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
3D model of MCTR2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
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
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
Admin
Created at
17th Sep 2020
Updated at
17th Sep 2020