Compounds > 17,18-epoxy-5,8,11,14-eicosatetraenoic acid
Page last updated: 2024-11-12

17,18-epoxy-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 Market Indicators

Description

17,18-epoxy-5,8,11,14-eicosatetraenoic acid: can be metabolized to novel epoxyprostaglandins [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID16061089
CHEMBL ID1802674
CHEBI ID72853
SCHEMBL ID655399
MeSH IDM0191688

Synonyms (20)

Synonym
(+/-)-17(18)-epoxy-5z,8z,11z,14z-eicosatetraenoic acid
LMFA03000004
17r,18s-epoxy-5z,8z,11z,14z-icosatetraenoic acid
(5e,8e,11e,14e)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid
chebi:72853 ,
CHEMBL1802674
17,18-eetetr
17,18-eeq
17,18-epoxyicosatetraenoic acid
(5z,8z,11z,14z)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid
17,18-epoxyeicosatetraenoic acid
17,18-epete
17,18-epoxy-5,8,11,14-eicosatetraenoic acid
SCHEMBL655399
17r,18s-epoxy-5z,8z,11z,14z-icosatetraenoate
(5z,8z,11z,14z)-(17r,18s)-17,18-epoxyicosa-5,8,11,14-tetraenoate
17,18-epoxy-5,8,11,14-eicosatetraenoate
17r,18s-epoxy-5z,8z,11z,14z-eicosatetraenoate
(5e,8e,11e,14e)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoate
Q27140189
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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
EpETEAn epoxy fatty acid obtained by formal epoxidation of one of the double bonds of any icosapentaenoic acid.
[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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID606174Metabolic stability in rat liver homogenates assessed as hydroxylation of compound by LC-MS analysis2011Journal of medicinal chemistry, Jun-23, Volume: 54, Issue:12
17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues.
AID606164Negative chronotropic activity in neonatal Wistar rat Cardiomyocytes assessed as change in heart beating at 30 nM and at 37 degC after 5 mins2011Journal of medicinal chemistry, Jun-23, Volume: 54, Issue:12
17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues.
AID606173Metabolic stability in rat liver homogenates assessed as epoxidation of compound by LC-MS analysis2011Journal of medicinal chemistry, Jun-23, Volume: 54, Issue:12
17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues.
AID606172Metabolic stability in rat liver homogenates assessed as formation of vic-diol 4 by LC-MS analysis2011Journal of medicinal chemistry, Jun-23, Volume: 54, Issue:12
17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues.
AID606175Metabolic stability in rat liver homogenates after 30 mins by LC-MS analysis2011Journal of medicinal chemistry, Jun-23, Volume: 54, Issue:12
17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (8.33)18.2507
2000's4 (16.67)29.6817
2010's14 (58.33)24.3611
2020's4 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.86

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 Index11.86 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
14,15-epoxy-5,8,11-eicosatrienoic acid
14,15-epoxy-5,8,11-eicosatrienoic acid: RN given refers to cpd without isomeric designation		2.0510long-chain fatty acid
glyburide
Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.		2.0510monochlorobenzenes;
N-sulfonylurea		anti-arrhythmia drug;
EC 2.7.1.33 (pantothenate kinase) inhibitor;
EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor;
hypoglycemic agent
alkenes
[no description available]		2.0610
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.110D-glucopyranoseepitope;
mouse metabolite
thromboxanes
thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.		2.0810
prostaglandins b
Prostaglandins B: Physiologically active prostaglandins found in many tissues and organs. They are potent pressor substances and have many other physiological activities.		1.9810
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		2.0210icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
eicosapentaenoic acid
icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.		3.360icosapentaenoic acid;
omega-3 fatty acid		anticholesteremic drug;
antidepressant;
antineoplastic agent;
Daphnia galeata metabolite;
fungal metabolite;
micronutrient;
mouse metabolite;
nutraceutical
ovalbumin
Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.		2.0710
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.		2.4420fatty acid 20:3;
long-chain fatty acid		fungal metabolite;
human metabolite;
nutraceutical
thromboxane b3
thromboxane B3 : A member of the class of thromboxanes B that is (5Z,13E,17Z)-thromboxa-5,13,17-trien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.		2.0810thromboxanes Bhuman metabolite;
mouse metabolite
19-hydroxy-5,8,11,14-eicosatetraenoic acid
19-hydroxy-5,8,11,14-eicosatetraenoic acid: potent stimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer		2.0210
5-hydroxy-6,8,11,14,17-eicosapentaenoic acid
5-hydroxy-6,8,11,14,17-eicosapentaenoic acid: RN given refers to (E,Z,Z,Z,Z)-isomer; RN for cpd without isomeric designation not available 4/89. 5-HEPE : A hydroxyicosapentaenoic acid that consists of 6E,8Z,11Z,14Z,17Z-icosapentaenoic acid with the hydroxy group located at position 5.		2.1510HEPEmouse metabolite
n-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide
N-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide: inhibits rat renal microsomal arachidonic acid epoxidation		2.0510
iberiotoxin
[no description available]		2.0510
1-eicosapentaenoylglycerol
1-eicosapentaenoylglycerol: structure in first source		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		03.0440
Cardiovascular Stroke
[description not available]		02.2110
Myocardial Infarction
NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).		02.2110
Innate Inflammatory Response
[description not available]		02.6620
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.6620
Obesity
A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).		02.3110
Fatty Liver, Nonalcoholic
[description not available]		02.1510
Non-alcoholic Fatty Liver Disease
Fatty liver finding without excessive ALCOHOL CONSUMPTION.		02.1510
Breast Cancer
[description not available]		02.1510
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.1510
Asthma, Bronchial
[description not available]		02.5220
Eosinophilia, Tropical
[description not available]		02.1710
Asthma
A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).		02.5220
Eosinophilia
Abnormal increase of EOSINOPHILS in the blood, tissues or organs.		02.1710
Contact Dermatitis
[description not available]		02.1710
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		02.1710
Primary Peritonitis
[description not available]		02.110
Peritonitis
INFLAMMATION of the PERITONEUM lining the ABDOMINAL CAVITY as the result of infectious, autoimmune, or chemical processes. Primary peritonitis is due to infection of the PERITONEAL CAVITY via hematogenous or lymphatic spread and without intra-abdominal source. Secondary peritonitis arises from the ABDOMINAL CAVITY itself through RUPTURE or ABSCESS of intra-abdominal organs.		02.110
Choroid Neovascularization
[description not available]		02.110
Age-Related Macular Degeneration
[description not available]		02.110
Macular Degeneration
Degenerative changes in the RETINA usually of older adults which results in a loss of vision in the center of the visual field (the MACULA LUTEA) because of damage to the retina. It occurs in dry and wet forms.		02.110
Experimental Lung Inflammation
Inflammation of any part, segment or lobe, of the lung parenchyma.		02.4720
Pneumonia
Infection of the lung often accompanied by inflammation.		02.4720
Injury, Ischemia-Reperfusion
[description not available]		02.4820
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		02.4820
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.0710
Muscle Relaxation
That phase of a muscle twitch during which a muscle returns to a resting position.		02.0710
Bronchial Hyperreactivity
Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.		02.0710