Compounds > 12-hydroxy-8,10-heptadecadienoic acid
Page last updated: 2024-12-10

12-hydroxy-8,10-heptadecadienoic acid

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

Description

12-hydroxy-8,10-heptadecadienoic acid (12-HHT) is a **fatty acid** that is a **metabolite of arachidonic acid**. It is formed by the enzyme **12-lipoxygenase**, which is found in various tissues and cells throughout the body, particularly in platelets.

Here's why 12-HHT is important in research:

**1. Role in Platelet Aggregation and Thrombosis:**
- 12-HHT plays a crucial role in **platelet aggregation**, the process by which platelets clump together to form a clot.
- It is a potent **agonist** of the **thromboxane A2 receptor**, a key player in platelet activation and thrombus formation.
- Research on 12-HHT helps understand the mechanisms of **hemostasis** (blood clotting) and **thrombosis** (blood clot formation in blood vessels), potentially leading to new treatments for **cardiovascular diseases**.

**2. Inflammation and Immune Response:**
- 12-HHT is also involved in **inflammatory responses**.
- It can act as a **mediator** of inflammation by activating **neutrophils** (white blood cells involved in fighting infections) and promoting the release of inflammatory cytokines.
- Research on 12-HHT explores its role in **inflammatory diseases**, including arthritis, asthma, and inflammatory bowel disease.

**3. Potential Therapeutic Targets:**
- The biological activity of 12-HHT makes it a potential target for the development of new **drugs** for various conditions.
- Researchers are investigating the use of 12-HHT antagonists or inhibitors to prevent or treat **thrombosis**, **inflammation**, and other diseases.

**4. Understanding Lipid Metabolism:**
- 12-HHT is a **biomarker** for the activity of 12-lipoxygenase, an enzyme involved in the metabolism of **arachidonic acid**.
- Studying 12-HHT levels in different tissues and conditions can help understand the role of **lipid metabolism** in various physiological and pathological processes.

**5. Biological Signaling:**
- 12-HHT acts as a **signaling molecule**, affecting various cellular processes, including **cell growth**, **differentiation**, and **apoptosis**.
- Research on 12-HHT expands our understanding of **cell signaling pathways** and the intricate network of molecular interactions within cells.

In conclusion, 12-hydroxy-8,10-heptadecadienoic acid is a fascinating molecule with diverse biological activities. Research on 12-HHT contributes to our understanding of platelet function, inflammatory processes, lipid metabolism, and cell signaling, potentially leading to the development of new therapeutic strategies for a wide range of diseases.

12-hydroxy-8,10-heptadecadienoic acid: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5312764
CHEMBL ID86565
CHEBI ID168099
SCHEMBL ID231193
MeSH IDM0085050

Synonyms (9)

Synonym
CHEMBL86565
15514-88-2
CHEBI:168099
(8e,10e)-12-hydroxyheptadeca-8,10-dienoic acid
LMFA01050194 ,
12-hydroxy-8e,10e-heptadecadienoic acid
8,10-heptadecadienoic acid, 12-hydroxy-
12-hydroxy-8,10-heptadecadienoic acid
SCHEMBL231193

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves performed with thrombin and collagen revealed that increased stimulation resulted in higher ratios of 12-HETE/HHT."( Differential effect of external calcium on the oxygenated metabolism of endogenous and exogenous arachidonic acid in platelets.
Lagarde, M; Velardo, B, 1985)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
long-chain fatty acidA fatty acid with a chain length ranging from C13 to C22.
[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 (1)

Assay IDTitleYearJournalArticle
AID7106Compound was evaluated for the inhibition of rat basophilic leukemia-1 (RBL-1) 5-Lipoxygenase at 10 uM1987Journal 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (100.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.50

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 Index12.50 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.50)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		1.9610benzoic 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
phenidone
phenidone: photographic developer; RN given refers to parent cpd; structure		1.9710
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		2.3720dialdehydebiomarker
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.		1.9610icosa-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
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.		1.9610fatty acid 20:3;
long-chain fatty acid		fungal metabolite;
human metabolite;
nutraceutical
15-keto-5,8,11,13-eicosatetraenoic acid
15-keto-5,8,11,13-eicosatetraenoic acid: RN given refers to (E,Z,Z,Z)-isomer; RN for cpd without isomeric designation not available 3/88. 15-oxo-ETE : An oxoicosatetraenoic acid having (5Z,8Z,11Z,13E) double bond stereochemistry, and an oxo group in position 15.		1.9710oxoicosatetraenoic acidhuman metabolite
alprostadil
[no description available]		1.9610prostaglandins Eanticoagulant;
human metabolite;
platelet aggregation inhibitor;
vasodilator agent
15-hydroxy-5,8,11,13-eicosatetraenoic acid
15(S)-HETE : An optically active form of 15-HETE having 15(S)-configuration..		1.9710(5Z,8Z,11Z,13E)-15-HETEhuman metabolite;
mouse metabolite
prostaglandin g2
[no description available]		1.9710prostaglandins Ghuman metabolite;
mouse metabolite
6-ketoprostaglandin f1 alpha
6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.		1.9510prostaglandins Falphahuman metabolite;
mouse metabolite
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, (s)-(e,z,z,z)-isomer
HPETE : Mono-hydroperoxy (e)icosatetraenoic acids (HPETEs) are the primary products of lipoxygenase-catalysed oxygenation of arachidonic acid.. 15(S)-HPETE : The (S)-enantiomer of 15-HPETE.		1.971015-HPETEmouse metabolite
prostaglandin f1
prostaglandin F1: was EN to PROSTAGLANDINS F (75-81); RN given refers to (9 alpha,11 alpha,13E,15S)-isomer		1.9610prostaglandins Falphahuman 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.		1.9610thromboxanes Bhuman 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)		1.9610
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid: RN given refers to cpd without isomeric designation; (S-(E,Z,Z,Z))-isomer caused dose-dependent constriction of cat coronary arteries; structure in first source. 15-HPETE : A HPETE that consists of (5Z,8Z,11Z,13E)-icosatetraenoic acid in which the hydroperoxy group is located at position 15.		1.9510HPETEhuman xenobiotic metabolite
13(S)-HODE
13(S)-HODE : An HODE (hydroxyoctadecadienoic acid) in which the double bonds are at positions 9 and 11 (E and Z geometry, respectively) and the hydroxy group is at position 13 (with S-configuration).		1.9710HODEantineoplastic agent;
human xenobiotic metabolite;
mouse metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Leukemia
[description not available]		01.9710