Structure Database (LMSD)
Common Name
AT-Resolvin D1
Systematic Name
7S,8R,17R-trihydroxy-4Z,9E,11E,13Z,15E,19Z-docosahexaenoic acid
Synonyms
- AT-RvD1
LM ID
LMFA04030005
Formula
Exact Mass
Calculate m/z
376.224975
Sum Composition
Status
Curated
3D model of AT-Resolvin D1
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 D1 (RvD1) is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase.1 17(R)-RvD1 is an aspirin-triggered epimer of RvD1 that reduces human polymorphonuclear leukocyte (PMN) transendothelial migration, the earliest event in acute inflammation, with equipotency to RvD1 (EC50 = ~30 nM).3 17(R)-RvD1 exhibits a dose-dependent reduction in leukocyte infiltration in a mouse model of peritonitis with maximal inhibition of ~35% at a 100 ng dose.3 In contrast to RvD1, the aspirin-triggered form resists rapid inactivation by eicosanoid oxidoreductases.
This information has been provided by Cayman Chemical
References
1. Hong, S., Gronert, K., Devchand, P.R., et al. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation. The Journal of Biological Chemisty 278(17), 14677-14687 (2003).
2. Ariel, A., and Serhan, C.N. Resolvins and protectins in the termination program of acute inflammation. Trends Immunol. 28(4), 176-183 (2007).
3. Sun, Y.P., Oh, S.F., Uddin, J., et al. Resolvin D1 and its aspirin-triggered 17R epimer stereochemical assignments, anti-inflammatory properties, and enzymatic inactivation. The Journal of Biological Chemisty 282(13), 9323-9334 (2007).
String Representations
InChiKey (Click to copy)
OIWTWACQMDFHJG-BJEBZIPWSA-N
InChi (Click to copy)
InChI=1S/C22H32O5/c1-2-3-9-14-19(23)15-10-6-4-5-7-11-16-20(24)21(25)17-12-8-13-18-22(26)27/h3-12,15-16,19-21,23-25H,2,13-14,17-18H2,1H3,(H,26,27)/b6-4-,7-5+,9-3-,12-8-,15-10+,16-11+/t19-,20-,21+/m1/s1
SMILES (Click to copy)
C(CC/C=C\C[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[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
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