Classification Term: 1796

Hydroxyeicosatetraenoic acids (ontology term: CHEMONTID:0000046)

Eicosanoic acids with an attached hydroxyl group and four CC double bonds." []

found 39 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Eicosanoids

Child Taxonomies: Lipoxins

8-HETE

(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593, 9113987) [HMDB] 8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593, 9113987).

   

16(R)-HETE

(5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


16(R)-HETE is a metabolite of arachidonic acid, metabolized by the enzyme Cytochrome P450, family 2, subfamily C [EC:1.14.13.80 1.14.13.48 1.14.13.49]. 16(R)-HETE is an endogenous lipidic inhibitor of human neutrophil inhibitor of adhesion and aggregation activity. Human polymorphonuclear leukocytes (PMNs) produce 16(R)-HETE that modulates their function. HETEs have different biological properties based on sites of production and can be stored in tissue lipids and released in response to hormonal stimuli. Eicosanoids generated during the actions of growth factors and vasoconstrictors can modulate disease processes by affecting vascular homeostasis, inflammation, cellular growth, apoptosis and oxidant stress. In lung, the presence of these eicosanoids in the pulmonary vasculature and airways, including effects on pulmonary vascular and bronchial smooth muscle tone and airway epithelial ion transport. (PMID: 16258232, 14626496, 12681244, 11123211, 14552765, 11126912) [HMDB] 16(R)-HETE is a metabolite of arachidonic acid, metabolized by the enzyme Cytochrome P450, family 2, subfamily C [EC:1.14.13.80 1.14.13.48 1.14.13.49]. 16(R)-HETE is an endogenous lipidic inhibitor of human neutrophil inhibitor of adhesion and aggregation activity. Human polymorphonuclear leukocytes (PMNs) produce 16(R)-HETE that modulates their function. HETEs have different biological properties based on sites of production and can be stored in tissue lipids and released in response to hormonal stimuli. Eicosanoids generated during the actions of growth factors and vasoconstrictors can modulate disease processes by affecting vascular homeostasis, inflammation, cellular growth, apoptosis and oxidant stress. In lung, the presence of these eicosanoids in the pulmonary vasculature and airways, including effects on pulmonary vascular and bronchial smooth muscle tone and airway epithelial ion transport. (PMID: 16258232, 14626496, 12681244, 11123211, 14552765, 11126912).

   

19(S)-HETE

(5Z,8Z,11Z,14Z)-(19S)-19-Hydroxyeicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


19(S)-HETE is an intermediate in Arachidonic acid metabolism. 19(S)-HETE is converted from Arachidonic acid via the enzyme CYP2U and Unspecific. Monooxygenase. (EC:1.14.14.1). 19(S)-HETE is an intermediate in Arachidonic acid metabolism. 19(S)-HETE is converted from Arachidonic acid via the enzyme CYP2U and Unspecific

   

12-HETE

(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyeicosa-5,8,10,14-tetraenoic acid

C20H32O3 (320.2351322)


12-Hydroxyeicosatetraenoic acid (CAS: 71030-37-0), also known as 12-HETE, is an eicosanoid, a 5-lipoxygenase metabolite of arachidonic acid. 5-Lipoxygenase (LO)-derived leukotrienes are involved in inflammatory glomerular injury. LO product 12-HETE is associated with the pathogenesis of hypertension and may mediate angiotensin II and TGFbeta induced mesangial cell abnormality in diabetic nephropathy. 12-HETE is markedly elevated in the psoriatic lesions. 12-HETE is a vasoconstrictor eicosanoid that contributes to high blood pressure in (renovascular) hypertension and pregnancy-induced hypertension. A significant percentage of patients suffering from a selective increase in plasma LDL cholesterol (type IIa hyperlipoproteinemia) exhibits increased platelet reactivity. This includes enhanced platelet responsiveness against a variety of platelet-stimulating agents ex vivo and enhanced arachidonic acid metabolism associated with increased generation of arachidonic acid metabolites such as 12-HETE, and secretion of platelet-storage products (PMID: 7562532, 12480795, 17361113, 8498970, 1333255, 2119633). 12-HETE 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 tumour cell metastatic potential through activation of protein kinase C. 12-HETE has a diversity of biological actions and is generated by a number of tissues including the renal glomerulus and the vasculature. 12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. 12-HETE is a neuromodulator that is synthesized during ischemia. Its neuronal effects include attenuation of calcium influx and glutamate release as well as inhibition of AMPA receptor (AMPA-R) activation. 12-HETE is found to be associated with peroxisomal biogenesis defect and Zellweger syndrome, which are inborn errors of metabolism.

