LIPID MAPS

Structure Database (LMSD)

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Common Name

5-HPETE

Systematic Name

5-hydroperoxyeicosa-6E,8Z,11Z,14Z-tetraenoic acid

Synonyms

(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

LM ID

LMFA03060108

Formula

C₂₀H₃₂O₄

Exact Mass

Calculate m/z

336.230061

Sum Composition

FA 20:4;O2

Status

Curated

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View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

5(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of 5-LO on arachidonic acid. It is metabolized to leukotriene A4 (LTA4), a key intermediate in the formation of LTs.¹ 5(S)-HpETE (1 µM) mediates the induction of the proto-oncogene c-fos in TNF-stimulated TA1 cells.²

This information has been provided by Cayman Chemical

References

1. Shimizu, T., Rådmark, O., and Samuelsson, B. Enzyme with dual lipoxygenase activities catalyzes leukotriene A4 synthesis from arachidonic acid. Proc. Natl. Acad. Sci. USA 81, 689-693 (1984).

2. Haliday, E.M., Ramesha, C.S., and Ringold, G. TNF induces c-fos via a novel pathway requiring conversion of arachidonic acid to a lipoxygenase metabolite. EMBO J. 10, 109-115 (1991).

String Representations

InChiKey (Click to copy)

JNUUNUQHXIOFDA-XTDASVJISA-N

InChi (Click to copy)

InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+

SMILES (Click to copy)

C(/C/C=C\C/C=C\CCCCC)=C/C=C/C(OO)CCCC(=O)O