5-HETE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H32O3
Molecular Weight	320.4663
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O

InChI

InChIKey=KGIJOOYOSFUGPC-JGKLHWIESA-N

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H32O3
Molecular Weight	320.4663
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	4
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
5-, 12- and 15-Hydroxyeicosatetraenoic acids induce cellular hypertrophy in the human ventricular cardiomyocyte, RL-14 cell line, through MAPK- and NF-κB-dependent mechanism.	2016-02	25600587
Group VIA Phospholipase A2 (iPLA2β) Modulates Bcl-x 5'-Splice Site Selection and Suppresses Anti-apoptotic Bcl-x(L) in β-Cells.	2015-04-24	25762722
Inhibition of soluble epoxide hydrolase enhances the anti-inflammatory effects of aspirin and 5-lipoxygenase activation protein inhibitor in a murine model.	2010-03-15	19896470
Structural requirements for activation of the 5-oxo-6E,8Z, 11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) receptor: identification of a mead acid metabolite with potent agonist activity.	2008-05	18292294
A rat air pouch model for evaluating the efficacy and selectivity of 5-lipoxygenase inhibitors.	2008-04-14	18295198
TG1019/OXE, a Galpha(i/o)-protein-coupled receptor, mediates 5-oxo-eicosatetraenoic acid-induced chemotaxis.	2005-09-09	16039985
Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE.	2005-05-17	15893379
Platelets abrogate leukotriene B(4) generation by human blood neutrophils stimulated with monosodium urate monohydrate or f-Met-Leu-Phe in vitro.	2003-04	12695552
Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils.	2003-03	12606753
Identification of a novel human eicosanoid receptor coupled to G(i/o).	2002-08-30	12065583
Chemical and biological characterization of oxo-eicosatetraenoic acids.	1994-12-15	7803484
Stimulation of human neutrophils by 5-oxo-6,8,11,14-eicosatetraenoic acid by a mechanism independent of the leukotriene B4 receptor.	1993-05-05	8387490
Quantitative changes of hydroxyacid formation during platelet-neutrophil interaction.	1993-03	8383163
Diethyldithiocarbamate (ditiocarb sodium) effect on arachidonic acid metabolism in human mononuclear cells. Glutathione peroxidase-like activity.	1992-03-17	1314059
The skin in mastocytosis.	1991-03	1672136
Selective conversion and esterification of monohydroxyeicosatetraenoic acids by human vascular smooth muscle cells: relevance to smooth muscle cell proliferation.	1991-01	1984423
[A kinetic scheme of human neutrophil 5-lipoxygenase activity].	1990-10	1964097
Transcellular lipoxygenase metabolism between monocytes and platelets.	1989-09-15	2550547
Dual stimulation of phospholipase activity in human monocytes. Role of calcium-dependent and calcium-independent pathways in arachidonic acid release and eicosanoid formation.	1988-06-01	2836505
Requirement of free arachidonic acid for leukotriene B4 biosynthesis by 12-hydroperoxyeicosatetraenoic acid-stimulated neutrophils.	1986-07-31	3017333
In vitro synthesis of 12-hydroxy-eicosatetraenoic acid is increased in uninvolved psoriatic epidermis.	1986-07	3088130
Leukotriene C4 production by murine mast cells: evidence of a role for extracellular leukotriene A4.	1985-10	2995976
Production of metabolic products of arachidonic acid during cell-cell interactions.	1984-09	6088611
Arachidonic acid metabolism by human monocytes. Studies with platelet-depleted cultures.	1983-08-01	6411852
[Cerebral vasospasm and lipid peroxidation--lipid peroxides in the cerebrospinal fluid after subarachnoid hemorrhage].	1982-12	7159548
Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes.	1980-11-13	6253824

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:04:56 GMT 2025` Edited by `admin` on `Mon Mar 31 22:04:56 GMT 2025`
Record UNII	467RNW8T91
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-HETE

Common Name

English

5(S)-HETE

Preferred Name

English

5-HYDROXYEICOSATETRAENOIC ACID

Systematic Name

English

5-HETE [MI]

Common Name

English

5-HETE, (S)-

Common Name

English

5(S)-HYDROXYEICOSATETRAENOIC ACID

Common Name

English

6,8,11,14-EICOSATETRAENOIC ACID, 5-HYDROXY-, (5S,6E,8Z,11Z,14Z)-

Systematic Name

English

5-HYDROXY-6,8,11,14-EICOSATETRAENOIC ACID

Systematic Name

English

5-L-HYDROXY-6,8,11,14-EICOSATETRAENOIC ACID

Common Name

English

5(S)-HYDROXY-6-TRANS-8,11,14-CIS-EICOSATETRAENOIC ACID

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C463