11.4Homo sapiens (human)
Polyunsaturated fatty acid lipoxygenase ALOX1512/15-lipoxygenase; Arachidonate 12-lipoxygenase, leukocyte-type; 12-LOX; 1.13.11.31; Arachidonate 15-lipoxygenase; 15-LOX; 15-LOX-1; 1.13.11.33; Arachidonate omega-6 lipoxygenase; Hepoxilin A3 synthase Alox15; 1.13.11.-; Linoleate 13S-lipoxygenase; 1.13.Homo sapiens (human)
Carbonyl reductase [NADPH] 1EC 1.1.1.184; 15-hydroxyprostaglandin dehydrogenase [NADP(+)]; 1.1.1.196; 1.1.1.197; 20-beta-hydroxysteroid dehydrogenase; NADPH-dependent carbonyl reductase 1; Prostaglandin 9-ketoreductase; PG-9-KR; Prostaglandin-E(2) 9-reductase; 1.1.1.189; Short chainHomo sapiens (human)
Thromboxane-A synthase TXA synthase; TXS; EC 5.3.99.5; Cytochrome P450 5A1; Hydroperoxy icosatetraenoate dehydratase; 4.2.1.152Homo sapiens (human)
Bifunctional epoxide hydrolase 2Homo sapiens (human)
Serum paraoxonase/lactonase 3EC 3.1.1.2; EC 3.1.1.81; EC 3.1.8.1Homo sapiens (human)
Dipeptidase 1EC 3.4.13.19; Beta-lactamase; 3.5.2.6; Dehydropeptidase-I; Microsomal dipeptidase; Renal dipeptidase; hRDPHomo sapiens (human)
Polyunsaturated fatty acid lipoxygenase ALOX15B15-lipoxygenase 2; 15-LOX-2; Arachidonate 15-lipoxygenase B; 15-LOX-B; 1.13.11.33; Arachidonate 15-lipoxygenase type II; Linoleate 13-lipoxygenase 15-LOb; 1.13.11.-Homo sapiens (human)
Serum paraoxonase/arylesterase 1PON 1; EC 3.1.1.2; EC 3.1.1.81; EC 3.1.8.1; Aromatic esterase 1; A-esterase 1; K-45; Serum aryldialkylphosphatase 1Homo sapiens (human)
Fatty-acid amide hydrolase 2EC 3.5.1.99; Amidase domain-containing protein; Anandamide amidohydrolase 2; Oleamide hydrolase 2Homo sapiens (human)
Dipeptidase 2EC 3.4.13.19Homo sapiens (human)
Dipeptidase 3EC 3.4.13.19Homo sapiens (human)
Arachidonate 12-lipoxygenase, 12R-type12R-LOX; 12R-lipoxygenase; EC 1.13.11.-; Epidermis-type lipoxygenase 12Homo sapiens (human)
15-hydroxyprostaglandin dehydrogenase [NAD(+)]15-PGDH; EC 1.1.1.141; Prostaglandin dehydrogenase 1; Short chain dehydrogenase/reductase family 36C member 1Homo sapiens (human)
Polyunsaturated fatty acid lipoxygenase ALOX12EC 1.13.11.-; Arachidonate (12S)-lipoxygenase; 12S-LOX; 12S-lipoxygenase; 1.13.11.31; Arachidonate (15S)-lipoxygenase; 1.13.11.33; Linoleate (13S)-lipoxygenase; Lipoxin synthase 12-LO; 3.3.2.-; Platelet-type lipoxygenase 12Homo sapiens (human)
Cytosolic phospholipase A2cPLA2; Phospholipase A2 group IVAHomo sapiens (human)
Leukotriene C4 synthaseLTC4 synthase; EC 4.4.1.20; Glutathione S-transferase LTC4; 2.5.1.-; Leukotriene-C(4) synthase; Leukotriene-C4 synthaseHomo sapiens (human)
Acyl-CoA wax alcohol acyltransferase 1EC 2.3.1.75; Diacylglycerol O-acyltransferase 2-like protein 3; Diacylglycerol acyltransferase 2; Long-chain-alcohol O-fatty-acyltransferase 1Homo sapiens (human)
Glutathione hydrolase 1 proenzymeEC 3.4.19.13; Gamma-glutamyltransferase 1; Gamma-glutamyltranspeptidase 1; GGT 1; 2.3.2.2; Leukotriene-C4 hydrolase; 3.4.19.14Homo sapiens (human)
Prostaglandin-H2 D-isomeraseEC 5.3.99.2; Beta-trace protein; Cerebrin-28; Glutathione-independent PGD synthase; Lipocalin-type prostaglandin-D synthase; L-PGDS; Prostaglandin-D2 synthase; PGD2 synthase; PGDS; PGDS2Homo sapiens (human)
Prostaglandin reductase 1PRG-1; 15-oxoprostaglandin 13-reductase; 1.3.1.48; Dithiolethione-inducible gene 1 protein; D3T-inducible gene 1 protein; DIG-1; Leukotriene B4 12-hydroxydehydrogenase; NAD(P)H-dependent alkenal/one oxidoreductase; 1.3.1.74Homo sapiens (human)
Serum paraoxonase/arylesterase 2PON 2; EC 3.1.1.2; EC 3.1.1.81; Aromatic esterase 2; A-esterase 2; Serum aryldialkylphosphatase 2Homo sapiens (human)
Prostamide/prostaglandin F synthaseProstamide/PG F synthase; Prostamide/PGF synthase; EC 1.11.1.20; Peroxiredoxin-like 2B; Protein FAM213BHomo sapiens (human)
Glutathione hydrolase 5 proenzymeEC 3.4.19.13; Gamma-glutamyl transpeptidase-related enzyme; GGT-rel; Gamma-glutamyltransferase 5; GGT 5; 2.3.2.2; Gamma-glutamyltransferase-like activity 1; Gamma-glutamyltranspeptidase 5; Leukotriene-C4 hydrolase; 3.4.19.14Homo sapiens (human)
Hydroperoxide isomerase ALOXE3Epidermis-type lipoxygenase 3; Epidermal LOX-3; e-LOX-3; eLOX-3; Hydroperoxy dehydratase ALOXE3; Hydroperoxy icosatetraenoate dehydratase; 4.2.1.152; Hydroperoxy icosatetraenoate isomerase; 5.4.4.7Homo sapiens (human)

