14-hydroxydocosahexaenoate profile

## 14-Hydroxydocosahexaenoate (14-HDHA): A Crucial Player in Inflammation and Cell Signaling

14-Hydroxydocosahexaenoate (14-HDHA) is a **metabolite of docosahexaenoic acid (DHA)**, a crucial omega-3 fatty acid found primarily in fatty fish. It's formed through a process called **hydroxylation**, where an oxygen atom is added to the DHA molecule. This seemingly simple change significantly alters its biological activity, making 14-HDHA a key player in various cellular processes.

### Why is 14-HDHA important for research?

Here's why 14-HDHA is a hot topic in research:

**1. Potential Role in Inflammation:**

* 14-HDHA has been shown to exhibit **anti-inflammatory properties**. Studies indicate it can suppress the production of pro-inflammatory cytokines (like TNF-α and IL-6) and promote the production of anti-inflammatory cytokines (like IL-10).
* This anti-inflammatory action suggests 14-HDHA could be beneficial in managing inflammatory conditions like rheumatoid arthritis, inflammatory bowel disease, and even neurodegenerative diseases.

**2. Modulation of Cell Signaling:**

* 14-HDHA can interact with various cell signaling pathways, including the **nuclear factor kappa B (NF-κB)** pathway, which plays a critical role in inflammation, immunity, and cell survival.
* By influencing these pathways, 14-HDHA may contribute to the regulation of diverse cellular functions like cell growth, differentiation, and apoptosis (programmed cell death).

**3. Potential Benefits in Brain Health:**

* 14-HDHA has been linked to improved cognitive function and protection against neurodegeneration. Studies suggest it might play a role in **neurogenesis** (formation of new neurons) and **synaptic plasticity** (strengthening of connections between neurons).
* This makes 14-HDHA a promising candidate for therapies targeting neurodegenerative disorders like Alzheimer's disease and Parkinson's disease.

**4. Potential for Therapeutic Applications:**

* The diverse biological activities of 14-HDHA have sparked interest in its therapeutic potential.
* Research is ongoing to explore its applications in various disease areas, including inflammation, neurodegeneration, cardiovascular disease, and cancer.

**5. Unraveling the Complexities of Omega-3 Metabolism:**

* Studying 14-HDHA helps us understand the intricate metabolic pathways of omega-3 fatty acids.
* This knowledge can be crucial in developing strategies for optimizing omega-3 intake and maximizing their health benefits.

### Challenges and Future Directions:

While 14-HDHA holds great promise, there are still limitations:

* More research is needed to fully elucidate its mechanisms of action and its specific effects on various diseases.
* Identifying ways to effectively deliver 14-HDHA to specific target tissues is essential for its therapeutic development.

Overall, 14-HDHA stands out as a potentially crucial molecule for research in various fields, particularly in understanding inflammation, cell signaling, and the benefits of omega-3 fatty acids. Continued research on this molecule could lead to significant breakthroughs in treating various human diseases.

14-hydroxydocosahexaenoic acid: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	6439735
MeSH ID	M0165563

Synonym
docosahexaenoic acid, 14-hydroxy-
14-hydroxydocosahexaenoate
86360-66-9
14-hydroxydocosahexaenoic acid
(2e,4e,6e,8e,10e,12e)-14-hydroxydocosa-2,4,6,8,10,12-hexaenoic acid

