Page last updated: 2024-11-10

5-hydroxy-6,8,11,14-eicosatetraenoic acid

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

Description

5(S)-HETE : A HETE having a (5S)-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds. [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]

5-HETE : A HETE having a 5-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds. [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 CID5280733
CHEMBL ID164813
CHEBI ID28209
SCHEMBL ID1476909
MeSH IDM0077607

Synonyms (55)

Synonym
6,8,11,14-eicosatetraenoic acid, 5-hydroxy-, (s-(e,z,z,z))-
5(s)-hydroxyeicosatetraenoic acid
CHEBI:28209 ,
(s)-(e,z,z,z)-5-hydroxyeicosa-6,8,11,14-tetraenoic acid
(5s,6e,8z,11z,14z)-5-hydroxyeicosa-6,8,11,14-tetraenoic acid
(5s,6e,8z,11z,14z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
5(s)-hydroxy-6(e),8(z),11(z),14(z)-eicosatetraenoic acid
5-(s)-hydroxyeicosatetraenoic acid
gtpl3390
5-hydroxyeicosatetraenoic acid
5-hydroxy-6,8,11,14-eicosatetraenoic acid
5s-hete
LMFA03060002
5s-hydroxy-6e,8z,11z,14z-eicosatetraenoic acid
BSPBIO_001443
5-hete
70608-72-9
(6e,8z,11z,14z)-(5s)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
5(s)-hete
5-hydroxyeicosatetraenoate
C04805
IDI1_033913
BCBCMAP01_000020
NCGC00161235-02
NCGC00161235-01
NCGC00161235-03
HMS1989I05
BML1-B01
HMS1791I05
HMS1361I05
CHEMBL164813 ,
bdbm50027525
SCHEMBL1476909
467rnw8t91 ,
unii-467rnw8t91
KGIJOOYOSFUGPC-JGKLHWIESA-N
6,8,11,14-eicosatetraenoic acid, 5-hydroxy-, (5s,6e,8z,11z,14z)-
5-l-hydroxy-6,8,11,14-eicosatetraenoic acid
5-hete, (s)-
5-hete [mi]
5(s)-hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid
HMS3402I05
5s-hydroxy-6,8,11,14-eicosatetraenoic acid
5(s)-hydroxyeicosatetraenoate
5-l-hydroxy-6,8,11,14-eicosatetraenoate
5-hydroxy-6,8,11,14-eicosatetraenoate
5(s)-hydroxy-6-trans-8,11,14-cis-eicosatetraenoate
5s-hydroxy-6,8,11,14-eicosatetraenoate
Q2823230
SR-01000946914-1
sr-01000946914
DTXSID701017281
5(s)-hete lipid maps(r) ms standard
CS-0059517
HY-113434

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The parent compound 4 is a selective, orally bioavailable 5-LO inhibitor which can serve as a useful reference standard for in vivo pharmacological studies involving leukotriene-mediated phenonmena."( 5-Lipoxygenase inhibitors: synthesis and structure-activity relationships of a series of 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-ones.
Basha, A; Bell, RL; Bhatia, PA; Bouska, JB; Brooks, CD; Carter, GW; Gunn, BP; Lanni, C; Ratajczyk, JD; Young, PR, 1996
)
0.29

