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
376.224976
Sum Composition
Status
Curated


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

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Resolvin D1 and its aspirin-triggered 17R epimer. Stereochemical assignments, anti-inflammatory properties, and enzymatic inactivation.,
J Biol Chem, 2007
Pubmed ID: 17244615

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

CHEBI ID
PubChem CID
Cayman ID
GuidePharm 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
25th Mar 2025