87173-80-6
Chemical Structure
5,6-Epoxyeicosatrienoic acid
Synonym(s): 5,6-EET; (±)5,6-EpETrE
- CAS No.: 87173-80-6
- Formula:C20H32O3
- Molecular Weight:320.47
IUPAC Name: 4-((2S,3R)-3-((2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl)oxiran-2-yl)butanoic acid
InChIKey: VBQNSZQZRAGRIX-GSKBNKFLSA-N
SMILES: OC(CCC[C@H]1[C@H](O1)C/C=C\C/C=C\C/C=C\CCCCC)=O
Biological Activity:
5,6-Epoxyeicosatrienoic acid (5,6-EET; (±) 5,6-EpETrE) is one of the four major epoxyeicosatrienoic acid (EET) isomers metabolized from Arachidonic acid (HY-109590). 5,6-Epoxyeicosatrienoic acid induces peripheral vasodilation and lowers blood pressure by inhibiting T-type calcium channels (Cav3.2: IC50 = 0.54 μM). 5,6-Epoxyeicosatrienoic acid causes vasoconstriction in hypoxic pulmonary blood vessels via activating Rho kinase in a membrane depolarization-dependent manner. 5,6-Epoxyeicosatrienoic acid induces mechanical pain by activating TRPA1. 5,6-Epoxyeicosatrienoic acid can be used in studies related to hypoxic pulmonary vasoconstriction, mechanical hyperalgesia and hypertension[1][2][3][4][5].
The product specifications provided below refer solely to the active content of 5,6-Epoxyeicosatrienoic acid.
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5,6-Epoxyeicosatrienoic acid | 99.07% | 5,6-Epoxyeicosatrienoic acid (5,6-EET; (±) 5,6-EpETrE) is one of the four major epoxyeicosatrienoic acid (EET) isomers metabolized from Arachidonic acid (HY-109590). 5,6-Epoxyeicosatrienoic acid induces peripheral vasodilation and lowers blood pressure by inhibiting T-type calcium channels (Cav3.2: IC50 = 0.54 μM). 5,6-Epoxyeicosatrienoic acid causes vasoconstriction in hypoxic pulmonary blood vessels via activating Rho kinase in a membrane depolarization-dependent manner. 5,6-Epoxyeicosatrienoic acid induces mechanical pain by activating TRPA1. 5,6-Epoxyeicosatrienoic acid can be used in studies related to hypoxic pulmonary vasoconstriction, mechanical hyperalgesia and hypertension. The product specifications provided below refer solely to the active content of 5,6-Epoxyeicosatrienoic acid. |
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5,6-Epoxyeicosatrienoic acid-d11 | 5,6-Epoxyeicosatrienoic acid-d11 (5,6-EET-d11) is deuterium labeled 5,6-Epoxyeicosatrienoic acid. 5,6-Epoxyeicosatrienoic acid is one of the four major epoxyeicosatrienoic acid (EET) isomers metabolized from Arachidonic acid (HY-109590). 5,6-Epoxyeicosatrienoic acid induces peripheral vasodilation and lowers blood pressure by inhibiting T-type calcium channels (Cav3.2: IC50 = 0.54 μM). 5,6-Epoxyeicosatrienoic acid causes vasoconstriction in hypoxic pulmonary blood vessels via activating Rho kinase in a membrane depolarization-dependent manner. 5,6-Epoxyeicosatrienoic acid induces mechanical pain by activating TRPA1. 5,6-Epoxyeicosatrienoic acid can be used in studies related to hypoxic pulmonary vasoconstriction, mechanical hyperalgesia and hypertension. | |||||||||||||||||||||
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Similarity Score 1.00
HY-1683825R(6S)-EET -
Similarity Score 1.00
HY-168382A5S(6R)-EET -
Similarity Score 0.97
HY-11351914R(15S)-EET -
Similarity Score 0.97
HY-150084(±)14,15-Epoxyeicosatrienoic acid -
Similarity Score 0.97
HY-N1297014S(15R)-EET -
Similarity Score 0.92
HY-169043(±)7(S),8(R)-EDT -
Similarity Score 0.91
HY-N1253016,17-EDT -
Similarity Score 0.89
HY-1500928(S),9(R)-EET -
Similarity Score 0.89
HY-179488(±)8(9)-EET -
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References
- [1]. Losapio JL, et al. 5,6-EET-induced contraction of intralobar pulmonary arteries depends on the activation of Rho-kinase. J Appl Physiol (1985). 2005;99(4):1391-1396.
- [2]. Stephenson AH, et al. 5,6-Epoxyeicosatrienoic acid reduces increases in pulmonary vascular resistance in the dog. Am J Physiol. 1998;275(1):H100-H109.
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[3]. Strielkov I, et al. Cytochrome P450 epoxygenase-derived 5,6-epoxyeicosatrienoic acid relaxes pulmonary arteries in normoxia but promotes sustained pulmonary vasoconstriction in hypoxia. Acta Physiol (Oxf). 2020 Sep;230(1):e13521.
- [4]. Sisignano M, et al. 5,6-EET is released upon neuronal activity and induces mechanical pain hypersensitivity via TRPA1 on central afferent terminals. J Neurosci. 2012;32(18):6364-6372.
- [5]. Cazade M, et al. 5,6-EET potently inhibits T-type calcium channels: implication in the regulation of the vascular tone. Pflugers Arch. 2014;466(9):1759-1768.
