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




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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
The role of Resolvin D1 in liver diseases.,
Prostaglandins Other Lipid Mediat, 2022
Pubmed ID: 35292355

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

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID

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
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Updated at
5th Feb 2024