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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 04:04:58 UTC
Update Date2017-10-23 19:04:09 UTC
HMDB IDHMDB0003733
Secondary Accession Numbers
  • HMDB03733
Metabolite Identification
Common NameResolvin D1
DescriptionResolvin D1 (RvD1) is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).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 term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. 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
7S,8,17S-Trihydroxy-docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoateHMDB
7S,8,17S-Trihydroxy-docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acidHMDB
RVD1HMDB
7,8,17-Trihydroxy-4,9,11,13,15,19-docosahexaenoic acidMeSH
RVD1 Fatty acidMeSH
Chemical FormulaC22H32O5
Average Molecular Weight376.4865
Monoisotopic Molecular Weight376.224974134
IUPAC Name(4Z,7S,9E,11E,13Z,15E,17S,19Z)-7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoic acid
Traditional Nameresolvin D1
CAS Registry NumberNot Available
SMILES
CC\C=C/C[C@H](O)\C=C\C=C/C=C/C=C/C(O)[C@@H](O)C\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C22H32O5/c1-2-3-9-14-19(23)15-10-6-4-5-7-11-16-20(24)21(25)17-12-8-13-18-22(26)27/h3-12,15-16,19-21,23-25H,2,13-14,17-18H2,1H3,(H,26,27)/b6-4-,7-5+,9-3-,12-8-,15-10+,16-11+/t19-,20?,21-/m0/s1
InChI KeyOIWTWACQMDFHJG-NJIQAZPPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Polyol
  • 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 DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.021 g/LALOGPS
logP4.66ALOGPS
logP3.22ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity115.78 m³·mol⁻¹ChemAxon
Polarizability42.86 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, Positivesplash10-07bf-2964000000-3cfbbd4a6208b19e902aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004j-6213197000-5eda0922138239f99e8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0009000000-6d91e25e362dd3938f52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0mi6-9547000000-ee7c5ac91dfdb52f97bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9421000000-6f76d241aa5fccdd6149View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-63b7cd0ebed5844b253fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7i-2459000000-91722c915dbc7e9cf847View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9550000000-49951d2854178f0090e6View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0000454 +/- 0.000027 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023219
KNApSAcK IDNot Available
Chemspider ID17216236
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061135
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 ]