Classification Term: 170929

Hydroxy-hydroperoxyeicosatetraenoic acids (ontology term: 18f23891943693316656825fd42c08ac)

found 33 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Eicosanoids

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

20-Hydroxyeicosatetraenoic acid

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

C20H32O3 (320.2351)


20-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor of renal, cerebral, and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase, and the mitogen-activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal, and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries. A fall in levels of 20-HETE contributes to the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries (PMID: 16258232). Metabolite produced during NADPH dependent enzymatic oxidation of arachidonic acid. Potent vasoconstrictor [CCD]

   

5-HETE

(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

C20H32O3 (320.2351)


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.

   

15(S)-HPETE

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

C20H32O4 (336.23)


15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983). D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

   

8(R)-HETE

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

C20H32O3 (320.2351)


A HETE having an (8R)-hydroxy group and (5Z)-, (9E)-, (11Z)- and (14Z)-double bonds.

   

12-Hydroperoxy-icosatetraenoic acid

12-hydroperoxyicosa-2,4,6,8-tetraenoic acid

C20H32O4 (336.23)


   

N-(2-Hydroxyethyl)eicosa-5,8,11,14-tetraenamide

N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid

C22H37NO2 (347.2824)


   

20-HETE

20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid

C20H32O3 (320.2351)


A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20.

   

5R-HETE

5R-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid

C20H32O3 (320.2351)


   

8R-HPETE

(5Z,9E,11Z,14Z)-(8R)-8-Hydroxyperoxyeicosa-5,9,11,14-tetraenoate

C20H32O4 (336.23)


   

15(S)-HPETE

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

C20H32O4 (336.23)


D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides The (S)-enantiomer of 15-HPETE. 15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983) [HMDB]

   

15-Oxo-ETE

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

C20H30O3 (318.2195)


An oxoicosatetraenoic acid having (5Z,8Z,11Z,13E) double bond stereochemistry, and an oxo group in position 15.

   

11R-HETE

(5Z,8Z,12E,14Z)-(11R)-Hydroxyeicosa-5,8,12,14-tetraenoic acid

C20H32O3 (320.2351)


An 11-HETE in which the chiral centre at position 11 has R-configuration.

   

ethyl 15-hydroxyicosa-5,8,11,13-tetraenoate

ethyl 15-hydroxyicosa-5,8,11,13-tetraenoate

C22H36O3 (348.2664)


   

(5s)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

(5s)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

C20H32O3 (320.2351)


   

(15r,16e)-15-hydroxytetracosa-6,9,12,16,18-pentaenoic acid

(15r,16e)-15-hydroxytetracosa-6,9,12,16,18-pentaenoic acid

C24H38O3 (374.2821)


   

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

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

C20H32O3 (320.2351)


   

ethyl (5z,8z,11z,13s,14z)-13-hydroxyicosa-5,8,11,14-tetraenoate

ethyl (5z,8z,11z,13s,14z)-13-hydroxyicosa-5,8,11,14-tetraenoate

C22H36O3 (348.2664)


   

(5e,8e,10e,12s,14e)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

(5e,8e,10e,12s,14e)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

C20H32O3 (320.2351)


   

(12e)-11-hydroxyicosa-5,8,12,14-tetraenoic acid

(12e)-11-hydroxyicosa-5,8,12,14-tetraenoic acid

C20H32O3 (320.2351)


   

(5e,8z,11e,14e)-8-hydroxyicosa-5,8,11,14-tetraenoic acid

(5e,8z,11e,14e)-8-hydroxyicosa-5,8,11,14-tetraenoic acid

C20H32O3 (320.2351)


   

11-hydroperoxyicosa-2,4,6,8-tetraenoic acid

11-hydroperoxyicosa-2,4,6,8-tetraenoic acid

C20H32O4 (336.23)


   

(6e,9e,12e,15r,16e,18z)-15-hydroxytetracosa-6,9,12,16,18-pentaenoic acid

(6e,9e,12e,15r,16e,18z)-15-hydroxytetracosa-6,9,12,16,18-pentaenoic acid

C24H38O3 (374.2821)


   

ethyl (5z,8z,11z,13e,15s)-15-hydroxyicosa-5,8,11,13-tetraenoate

ethyl (5z,8z,11z,13e,15s)-15-hydroxyicosa-5,8,11,13-tetraenoate

C22H36O3 (348.2664)


   

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

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

C20H32O3 (320.2351)


   

(11r)-11-hydroxyicosa-5,8,12,14-tetraenoic acid

(11r)-11-hydroxyicosa-5,8,12,14-tetraenoic acid

C20H32O3 (320.2351)


   

(5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid

(5z,8z,11z,14z)-n-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid

C22H37NO2 (347.2824)


   

(6e)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

(6e)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

C20H32O3 (320.2351)


   

methyl (5z,8z,10e,12s,14z)-12-hydroxyicosa-5,8,10,14-tetraenoate

methyl (5z,8z,10e,12s,14z)-12-hydroxyicosa-5,8,10,14-tetraenoate

C21H34O3 (334.2508)


   

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

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

C20H32O3 (320.2351)


   

(6z,9z,11s,12z)-11-hydroxyoctadeca-6,9,12-trienoic acid

(6z,9z,11s,12z)-11-hydroxyoctadeca-6,9,12-trienoic acid

C18H30O3 (294.2195)


   

methyl 12-hydroxyicosa-5,8,10,14-tetraenoate

methyl 12-hydroxyicosa-5,8,10,14-tetraenoate

C21H34O3 (334.2508)


   

ethyl 13-hydroxyicosa-5,8,11,14-tetraenoate

ethyl 13-hydroxyicosa-5,8,11,14-tetraenoate

C22H36O3 (348.2664)


   

(5e,8e,11r,12e,14e)-11-hydroxyicosa-5,8,12,14-tetraenoic acid

(5e,8e,11r,12e,14e)-11-hydroxyicosa-5,8,12,14-tetraenoic acid

C20H32O3 (320.2351)