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Structure Database (LMSD)

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Common Name

Protectin DX

Systematic Name

10S,17S-dihydroxy-4Z,7Z,11E,13Z,15E,19Z-docosahexaenoic acid

Synonyms

PDX
10S,17S-DiHDoHE
10S,17S-diHDHA

LM ID

LMFA04040003

Formula

C₂₂H₃₂O₄

Exact Mass

Calculate m/z

360.23006

Sum Composition

FA 22:6;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

10(S),17(S)-DiHDHA is a DHA metabolite, also referred to as protectin DX (PDX).¹ It is produced by an apparent double lipoxygenase (LO)-mediated reaction in murine peritonitis exudates, in suspensions of human leukocytes, or by soybean 15-LO incubated with DHA.^2,1 It differs from protectin D1 with respect to the stereochemistry of the C-10 hydroxyl and the double bond configuration at the 13 and 15 positions. 10(S),17(S)-DiHDHA blocks neutrophil infiltration in murine peritonitis by 20-25% at a dose of 1 ng/mouse.² It also inhibits platelet activation by both impairing thromboxane (TX) synthesis and TX receptor activation.^1,3

This information has been provided by Cayman Chemical

References

1. Serhan, C.N., Gotlinger, K., Hong, S., et al. Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: Assignments of dihydroxy-containing docosatrienes. J. Immunol. 176(3), 1848-1859 (2006).

2. Chen, P., Fenet, B., Michaud, S., et al. Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation. FEBS Lett. 583, 3478-3484 (2009).

3. Chen, P., Véricel, E., Lagarde, M., et al. Poxytrins, a class of oxygenated products from polyunsaturated fatty acids, potently inhibit blood platelet aggregation. FASEB J. 25, 382-388 (2011).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA.,
J Lipid Res, 2013

Pubmed ID: 23740966

Glycine max (#3847)

Magnoliopsida (#3398)

Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation.,
FEBS Lett, 2009

Pubmed ID: 19818771

String Representations

InChiKey (Click to copy)

CRDZYJSQHCXHEG-XLBFCUQGSA-N

InChi (Click to copy)

InChI=1S/C22H32O4/c1-2-3-10-15-20(23)17-12-8-9-13-18-21(24)16-11-6-4-5-7-14-19-22(25)26/h3,5-13,17-18,20-21,23-24H,2,4,14-16,19H2,1H3,(H,25,26)/b7-5-,9-8-,10-3-,11-6-,17-12+,18-13+/t20-,21-/m0/s1

SMILES (Click to copy)

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