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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:46 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002294
Secondary Accession Numbers
  • HMDB02294
Metabolite Identification
Common NameResolvin D2
DescriptionResolvin D2 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
Data?1582752242
Synonyms
ValueSource
RVD2HMDB
RVD2 CompoundHMDB
(4Z,7R,8E,10Z,12E,14E,17S,19Z)-7,16,17-Trihydroxy-4,8,10,12,14,19-docosahexaenoic acidHMDB
(4Z,7R,8E,10Z,12E,14E,17S,19Z)-7,16,17-Trihydroxydocosa-4,8,10,12,14,19-hexaenoateHMDB
Resolvin D2MeSH
Chemical FormulaC22H32O5
Average Molecular Weight376.4865
Monoisotopic Molecular Weight376.224974134
IUPAC Name(4Z,7R,8E,10Z,12E,14E,17S,19Z)-7,16,17-trihydroxydocosa-4,8,10,12,14,19-hexaenoic acid
Traditional Nameresolvin D2
CAS Registry Number82864-77-5
SMILES
CC\C=C/C[C@H](O)C(O)\C=C\C=C\C=C/C=C/[C@H](O)C\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C22H32O5/c1-2-3-9-16-20(24)21(25)17-12-7-5-4-6-10-14-19(23)15-11-8-13-18-22(26)27/h3-12,14,17,19-21,23-25H,2,13,15-16,18H2,1H3,(H,26,27)/b6-4-,7-5+,9-3-,11-8-,14-10+,17-12+/t19-,20-,21?/m0/s1
InChI KeyIKFAUGXNBOBQDM-GIINMYNKSA-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
  • 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
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
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP4.72ALOGPS
logP3.22ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.64ChemAxon
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
Polarizability42.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.15631661259
DarkChem[M-H]-194.86531661259
DeepCCS[M+H]+197.13830932474
DeepCCS[M-H]-194.7830932474
DeepCCS[M-2H]-228.67330932474
DeepCCS[M+Na]+203.85430932474
AllCCS[M+H]+201.332859911
AllCCS[M+H-H2O]+198.632859911
AllCCS[M+NH4]+203.732859911
AllCCS[M+Na]+204.432859911
AllCCS[M-H]-194.932859911
AllCCS[M+Na-2H]-197.132859911
AllCCS[M+HCOO]-199.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Resolvin D2CC\C=C/C[C@H](O)C(O)\C=C\C=C\C=C/C=C/[C@H](O)C\C=C/CCC(O)=O5395.8Standard polar33892256
Resolvin D2CC\C=C/C[C@H](O)C(O)\C=C\C=C\C=C/C=C/[C@H](O)C\C=C/CCC(O)=O3024.8Standard non polar33892256
Resolvin D2CC\C=C/C[C@H](O)C(O)\C=C\C=C\C=C/C=C/[C@H](O)C\C=C/CCC(O)=O3262.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Resolvin D2,1TMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O3384.6Semi standard non polar33892256
Resolvin D2,1TMS,isomer #2CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O)O[Si](C)(C)C3357.2Semi standard non polar33892256
Resolvin D2,1TMS,isomer #3CC/C=C\C[C@H](O)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C3423.9Semi standard non polar33892256
Resolvin D2,1TMS,isomer #4CC/C=C\C[C@H](O)C(O)/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C3314.7Semi standard non polar33892256
Resolvin D2,2TMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O)O[Si](C)(C)C3387.1Semi standard non polar33892256
Resolvin D2,2TMS,isomer #2CC/C=C\C[C@H](O[Si](C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C3417.1Semi standard non polar33892256
Resolvin D2,2TMS,isomer #3CC/C=C\C[C@H](O[Si](C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C3330.0Semi standard non polar33892256
Resolvin D2,2TMS,isomer #4CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3390.4Semi standard non polar33892256
Resolvin D2,2TMS,isomer #5CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3313.6Semi standard non polar33892256
Resolvin D2,2TMS,isomer #6CC/C=C\C[C@H](O)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3354.0Semi standard non polar33892256
Resolvin D2,3TMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3380.2Semi standard non polar33892256
Resolvin D2,3TMS,isomer #2CC/C=C\C[C@H](O[Si](C)(C)C)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3304.9Semi standard non polar33892256
Resolvin D2,3TMS,isomer #3CC/C=C\C[C@H](O[Si](C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3345.3Semi standard non polar33892256
Resolvin D2,3TMS,isomer #4CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3324.5Semi standard non polar33892256
Resolvin D2,4TMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3313.9Semi standard non polar33892256
