14,15-episulfide eicosatrienoic acid profile

## 14,15-Episulfide Eicosatrienoic Acid (14,15-EpETE)

14,15-EpETE is a **sulfur-containing fatty acid** that is a **metabolite of arachidonic acid**. It's formed by the enzyme **cytochrome P450**, specifically the CYP2J2 isoform. This means it's a member of the **eicosanoid family**, which includes prostaglandins, leukotrienes, and thromboxanes, all involved in a variety of biological processes.

**What makes it special?**

* **Unique structure:** 14,15-EpETE features a **sulfur bridge** between carbons 14 and 15 of its eicosatrienoic acid backbone. This unique structure gives it distinct properties compared to other eicosanoids.
* **Biological activity:** 14,15-EpETE is known to have **anti-inflammatory**, **pro-resolving**, and **anti-tumor** effects. It also seems to be involved in **blood pressure regulation** and **vascular function**.

**Why is it important for research?**

1. **Potential therapeutic target:** Its diverse biological activity makes it an attractive target for developing new drugs for various diseases, including:
* **Inflammation:** 14,15-EpETE's anti-inflammatory properties could be harnessed for treating inflammatory conditions like rheumatoid arthritis or inflammatory bowel disease.
* **Cancer:** Its potential to inhibit tumor growth makes it an area of study for developing new cancer therapies.
* **Cardiovascular diseases:** Its role in blood pressure regulation and vascular function suggests its potential for treating hypertension and other cardiovascular issues.

2. **Understanding inflammatory pathways:** Studying the mechanisms of action of 14,15-EpETE can help researchers understand how the body controls inflammation and tissue repair, leading to more effective treatment strategies.

3. **Developing new analytical tools:** The unique structure of 14,15-EpETE requires specific analytical methods for detection and quantification. This research can lead to the development of new tools for studying this and other sulfur-containing lipids, which are often overlooked in conventional lipidomics analyses.

**Challenges:**

* **Limited understanding:** Despite its promising potential, our knowledge about 14,15-EpETE's detailed mechanisms of action and its role in various biological processes is still limited.
* **Lack of specific inhibitors:** Currently, there are no specific inhibitors for the enzymes responsible for 14,15-EpETE production, which hinders targeted research.

**Future Research:**

* **More in-depth studies** are needed to understand the specific roles of 14,15-EpETE in different cell types and tissues.
* **Development of specific inhibitors** to modulate its production and study its effects in vivo.
* **Clinical trials** to evaluate its therapeutic potential in human diseases.

Overall, 14,15-EpETE is a fascinating lipid with promising therapeutic potential. Further research is crucial to understand its full biological activity and pave the way for its translation into clinical applications.

14,15-episulfide eicosatrienoic acid: inhibits ionophore but not thrombin-induced platelet aggregation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	6438816
MeSH ID	M0184763

Synonym
14,15-episulfide eicosatrienoic acid
(5e,8e,11e)-13-[(3s)-3-pentylthiiran-2-yl]trideca-5,8,11-trienoic acid
98893-66-4
14,15 epoxyeicosa-5(z)-enoic acid
14,15-cis-episulfide-eicosatrienoic acid
5,8,11-tridecatrienoic acid, 13-(3-pentylthiiranyl)-, (2alpha(5z,8z,11z),3alpha)-