Compounds (68)

CompoundDescription
hydronium ion
GlutathioneA tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides.
NADH
CalciumA basic element found in nearly all tissues. It is a member of the alkaline earth family of metals with the atomic symbol Ca, atomic number 20, and atomic weight 40. Calcium is the most abundant mineral in the body and combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes.
ironA metallic element with atomic symbol Fe, atomic number 26, and atomic weight 55.85. It is an essential constituent of HEMOGLOBINS; CYTOCHROMES; and IRON-BINDING PROTEINS. It plays a role in cellular redox reactions and in the transport of OXYGEN.
ZincA metallic element of atomic number 30 and atomic weight 65.38. It is a necessary trace element in the diet, forming an essential part of many enzymes, and playing an important role in protein synthesis and in cell division. Zinc deficiency is associated with ANEMIA, short stature, HYPOGONADISM, impaired WOUND HEALING, and geophagia. It is known by the symbol Zn.
Glutathione DisulfideA GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.
dinoprostoneThe most common and most biologically active of the mammalian prostaglandins. It exhibits most biological activities characteristic of prostaglandins and has been used extensively as an oxytocic agent. The compound also displays a protective effect on the intestinal mucosa.
dinoprostA naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.
epoprostenolA prostaglandin that is a powerful vasodilator and inhibits platelet aggregation. It is biosynthesized enzymatically from PROSTAGLANDIN ENDOPEROXIDES in human vascular tissue. The sodium salt has been also used to treat primary pulmonary hypertension (HYPERTENSION, PULMONARY).
adenosine diphosphateAdenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.
MagnesiumA metallic element that has the atomic symbol Mg, atomic number 12, and atomic weight 24.31. It is important for the activity of many enzymes, especially those involved in OXIDATIVE PHOSPHORYLATION.
WaterA clear, odorless, tasteless liquid that is essential for most animal and plant life and is an excellent solvent for many substances. The chemical formula is hydrogen oxide (H2O). (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)
OxygenAn element with atomic symbol O, atomic number 8, and atomic weight [15.99903; 15.99977]. It is the most abundant element on earth and essential for respiration.
salicylatesThe salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.
malondialdehydeThe dialdehyde of malonic acid.
nadA coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed)
NADPNicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed)
NADPNicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed)
prostaglandin h2A cyclic endoperoxide intermediate produced by the action of CYCLOOXYGENASE on ARACHIDONIC ACID. It is further converted by a series of specific enzymes to the series 2 prostaglandins.
n(1)-methylnicotinamideRN given refers to parent cpd
leukotriene a4(2S-(2 alpha,3 beta(1E,3E,5Z,8Z)))-3-(1,3,5,8-Tetradecatetraenyl)oxiranebutanoic acid. An unstable allylic epoxide, formed from the immediate precursor 5-HPETE via the stereospecific removal of a proton at C-10 and dehydration. Its biological actions are determined primarily by its metabolites, i.e., LEUKOTRIENE B4 and cysteinyl-leukotrienes. Alternatively, leukotriene A4 is converted into LEUKOTRIENE C4 by glutathione-S-transferase or into 5,6-di-HETE by the epoxide-hydrolase. (From Dictionary of Prostaglandins and Related Compounds, 1990)
leukotriene b4The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990)
leukotriene c4The conjugation product of LEUKOTRIENE A4 and glutathione. It is the major arachidonic acid metabolite in macrophages and human mast cells as well as in antigen-sensitized lung tissue. It stimulates mucus secretion in the lung, and produces contractions of nonvascular and some VASCULAR SMOOTH MUSCLE. (From Dictionary of Prostaglandins and Related Compounds, 1990)
thromboxane a2An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).
