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17 (R) -Resolvin D1

CAT: 0931-T35946-01Size: 10 µgDry Ice: NoHazardous: No
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CAT#:0931-T35946-01Size:10 µg
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CAS Number
528583-91-7
Target
Others, TRP/TRPV Channel
Related Pathways
Others, Membrane transporter/Ion channel
Bioactivity
Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid and docosahexaenoic acid.[1] In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state.[2] Resolvin D1 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. Analytical and biological comparisons of synthetic 17 (R) -RvD1 with endogenously derived 17 (R) -RvD1 have confirmed its identity as matching the natural product.[4]
Smiles
CC\C=C/C[C@@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)C\C=C/CCC(O)=O
Molecular Formula
C22H32O5
Molecular Weight
376.493
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

aspirin-triggered resolvin D1

Aspirin-triggered resolvin D1 is a member of the class of resolvins that consists of docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid carrying three hydroxy substituents at positions 7, 8, and 17 (the 7S,8R,17S-stereoisomer). It has a role as an antiviral agent, an analgesic, an anti-allergic agent, an anti-inflammatory agent, a nephroprotective agent, a human xenobiotic metabolite and a TGFbeta receptor antagonist. It is a resolvin, a secondary allylic alcohol and a hydroxy polyunsaturated fatty acid.

CAS Number528583-91-7
PubChem CID16126783
IUPAC Name(4Z,7S,8R,9E,11E,13Z,15E,17R,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoic acid
Molecular FormulaC22H32O5
Molecular Weight376.5
XLogP3.1
Topological Polar Surface Area98
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count14
Heavy Atom Count27
Formal Charge0
Complexity555
SMILES
CC/C=C\C[C@H](/C=C/C=C\C=C\C=C\[C@H]([C@H](C/C=C\CCC(=O)O)O)O)O
InChI
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
InChIKey
OIWTWACQMDFHJG-BJEBZIPWSA-N
Chemical Structure
2D Structure
2D structure of aspirin-triggered resolvin D1
CAS: 528583-91-7
CID: 16126783
Formula: C22H32O5
MW: 376.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight376.5
XLogP33.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count14
Exact Mass376.22497412
Monoisotopic Mass376.22497412
Topological Polar Surface Area98 Ų
Heavy Atom Count27
Formal Charge0
Complexity555
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count6
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
QJB53270Resolvin E2
HY-113533Resolvin D4
HY-114041-01Resolvin E1
464623-01Resolvin D2
439859-01Resolvin D5
MBS5801195Resolvin D3
MBS5768152Resolvin D1

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