   

15-HETE

15-Hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(e,Z,Z,Z))-isomer

C20H32O3 (320.2351322)


15-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12-, and 15-lipoxygenase (LO) pathways. The 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro, 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation, and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE also has some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells (PMID: 11104340). 15(S)-HETE is found to be associated with Zellweger syndrome, which is an inborn error of metabolism. 15(S)-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12- and 15-lipoxygenase (LO) pathways. 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE has also some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. (PMID: 11104340) [HMDB] 15(S)-HETE. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=54845-95-3 (retrieved 2024-07-10) (CAS RN: 54845-95-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

5-HETE

5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomer

C20H32O3 (320.23513219999995)


5-Hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.; 5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in Arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then it is converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback. 5-HETE is found in corn. 5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.

   

9-HETE

(5Z,7E,11Z,14Z)-(9S)-9-Hydroxyeicosa-5,7,11,14-tetraenoic acid

C20H32O3 (320.2351322)


9-HETE, which is a product of free radical-mediated arachidonic acid oxidation, is significantly elevated in patients with angiographically defined CAD. (PMID: 17145556). 9-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. [HMDB] 9-HETE, which is a product of free radical-mediated arachidonic acid oxidation, is significantly elevated in patients with angiographically defined CAD. (PMID: 17145556). 9-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid.

   

11(R)-HETE

11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer

C20H32O3 (320.23513219999995)


11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853, 8555273) [HMDB] 11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853, 8555273).

   

18-Hydroxyarachidonic acid

(5Z,8Z,11Z,14Z,18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


(18R)-Hydroxyarachidonate is a substrate for CYP4F8 or leukotriene-B4 20-monooxygenase (EC 1.14.13.30). This enzyme hydroxylates arachdonic acid (20:4n-6) to (18R)-hydroxyarachidonate in the endoplasmic reticulum. This reaction is irreversible. CYP4F8 is a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved in drug metabolism and synthesis of cholesterol, steroids and other lipids. This protein localizes to the endoplasmic reticulum and functions as a 19-hydroxylase of prostaglandins in seminal vesicles. In particular, CYP4F8 catalyzes the 2-hydroxylation of PGH1 and PGH2, which will lead to biosynthesis of the two main PGs of human seminal fluid, (19R)-hydroxy-PGE1 and (19R)-hydroxy-PGE2 (PMID: 10791960). 18-Hydroxyarachidonic acid is an intermediate in eicosanoid metabolism. [HMDB] (18R)-Hydroxyarachidonate is a substrate for CYP4F8 or leukotriene-B4 20-monooxygenase (EC 1.14.13.30). This enzyme hydroxylates arachdonic acid (20:4n-6) to (18R)-hydroxyarachidonate in the endoplasmic reticulum. This reaction is irreversible. CYP4F8 is a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved in drug metabolism and synthesis of cholesterol, steroids and other lipids. This protein localizes to the endoplasmic reticulum and functions as a 19-hydroxylase of prostaglandins in seminal vesicles. In particular, CYP4F8 catalyzes the 2-hydroxylation of PGH1 and PGH2, which will lead to biosynthesis of the two main PGs of human seminal fluid, (19R)-hydroxy-PGE1 and (19R)-hydroxy-PGE2 (PMID: 10791960). 18-Hydroxyarachidonic acid is an intermediate in eicosanoid metabolism.

   

17-HETE

(5Z,8Z,11Z,14Z)-17-Hydroxyeicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (?)17-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid that has stereospecific effects on sodium transport in the kidney. At a concentration of 2 ?M the (S)-enantiomer of 17-HETE inhibits proximal tubule ATPase activity by as much as 70\\%, whereas the (R)-isomer is inactive [HMDB] Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)17-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid that has stereospecific effects on sodium transport in the kidney. At a concentration of 2 ¬µM the (S)-enantiomer of 17-HETE inhibits proximal tubule ATPase activity by as much as 70\\%, whereas the (R)-isomer is inactive.

