Structure Database (LMSD)
Common Name
Neuroprotectin D1-d5
Systematic Name
10R,17S-dihydroxy-4Z,7Z,11E,13E,15Z,19Z-docosahexaenoic-21,21,22,22,22-d5 acid
Synonyms
- NPD1-d5
- Protectin D1-d5
- PD1-d5
3D model of Neuroprotectin D1-d5
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Protectin D1-d5 is intended for use as an internal standard for the quantification of protectin D1 by GC- or LC-MS. 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. 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
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
synthetic construct
(#32630)
Synthetic deuterated standard
String Representations
InChiKey (Click to copy)
CRDZYJSQHCXHEG-XYVLOPPUSA-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/i1D3,2D2
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\C([2H])([2H])C([2H])([2H])[2H])(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
Aromatic Rings
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
4th Dec 2024
Updated at
5th Dec 2024