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Arachidonic acid (AA, ARA) oxylipin metabolism

Proteins (0)

Compounds (63)

CompoundDescription
aspirinThe prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5)
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).
8,15-leukotriene B4RN given refers to cpd without isomeric designation; structure in first source
8-hydroperoxyeicosatetraenoic acid
5,20-dihydroxy-6,8,11,14-eicosatetraenoic acid
10-hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acidstructure in 2nd source
arachidonic acidAn unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
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.
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-keto-13,14-dihydroprostaglandin e2RN given refers to (5Z,11alpha)-isomer; structure in first source
15-ketoprostaglandin e2metabolite of PGE2; RN given refers to (5Z,11alpha,13E)-isomer
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
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 b2RN given refers to (5Z,13E,15S)-isomer
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.
15-ketoprostaglandin f2alpha
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
lipoxin B4structure in first source
leukotriene f-4formed by transpeptidation of leukotriene E
13,14-dihydro-15-ketoprostaglandin d2PGD2 metabolite; RN given refers to (5Z,9alpha)-isomer
15-keto-13,14-dihydroprostaglandin f2alphamain metabolite of PGF2alpha in plasma after allergen provoked asthma; RN given refers to (5Z,9alpha,11alpha)-isomer; structure
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).
2,3-dinor-thromboxane b2
11,12-dihydroxyeicosatrienoic acid
14,15-dihydroxyeicosatrienoic acid
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
5,15-dihydroxy-6,8,11,13-eicosatetraenoic acidRN given refers to (6,13-trans) & (8,11-cis)-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
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
11-hydroperoxyeicosa-5,8,12,14-tetraenoic acid
5,6-epoxy-8,11,14-eicosatrienoic acidRN given refers to cpd without isomeric designation
8,9-epoxyeicosatrienoic acidRN given refers to cpd without isomeric designation
14,15-epoxy-5,8,11-eicosatrienoic acidRN given refers to cpd without isomeric designation
8,11,12-trihydroxy-5,9,14-eicosatrienoic acidstructure
trioxilin B3structure in first source
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
12-hydroxy-5,8,10-heptadecatrienoic acidmetabolite of arachidonic acid in blood platelet suspension; RN given refers to cpd without isomeric designation
15-hydroperoxy-5,8,11,13-eicosatetraenoic acidRN given refers to cpd without isomeric designation; (S-(E,Z,Z,Z))-isomer caused dose-dependent constriction of cat coronary arteries; structure in first source
18-hydroxy-5,8,11,14-eicosatetraenoic acidstructure given in first source
15-epi-lipoxin A4
11 alpha-hydroxy-9,15-dioxo-2,3,4,5,20-pentanor-19-carboxyprostanoic acidmajor urinary metabolite of PGE in man
prostaglandin A2RN given refers to (5Z,13E,15S)-isomer
eoxin c4structure in first source
eoxin D4
12,20-dihydroxy-5,8,10,14-eicosatetraenoic acid
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