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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.