Structure Database (LMSD)

Common Name
MCTR2
Systematic Name
13R-(S-cysteinylglycinyl)-14S-hydroxy-4Z,7Z,9E,11E,16Z,19Z-docosahexaenoic acid
Synonyms
  • 13-cysteinylglycinyl-maresin 2
  • Maresin Conjugates in Tissue Regeneration 2
  • Maresin Sulfido Conjugate 2
LM ID
LMFA04050006
Formula
Exact Mass
Calculate m/z
520.26071
Status
Curated

Classification

Biological Context

Maresin conjugates in tissue regeneration 2 (MCTR2) is a specialized pro-resolving mediator (SPM) synthesized from docosahexaenoic acid (DHA) in macrophages at the site of inflammation.1,2 DHA is oxidized to maresin 1 (MaR1), which is converted to MCTR1 by glutathione S-transferase Mu 4 or leukotriene C4 synthase then to MCTR2 by γ-glutamyl transferase.3 MCTR2 accelerates tissue regeneration in planaria (1 and 100 nM).2 Pretreatment with MCTR2 prior to E. coli administration reduces neutrophil infiltration, shortens the inflammatory resolution period, and increases phagocytosis of E. coli by macrophages.2 When administered at a dose of 100 ng 12h post E. coli infection in a mouse model of peritonitis, MCTR2 selectively reduced the amount of the eicosanoids PGD2 and PGF2α in the exudate.2

This information has been provided by Cayman Chemical

References

1. Serhan, C.N. Novel pro-resolving lipid mediators in inflammation are leads for resolution physiology. Nature 510(7503), 92-101 (2014).
2. Dalli, J., Vlasakov, I., Riley, I.R., et al. Maresin conjugates in tissue regeneration biosynthesis enzymes in human macrophages. Proc. Natl. Acad. Sci. USA 113(43), 12232-12237 (2016).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Maresin conjugates in tissue regeneration biosynthesis enzymes in human macrophages.,
Proc Natl Acad Sci U S A, 2016
Pubmed ID: 27791009

String Representations

InChiKey (Click to copy)
CPBQPRBQBDLLLA-VZUSUAOUSA-N
InChi (Click to copy)
InChI=1S/C27H40N2O6S/c1-2-3-4-5-11-14-17-23(30)24(36-21-22(28)27(35)29-20-26(33)34)18-15-12-9-7-6-8-10-13-16-19-25(31)32/h3-4,6-7,9-15,18,22-24,30H,2,5,8,16-17,19-21,28H2,1H3,(H,29,35)(H,31,32)(H,33,34)/b4-3-,7-6-,12-9+,13-10-,14-11-,18-15+/t22-,23-,24+/m0/s1
SMILES (Click to copy)
C(CC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)NCC(O)=O)N)[C@@H](O)C/C=C\C/C=C\CC)(=O)O

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 545.15
Topological Polar Surface Area 149.95
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 8
logP 5.19
Molar Refractivity 149.24

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Created at
17th Sep 2020
Updated at
17th Sep 2020