Page last updated: 2024-12-10

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

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

Description

## 15-Hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE)

**What it is:** 15-HETE is a **hydroxy fatty acid** derived from the oxidation of **arachidonic acid**, a type of omega-6 fatty acid commonly found in cell membranes.

**How it's formed:** It's produced by the enzyme **15-lipoxygenase** (15-LOX), a key player in the arachidonic acid cascade.

**Importance in research:**

15-HETE has been implicated in a wide range of biological processes, making it a significant focus of research across different fields:

* **Inflammation and Immune Response:** 15-HETE can contribute to both pro-inflammatory and anti-inflammatory effects. It influences leukocyte adhesion, neutrophil activation, and cytokine production, suggesting its involvement in various inflammatory conditions.
* **Cancer:** Studies suggest 15-HETE can influence cancer cell growth, proliferation, angiogenesis, and metastasis. Its potential role in cancer progression and potential therapeutic targets are actively investigated.
* **Cardiovascular Disease:** 15-HETE impacts vascular tone, platelet aggregation, and blood pressure regulation. Its involvement in the development and progression of cardiovascular diseases is under investigation.
* **Neurological Disorders:** 15-HETE has been associated with neuronal damage and neuroinflammation, potentially contributing to conditions like Alzheimer's disease and Parkinson's disease.
* **Metabolic Disorders:** 15-HETE can affect insulin sensitivity, lipid metabolism, and glucose homeostasis, potentially impacting metabolic disorders like diabetes.

**Potential Therapeutic Applications:**

* 15-HETE's diverse biological activities have led to research exploring its potential therapeutic applications:
* **Anti-cancer therapy:** Targeting 15-HETE pathways might offer new avenues for cancer treatment.
* **Anti-inflammatory agents:** Modulating 15-HETE levels could be beneficial in managing inflammatory diseases.
* **Cardiovascular protection:** Developing strategies to control 15-HETE levels could offer cardiovascular protection.
* **Neuroprotective agents:** Targeting 15-HETE production might offer potential neuroprotective benefits.

**Ongoing Research:**

The exact mechanisms by which 15-HETE exerts its effects are still being investigated. Researchers are actively trying to:

* Determine the precise cellular signaling pathways activated by 15-HETE.
* Develop specific inhibitors of 15-LOX to control 15-HETE production.
* Explore the potential therapeutic applications of 15-HETE and its modulation.

**In conclusion, 15-HETE is a crucial molecule with significant biological implications. Its role in various physiological processes, including inflammation, cancer, cardiovascular health, and neurological function, makes it a vital subject of ongoing research, with potential for future therapeutic interventions.**

## 15-Hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE)

15-HETE is a **lipid mediator** derived from the metabolism of arachidonic acid by the enzyme **15-lipoxygenase (15-LOX)**. It is a potent bioactive molecule with a variety of physiological and pathological roles.

### Importance in Research:

15-HETE is a key player in diverse biological processes, making it a focus of research in many areas. Here are some key reasons why it is important:

* **Inflammation:** 15-HETE can both promote and suppress inflammation, depending on the context. It can contribute to the inflammatory response by attracting immune cells and promoting the release of inflammatory mediators. However, it can also exert anti-inflammatory effects by inhibiting the production of other inflammatory mediators.
* **Cardiovascular disease:** 15-HETE has been implicated in the development and progression of cardiovascular disease. It can contribute to atherosclerosis by promoting platelet aggregation, vascular smooth muscle cell proliferation, and inflammation. However, it may also have protective effects in the cardiovascular system, depending on the specific context.
* **Cancer:** 15-HETE has been linked to both cancer development and suppression. It can promote cancer cell growth and proliferation in certain cancers, but it can also inhibit cancer cell growth in others. The role of 15-HETE in cancer remains complex and requires further investigation.
* **Neurological function:** 15-HETE plays a role in neuronal signaling and can influence neurotransmission. It has been implicated in the development of neurodegenerative diseases like Alzheimer's and Parkinson's disease, as well as in the pathogenesis of stroke.
* **Other roles:** 15-HETE is also involved in various other biological processes, including wound healing, immune response, and renal function.

**Research on 15-HETE focuses on understanding its diverse biological effects, its role in disease development, and its potential as a therapeutic target.** Researchers are investigating how to modulate 15-HETE levels in the body to treat various diseases, including cancer, cardiovascular disease, and inflammatory disorders.

### Summary:

15-HETE is a key player in various biological processes, including inflammation, cardiovascular disease, cancer, and neurological function. Research on this molecule is essential for understanding its diverse roles and for developing novel therapeutic strategies targeting 15-HETE pathways.

15-hydroxy-5,8,11,13-eicosatetraenoic acid: potent & selective inhibitor of platelet lipoxygenase; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

15(S)-HETE : An optically active form of 15-HETE having 15(S)-configuration.. [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 CID5353283
SCHEMBL ID1478265
MeSH IDM0085804
PubMed CID5280724
CHEMBL ID594621
CHEBI ID15558
SCHEMBL ID994674
MeSH IDM0085804

Synonyms (70)

