Structure Database (LMSD)
Common Name
Neuroprotectin D1
Systematic Name
10R,17S-dihydroxy-4Z,7Z,11E,13E,15Z,19Z-docosahexaenoic acid
Synonyms
- NPD1
- Protectin D1
- PD1
LM ID
LMFA04040001
Formula
Exact Mass
Calculate m/z
360.23006
Sum Composition
Status
Curated
3D model of Neuroprotectin D1
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Protectin D1 is a specialized pro-resolving mediator (SPM) synthesized from docosahexaenoic acid (DHA).1 DHA is oxidized to 16S,17S-epoxy-protectin, which is converted to protectin D1 enzymatically. Protectin D1 increases phagocytosis of apoptotic polymorphonuclear leukocytes (PMNs) by macrophages in a non-phlogistic manner and is generated in vitro during macrophage-apoptotic interactions.2 It enhances phagocytosis in mice after 24 hours, but not at the initiation or peak of inflammation. It also decreases PMN infiltration in a zymosan-induced mouse model of inflammation when administered at a dose of 300 ng per animal. Protectin D1 (200 µg, i.v.) inhibits increases in neutrophil counts in bronchoalveolar fluid (BALF) and lung myeloperoxidase activity in a mouse model of pulmonary injury and inflammation induced by intratracheal LPS instillation.3 It also decreases pulmonary edema and promotes neutrophil apoptosis in BALF.
This information has been provided by Cayman Chemical
References
1. Li, X., Li, C., Liang, W., et al. Protectin D1 promotes resolution of inflammation in a murine model of lipopolysaccharide-induced acute lung injury via enhancing neutrophil apoptosis. Chin. Med. J. (Engl.) 127(5), 810-814 (2014).
2. Rodriguez, A.R., and Spur, B.W. Total synthesis of pro-resolving and tissue-regenerative protectin sulfido-conjugates. Tetrahedron Lett. 56(42), 5811-5815 (2015).
References
String Representations
InChiKey (Click to copy)
CRDZYJSQHCXHEG-SFVBTVKNSA-N
InChi (Click to copy)
InChI=1S/C22H32O4/c1-2-3-10-15-20(23)17-12-8-9-13-18-21(24)16-11-6-4-5-7-14-19-22(25)26/h3,5-13,17-18,20-21,23-24H,2,4,14-16,19H2,1H3,(H,25,26)/b7-5-,9-8+,10-3-,11-6-,17-12-,18-13+/t20-,21+/m0/s1
SMILES (Click to copy)
C(CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)C/C=C\CC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
405.84
Topological Polar Surface Area
77.76
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
5.06
Molar Refractivity
108.89
Admin
Created at
-
Updated at
27th Jan 2022