LIPID MAPS

Structure Database (LMSD)

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Common Name

17-oxo-DPA

Systematic Name

17-oxo-7Z,10Z,13Z,15E,19Z-docosapentaenoic acid

Synonyms

EFOX
17-oxo-7(Z),10(Z),13(Z),15(E),19(Z)-DPA
17-oxo-DPE (DPA n-3)

LM ID

LMFA04000109

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-oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DPA that is produced endogenously by aspirin-enhanced COX-2 activity.^1,2 It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 µM).²

This information has been provided by Cayman Chemical

References

1. Jie, M.S.F.L.K., and Pasha, M.K. Fatty acids, fatty acid analogues and their derivatives. Nat. Prod. Rep. 607-629 (1998).

2. Groeger, A.L., Cipollina, C., Cole, M.P., et al. Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids. Nat. Chem. Biol. (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids.,
Nat Chem Biol, 2010

Pubmed ID: 20436486

String Representations

InChiKey (Click to copy)

PWVSFTLICCBISU-UCMLWGQMSA-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/h3,5-8,11,13,15-16,19H,2,4,9-10,12,14,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,15-3-,19-16+

SMILES (Click to copy)

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