LIPID MAPS

Structure Database (LMSD)

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Common Name

19(20)-EpDPE

Systematic Name

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

Synonyms

(+/-)19(20)-EpDPA
(+/-)19,20-epoxy DPA

LM ID

LMFA04000038

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

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View spectra on LIPID MAPS Standard Spectra DB

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

Classification

Biological Context

(±)-19(20)-EpDPA is an epoxide metabolite of docosahexaenoic acid (DHA).¹ It is formed from DHA by various cytochrome P450 (CYP) isoforms. In vivo, (±)-19(20)-EpDPA (100 ng/animal, i.p.) suppresses hepatic crown-like structure (hCLS) formation and liver fibrosis in wild-type, but not GPR120-deficient, mice in a model of non-alcoholic steatohepatitis (NASH) induced by high-fat diet and carbon tetrachloride (CCl4).² Intraplantar administration of (±)-19(20)-EpDPA induces acute mechanical hyperalgesia in mice, an effect that can be blocked by the transient receptor potential ankyrin 1 (TRPA1) inhibitor A-967079.3

This information has been provided by Cayman Chemical

References

1. Lucas, D., Goulitquer, S., Marienhagen, J., et al. Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450. J. Lipid Res. 51(5), 1125-1133 (2010).

2. Aoki, H., Isobe, Y., Yoshida, M., et al. Enzymatically-epoxidized docosahexaenoic acid, 19,20-EpDPE, suppresses hepatic crown-like structure formation and nonalcoholic steatohepatitis fibrosis through GPR120. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1868(3), 159275 (2023).

3. Sun, L., Zhang, J., Niu, C., et al. CYP1B1-derived epoxides modulate the TRPA1 channel in chronic pain. Acta Pharm. Sinica B 1-14 (2022).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450.,
J Lipid Res, 2010

Pubmed ID: 19965576

String Representations

InChiKey (Click to copy)

OSXOPUBJJDUAOJ-MBYQGORISA-N

InChi (Click to copy)

InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/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\CC1OC1CC)(=O)O