LIPID MAPS

Structure Database (LMSD)

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

Maresin 1-d5

Systematic Name

7R,14S-dihydroxy-4Z,8E,10E,12Z,16Z,19Z-docosahexaenoic-21,21,22,22,22-d5 acid

Synonyms

Mar1-d5

LM ID

LMFA04050008

Formula

C₂₂H₂₇D₅O₄

Exact Mass

Calculate m/z

365.261444

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Maresin 1-d5 is intended for use as an internal standard for the quantification of maresin 1 by GC- or LC-MS. Maresin 1 is a member of the specialized pro-resolving mediator (SPM) family of bioactive lipids.¹ It is produced from docosahexaenoic acid (DHA) in human peripheral blood mononuclear cells (PBMCs). Maresin 1 (100 nM) reduces TNF-α-induced increases in reactive oxygen species (ROS) in primary human vascular smooth muscle and endothelial cells.² It decreases disease severity, neutrophil infiltration, and intestinal crypt damage in a mouse model of colitis induced by dextran sulfate (DSS) when administered at doses of 0.3 and 1 µg/animal.³ Maresin 1 (0.1, 1, and 10 ng/animal) inhibits increases in inflammatory exudate polymorphonuclear (PMN) neutrophil infiltration in a mouse model of peritonitis induced by zymosan A.¹ It has been found in the synovial fluid of rheumatoid arthritis patients.⁴

This information has been provided by Cayman Chemical

References

1. Serhan, C.N., Dalli, J., Karamnov, S., et al. Macrophage proresolving mediator maresin 1 stimulates tissue regeneration and controls pain. FASEB J. 26(4), 1755-1765 (2012).

2. Chetterjee, A., Sharma, A., Chen, M., et al. The pro-resolving lipid mediator maresin 1 (MaR1) attenuates inflammatory signaling pathways in vascular smooth muscle and endothelial cells. PLoS One 9(11), 1-11 (2014).

3. Marcon, R., Bento, A.F., Dutra, R.C., et al. Maresin 1, a proresolving lipid mediator derived from omega-3 polyunsaturated fatty acids, exerts protective actions in murine models of colitis. J. Immunol. 191(8), 4288-4298 (2013).

4. Giera, M., Ioan-Facsinay, A., Toes, R., et al. Lipid and lipid mediator profiling of human synovial fluid in rheumatoid arthritis patients by means of LC-MS/MS. Biochim. Biophys. Acta 1821(11), 1415-1424 (2012).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

HLHYXXBCQOUTGK-MUCARDRFSA-N

InChi (Click to copy)

InChI=1S/C22H32O4/c1-2-3-4-5-6-10-15-20(23)16-11-7-8-12-17-21(24)18-13-9-14-19-22(25)26/h3-4,6-13,16-17,20-21,23-24H,2,5,14-15,18-19H2,1H3,(H,25,26)/b4-3-,8-7+,10-6-,13-9-,16-11-,17-12+/t20-,21-/m0/s1/i1D3,2D2

SMILES (Click to copy)

C(CC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)C/C=C\C/C=C\C([2H])([2H])C([2H])([2H])[2H])(=O)O