82337-46-0
Chemical Structure
12(R)-HETE
- CAS No.: 82337-46-0
- Formula:C20H32O3
- Molecular Weight:320.47
IUPAC Name: (R,5Z,8Z,10E,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
InChIKey: ZNHVWPKMFKADKW-ZYBDYUKJSA-N
SMILES: CCCCC/C=C\C[C@H](/C=C/C=C\C/C=C\CCCC(O)=O)O
Biological Activity: 12(R)-HETE is a CYP-dependent arachidonic acid metabolite that acts as a proinflammatory lipid mediator. 12 (R)-HETE widely exists in various tissues including the eye, skin and liver. In the cornea, 12(R)-HETE is metabolized via pathways such as β-oxidation into the precursor of 12(R)-HETrE. Without direct receptor binding, 12(R)-HETE indirectly activates AHR-mediated target gene transcription, while inhibiting the enzymatic activity of Na+,K+-ATPase and the intracellular calcium elevation induced by TP agonists. 12(R)-HETE also possesses multiple physiological effects such as chemotaxis, proangiogenesis, vasodilation, natriuresis, diuresis and intraocular pressure reduction, and can be widely used in studies related to psoriasis, inflammatory skin diseases and ocular inflammation[1][2][3].
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12(R)-HETE | 99.68% | 12(R)-HETE is a CYP-dependent arachidonic acid metabolite that acts as a proinflammatory lipid mediator. 12 (R)-HETE widely exists in various tissues including the eye, skin and liver. In the cornea, 12(R)-HETE is metabolized via pathways such as β-oxidation into the precursor of 12(R)-HETrE. Without direct receptor binding, 12(R)-HETE indirectly activates AHR-mediated target gene transcription, while inhibiting the enzymatic activity of Na+,K+-ATPase and the intracellular calcium elevation induced by TP agonists. 12(R)-HETE also possesses multiple physiological effects such as chemotaxis, proangiogenesis, vasodilation, natriuresis, diuresis and intraocular pressure reduction, and can be widely used in studies related to psoriasis, inflammatory skin diseases and ocular inflammation. | ||||||||||||||||||||
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- [1]. Chiaro C R, et al. 12 (R)-Hydroxy-5 (Z), 8 (Z), 10 (E), 14 (Z)-eicosatetraenoic acid [12 (R)-HETE], an arachidonic acid derivative, is an activator of the aryl hydrocarbon receptor[J]. Molecular pharmacology, 2008, 74(6): 1649-1656.
- [2]. Siangjong L, et al. Endothelial 12(S)-HETE vasorelaxation is mediated by thromboxane receptor inhibition in mouse mesenteric arteries. Am J Physiol Heart Circ Physiol. 2013;304(3):H382-H392. [Content Brief]
- [3]. Nishimura M, et al. Metabolism of 12 (R)-hydroxy-5, 8, 10, 14-eicosatetraenoic acid (12 (R)-HETE) in corneal tissues: formation of novel metabolites[J]. Archives of biochemistry and biophysics, 1991, 290(2): 326-335.
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