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17 (R) -Resolvin D3

CAT: 0931-T85108-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0931-T85108-01Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
1427475-53-3
Target
Drug Metabolite, Others
Related Pathways
Metabolism, Others
Bioactivity
17 (R) -Resolvin D3 (17 (R) -RvD3) is an aspirin-triggered epimer of resolvin D3, produced from docosahexaenoic acid (DHA) through the action of COX-2 in the presence of aspirin, via a 17 (R) -hydroperoxy DHA (17 (R) -HDHA) intermediary. Identified in mouse inflammatory exudates, 17 (R) -RvD3 notably inhibits the transmigration of isolated human polymorphonuclear cells (PMNs) and fosters the efferocytosis of apoptotic PMNs by macrophages. Furthermore, in a mouse model of zymosan-induced peritonitis, 17 (R) -RvD3 administration (10 ng/animal) significantly curtails neutrophil infiltration into the peritoneal cavity and modulates cytokine levels by reducing IL-6 and increasing IL-10 in the inflammatory exudate. It engages GPR32, evidenced by activation in a β-arrestin reporter assay and augments phagocytosis more effectively in CHO cells overexpressing GPR32 compared to controls. Additionally, 17 (R) -RvD3 enhances the clearance of etoposide-induced tumor cell debris by monocyte-derived macrophages in H460 human lung carcinoma.
Smiles
C([C@H](/C=C/C=C/C=C\[C@H](CCC(O)=O)O)O)/C=C\C=C\[C@@H](C/C=C\CC)O
Molecular Formula
C22H32O5
Molecular Weight
376.49
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

AT-Resolvin D3

Aspirin-triggered resolvin D3 is a member of the class of resolvins that is (5Z,7E,9E,13Z,15E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 4, 11 and 17 (the 4S,11R,17R-stereoisomer). It has a role as an anti-inflammatory agent and a human xenobiotic metabolite. It is a resolvin, a secondary allylic alcohol, a hydroxy polyunsaturated fatty acid and a triol.

CAS Number1427475-53-3
PubChem CID77845952
IUPAC Name(4S,5Z,7E,9E,11R,13Z,15E,17R,19Z)-4,11,17-trihydroxydocosa-5,7,9,13,15,19-hexaenoic acid
Molecular FormulaC22H32O5
Molecular Weight376.5
XLogP2.9
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@H](/C=C/C=C/C=C\[C@H](CCC(=O)O)O)O)O
InChI
InChI=1S/C22H32O5/c1-2-3-7-12-19(23)14-10-6-11-15-20(24)13-8-4-5-9-16-21(25)17-18-22(26)27/h3-11,13-14,16,19-21,23-25H,2,12,15,17-18H2,1H3,(H,26,27)/b5-4+,7-3-,11-6-,13-8+,14-10+,16-9-/t19-,20+,21-/m1/s1
InChIKey
QBTJOLCUKWLTIC-AXRBAIMGSA-N
Chemical Structure
2D Structure
2D structure of AT-Resolvin D3
CAS: 1427475-53-3
CID: 77845952
Formula: C22H32O5
MW: 376.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight376.5
XLogP32.9
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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