Page last updated: 2024-11-07

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

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

20-hydroxy-5,8,11,14-eicosatetraenoic acid: stimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

20-HETE : A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5283157
CHEMBL ID4085458
CHEBI ID34306
SCHEMBL ID505713
MeSH IDM0157282

Synonyms (32)

Synonym
CHEBI:34306
20-hydroxyarachidonic acid
20-hydroxy-5,8,11,14-eicosatetraenoic acid
5,8,11,14-eicosatetraenoic acid, 20-hydroxy-, (all-z)-
20-hydroxy-5z,8z,11z,14z-eicosatetraenoic acid
LMFA03060009
20-hete
20-hydroxy arachidonic acid
20-hydroxyicosatetraenoic acid
(5z,8z,11z,14z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid
79551-86-3
20-hydroxyeicosatetraenoic acid
20-hydroxy-(5z,8z,11z,14z)-eicosatetraenoic acid, ~100 mug/ml in ethanol, >=90% (hplc)
5,8,11,14-eicosatetraenoicacid, 20-hydroxy-, (5z,8z,11z,14z)-
20-hydroxy-(5z,8z,11z,14z)-eicosatetraenoic acid
gtpl4103
HY-15598
CS-1451
SCHEMBL505713
AKOS027327565
20-hydroxyicosatetraenoate
20-hydroxy-5z,8z,11z,14z-eicosatetraenoate
(all-z)-20-hydroxy-5,8,11,14-eicosatetraenoic acid
20-hydroxy-5,8,11,14-eicosatetraenoate
(all-z)-20-hydroxy-5,8,11,14-eicosatetraenoate
DTXSID601009895
20-hydroxyeicosatetraeonic acid
sr-01000946981
SR-01000946981-1
Q21099666
20-hydroxy-5(z),8(z),11(z),14(z)-eicosatetraenoic acid
CHEMBL4085458

