Structure Database (LMSD)

Common Name
Maresin 2-d5
Systematic Name
13R,14S-dihydroxy-4Z,7Z,9E,11E,16Z,19Z-docosahexaenoic-21,21,22,22,22-d5 acid
Synonyms
  • 13R,14S-diHDHA-d5
  • 13R,14S-dihydroxy Docosahexaenoic Acid-d5
  • MaR2-d5
LM ID
LMFA04050009
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

Category
Main Class
Sub Class
Fatty Acyls [FA]
Docosanoids [FA04]
Maresins [FA0405]

Biological Context

Maresin 2-d5 (MaR2-d5) contains 5 deuterium atoms at the 21, 21, 22, 22, and 22 positions. It is intended for use as an internal standard for the quantification of MaR2 by GC- or LC-MS. MaR2 is a 13R,14S-dihydroxy DHA formed by recombinant human macrophage 12-lipoxygenase and soluble epoxide hydrolase co-incubated with DHA.1 At 1 ng/mouse, MaR2 was shown to reduce neutrophil infiltration by 40% in a mouse model of peritonitis, and at 10 pM, MaR2 can enhance human macrophage phagocytosis of zymosan A by 90%.1

This information has been provided by Cayman Chemical

References

1. Deng, B., Wang, C.W., Arnardottir, H.H., et al. Maresin biosynthesis and identification of maresin 2, a new anti-inflammatory and pro-resolving mediator from human macrophages. PLoS One 9(7), (2014).
1. Deng, B., Wang, C.W., Arnardottir, H.H., et al. Maresin biosynthesis and identification of maresin 2, a new anti-inflammatory and pro-resolving mediator from human macrophages. PLoS One 9(7), (2014).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
ALWYOLKNLLFCAY-VLKIHEMDSA-N
InChi (Click to copy)
InChI=1S/C22H32O4/c1-2-3-4-5-11-14-17-20(23)21(24)18-15-12-9-7-6-8-10-13-16-19-22(25)26/h3-4,6-7,9-15,18,20-21,23-24H,2,5,8,16-17,19H2,1H3,(H,25,26)/b4-3-,7-6-,12-9+,13-10-,14-11-,18-15+/t20-,21+/m0/s1/i1D3,2D2
SMILES (Click to copy)
C(CC/C=C\C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)C/C=C\C/C=C\C([2H])([2H])C([2H])([2H])[2H])(=O)O

Other Databases

PubChem CID
162640727
Cayman ID
20757

Calculated Physicochemical Properties

Heavy Atoms 26
Rings
Aromatic Rings
Rotatable Bonds 14
Van der Waals Molecular Volume 405.84
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 5.06
Molar Refractivity 108.89

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Created at
25th Mar 2025
Updated at
25th Mar 2025