Structure Database (LMSD)
Common Name
Resolvin D1
Systematic Name
7S,8R,17S-trihydroxy-4Z,9E,11E,13Z,15E,19Z-docosahexaenoic acid
Synonyms
- RvD1
LM ID
LMFA04030011
Formula
Exact Mass
Calculate m/z
376.224975
Sum Composition
Status
Curated
3D model of Resolvin D1
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Resolvin D1 (RvD1) is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase.1 A 17(R)-epimer of RvD1 can also be generated in aspirin-treated samples.2 Both RvD1 and its 17(R)-configuration reduce human polymorphonuclear leukocyte (PMNL) transendothelial migration, the earliest event in acute inflammation, with EC50 values of ~30 nM.3 RvD1 and its aspirin-triggered form also exhibit a dose-dependent reduction in leukocyte infiltration in a mouse model of peritonitis with a maximal inhibition of ~35% at a 10-100 ng dose.3
This information has been provided by Cayman Chemical
References
2. 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).
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).
References
String Representations
InChiKey (Click to copy)
OIWTWACQMDFHJG-CCFUIAGSSA-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-/m0/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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Created at
-
Updated at
5th Feb 2024