LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

(+/-)-15-HEPE

Systematic Name

(+/-)-15-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid

Synonyms

LM ID

LMFA03070032

Formula

C₂₀H₃₀O₃

Exact Mass

Calculate m/z

318.219495

Sum Composition

FA 20:5;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

Classification

Biological Context

(±)15-HEPE is a racemic mixture of the monohydroxy fatty acids 15(R)-HEPE and 15(S)-HEPE . 15(S)-HEPE is formed from EPA via a 15(S)-HpEPE intermediate, which is produced by 15-lipoxygenase (15-LO) and reduced by glutathione peroxidase (GPX).^1,2 (±)15-HEPE is active against P. acnes and S. aureus (MICs = 128 and 512 mg/L, respectively).³ It inhibits aggregation of isolated rat neutrophils induced by the formyl peptide receptor agonist fMLP (IC50 = 4.7 µM).⁴ Bronchoalveolar lavage fluid (BALF) levels of (±)15-HEPE are increased in patients with allergic asthma or COVID-19.5,6

This information has been provided by Cayman Chemical

References

1. Lam, B., Marcinkiewicz, E., and Wong, P.Y.-K. Transformation of 15-hydroperoxyeicosapentaenoic acid into mono- and dihydroxyeicosapentaenoic acids by human platelets. Drugs affecting leukotrienes and other eicosanoid pathways 167-180 (1985).

2. Desbois, A.P., and Lawlor, K.C. Antibacterial activity of long-chain polyunsaturated fatty acids against Propionibacterium acnes and Staphylococcus aureus. Mar. Drugs 11(11), 4544-4557 (2013).

3. Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

4. Tan, L., Xin, X., Zhai, L., et al. Drosophila fed ARA and EPA yields eicosanoids, 15S-hydroxy-5Z,8Z, 11Z, 13E-eicosatetraenoic acid, and 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid. Lipids 51(4), 435-449 (2016).

5. Lundström, S.L., Yang, J., Källberg, H.J., et al. Allergic asthmatics show divergent lipid mediator profiles from healthy controls both at baseline and following birch pollen provocation. PLoS One 7(3), e33780 (2012).

6. Miller, C., Yamaguchi, R.Y., and Ziboh, V.A. Guinea pig epidermis generates putative anti-inflammatory metabolites from fish oil polyunsaturated fatty acids. Lipids 24(12), 998-1003 (1989).

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)

WLKCSMCLEKGITB-XWJJKCKWSA-N

InChi (Click to copy)

InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h3-5,8-11,13-14,17,19,21H,2,6-7,12,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,13-3-,17-14+

SMILES (Click to copy)

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