Synonym
73945-47-8
15-hydroxy-5,8,11,13-eicosatetraenoic acid
(5e,8e,11e,13e)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
SCHEMBL1478265
5,8,11,13-eicosatetraenoic acid, 15-hydroxy-
sodiumdiamylsulfosuccinate
gtpl3401
CHEBI:15558 ,
15(s)-hydroxyeicosatetraenoic acid
(5z,8z,11z,13e,15s)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
icomucret
(5z,8z,11z,13e,15s)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid
15s-hete
(5z,8z,11z,13e,15s)-15-hydroxy-5,8,11,13-eicosatetraenoic acid
(15s)-hydroxyeicosa-(5z,8z,11z,13e)-tetraenoic acid
(15s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoic acid
LMFA03060001
15s-hydroxy-5z,8z,11z,13e-eicosatetraenoic acid
(5z,8z,11z,13e)-(15s)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
54845-95-3
15(s)-hete
C04742
(15s)-15-hydroxy-5,8,11-cis-13-trans-eicosatetraenoate
(15s)-15-hydroxy-5,8,11-cis-13-trans-icosatetraenoate
15 hete
15-hete
15(s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoic acid, ~150 mug/ml in ethanol, >=97.0% (hplc)
IDI1_033807
BSPBIO_001337
NCGC00161242-01
NCGC00161242-02
NCGC00161242-03
HMS1989C19
BML1-B09
D08931
icomucret (usan)
HMS1791C19
HMS1361C19
al-12959
CHEMBL594621
unii-44jhk6g39q
44jhk6g39q ,
icomucret [usan:inn]
15(s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoic acid
(15s,5z,8z,11z,13e)-15-hydroxyeicosatetraenoic acid
(s)-15-hete
5,8,11,13-eicosatetraenoic acid, 15-hydroxy-, (5z,8z,11z,13e,15s)-
icomucret [usan]
icomucret [inn]
bdbm50421764
SCHEMBL994674
HMS3402C19
(15s)-15-hydroxy-5,8,11-cis-13-trans-icosatetraenoic acid
(15s,5z,8z,11z,13e)-15-hydroxyeicosatetraenoate
(15s)-15-hydroxy-5,8,11-cis-13-trans-eicosic acid
(15s)-15-hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid
(5z,8z,11z,13e)-(15s)-15-hydroxyicosa-5,8,11,13-tetraenoate
15s-hydroxy-5z,8z,11z,13e-eicosatetraenoate
15(s)-hydroxy-(5z,8z,11z,13e)-eicosatetraenoate
5z,8z,11z,13e,15s)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
SR-01000946930-1
sr-01000946930
Q21099561
15(s)-hydroxy-5(z),8(z),11(z),13(e)-eicosatetraenoic acid
15(s)-hydroxyeicosa-5z,8z,11z,13e-tetraenoic acid
STARBLD0018619
CS-0059635
HY-113336
DTXSID101031956
AKOS040752060

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response studies showed that both lipoxin A and lipoxin B inhibit, at submicromolar concentrations (ID50 10(-7) M), NK cell activity assayed against K562 target cells."( Action of novel eicosanoids lipoxin A and B on human natural killer cell cytotoxicity: effects on intracellular cAMP and target cell binding.
Ng, J; Ramstedt, U; Samuelsson, B; Serhan, CN; Wigzell, H, 1985
)
0.27
" In dose-response studies using TRH concentrations of 10(-6) M to 10(-12) M, the highest level of 9 HETE release was obtained at 10(-11) M TRH and the highest release of 15 HETE was at 10(-9) M TRH."( Arachidonic acid metabolism in a cloned strain of rat pituitary tumor cells: correlation between 15 hydroxyeicosatetraenoic acid release and the prolactin secretory process.
Chavis, C; Crastes de Paulet, A; Damon, M; Rabier, M, 1987
)
0.27
" 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
" There was no evidence of tachyphylaxis following repeated topical ocular dosing of 15(S)-HETE."( Corneal protection by the ocular mucin secretagogue 15(S)-HETE in a rabbit model of desiccation-induced corneal defect.
Gamache, DA; Miller, ST; Spellman, JM; Wei, ZY; Weimer, LK; Yanni, JM, 2002
)
0.31
[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
(5Z,8Z,11Z,13E)-15-HETEA HETE that is (5Z,8Z,11Z,13E)-15-hydroxyicosa-5,8,11,13-tetraenoic acid bearing a hydroxy substituent at position 15.
[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 15-eicosatetraenoic acid derivatives314
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 cyclooxygenases (COX)137
Eicosanoid metabolism via lipoxygenases (LOX)040
Selenium micronutrient network095
Eicosanoid synthesis026

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency44.66840.003245.467312,589.2998AID2517
[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-lipoxygenaseRattus norvegicus (Norway rat)IC50 (µMol)5.35000.00462.018210.0000AID6781; AID6794; AID6809
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID6794Inhibition of rat basophilic leukemia-1 (RBL-1) 5-lipoxygenase1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues.
AID455093Inhibition of soybean LO1 assessed as increase in arachidonic acid/linoleic acid ratio by substrate specificity assay2009Bioorganic & medicinal chemistry, Sep-15, Volume: 17, Issue:18
Substrate specificity effects of lipoxygenase products and inhibitors on soybean lipoxygenase-1.
AID6781Inhibition of rat neutrophil 5- Lipoxygenase (5-LO)1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Substituted arylmethyl phenyl ethers. 1. A novel series of 5-lipoxygenase inhibitors and leukotriene antagonists.
AID6809In vitro inhibitory activity against RBL-1 5-LO1987Journal of medicinal chemistry, Mar, Volume: 30, Issue:3
Hydroxamic acid inhibitors of 5-lipoxygenase.
AID1346050Human BLT2 receptor (Leukotriene receptors)2001The Journal of biological chemistry, Apr-13, Volume: 276, Issue:15
Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (728)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990209 (28.71)18.7374
1990's269 (36.95)18.2507
2000's115 (15.80)29.6817
2010's125 (17.17)24.3611
2020's10 (1.37)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.01

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 Index12.01 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.09 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.01)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials13 (1.75%)5.53%
Trials0 (0.00%)5.53%
Reviews21 (2.83%)6.00%
Reviews0 (0.00%)6.00%
Case Studies1 (0.13%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other707 (95.28%)84.16%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]