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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 03:26:19 UTC
Update Date2022-03-07 02:49:19 UTC
HMDB IDHMDB0003689
Secondary Accession Numbers
  • HMDB03689
Metabolite Identification
Common NameNeuroprotectin D1
DescriptionNeuroprotectin D1 is an autacoid protectin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. They require enzymatic generation from docosanoids, oxygenated products from docosahexaenoic acid (DHA), which specifically possess a conjugated triene double-bond system in their structures, are denoted protectins. The protectins demonstrate anti-inflammatory and neuroprotective actions in vivo. Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The terms protectin and neuroprotectin [the term applied to protectin that is generated in the neural tissues] were introduced given the anti-inflammatory and protective actions of the 10,17-docosatriene in neural systems, stroke, and animal models of Alzheimer's disease. The prefix in neuroprotectin (NPD1) provides a local pathway address for the biosynthesis and action of this molecule. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimer's disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225 ).
Structure
Thumb
Synonyms
ValueSource
(4Z,7Z,10R,11E,13E,15Z,17S,19Z)-10,17-Dihydroxydocosahexaenoic acidChEBI
(N)PD1ChEBI
(Neuro)protectin D1ChEBI
10(R),17(S)-Dihydroxydocosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acidChEBI
NPD1ChEBI
PD1ChEBI
(4Z,7Z,10R,11E,13E,15Z,17S,19Z)-10,17-DihydroxydocosahexaenoateGenerator
10(R),17(S)-Dihydroxydocosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoateGenerator
10R,17S-Dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoateHMDB
10R,17S-Dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acidHMDB, MeSH
Protectin D1MeSH, HMDB
Neuroprotectin D1ChEBI
Chemical FormulaC22H32O4
Average Molecular Weight360.4871
Monoisotopic Molecular Weight360.230059512
IUPAC Name(4Z,7Z,10R,11E,13E,15Z,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoic acid
Traditional Nameneuroprotectin D1
CAS Registry NumberNot Available
SMILES
CC\C=C/C[C@H](O)\C=C/C=C/C=C/[C@H](O)C\C=C/C\C=C/CCC(O)=O
InChI Identifier
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
InChI KeyCRDZYJSQHCXHEG-SFVBTVKNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13171083
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProtectin_D1
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID138655
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Serhan CN: Resolution phase of inflammation: novel endogenous anti-inflammatory and proresolving lipid mediators and pathways. Annu Rev Immunol. 2007;25:101-37. [PubMed:17090225 ]