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
LM ID
LMFA04040007
Formula
Exact Mass
Calculate m/z
365.261444
Status
Curated

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

PubChem CID
Cayman ID

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

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Created at
4th Dec 2024
Updated at
5th Dec 2024