An active metabolite of eicosapentaenoic acid and an S1P1 agonist
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(±)17(18)-EpETE

Item No. 50861

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(17S,18R)-epoxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
Synonyms
  • (±)17(18)-EEQ
  • (±)17(18)-epoxy-5(Z),8(Z)
  • (±)17(18)-epoxy-all-cis-5,8,11,14-Eicosatetraenoic Acid
  • (±)17(18)-Epoxyeicosatetraenoic Acid
  • 11(Z),14(Z)-ETE
  • FA 20:5;O
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥90%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
CC[C@@H]1[C@@H](O1)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O.CC[C@H]2[C@H](O2)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/2C20H30O3/c2*1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22/h2*3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)/b2*5-3-,8-6-,11-9-,14-12-/t18-,19+;18-,19-/m01/s1
InChi Key
KWSANWNLWZVOSU-LGROVTKTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $69

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    50 µg

    $130

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    100 µg

    $233

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    500 µg

    $955

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    Product Description

    (±)17(18)-EpETE is an active metabolite of the ω-3 fatty acid eicosapentaenoic acid (EPA; Item Nos. 90110 | 90110.1 | 21908) formed via epoxidation of the 17,18 double bond by the cytochrome P450 (CYP) isoform CYP1A2 and an agonist of sphingosine-1-phosphate receptor 1 (S1P1).1,2 It binds to S1P1 (Ki = 0.57 nM) and activates S1P1 in a bioluminescence resonance energy transfer (BRET) assay using HEK293T cells expressing human S1P1 (EC50 = 8.93).1 (±)17(18)-EpETE (100 nM) also increases outward potassium efflux in rat vascular smooth muscle cells expressing large-conductance calcium-activated potassium channels (KCa1.1/BK).3 It inhibits oscillatory shear stress- or TNF-α-induced increases in vascular cell adhesion molecule-1 (VCAM1) levels in human umbilical vein endothelial cells (HUVECs) in a concentration-dependent manner.1 (±)17(18)-EpETE (1 µM) increases levels of phosphorylated endothelial nitric oxide synthase (eNOS), as well as prevents TNF-α-induced increases in levels of IκBα and phosphorylated levels of IKKα and p65 in HUVECs. In vivo, (±)17(18)-EpETE decreases tissue levels of VCAM1 and intracellular adhesion molecule-1 (ICAM1) and reduces the number of atherosclerotic lesions in the carotid arteries of wild-type but not S1pr1-/- mice in a model of atherosclerosis induced by arterial ligation and the Pcsk9 mutant Pcsk9N377Y.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhou, T., Cheng, J., He, S., et al. The sphingosine-1-phosphate receptor 1 mediates the atheroprotective effect of eicosapentaenoic acid. Nat. Metab. 6(8), 1566-1583 (2024).

    2. Isobe, Y., Itagaki, M., ito, Y., et al. Comprehensive analysis of the mouse cytochrome P450 family responsible for omega-3 epoxidation of eicosapentaenoic acid. Sci. Rep. 8(1), 7954 (2018).

    3. Lauterbach, B., Barbosa-Sicard, E., Wang, M.H., et al. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39(2 Pt. 2), 609-613 (2002).

    Product Citations

    Walker, R.E., Savinova, O.V., Pedersen, T.L., et al. Effects of inflammation and soluble epoxide hydrolase inhibition on oxylipin composition of very low-density lipoproteins in isolated perfused rat livers. Physiol. Rep. 9(4), e14480 (2021).

    Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (2017).

    McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides. Proc. Natl. Acad. Sci. USA 114(30), E6034-E6043 (2017).

    Aoyagi, R., Ikeda, K., Isobe, Y., et al. Comprehensive analyses of oxidized phospholipids using a measured MS/MS spectra library. J. Lipid. Res. 58(11), 2229-2237 (2017).