   

8,15-DiHETE

(5Z,9E,11Z,13E)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid

C20H32O4 (336.2300472)


8,15-DiHETE is a double oxidation product of arachadonic acid. It is generated through the action of 15-lipoxygenase (PMID: 8334154). 8,15-DiHETE is also known as eosinophil chemotactic factor of anaphylaxis (ECF-A). In particular it is able to selectively attract eosinophils and neutrophils from mixed leukocyte populations.Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 8,15-DiHETE is a double oxidation product of arachadonic acid. It is generated through the action of 15-lipoxygenase (PMID: 8334154). 8,15-DiHETE is also known as eosinophil chemotactic factor of anaphylaxis (ECF-A). In particular it is able to selectively attract eosinophils and neutrophils from mixed leukocyte populations.

   

12,20-DiHETE

(5Z,8Z,10E,14Z)-12,20-dihydroxyicosa-5,8,10,14-tetraenoic acid

C20H32O4 (336.2300472)


This compound belongs to the family of Hydroxyeicosatetraenoic Acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.......

   

14,15-DiHETE

(5Z,8Z,11Z,17Z)-14,15-dihydroxyicosa-5,8,11,17-tetraenoic acid

C20H32O4 (336.2300472)


14,15-DiHETE is an oxygenated lipid found in human blood. This fatty acyl belongs to the main class of eicosanoids and the sub class of hydroxy/hydroperoxyeicosatetraenoic acids. (Lipid Maps) [HMDB] 14,15-DiHETE is an oxygenated lipid found in human blood. This fatty acyl belongs to the main class of eicosanoids and the sub class of hydroxy/hydroperoxyeicosatetraenoic acids. (Lipid Maps).

   

5,15-DiHETE

(5S,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoic acid

C20H32O4 (336.2300472)


5,15-DiHETE or 5,15-dihydroxyeicosatetraenoic acid is a double oxidation product of arachadonic acid. (PMID: 6817003). It is produced by the action of lipoxygenases (specifically 5-lipoxygenase and 15 lipoxygenase) in the liver and in neutrophils. [HMDB] 5,15-DiHETE or 5,15-dihydroxyeicosatetraenoic acid is a double oxidation product of arachadonic acid. (PMID: 6817003). It is produced by the action of lipoxygenases (specifically 5-lipoxygenase and 15 lipoxygenase) in the liver and in neutrophils.

   

17,18-DiHETE

(5Z,8Z,11Z,14Z)-17,18-Dihydroxyeicosa-5,8,11,14-tetraenoic acid

C20H32O4 (336.2300472)


17,18-DiHETE is an oxygenated lipid found in human blood. This fatty acyl belongs to the main class of eicosanoids and sub class of hydroxy/hydroperoxyeicosatetraenoic acids. (Lipid Maps) [HMDB] 17,18-DiHETE is an oxygenated lipid found in human blood. This fatty acyl belongs to the main class of eicosanoids and sub class of hydroxy/hydroperoxyeicosatetraenoic acids. (Lipid Maps).

   

13-HETE

(5Z,8Z,11Z,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


13-Hydroxyeicosatetraenoic acid is one of the main metabolites of 15-lipoxygenases (15-LOXs), are endogenous ligands of PPARr. It can inhibit cell proliferation and induce apoptosis in several types of human cancer. 13-HETE is an arachidonic acid metabolite in rat liver microsomes, and is a metabolite of red algae.Hydroxyeicosatetraenoic acids (HETEs) are formed in numerous cell types by enzymatically-mediated hydroxylation of arachidonic acid. There are three distinct enzymes involved in HETE biosynthesis:lipoxygenase (LOX), prostaglandin H (PGH) synthase, and cytochrome P-450. LOX- and PGH-synthase-mediated arachidonic acid metabolism is normally highly stereoselective. 13-Hydroxyeicosatetraenoic acid is one of the main metabolites of 15-lipoxygenases (15-LOXs), are endogenous ligands of PPARr. It can inhibit cell proliferation and induce apoptosis in several types of human cancer

