Structure Database (LMSD)

Common Name
17R,18S-EpETE
Systematic Name
17R,18S-epoxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
Synonyms
  • (5Z,8Z,11Z,14Z)-(17R,18S)-17,18-Epoxyicosa-5,8,11,14-tetraenoic acid
LM ID
LMFA03000006
Formula
C20H30O3
Exact Mass
Calculate m/z
318.219496
Sum Composition
FA 20:5;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Other Eicosanoids [FA0300]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Epoxy fatty acids [FA0107]

Biological Context

17R(18S)-EpETE is an oxylipin and a cytochrome P450 metabolite of eicosapentaenoic acid (EPA).1,2 17R(18S)-EpETE is an activator of large-conductance calcium-activated potassium (KCa1.1/BK) channels, increasing the potassium current amplitude by 15-fold in isolated rat cerebral artery vascular smooth muscle cells (VSMCs) at +60 mV when used at a concentration of 50 nM.2 It has negative chronotropic effects in isolated neonatal rat cardiomyocytes (NRCMs; EC50 = ~1-2 nM) and prevents calcium-induced increases in the spontaneous beating of NRCMs.3,4

This information has been provided by Cayman Chemical

References

1. 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).
2. Schwarz, D., Kisselev, P., Ericksen, S.S., et al. Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: Highly steroselective formation of 17(R), 18(S)-epoxyeicosatetraenoic acid. Biochem. Pharmacol. 67(8), 1445-1457 (2004).
3. Arnold, C., Markovic, M., Blossey, K., et al. Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of omega-3 fatty acids. The Journal of Biological Chemisty 285(43), 32720-32733 (2010).
4. Falck, J.R., Wallukat, G., Puli, N., et al. 17(R),18(S)-Epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: Structure-activity relationships and stable analogues. J. Med. Chem. 54(12), 4109-4118 (2011).

String Representations

InChiKey (Click to copy)
GPQVVJQEBXAKBJ-VDTDYMMTSA-N
InChi (Click to copy)
InChI=1S/C20H30O3/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)/b5-3-,8-6-,11-9-,14-12-/t18-,19+/m0/s1
SMILES (Click to copy)
C(=C/C/C=C\C/C=C\C/C=C\CCCC(=O)O)/C[C@H]1O[C@H]1CC

Other Databases

KEGG ID
C13843
HMDB ID
HMDB10212
CHEBI ID
76953
PubChem CID
5282277
SwissLipids ID
SLM:000389389
Cayman ID
28630

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 355.37
Topological Polar Surface Area 49.83
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 5.78
Molar Refractivity 96.49

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Updated at
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