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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 03:26:19 UTC
Update Date2017-12-07 01:52:40 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
10R,17S-Dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoateHMDB
10R,17S-Dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acidHMDB
NPD1HMDB
Protectin D1MeSH
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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP4.95ALOGPS
logP4.29ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity114.42 m³·mol⁻¹ChemAxon
Polarizability41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6968000000-42e1438e64f55c9f245aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-08i9-7102390000-328e3d7ee2985bc30985View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0019000000-a7f57dc37b7f53e2c011View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-3489000000-de7442657d44b0899c71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kal-9280000000-fae78fa064c3e0305660View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-0009000000-c9399c4361cff827f71dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-1129000000-13f3fb05ea5906bdabc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9331000000-a208007b61b44d2fe4d1View in MoNA
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
FoodDB IDFDB023215
KNApSAcK IDNot Available
Chemspider ID13171083
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16042541
PDB IDNot Available
ChEBI 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 ]