LIPID MAPS

Structure Database (LMSD)

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Common Name

22-HDHA

Systematic Name

22-hydroxy-4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid

Synonyms

22-OH DHA
22-HDoHE

LM ID

LMFA01050604

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

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

Classification

Biological Context

22-HDHA is an oxidation product of docosahexaenoic acid (DHA).¹ In vitro, it is formed upon incubation of rat liver microsomes with DHA and NADPH and also by the human cytochrome P450 (CYP) isoform CYP4F3B in BTI-TN-5B1-4 microsomes.^1,2 Serum levels of 22-HDHA increase following dietary DHA supplementation in humans.³

This information has been provided by Cayman Chemical

References

1. 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).

2. Harmon, S.D., Fang, X., Kaduce, T.L., et al. Oxygenation of ω-3 fatty acids by human cytochrome P450 4F3B: Effect on 20-hydroxyeicosatetraenoic acid production. Prostaglandins Leukot. Essent. Fatty Acids 75(3), 169-177 (2006).

3. Fischer, R., Konkel, A., Mehling, H., et al. Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway. J. Lipid Res. 55(6), 1150-1164 (2014).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production.,
Prostaglandins Leukot Essent Fatty Acids, 2006

Pubmed ID: 16820285

String Representations

InChiKey (Click to copy)

DTRUULZFBQUZPD-OAKYPOHLSA-N

InChi (Click to copy)

InChI=1S/C22H32O3/c23-21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-22(24)25/h2-5,8-11,14-17,23H,1,6-7,12-13,18-21H2,(H,24,25)/b4-2-,5-3-,10-8-,11-9-,16-14-,17-15-

SMILES (Click to copy)

C(=C/C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCO)/CCC(=O)O