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Structure Database (LMSD)

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Common Name

8S-HETE

Systematic Name

8S-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid

Synonyms

8-HETE

LM ID

LMFA03060006

Formula

C₂₀H₃₂O₃

Exact Mass

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320.235145

Sum Composition

FA 20:4;O

Status

Curated

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Classification

Biological Context

8(S)-HETE is a major lipoxygenase product in PMA-treated murine epidermis.¹ It activates mouse keratinocyte protein kinase C with an IC50 of 100 µM.² 8(S)-HETE also activates PPARα selectively at concentrations as low as 0.3 µM.³ Stereochemical assignment of the (S) enantiomer is based on comparison of chiral HPLC retention times to published results.⁴

This information has been provided by Cayman Chemical

References

1. Hughes, M.A., and Brash, A.R. Investigation of the mechanism of biosynthesis of 8-hydroxyeicosatetraenoic acid in mouse skin. Biochim. Biophys. Acta 1081(3), 347-354 (1991).

2. Lo, H.H., Bartek, G.A., and Fischer, S.M. In vitro activation of mouse skin protein kinase C by fatty acids and their hydroxylated metabolites. Lipids 29(8), 547-553 (1994).

3. Yu, K., Bayona, W., Kallen, C.B., et al. Differential activation of peroxisome proliferator-activated receptors by eicosanoids. The Journal of Biological Chemisty 270(41), 23975-23983 (1995).

4. Schneider, C., Yu, Z., Boeglin, W.E., et al. Enantiomeric separation of hydroxy and hydroperoxy eicosanoids by chiral column chromatography. Methods Enzymol. 433, 145-157 (2007).

String Representations

InChiKey (Click to copy)

NLUNAYAEIJYXRB-VYOQERLCSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1

SMILES (Click to copy)

C(=C/CCCC(=O)O)/C[C@H](O)/C=C/C=C\C/C=C\CCCCC