Resolvin D2,1TBDMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O3612.5Semi standard non polar33892256
Resolvin D2,1TBDMS,isomer #2CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C3601.0Semi standard non polar33892256
Resolvin D2,1TBDMS,isomer #3CC/C=C\C[C@H](O)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C3657.1Semi standard non polar33892256
Resolvin D2,1TBDMS,isomer #4CC/C=C\C[C@H](O)C(O)/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C3561.4Semi standard non polar33892256
Resolvin D2,2TBDMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C3838.0Semi standard non polar33892256
Resolvin D2,2TBDMS,isomer #2CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C3862.7Semi standard non polar33892256
Resolvin D2,2TBDMS,isomer #3CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C3777.1Semi standard non polar33892256
Resolvin D2,2TBDMS,isomer #4CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3844.8Semi standard non polar33892256
Resolvin D2,2TBDMS,isomer #5CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3769.2Semi standard non polar33892256
Resolvin D2,2TBDMS,isomer #6CC/C=C\C[C@H](O)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3823.0Semi standard non polar33892256
Resolvin D2,3TBDMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4097.8Semi standard non polar33892256
Resolvin D2,3TBDMS,isomer #2CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C/C=C/C=C\C=C\[C@H](O)C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4040.0Semi standard non polar33892256
Resolvin D2,3TBDMS,isomer #3CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4068.8Semi standard non polar33892256
Resolvin D2,3TBDMS,isomer #4CC/C=C\C[C@H](O)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4057.4Semi standard non polar33892256
Resolvin D2,4TBDMS,isomer #1CC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C/C=C/C=C\C=C\[C@@H](C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4264.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Resolvin D2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-5595000000-26ab42a98e41df2bfed02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Resolvin D2 GC-MS (4 TMS) - 70eV, Positivesplash10-004j-8310898000-42d39b76a878f133b4372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Resolvin D2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Resolvin D2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 10V, Positive-QTOFsplash10-0a4l-0019000000-cc846ee4dc598df36b232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 20V, Positive-QTOFsplash10-016u-9287000000-8a330b98dfde62df49a92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 40V, Positive-QTOFsplash10-0uxr-9351000000-80ce2f4beee59ac7be182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 10V, Negative-QTOFsplash10-004i-0009000000-19b2fd7eb7c8fb7e51d32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 20V, Negative-QTOFsplash10-0a4i-4159000000-2a165dc7ddd5d24057572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 40V, Negative-QTOFsplash10-0a4i-9240000000-6cdfab92ec5f8d77f8ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 10V, Positive-QTOFsplash10-052f-1019000000-beeb40b975449fe809d92021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 20V, Positive-QTOFsplash10-0006-6697000000-f29701744359c0353f8a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 40V, Positive-QTOFsplash10-001i-5940000000-c5b9c58a4d6c2d9e51222021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 10V, Negative-QTOFsplash10-056r-0019000000-76542daa6f42db069ce12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 20V, Negative-QTOFsplash10-0a70-0159000000-cbe90d6df4027e425b882021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Resolvin D2 40V, Negative-QTOFsplash10-052k-9372000000-5790253dd271949b6de22021-09-25Wishart LabView Spectrum
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 IDFDB022952
KNApSAcK IDNot Available
Chemspider ID17216185
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkResolvin
METLIN IDNot Available
PubChem Compound16061136
PDB IDNot Available
ChEBI IDNot Available
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 ]