20-HETE

Names

[ Name ]:
20-HETE

[Synonym ]:
20-hydroxy-5,8,11,14-eicosatetraenoic acid
20-HETE
20-Hydroxyicosatetraenoic acid
5,8,11,14-Eicosatetraenoic acid, 20-hydroxy-, (5Z,8Z,11Z,14Z)-
DSR-II-247-30
(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid
20-Hydroxyeicosatetraenoic acid
20-Hydroxyicosatetraenoate
20-Hydroxy arachidonic acid
(5Z,8Z,11Z,14Z)-20-Hydroxy-5,8,11,14-icosatetraenoic acid

Biological Activity

[Description]:

20-HETE(20-hydroxy Arachidonic Acid) is a potent vasoconstrictor produced in vascular smooth muscle (VSM) cells. It depolarizes VSM by blocking the open-state probability of Ca2+-activated K+-channels.IC50 Value:Target: 20-Hydroxyeicosatetraenoic acid (20-HETE) is a cytochrome P450-derived arachidonic acid metabolite that has been shown to increase smooth muscle contractions and proliferation, stimulate endothelial dysfunction and activation and promote hypertension. in vitro: Addition of 20-HETE to the bath (1-100 nM), reduced the frequency of opening of the large-conductance Ca(2+)-activated K+ channel recorded using cell-attached patches on VSM [1]. In kidney, 20-HETE induces diuresis by inhibiting Na+-K+-ATPase in proximal tubules and Na+/K+/Cl+ cotransporter in the thick ascending limb of Henle's loop [2].in vivo: In Cyp4a14(-/-) mice, which display androgen-driven and 20-HETE-dependent hypertension, treatment with20-HETE antagonist abolished remodeling of renal resistance arteries measured as media thickness (24±1 vs. 15±1μm) and M/L (0.29±0.03 vs. 0.17±0.01) [4]. The transgenic mice had overexpressed hepatic CYP4F2, high hepatic 20-HETE and fasting plasma glucose levels but normal insulin level. The GP activity was increased and the cAMP/PKA-PhK-GP pathway was activated in the transgenic mice compared with wild-type mice [5]. Clinical trial: Mechanisms of Response to Diesel Exhaust in Subjects With Asthma. Phase not specified

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

[Target]

Human Endogenous Metabolite

[References]

[1]. Zou AP, Fleming JT, Falck JR, 20-HETE is an endogenous inhibitor of the large-conductance Ca(2+)-activated K+ channel in renal arterioles. Am J Physiol. 1996 Jan;270(1 Pt 2):R228-37.

[2]. Schwartzman M, Ferreri NR, Carroll MA, Renal cytochrome P450-related arachidonate metabolite inhibits (Na+ + K+)ATPase. Nature. 1985 Apr 18-24;314(6012):620-2.

[3]. Ding Y, Wu CC, Garcia V, 20-HETE INDUCES REMODELING OF RENAL RESISTANCE ARTERIES INDEPENDENT OF BLOOD PRESSURE ELEVATION IN HYPERTENSION. Am J Physiol Renal Physiol. 2013 Jul 3. [Epub ahead of print]

[4]. Lai G, Wu J, Liu X, 20-HETE induces hyperglycemia through the cAMP/PKA-PhK-GP pathway. Mol Endocrinol. 2012 Nov;26(11):1907-16.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
482.0±33.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₃₂O₃

[ Molecular Weight ]:
320.47

[ Flash Point ]:
259.4±21.9 °C

[ Exact Mass ]:
320.235138

[ PSA ]:
57.53000

[ LogP ]:
4.91

[ Vapour Pressure ]:
0.0±2.7 mmHg at 25°C

[ Index of Refraction ]:
1.515

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P305 + P351 + P338-P370 + P378-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
F: Flammable;Xi: Irritant;

[ Risk Phrases ]:
11-36/37/38

[ Safety Phrases ]:
16-26-36

[ RIDADR ]:
UN 1170 3/PG 2

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

HMDB: a knowledgebase for the human metabolome.

Nucleic Acids Res. 37(Database issue) , D603-10, (2009)

The Human Metabolome Database (HMDB, http://www.hmdb.ca) is a richly annotated resource that is designed to address the broad needs of biochemists, clinical chemists, physicians, medical geneticists, ...

The human serum metabolome.

PLoS ONE 6(2) , e16957, (2011)

Continuing improvements in analytical technology along with an increased interest in performing comprehensive, quantitative metabolic profiling, is leading to increased interest pressures within the m...

IGF-1 deficiency impairs cerebral myogenic autoregulation in hypertensive mice.

J. Cereb. Blood Flow Metab. 34(12) , 1887-97, (2014)

Aging impairs autoregulatory protection in the brain, exacerbating hypertension-induced cerebromicrovascular injury, neuroinflammation, and development of vascular cognitive impairment. Despite the im...