LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)-17-HDoHE

Systematic Name

(+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid

Synonyms

(+/-)-17-HDHA

LM ID

LMFA04000032

Formula

C₂₂H₃₂O₃

Exact Mass

Calculate m/z

344.235146

Sum Composition

FA 22:6;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

(±)17-HDHA is an autoxidation product of docosahexaenoic acid (DHA) in vitro.^1,2 It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes.^3,4,5 17(S)-HDHA could be produced by enzymatic oxidation of DHA using soybean lipoxygenase (LO) and is the putative product of mammalian 15-LOs.⁵ 17(S)-HDHA was shown to be an inhibitor of U-46619 -induced rabbit and rat aortic smooth muscle contraction with IC50 values of 4.9 and 7.2 µM, respectively.⁶ (±)17-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

This information has been provided by Cayman Chemical

References

1. Kim, H.Y., Karanian, J.W., Shingu, T., et al. Sterochemical analysis of hydroxylated docosahexaenoates produced by human platelets and rat brain homogenate. Prostaglandins 40(5), 473-490 (1990).

2. Reynaud, D., Thickitt, C.P., and Pace-Asciak, C.R. Facile preparation and structural determination of monohydroxy derivatives of docosahexaenoic acid (HDoHE) by α-tocopherol-directed autoxidation. Anal. Biochem. 214(1), 165-170 (1993).

3. Yamane, M., Abe, A., and Yamane, S. High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate. J. Chromatogr. 652(2), 123-136 (1994).

4. Karanian, J.W., Kim, H.Y., and Salem, N., Jr. Inhibitory effects of n-6 and n-3 hydroxy fatty acids on thromboxane (U46619)-induced smooth muscle contraction. J. Pharmacol. Exp. Ther. 270(3), 1105-1109 (1994).

5. VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. J. Biol. Chem. 259(9), 5776-5783 (1984).

6. VanRollins, M., and Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate. J. Lipid Res. 25(5), 507-517 (1984).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

SWTYBBUBEPPYCX-VIIQGJSXSA-N

InChi (Click to copy)

InChI=1S/C22H32O3/c1-2-3-15-18-21(23)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(24)25/h3,5-8,11-16,19,21,23H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+

SMILES (Click to copy)

C(CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(O)C/C=C\CC)(=O)O