Classification Term: 168150

Hydroxy/hydroperoxyeicosatrienoic acids [FA0305] (ontology term: 61a15fe314cfbcabaf83d144e9c472a7)

Hydroxy/hydroperoxyeicosatrienoic acids [FA0305]

found 20 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Eicosanoids [FA03]

Child Taxonomies: There is no child term of current ontology term.

14,15-DiHETrE

(±)14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoic acid

C20H34O4 (338.24569640000004)


14,15-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. Regulation of P450 eicosanoid levels is determined by many factors, including the induction or repression of the P450 enzymes responsible for their formation. Fibrate drugs are part of a diverse group of compounds known as peroxisome proliferators, which also include herbicides and phthalate ester plasticizers. Peroxisome proliferators act via peroxisome proliferator-activated receptor (PPAR ). This receptor is a member of the PPAR nuclear receptor family that also consists of the PPAR and PPAR isoforms. PPAR is mainly expressed in the heart, liver, and kidney, whereas the expression of PPAR is predominantly in the adipose tissue. The biological role of PPAR as a lipid sensor has been well established. 14,15-DiHETrE is a potent activators of PPAR and PPAR . shown to induce the binding of PPAR to a peroxisome proliferator response element (PPRE). Furthermore, 14,15-DiHETrE behaves like peroxisome proliferators in that is able to alter apoA-I and apoA-II mRNA expression. 14,15-DiHETrE is the most potent PPARalpha activator in a COS-7 cell expression system producing a 12-fold increase in PPARalpha-mediated luciferase activity. (PMID: 17431031, 16113065) [HMDB] 14,15-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. Regulation of P450 eicosanoid levels is determined by many factors, including the induction or repression of the P450 enzymes responsible for their formation. Fibrate drugs are part of a diverse group of compounds known as peroxisome proliferators, which also include herbicides and phthalate ester plasticizers. Peroxisome proliferators act via peroxisome proliferator-activated receptor (PPAR). This receptor is a member of the PPAR nuclear receptor family that also consists of the PPAR and PPAR isoforms. PPAR is mainly expressed in the heart, liver, and kidney, whereas the expression of PPAR is predominantly in the adipose tissue. The biological role of PPAR as a lipid sensor has been well established. 14,15-DiHETrE is a potent activators of PPAR and PPAR, shown to induce the binding of PPAR to a peroxisome proliferator response element (PPRE). Furthermore, 14,15-DiHETrE behaves like peroxisome proliferators in that is able to alter apoA-I and apoA-II mRNA expression. 14,15-DiHETrE is the most potent PPARalpha activator in a COS-7 cell expression system producing a 12-fold increase in PPARalpha-mediated luciferase activity. (PMID: 17431031, 16113065).

   

11,12,15-THETA

(5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoic acid

C20H34O5 (354.24061140000003)


11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). 11,12,15-THETA is an endothelium-derived relaxing factor. Acetylcholine stimulates AA release from membrane phospholipids of vascular endothelial cells (ECs). AA is released from phosphatidylcholine (PC) and phosphatidylethanolamine (PE) by phospholipase A2 (PLA2), or from phosphatidylinositol (PI) by phospholipase C (PLC) pathway. The diacylglycerol (DAG) lipase can convert DAG into 2-arachidonoylglycerol from which free AA can be released by monoacylglycerol (MAG) lipase or fatty acid amidohydrolase (FAAH). 11,12,15-THETA mediates the acetylcholine-induced vaso-relaxation, via activation of the K+ channels to hyperpolarize the smooth muscle membrane and induce relaxation. (PMID: 12907422, 16024567, 15388505, 14622984) [HMDB] 11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). 11,12,15-THETA is an endothelium-derived relaxing factor. Acetylcholine stimulates AA release from membrane phospholipids of vascular endothelial cells (ECs). AA is released from phosphatidylcholine (PC) and phosphatidylethanolamine (PE) by phospholipase A2 (PLA2), or from phosphatidylinositol (PI) by phospholipase C (PLC) pathway. The diacylglycerol (DAG) lipase can convert DAG into 2-arachidonoylglycerol from which free AA can be released by monoacylglycerol (MAG) lipase or fatty acid amidohydrolase (FAAH). 11,12,15-THETA mediates the acetylcholine-induced vaso-relaxation, via activation of the K+ channels to hyperpolarize the smooth muscle membrane and induce relaxation. (PMID: 12907422, 16024567, 15388505, 14622984).

