Structure Database (LMSD)

Common Name
Resolvin D1-d5
Systematic Name
7S,8R,17S-trihydroxy-4Z,9E,11E,13Z,15E,19Z-docosahexaenoic-21,21,22,22,22-d5 acid
Synonyms
  • RvD1-d5
LM ID
LMFA04030017
Formula
Exact Mass
Calculate m/z
381.256359
Status
Curated

Classification

Biological Context

Resolvin D1-d5 (RvD1-d5) is intended for use as an internal standard for the quantification of RvD1 by GC- or LC-mass spectrometry. 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 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.3 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.4 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.4

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
OIWTWACQMDFHJG-CLQVKFETSA-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/i1D3,2D2
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\C([2H])([2H])C([2H])([2H])[2H])(=O)O

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 27
Rings
Aromatic Rings
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
4th Dec 2024
Updated at
5th Dec 2024