LIPID MAPS

Structure Database (LMSD)

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Common Name

5S-HETE-d8

Systematic Name

5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5,6,8,9,11,12,14,15-d8)

Synonyms

LM ID

LMFA03060005

Formula

C₂₀H₂₄D₈O₃

Exact Mass

Calculate m/z

328.285361

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

5(S)-HETE-d8 is intended for use as an internal standard for the quantification of 5-HETE by GC- or LC-MS. (±)5-HETE is formed via non-enzymatic oxidation of arachidonic acid .¹ 5(S)- and 5(R)-HETE are formed by lipoxygenase-mediated oxidation of arachidonic acid.^2,3

This information has been provided by Cayman Chemical

References

1. Astarita, G., Kendall, A.C., Dennis, E.A., et al. Targeted lipidomics strategies for oxygenated metabolites of polyunsaturated fatty acid. Biochim. Biophys. Acta 1851(4), 456-468 (2015).

2. Hada, T., Swift, L.L., and Brash, A.R. Discovery of 5R-lipoxygenase activity in oocytes of the surf clam, Spisula solidissima. Biochim. Biophys. Acta 1346(2), 109-119 (1997).

3. Dodge, W., and Thomas, M. The effect of 5-hydroxyeicosatetraenoic acid on the proliferation of granulocyte progenitors and embryonic fibroblasts of the chick. Biochem. Biophys. Res. Commun. 131(2), 731-735 (1985).

References

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

KGIJOOYOSFUGPC-IWMWOOIASA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1/i6D,7D,9D,10D,12D,13D,16D,19D

SMILES (Click to copy)

C(O)(=O)CCC[C@]([2H])(O)/C(/[2H])=C/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\CCCCC