LIPID MAPS

Structure Database (LMSD)

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Common Name

19,20-DiHDPE

Systematic Name

(+/-)-19,20-dihydroxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid

Synonyms

19,20-DiHDPA

LM ID

LMFA04000043

Formula

C₂₂H₃₄O₄

Exact Mass

Calculate m/z

362.245711

Sum Composition

FA 22:5;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Biological Context

Docosahexaenoic acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain.¹ (±)19(20)-DiHDPA is one of the major metabolites produced when DHA is incubated with NADPH-supplemented rat liver microsomes.² DHA is also slowly metabolized by monkey seminal vesicles to (±)19(20)-DiHDPA.³ The route of production likely proceeds through cytochrome P450-catalyzed epoxidation at the ω-3 double bond, followed by conversion to the vicinal diols by epoxide hydrolase.^2,3

This information has been provided by Cayman Chemical

References

1. Salem, N., Kim, H.Y., and Yergey, J.A. Docosahexaenoic acid: Membrane function and metabolism. Health effects of polyunsaturated fatty acids in seafoods 263-317 (1986).

2. VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. The Journal of Biological Chemisty 259(9), 5776-5783 (1984).

3. Oliw, E.H., and Sprecher, H.W. Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: Isolation and biosynthesis of omega-3 epoxides. Biochim. Biophys. Acta 1086(3), 287-294 (1991).

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)

FFXKPSNQCPNORO-MBYQGORISA-N

InChi (Click to copy)

InChI=1S/C22H34O4/c1-2-20(23)21(24)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(25)26/h3-4,7-10,13-16,20-21,23-24H,2,5-6,11-12,17-19H2,1H3,(H,25,26)/b4-3-,9-7-,10-8-,15-13-,16-14-

SMILES (Click to copy)

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