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (12.50)	18.2507
2000's	7 (43.75)	29.6817
2010's	7 (43.75)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	16 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	2.07	1	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
14,15-epoxy-5,8,11-eicosatrienoic acid 14,15-epoxy-5,8,11-eicosatrienoic acid: RN given refers to cpd without isomeric designation	3.13	5	long-chain fatty acid
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.06	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.03	1	dichlorobenzene; ether; imidazoles
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.03	1	adamantanes; polycyclic alkane
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	1.98	1	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.15	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	2.06	1	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
bradykinin [no description available]	2.45	2	oligopeptide	human blood serum metabolite; vasodilator agent
nitroarginine Nitroarginine: An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6). N(gamma)-nitro-L-arginine : An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.	2.06	1	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	1.98	1	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2.05	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
sc 560 SC560 : A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-methoxyphenyl, trifluoromethyl and 4-chlorophenyl groups, respectively. Unlike many members of the diaryl heterocycle class of cyclooxygenase (COX) inhibitors, SC-560 is selective for COX-1.	2.07	1	aromatic ether; monochlorobenzenes; organofluorine compound; pyrazoles	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; cyclooxygenase 1 inhibitor; non-steroidal anti-inflammatory drug
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.07	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
8,11,14-eicosatrienoic acid 8,11,14-Eicosatrienoic Acid: A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.. all-cis-icosa-8,11,14-trienoic acid : An icosatrienoic acid having three cis double bonds at positions 8, 11 and 14.	4.18	16	fatty acid 20:3; long-chain fatty acid	fungal metabolite; human metabolite; nutraceutical
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	1.97	1	thromboxanes B	human metabolite; mouse metabolite
14,15-dihydroxyeicosatrienoic acid (5Z,8Z,11Z)-14,15-dihydroxyicosatrienoic acid : A DHET obtained by formal dihydroxylation across the 14,15-double bond of arachidonic acid.	2.07	1	DHET; diol; secondary allylic alcohol	mouse metabolite
adenosine-3',5'-cyclic phosphorothioate adenosine-3',5'-cyclic phosphorothioate: RP-cAMP-S is a protein kinase A inhibitor; SP-cAMP-S is a protein kinase A agonist. (Sp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Sp-stereoisomer).. (Rp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Rp-stereoisomer).	2.03	1	nucleoside 3',5'-cyclic phosphorothioate
n-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide N-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide: inhibits rat renal microsomal arachidonic acid epoxidation	2.45	2
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	1.97	1	benzoxazole
icatibant icatibant: a potent bradykinin (B2) receptor antagonist; WIN 65365 is an L-Tic(7) stereoisomer. icatibant : A ten-membered synthetic oligopeptide consisting of D-Arg, Arg, Pro, Hyp, Gly, Thi, Ser, D-Tic, Oic, and Arg residues joined in sequrence. A bradykinin receptor antagonist used as its acetate salt for the treatment of acute attacks of hereditary angioedema in adult patients.	2.06	1
11,12-epoxy-5,8,14-eicosatrienoic acid 11,12-epoxy-5,8,14-eicosatrienoic acid: RN given refers to cpd without isomeric designation. (11S,12R)-EET : An 11,12-EET in which the epoxy moiety has 11S,12R-configuration.. 11,12-EET : An EET obtained by formal epoxidation of the 11,12-double bond of arachidonic acid.	2.15	1	11,12-EET	human xenobiotic metabolite
charybdotoxin [no description available]	2.03	1

Condition	Relationship Strength	Studies
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.49	2
Injury, Myocardial Reperfusion [description not available]	2.49	2
Active Hyperemia [description not available]	2.05	1
Hyperemia The presence of an increased amount of blood in a body part or an organ leading to congestion or engorgement of blood vessels. Hyperemia can be due to increase of blood flow into the area (active or arterial), or due to obstruction of outflow of blood from the area (passive or venous).	2.05	1
Cardiovascular Stroke [description not available]	2.06	1
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.06	1
Metabolic Acidosis [description not available]	2.07	1
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	2.07	1
Chronic Kidney Diseases [description not available]	2.07	1
Cirrhosis [description not available]	2.07	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.07	1
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.07	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.03	1
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.04	1
Cerebral Ischemia [description not available]	2.04	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.04	1
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.04	1

14,15-episulfide eicosatrienoic acid

Description

Cross-References

Synonyms (6)

Research

Studies (16)

Market Indicators

Research Demand Index: 12.03

Study Types