   

10-HETE

(5Z,8Z,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


10-HETE is a HETE(Hydroxyeicosatetraenoic acid)with the hydroxy group located in C-10 position. The HETE metabolites are identified as omega-hydroxy derivatives and 10-HETE is one of the major products of NADPH-dependent arachidonic acid metabolism in rat liver microsomes. The conversion of arachidonic acid to HETE can be catalyzed via lipoxygenase ,cyclooxygenase or P-450 dependent route. [PMID: 7646075]. 10-HETE is a HETE(Hydroxyeicosatetraenoic acid)with the hydroxy group located in C-10 position. The HETE metabolites are identified as omega-hydroxy derivatives and 10-HETE is one of the major products of NADPH-dependent arachidonic acid metabolism in rat liver microsomes. The conversion of arachidonic acid to HETE can be catalyzed via lipoxygenase ,cyclooxygenase or P-450 dependent route.

   

18E-20-Oxo-20-CoA-LTE4

6-[(2-Amino-2-carboxyethyl)sulphanyl]-20-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5-hydroxy-20-oxoicosa-7,9,11,14,18-pentaenoic acid

C44H67N8O22P3S2 (1216.3024031999998)


18E-20-oxo-20-CoA-LTE4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4).Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939, 12432945, 6311078). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 18E-20-oxo-20-CoA-LTE4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4).Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939, 12432945, 6311078)

   

12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid

(5E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

C20H32O3 (320.23513219999995)


12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid, also known as 12-S-HETE or Acid, 12-S-hydroxyeicosatetraenoic, is classified as a member of the Hydroxyeicosatetraenoic acids. Hydroxyeicosatetraenoic acids are eicosanoic acids with an attached hydroxyl group and four CC double bonds. 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 12S-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid is an eicosanoid lipid molecule

   

15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid

(5Z,8Z,11Z,13E,15R)-15-hydroxyicosa-5,8,11,13-tetraenoic acid

C20H32O3 (320.23513219999995)


15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is also known as 15R-HETE. 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is an eicosanoid lipid molecule

   

18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid

(5Z,8Z,11Z,14Z)-18-Hydroxyeicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid is an eicosanoid lipid molecule. It is classified as a member of the hydroxyeicosatetraenoic acids. Hydroxyeicosatetraenoic acids are eicosanoic acids with an attached hydroxyl group and four CC double bonds. 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic.

   

7-HETE

(5Z,8Z,14Z)-7-hydroxyicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


7-HETE, also known as 7-Hydroxyeicosatetraenoic acid, is classified as a member of the Hydroxyeicosatetraenoic acids. Hydroxyeicosatetraenoic acids are eicosanoic acids with an attached hydroxyl group and four CC double bonds. 7-HETE is considered to be practically insoluble (in water) and acidic

   

8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid

(5Z,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid is also known as 8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-isomer. 8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid is an eicosanoid lipid molecule

   

5,20-DiHETE

(6E,8E,11E,14E)-5,20-dihydroxyicosa-6,8,11,14-tetraenoic acid

C20H32O4 (336.2300472)


5,20-DiHETE is also known as 5,20-Dihydroxy-6,8,11,14-eicosatetraenoic acid. 5,20-DiHETE is considered to be practically insoluble (in water) and acidic

   

5(S),11(R)-DiHETE

(5S,6E,8Z,11R,12E,14Z)-5,11-dihydroxyicosa-6,8,12,14-tetraenoic acid

C20H32O4 (336.2300472)


5(S),11(R)-DiHETE is also known as 5,11-DiHETE or 5S,11R-Dihydroxy-6E,8Z,12E,14Z-eicosatetraenoate. 5(S),11(R)-DiHETE is considered to be practically insoluble (in water) and acidic. 5(S),11(R)-DiHETE is an eicosanoid lipid molecule

   

5(S),15(R)-DiHETE(1-)

5(S),15(S)-Dihydroxy-6,13-trans-8,11-cis-eicosatetraenoic acid

C20H32O4 (336.2300472)


5(S),15(R)-DiHETE(1-) is considered to be practically insoluble (in water) and acidic