15-keto-5,8,11,13-eicosatetraenoic acidRN given refers to (E,Z,Z,Z)-isomer; RN for cpd without isomeric designation not available 3/88
15-hydroxy-5,8,11,13-eicosatetraenoic acidpotent & selective inhibitor of platelet lipoxygenase; RN given refers to cpd without isomeric designation
5-hydroxy-6,8,11,14-eicosatetraenoic acid
5,12,20-trihydroxy-6,8,10,14-eicosatetraenoic acidRN given refers to (S-(R*,R*-(E,E,Z,Z)))-isomer
arachidonic acid 5-hydroperoxide5-HPETE is used inconsistently in literature as syn for cpds with various tetraene locants; RN given refers to (6,8,11,14)-isomer; RN in CA Vol 91 Form Index for (E,Z,Z,Z)-isomer: 70968-82-0; RN for (5,8,11,13)-isomer: 71133-12-5; in Merck, arachidonic acid is the (5,8,11,14)-isomer
12-oxoleukotriene B4structure given in first source
20-carboxyleukotriene b4metabolite of leukotriene B4
leukotriene d4One of the biologically active principles of SRS-A. It is generated from LEUKOTRIENE C4 after partial hydrolysis of the peptide chain, i.e., cleavage of the gamma-glutamyl portion. Its biological actions include stimulation of vascular and nonvascular smooth muscle, and increases in vascular permeability. (From Dictionary of Prostaglandins and Related Compounds, 1990)
leukotriene e4A biologically active principle of SRS-A that is formed from LEUKOTRIENE D4 via a peptidase reaction that removes the glycine residue. The biological actions of LTE4 are similar to LTC4 and LTD4. (From Dictionary of Prostaglandins and Related Compounds, 1990)
prostaglandin a2RN given refers to (5Z,13E,15S)-isomer
prostaglandin b2RN given refers to (5Z,13E,15S)-isomer
prostaglandin g2
9-deoxy-delta-9-prostaglandin d2has potent antineoplastic & weak smooth muscle contracting activities; structure given in first source
9-deoxy-9,10-didehydro-12,13-didehydro-13,14-dihydroprostaglandin d2PGD2 metabolite in human plasma
DinoprostA naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.
6-ketoprostaglandin f1 alphaThe physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.
11-dehydro-thromboxane b2structure given in first source
arachidonic acid omega-9 hydroperoxide
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, (s)-(e,z,z,z)-isomer
anandamide
thromboxane b2A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).
12-hydroxy-5,8,10-heptadecatrienoic acidmetabolite of arachidonic acid in blood platelet suspension; RN given refers to cpd without isomeric designation
12-hydroxy-5,8,10,14-eicosatetraenoic acidA lipoxygenase metabolite of ARACHIDONIC ACID. It is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumor cell metastatic potential through activation of protein kinase C. (J Pharmacol Exp Ther 1995; 274(3):1545-51; J Natl Cancer Inst 1994; 86(15):1145-51)
20-hydroxy-5,8,11,14-eicosatetraenoic acidstimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer
5-oxo-6,8,11,14-eicosatetraenoic acidRN given is for cpd without isomeric designation; an arachidonate metabolite which stimulates neutrophils to mobilize Ca and promotes PMN degranulation responses
12-keto-5,8,11,13-eicosatetraenoic acid
15-hydroxy-5,8,11,13-eicosatetraenoic acidpotent & selective inhibitor of platelet lipoxygenase; RN given refers to cpd without isomeric designation
5,6-epoxy-8,11,14-eicosatrienoic acidRN given refers to cpd without isomeric designation
8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid
15-deoxy-delta(12,14)-prostaglandin j215-deoxy-PGJ2 is also available; check for double bonds (indicated by delta) at 12 and 14 positions
glutamate
adenosine triphosphateAn adenine nucleotide containing three phosphate groups esterified to the sugar moiety. In addition to its crucial roles in metabolism adenosine triphosphate is a neurotransmitter.
18-carboxy-19,20-dinorleukotriene B4structure given in first source
20-aldehyde leukotriene B4
ethanolamineA viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorimetric reagent, and to remove CO2 and H2S from natural gas and other gases.
5-hydroxy-6,8,11,14-eicosatetraenoic acid
19-hydroxy-5,8,11,14-eicosatetraenoic acidpotent stimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer
Coenzyme A
eoxin c4structure in first source
eoxin D4
prostaglandin d2The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.
eoxin E4
creolinfrom refined coal tar oils