LIPID MAPS

Structure Database (LMSD)

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Common Name

9(S)-HETE-d8

Systematic Name

9S-hydroxy-eicosa-5Z,7E,11Z,14Z-tetraenoic-5,6,8,9,11,12,14,15-d8 acid

Synonyms

9(S)-Hydroxyeicosatetraenoic Acid-d8

LM ID

LMFA03060122

Formula

C₂₀H₂₄D₈O₃

Exact Mass

Calculate m/z

328.285359

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

9(S)-HETE-d8 is intended for use as an internal standard for the quantification of 9-HETE by GC- or LC-MS. (±)9-HETE is formed by lipid peroxidation of arachidonic acid.¹ 9(S)-HETE and 9(R)-HETE are formed via oxidation of arachidonic acid by rat liver microsomal cytochrome P450 (CYP) in a non-stereoselective manner.²

This information has been provided by Cayman Chemical

References

1. Powell, W.S., and Rokach, J. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochim. Biophys. Acta 1851(4), 340-355 (2014).

2. Capdevila, J., Yadagiri, P., Manna, S., et al. Absolute configuration of the hydroxyeicosatetraenoic acids (HETEs) formed during catalytic oxygenation of arachidonic acid by microsomal cytochrome P-450. Biochem. Biophys. Res. Commun. 141(3), 1007-1011 (1986).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

KATOYYZUTNAWSA-KTKFBEHZSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9-,13-10-,17-14+/t19-/m0/s1/i6D,7D,9D,10D,11D,13D,17D,19D

SMILES (Click to copy)

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