Dosage Studied

ExcerptRelevanceReference
" A dose-response curve was constructed and revealed that the above changes became evident when the platelet number exceeded 10(7)."( Transcellular lipoxygenase metabolism between monocytes and platelets.
Bigby, TD; Meslier, N, 1989
)
0.28
" PGF-A enhanced both mucous glycoprotein release and the 5- and 15-lipoxygenation of arachidonic acid as well as the formation of leukotriene B4 (LTB4) with similar dose-response relationships."( Prostaglandin-generating factor of anaphylaxis induces mucous glycoprotein release and the formation of lipoxygenase products of arachidonate from human airways.
Goetzl, EJ; Kaliner, M; Marom, Z; Shelhamer, JH; Steel, L, 1984
)
0.27
" Dose-response curves for both isomers through cellular monolayers had the same shapes, but 5(R)-HETE was more potent than 5(S)-HETE."( 5-Hydroxyeicosatetraenoic acid (HETE)-induced neutrophil transcellular migration is dependent upon enantiomeric structure.
Bittleman, DB; Casale, TB, 1995
)
0.29
" Although its ability to inhibit the cyclooxygenase pathway was readily observed in whole blood and in vivo, tenidap's 5-LO blockade could not be demonstrated by ionophore stimulated human blood, nor after oral dosing in rat models in which peritoneal leukotriene products were measured after challenge with three different stimuli."( Tenidap inhibits 5-lipoxygenase product formation in vitro, but this activity is not observed in three animal models.
Carty, TJ; Cheng, JD; Ernest, MJ; Eskra, JD; Griffiths, RJ; Joseph, PA; Kadin, SB; Loose, LD; Moore, PF; Murase, S; Nagahisa, A; Pazoles, PP; Pillar, JS; Sweeney, FJ, 1997
)
0.3
" Dose-response studies indicated that 5-HPETE was a potent (IC25 = 10(-8) M) inhibitor of Na+, K(+)-ATPase activity."( 5-HPETE is a potent inhibitor of neuronal Na+, K(+)-ATPase activity.
Foley, TD, 1997
)
0.3
" This study evaluated the effect of n-3 PUFA in a low, but recommended cardioprotective dosage on the formation of 5-lipoxygenase pathway metabolites in overweight subjects."( The effect of low-dose marine n-3 fatty acids on the biosynthesis of pro-inflammatory 5-lipoxygenase pathway metabolites in overweight subjects: a randomized controlled trial.
Aardestrup, I; Gammelmark, A; Madsen, T; Nielsen, MS; Obel, T; Schmidt, EB, 2012
)
0.38
[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 (1)

ClassDescription
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 (49)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Fatty acid metabolism113203
Arachidonic acid metabolism3682
Synthesis of 5-eicosatetraenoic acids615
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
Arachidonic acid (AA, ARA) oxylipin metabolism076
Folic acid network070
Selenium micronutrient network095
Eicosanoid synthesis026

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Microtubule-associated protein tauHomo sapiens (human)Potency0.12590.180013.557439.8107AID1460
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency11.22021.000010.475628.1838AID1457
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)IC50 (µMol)2.00000.00011.68479.3200AID6952
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
negative regulation of endothelial cell proliferationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte chemotaxis involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte migration involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
humoral immune responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of bone mineralizationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
dendritic cell migrationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
glucose homeostasisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
long-chain fatty acid biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of fat cell differentiationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of insulin secretionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of vascular wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory response to woundingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cytokine production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cellular response to oxidative stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene A4 biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of reactive oxygen species biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of sprouting angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cellPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxin biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
arachidonate 5-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 12(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
iron ion bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
protein bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
hydrolase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
extracellular spacePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelope lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nucleoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
cytosolPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear matrixPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear membranePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
secretory granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
perinuclear region of cytoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
ficolin-1-rich granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID6952Inhibitory activity against 5-lipoxygenase1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Synthesis and 5-lipoxygenase inhibitory activities of eicosanoid compounds.
AID1346064Human OXE receptor (Leukotriene receptors)1994Biochimica et biophysica acta, Dec-15, Volume: 1201, Issue:3
Chemical and biological characterization of oxo-eicosatetraenoic acids.
AID1346064Human OXE receptor (Leukotriene receptors)2005Biochemical and biophysical research communications, Sep-09, Volume: 334, Issue:4
TG1019/OXE, a Galpha(i/o)-protein-coupled receptor, mediates 5-oxo-eicosatetraenoic acid-induced chemotaxis.
AID1346064Human OXE receptor (Leukotriene receptors)1993The Journal of biological chemistry, May-05, Volume: 268, Issue:13
Stimulation of human neutrophils by 5-oxo-6,8,11,14-eicosatetraenoic acid by a mechanism independent of the leukotriene B4 receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (641)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990287 (44.77)18.7374
1990's222 (34.63)18.2507
2000's72 (11.23)29.6817
2010's45 (7.02)24.3611
2020's15 (2.34)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 7.84

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index7.84 (24.57)
Research Supply Index6.48 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (7.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (0.77%)5.53%
Reviews18 (2.78%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other625 (96.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]