LIPID MAPS

Structure Database (LMSD)

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Common Name

5S-HETE di-endoperoxide

Systematic Name

5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid

Synonyms

LM ID

LMFA03000011

Formula

C₂₀H₃₄O₈

Exact Mass

Calculate m/z

402.22537

Sum Composition

FA 20:3;O6

Status

Active

Show lipids differing only in stereochemistry/bond geometry

Main

Classification

String Representations

InChiKey (Click to copy)

DOXGUXRZAOCYPM-IPIAXWAYSA-N

InChi (Click to copy)

InChI=1S/C20H34O8/c1-2-3-4-6-14(21)9-11-16-18-13-19(28-27-18)17(26-25-16)12-10-15(22)7-5-8-20(23)24/h10,12,14-19,21-22H,2-9,11,13H2,1H3,(H,23,24)/b12-10+/t14-,15-,16-,17-,18+,19-/m0/s1

SMILES (Click to copy)

[C@@H]12OO[C@@H]([C@H](CC[C@@H](O)CCCCC)OO[C@H]1/C=C/[C@@H](O)CCCC(=O)O)C2

References

Reference

Convergence of the 5-LOX and COX-2 pathways:
heme-catalyzed cleavage of the 5S-HETE-derived di-endoperoxide into aldehyde fragments.
Griesser M, Boeglin WE, Suzuki T, Schneider C.
J Lipid Res. 2009 Dec;50(12):2455-62