Structure Database (LMSD)
Common Name
Resolvin D2
Systematic Name
7S,16R,17S-trihydroxy-4Z,8E,10Z,12E,14E,19Z-docosahexaenoic acid
Synonyms
- RvD2
LM ID
LMFA04030001
Formula
Exact Mass
Calculate m/z
376.224975
Sum Composition
Status
Curated
3D model of Resolvin D2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).1 In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state.2 Resolvin D2 (RvD2) is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase and functions to dampen excessive neutrophil trafficking to sites of inflammation.3 It reduces zymosan-stimulated PMN infiltration by 70% at doses as low as 10 pg per mouse and significantly reduces PAF-stimulated leukocyte adherence and emigration at 1 nM.3 Also, by stimulating nitric oxide production, RvD2 dose dependently decreases leukocyte-endothelial interactions. In a mouse model of sepsis, RvD2 reduces leukocyte and PMN infiltration, decreases production of pro-inflammatory cytokines, and promotes phagocyte-mediated bacterial clearance.3
This information has been provided by Cayman Chemical
References
2. Ariel, A., and Serhan, C.N. Resolvins and protectins in the termination program of acute inflammation. Trends Immunol. 28(4), 176-183 (2007).
References
String Representations
InChiKey (Click to copy)
IKFAUGXNBOBQDM-XFMPMKITSA-N
InChi (Click to copy)
InChI=1S/C22H32O5/c1-2-3-9-16-20(24)21(25)17-12-7-5-4-6-10-14-19(23)15-11-8-13-18-22(26)27/h3-12,14,17,19-21,23-25H,2,13,15-16,18H2,1H3,(H,26,27)/b6-4-,7-5+,9-3-,11-8-,14-10+,17-12+/t19-,20+,21-/m1/s1
SMILES (Click to copy)
C(CC/C=C\C[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)C/C=C\CC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
414.63
Topological Polar Surface Area
97.99
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
5
logP
4.32
Molar Refractivity
110.79
Admin
Created at
-
Updated at
5th Feb 2024