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The present study evaluated whether reactive oxygen species-induced alterations in bioavailability of 20-HETE in the kidney contribute to the antihypertensive and renoprotective actions of antioxidant therapy with Tempol in the Dahl salt-sensitive (DS) rat."( Contributions of 20-HETE to the antihypertensive effects of Tempol in Dahl salt-sensitive rats.
Hoagland, KM; Maier, KG; Roman, RJ, 2003
)
0.32
"Nitric oxide (NO), generated from L-arginine by endothelial nitric oxide synthase (eNOS), is a key endothelial-derived factor whose bioavailability is essential to the normal function of the endothelium."( 20-hydroxyeicosatetraenoic acid causes endothelial dysfunction via eNOS uncoupling.
Cheng, J; Falck, JR; Narsimhaswamy, D; Ou, JS; Pritchard, KA; Schwartzman, ML; Singh, H, 2008
)
0.35
" Long-lasting high sodium intake lowers NO bioavailability and promotes systemic and intrarenal vasoconstrictor activity of 20-HETE."( Cytochrome P-450 metabolites in renal circulation and excretion--interaction with the nitric oxide (NO) system.
Kompanowska-Jezierska, E; Kuczeriszka, M, 2008
)
0.35
" Inhibition in TGR of 20-HETE formation combined with enhanced bioavailability of EETs attenuated the development of hypertension, cardiac hypertrophy, proteinuria, glomerular hypertrophy and sclerosis as well as renal tubulointerstitial injury."( Combined inhibition of 20-hydroxyeicosatetraenoic acid formation and of epoxyeicosatrienoic acids degradation attenuates hypertension and hypertension-induced end-organ damage in Ren-2 transgenic rats.
Certíková Chábová, V; Cervenka, L; Falck, JR; Hammock, BD; Imig, JD; Kompanowska-Jezierska, E; Kopkan, L; Kramer, HJ; Kujal, P; Sadowski, J; Vanecková, I; Vanourková, Z; Vernerová, Z; Walkowska, A, 2010
)
0.36
" A previous study indicated that bioavailability of cytochrome P-450 metabolites epoxyeicosatrienoic acids (EETs) is decreased while that of 20-hydroxyeicosatetraenoic acids (20-HETE) is increased in this model."( Role of cytochrome P-450 metabolites in the regulation of renal function and blood pressure in 2-kidney 1-clip hypertensive rats.
Cervenka, L; Hammock, BD; Husková, Z; Hwang, SH; Imig, JD; Kopkan, L; Kramer, HJ; Sporková, A; Varcabová, S, 2011
)
0.37
" Vascular relaxation responses to the NO donor C(5)FeN(6)Na(2)O were intact in both SS and SS-5(BN) rats and unaffected by the acute addition of DDMS, indicating that the vascular dysfunction of the SS rat is due to a reduced bioavailability of NO instead of failure of the VSMCs (vascular smooth muscle cells) to respond to the vasodilator."( Introgression of Brown Norway CYP4A genes on to the Dahl salt-sensitive background restores vascular function in SS-5(BN) consomic rats.
Falck, JR; Lombard, JH; Lukaszewicz, KM; Manthati, VL, 2013
)
0.39
" Increasing epoxyeicosanoid bioavailability by inhibiting their degradation induced a tocolytic effect in the non-pregnant group (20%) and in inflammation-induced condition (40%)."( Effect of cytochrome P-450 epoxygenase and hydroxylase metabolites on rat myometrium contractility in non-pregnancy, late pregnancy and late pregnancy under inflammatory conditions.
Berthiaume, M; Corriveau, S; Girard, I; Nolin, MA; Pasquier, JC; Rousseau, E, 2014
)
0.4
" In summary, in combination with NO, the increased EET bioavailability as a function of genetic deletion and/or downregulation of sEH accounts for the female-favorable attenuation of pressure-induced vasoconstriction."( Female-favorable attenuation of coronary myogenic constriction via reciprocal activations of epoxyeicosatrienoic acids and nitric oxide.
Froogh, G; Huang, A; Jiang, H; Kandhi, S; Le, Y; Luo, M; Qin, J; Sun, D, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" The potentiating effect of 20-HETE resulted in a shifting to the left of the dose-response curve to Epo."( Modulation of erythropoiesis by novel human bone marrow cytochrome P450-dependent metabolites of arachidonic acid.
Abraham, NG; Falck, JR; Feldman, E; Lutton, JD; Schwartzman, ML, 1991
)
0.28
" Arteries were contracted with noradrenaline and then exposed to one cumulative dose-response curve to acetylcholine in absence (control) or in presence of indomethacin, (N-[2-cyvlohexyloxy)-4-nitrophenyl]-methanesulfonamide) (NS 398) or 4-hydroxy-2,2,6,6-tetraethylpiperidine-N-oxyl (tempol)."( Endothelial dysfunction and improvement of the angiotensin II-reactivity in hypercholesterolemic rabbits: role of cyclooxygenase metabolites.
Coviello, A; de Bruno, MP; Jerez, S; Sierra, L, 2008
)
0.35
"5-15 mg/kg), the effective dosage range of diclofenac was identified (> 5 mg/kg/day)."( Dose-dependency of the cardiovascular risks of non-steroidal anti-inflammatory drugs.
Ahmed, SA; Al-Lawati, H; Jamali, F, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
hydroxy monocarboxylic acidAny monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent.
HETEAny monohydroxylated icosanoid having four double bonds.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (52)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Fatty acid metabolism113203
Arachidonic acid metabolism3682
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)08
Arachidonic Acid Metabolism2966
Leukotriene C4 Synthesis Deficiency2966
Piroxicam Action Pathway2967
Acetylsalicylic Acid Action Pathway2967
Etodolac Action Pathway2967
Ketoprofen Action Pathway2967
Ibuprofen Action Pathway5076
Rofecoxib Action Pathway2967
Diclofenac Action Pathway2967
Sulindac Action Pathway2967
Celecoxib Action Pathway3573
Ketorolac Action Pathway2967
Suprofen Action Pathway2967
Bromfenac Action Pathway2967
Indomethacin Action Pathway3067
Mefenamic Acid Action Pathway2967
Oxaprozin Action Pathway2967
Nabumetone Action Pathway2967
Naproxen Action Pathway2967
Diflunisal Action Pathway2967
Meloxicam Action Pathway2967
Valdecoxib Action Pathway2967
Antipyrine Action Pathway2967
Antrafenine Action Pathway2967
Carprofen Action Pathway2967
Etoricoxib Action Pathway2967
Fenoprofen Action Pathway2967
Flurbiprofen Action Pathway2967
Magnesium Salicylate Action Pathway2967
Lumiracoxib Action Pathway2967
Lornoxicam Action Pathway2967
Phenylbutazone Action Pathway2967
Nepafenac Action Pathway2967
Trisalicylate-Choline Action Pathway2967
Tolmetin Action Pathway2967
Tiaprofenic Acid Action Pathway2967
Tenoxicam Action Pathway2967
Salsalate Action Pathway2967
Salicylate-Sodium Action Pathway2967
Salicylic Acid Action Pathway2967
Acetaminophen Action Pathway2967
Eicosanoid metabolism via cytochrome P450 monooxygenases pathway113
RAS and bradykinin pathways in COVID-19113
Arachidonic acid (AA, ARA) oxylipin metabolism076
Angiotensin II signaling (acute) in thick ascending limbs08
Eicosanoid metabolism via cytochrome P450 monooxygenases213
Vascular smooth muscle contraction013
Arachidonic acid metabolism via CYP (Cytochromoe P450) pathway014

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1434437Agonist activity at recombinant mouse TRPV1 expressed in HEK293 cells assessed as increase in calcium influx up to 10 uM measured for 380 sec by Fluo-4 dye based FLIPR assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.
AID1434434Induction of mechanical allodynia in Sprague-Dawley rat assessed as decrease in contralateral hind paw withdrawal threshold at 3 ug administered as intraplantar injection measured up to 150 mins post dose by Von Frey assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.
AID1434433Induction of mechanical allodynia in Sprague-Dawley rat assessed as decrease in ipsilateral hind paw withdrawal threshold administered as intraplantar injection measured up to 150 mins post dose by Von Frey assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.
AID1434439Inhibition of ovine COX1 at 100 uM using arachidonic acid as substrate after 2 mins by fluorometric substrate-based fluorescence assay relative to control2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.
AID1434440Inhibition of human COX2 at 100 uM using arachidonic acid as substrate after 2 mins by fluorometric substrate-based fluorescence assay relative to control2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.
AID1434432Induction of mechanical allodynia in Sprague-Dawley rat assessed as decrease in withdrawal threshold at 1 ug administered as intraplantar injection measured up to 150 mins post dose by Von Frey assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (618)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (0.49)18.7374
1990's81 (13.11)18.2507
2000's278 (44.98)29.6817
2010's219 (35.44)24.3611
2020's37 (5.99)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials13 (2.03%)5.53%
Reviews65 (10.16%)6.00%
Case Studies0 (0.00%)4.05%
Observational2 (0.31%)0.25%
Other560 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]