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

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: assignments of dihydroxy-containing docosatrienes.,
J Immunol, 2006
Pubmed ID: 16424216

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

HMDB ID
CHEBI ID
PubChem CID
Cayman ID

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

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Created at
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Updated at
27th Jan 2022