   

12R-HETrE

12R-hydroxy-5Z,8Z,12Z-eicosatrienoic acid

C20H34O3 (322.25078140000005)


   

FA 20:4;O3

4-((1S,2S,5R)-5-hydroxy-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl)-3-oxocyclopentyl)butanoic acid

C20H32O5 (352.2249622)


D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents

   

FA 21:4;O6

methyl 9,11-epidioxy-12,15-dihydroperoxy-5,7,13-eicosatrienoate

C21H34O8 (414.2253564)


   

FA 20:3;O

(11Z,14Z)-16-(3-Ethyl-2-oxiranyl)-11,14-hexadecadienoic acid

C20H34O3 (322.25078140000005)


   

FA 20:3;O2

(5R,8E,10E,12R,14Z)-5,12-dihydroxyicosa-8,10,14-trienoic acid

C20H34O4 (338.24569640000004)


   

FA 20:3;O3

7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid

C20H34O5 (354.24061140000003)


D012102 - Reproductive Control Agents > D000019 - Abortifacient Agents D012102 - Reproductive Control Agents > D010120 - Oxytocics

   

12-HHT

12S-hydroxy-5Z,8E,10E-heptadecatrienoic acid

C17H28O3 (280.2038338)


   

5,6-DHET

(8Z,11Z,14Z)-5,6-Dihydroxyeicosa-8,11,14-trienoic acid

C20H34O4 (338.24569640000004)


A DHET obtained by formal dihydroxylation across the 5,6-double bond of arachidonic acid.

   

5S-HETrE

5S-hydroxy-6E,8Z,11Z-eicosatrienoic acid

C20H34O3 (322.25078140000005)


   

8,9-DHET

(5Z,11Z,14Z)-8,9-Dihydroxyeicosa-5,11,14-trienoic acid

C20H34O4 (338.24569640000004)


   

15S-HETrE

15S-hydroxy-8Z,11Z,13E-eicosatrienoic acid

C20H34O3 (322.25078140000005)


   

8S-HETrE

8S-hydroxy-9E,11Z,14Z-eicosatrienoic acid

C20H34O3 (322.25078140000005)


   

(+/-)14,15-EpETrE-(d8)

14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid-(d8)

C20H24D8O3 (328.285349624)


   

(+/-)8,9-EpETrE-(d8)

8,9-epoxy-5Z,11Z,14Z-eicosatrienoic acid-(d8)

C20H24D8O3 (328.285349624)


   

15-HETrE

(8Z,11Z,13E)-15-hydroxyeicosa-8,11,13-trienoic acid;15-hydroxy-8Z,11Z,13E-eicosatrienoic acid;15-hydroxy-8Z,11Z,13E-icosatrienoic acid;15-hydroxyeicosa-8Z,11Z,13E-trienoic acid;15-hydroxyicosa-8Z,11Z,13E-trienoic acid

C20H34O3 (322.25078140000005)


A hydroxyeicosatrienoic acid that consists of 8Z,11Z,13E-icosatrienoic acid bearing an additional 15-hydroxy substituent.

   

5-HETrE

(6E,8Z,11Z)-5-hydroxyeicosa-6,8,11-trienoic acid;5-hydroxy-6E,8Z,11Z-eicosatrienoic acid;5-hydroxy-6E,8Z,11Z-icosatrienoic acid

C20H34O3 (322.25078140000005)


A hydroxyeicosatrienoic acid that consists of 6E,8Z,11Z-eicosatrienoic acid bearing a 5-hydroxy substituent.

   

8-HETrE

(9E,11Z,14Z)-8-hydroxyeicosa-9,11,14-trienoic acid;8-hydroxy-9E,11Z,14Z-eicosatrienoic acid;8-hydroxy-9E,11Z,14Z-icosatrienoic acid

C20H34O3 (322.25078140000005)


A hydroxyeicosatrienoic acid that consists of 9E,11Z,14Z-eicosatrienoic acid bearing an 8-hydroxy substituent.

   

12-KHT

12-oxo-5Z,8E,10E-heptadecatrienoic acid

C17H26O3 (278.1881846)