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (12.50)	18.7374
1990's	2 (12.50)	18.2507
2000's	1 (6.25)	29.6817
2010's	7 (43.75)	24.3611
2020's	4 (25.00)	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	3 (18.75%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	13 (81.25%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	3.5	1	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.31	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
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.	4.44	3	0	D-glucopyranose	epitope; mouse metabolite
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.	1.97	1	0	icosa-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.	8.57	13	2	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
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.	4.44	3	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.13	1	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	2.31	1	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	1.98	1	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
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	0	thromboxanes B	human metabolite; mouse metabolite
20-hydroxy-5,8,11,14-eicosatetraenoic acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid: stimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer. 20-HETE : A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20.	2.31	1	0	HETE; hydroxy monocarboxylic acid	human metabolite; mouse metabolite
12-hydroxy-5,8,10,14-eicosatetraenoic acid 12-Hydroxy-5,8,10,14-eicosatetraenoic Acid: A lipoxygenase metabolite of ARACHIDONIC ACID. It is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumor cell metastatic potential through activation of protein kinase C. (J Pharmacol Exp Ther 1995; 274(3):1545-51; J Natl Cancer Inst 1994; 86(15):1145-51)	5.79	7	0
15-hydroxy-5,8,11,13-eicosatetraenoic acid 15-hydroxy-5,8,11,13-eicosatetraenoic acid: potent & selective inhibitor of platelet lipoxygenase; RN given refers to cpd without isomeric designation	1.97	1	0
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	1.98	1	0
17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid: RN given refers to (E,Z,Z,Z,Z,Z)-isomer; RN for cpd without isomeric designation not avail 3/90. (4Z,7Z,10Z,13Z,15E,19Z)-17-hydroxydocosahexaenoic acid : A hydroxydocosahexaenoic acid that consists of 4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid bearing an additional 17-hydroxy substituent.	8.27	10	3	hydroxydocosahexaenoic acid; secondary allylic alcohol	human xenobiotic metabolite
12-hydroxy-5,8,10,14,17-eicospentaenoic acid 12-hydroxy-5,8,10,14,17-eicospentaenoic acid: RN given refers to cpd without isomeric designation	5.71	6	0
18-hydroxy-5,8,11,14-eicosatetraenoic acid 18-hydroxy-5,8,11,14-eicosatetraenoic acid: structure given in first source	4.02	2	1
5s,12r,18r-trihydroxy-6z,8e,10e,14z,16e-eicosapentaenoic acid 5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-eicosapentaenoic acid: a bioactive oxygenated product of EPA, was identified in human plasma and prepared by total organic synthesis; structure in first source. resolvin E1 : A resolvin that is (6Z,8E,10E,14Z,16E)-icosa-6,8,10,14,16-pentaenoic acid which is substituted at positions 5, 12 and 18 by hydroxy groups (the 5S,12R,18R stereoisomer).	6.07	4	1	hydroxy polyunsaturated fatty acid; long-chain fatty acid; nonclassic icosanoid; resolvin; triol	anti-inflammatory agent; human xenobiotic metabolite
protectin d1 protectin D1: a docosahexaenoic acid-derived docosatriene protects human retinal pigment epithelial cells from oxidative stress; structure in first source. protectin D1 : A dihydroxydocosahexaenoic acid that is (4Z,7Z,11E,13E,15Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at positions 10 and 17 (the 10R,17S-stereoisomer). Protectin D1 is one of the specialised proresolving mediators. When produced in neural tissues, it is called neuroprotectin D1	4.44	3	0	dihydroxydocosahexaenoic acid; protectin; secondary allylic alcohol	anti-inflammatory agent; apoptosis inhibitor; hepatoprotective agent; human xenobiotic metabolite; neuroprotective agent; PPARgamma agonist; specialised pro-resolving mediator
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	1.97	1	0

Condition	Relationship Strength	Studies	Trials
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	3.97	2	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.29	3	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.31	1	0
Pneumonia Infection of the lung often accompanied by inflammation.	2.31	1	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	3.97	2	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	8.53	25	0
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	8.53	25	0
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).	8.69	28	0
Innate Inflammatory Response [description not available]	2.59	2	0
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.	2.59	2	0
Infections, Orthomyxoviridae [description not available]	3.06	1	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	3.06	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	3.53	1	1
Diabetes Mellitus, Adult-Onset [description not available]	3.94	2	1
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	3.56	1	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	3.94	2	1
Diathesis [description not available]	3.12	1	0
Insulin Sensitivity [description not available]	2.13	1	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.13	1	0
Primary Peritonitis [description not available]	6.33	9	0
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.	6.33	9	0
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.	2.67	3	0

14-hydroxydocosahexaenoate

Description

Cross-References

Synonyms (5)

Research

Studies (16)

Market Indicators

Research Demand Index: 12.48

Study Types