LIPID MAPS

Structure Database (LMSD)

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Common Name

17S-HDHA

Systematic Name

17S-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid

Synonyms

LM ID

LMFA04000012

Formula

C₂₂H₃₂O₃

Exact Mass

Calculate m/z

344.235145

Sum Composition

FA 22:6;O

Status

Curated

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Classification

Biological Context

17(S)-HDHA is a hydroxy fatty acid formed from docosahexaenoic acid (DHA) by 15-lipoxygenase (15-LO) and is a precursor to 17(S)-resolvins.^1,2 17(S)-HDHA inhibits platelet 12-LO (IC50 = 0.4 μM).² It inhibits TNF-α-induced expression of IL1B in a human glial cell line (IC50 = ~0.5 nM).¹ 17(S)-HDHA (100 nM) inhibits NOD-, LRR-, and pyrin domain-containing protein 3 (NLRP3) inflammasome formation induced by homocysteine in podocytes.³

This information has been provided by Cayman Chemical

References

1. Li, G., Chen, Z., Bhat, O.M., et al. NLRP3 inflammasome as a novel target for docosahexaenoic acid metabolites to abrogate glomerular injury. J. Lipid Res. 58(6), 1080-1090 (2017).

2. Mitchell, P.D., Hallam, C., Hemsley, P.E., et al. Inhibition of platelet 12-lipoxygenase by hydroxy-fatty acids. Biochem. Soc. Trans. 12, 839-841 (1984).

3. Hong, S., Gronert, K., Devchand, P.R., et al. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation. J. Biol. Chem. 278(17), 14677-14687 (2003).

String Representations

InChiKey (Click to copy)

SWTYBBUBEPPYCX-YTQNUIGOSA-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/h3,5-8,11-16,19,21,23H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+/t21-/m0/s1

SMILES (Click to copy)

C(CC/C=C\C/C=C\C/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CC)(=O)O