   

8,20-DiHETE

(5Z,11Z,14Z)-8,20-dihydroxyicosa-5,9,11,14-tetraenoic acid

C20H32O4 (336.2300472)


8,20-DiHETE is also known as 8,20-Dihydroxy-5Z,9E,11Z,14Z-eicosatetraenoate or (5Z,9E,11Z,14Z)-8,20-Dihydroxyicosatetraenoate. 8,20-DiHETE is considered to be practically insoluble (in water) and acidic

   

20-hydroxylipoxin A4

(5S,6R,7E,9E,11Z,15S)-5,6,15,20-tetrahydroxyicosa-7,9,11,13-tetraenoic acid

C20H32O6 (368.2198772)


20-hydroxylipoxin A4 is considered to be practically insoluble (in water) and acidic

   

(+/-)-11,12-Dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoic acid

(+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoic acid

C20H32O4 (336.2300472)


   

(12S)-12-Hydroxyicosa-2,4,6,8-tetraenoic acid

(12S)-12-Hydroxyicosa-2,4,6,8-tetraenoic acid

C20H32O3 (320.23513219999995)


   

(5E,8E,11E,14E)-19-Hydroxyicosa-5,8,11,14-tetraenoic acid

(5E,8E,11E,14E)-19-Hydroxyicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


   

11-Hydroxy-5Z,8Z,11E,14Z-eicosatetraenoic acid

11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer

C20H32O3 (320.23513219999995)


   

12(S)-Hydroxy-5,8,10,14-eicosatetraenoic acid

12(S)-Hydroxy-5,8,10,14-eicosatetraenoic acid

C20H32O3 (320.23513219999995)


12-hydroxyeicosatetraenoic acid (12-HETE) is an eicosanoid, a 5-lipoxygenase metabolite of arachidonic acid. 5-Lipoxygenase (LO)-derived leukotrienes are involved in inflammatory glomerular injury. LO product 12-HETE is associated with pathogenesis of hypertension, and may mediate angiotensin II and TGFbeta induced mesengial cell abnormality in diabetic nephropathy. 12-HETE is markedly elevated in the psoriatic lesions. 12-HETE is a vasoconstrictor eicosanoid that contribute to high blood pressure in (renovascular) hypertension and pregnancy-induced hypertension. A significant percentage of patients suffering from a selective increase in plasma LDL cholesterol (type IIa hyperlipoproteinaemia) exhibits increased platelet reactivity. This includes enhanced platelet responsiveness against a variety of platelet-stimulating agents ex vivo and enhanced arachidonic acid metabolism associated with increased generation of arachidonic acid metabolites such as 12-HETE, and secretion of platelet-storage products. (PMID: 7562532, 12480795, 17361113, 8498970,1333255, 2119633). 12-HETE 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 tumour cell metastatic potential through activation of protein kinase c. 12-HETE can be formed either in the 12-S or 12-R configuration. It has a diversity of biological actions and is generated by a number of tissues including the renal glomerulus and the vasculature. 12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. 12-HETE is a neuromodulator that is synthesized during ischemia. Its neuronal effects include attenuation of calcium influx and glutamate release as well as inhibition of AMPA receptor (AMPA-R) activation. 12-HETE is found in corn.

   

15-Hydroxy-5,8,11,13-eicosatetraenoic acid

15-Hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(e,Z,Z,Z))-isomer

C20H32O3 (320.23513219999995)


   

Eicosatetraenoic acid, 15-hydroxy-

15-hydroxyicosa-2,4,6,8-tetraenoic acid

C20H32O3 (320.23513219999995)


   

18-Hydroxyeicosatetraenoic acid

18-hydroxyicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.23513219999995)


   

19-Hydroxyeicosatetraenoic acid

19-hydroxyicosa-2,4,6,8-tetraenoic acid

C20H32O3 (320.23513219999995)


   

8-Hydroxy-5E,9Z,11Z,14Z-eicosatetraenoic acid

8-hydroxy-5E,9Z,11Z,14Z-eicosatetraenoic acid

C20H32O3 (320.23513219999995)


   

8S,15S-Dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid

8S,15S-dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid

C20H32O4 (336.2300472)