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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:27 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012534
Secondary Accession Numbers
  • HMDB12534
Metabolite Identification
Common Name11R-HEPE
Description11R-HEPE belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. Thus, 11R-hepe is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 11R-HEPE.
Structure
Data?1582753063
Synonyms
ValueSource
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoic acidChEBI
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-icosapentaenoic acidChEBI
(5Z,8Z,11R,12E,14Z,17Z)-11-Hydroxyicosapentaenoic acidChEBI
11R-Hydroxy-5Z,8Z,12E,14Z,17Z-eicosapentaenoic acidChEBI
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateGenerator
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-icosapentaenoateGenerator
(5Z,8Z,11R,12E,14Z,17Z)-11-HydroxyicosapentaenoateGenerator
11R-Hydroxy-5Z,8Z,12E,14Z,17Z-eicosapentaenoateGenerator
11(R)-Hydroxyeicosa-5Z,8Z,12E,14Z,17Z-pentaenoateHMDB
11(R)-Hydroxyeicosa-5Z,8Z,12E,14Z,17Z-pentaenoic acidHMDB
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,11R,12E,14Z,17Z)-11-hydroxyicosa-5,8,12,14,17-pentaenoic acid
Traditional Name11R-hepe
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C=C/[C@H](O)C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h3-4,6-7,9-11,13-14,16,19,21H,2,5,8,12,15,17-18H2,1H3,(H,22,23)/b4-3-,9-6-,10-7-,14-11-,16-13+/t19-/m0/s1
InChI KeyIDEHSDHMEMMYIR-DJWFCICMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosapentaenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosapentaenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.0032 g/LALOGPS
logP5.53ALOGPS
logP4.99ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability37.57 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]+188.18731661259
DarkChem[M-H]-189.86731661259
DeepCCS[M+H]+186.30330932474
DeepCCS[M-H]-183.94530932474
DeepCCS[M-2H]-216.98830932474
DeepCCS[M+Na]+192.39630932474
AllCCS[M+H]+185.532859911
AllCCS[M+H-H2O]+182.632859911
AllCCS[M+NH4]+188.332859911
AllCCS[M+Na]+189.132859911
AllCCS[M-H]-183.132859911
AllCCS[M+Na-2H]-184.732859911
AllCCS[M+HCOO]-186.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11R-HEPECC\C=C/C\C=C/C=C/[C@H](O)C\C=C/C\C=C/CCCC(O)=O4304.6Standard polar33892256
11R-HEPECC\C=C/C\C=C/C=C/[C@H](O)C\C=C/C\C=C/CCCC(O)=O2409.2Standard non polar33892256
11R-HEPECC\C=C/C\C=C/C=C/[C@H](O)C\C=C/C\C=C/CCCC(O)=O2603.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11R-HEPE,1TMS,isomer #1CC/C=C\C/C=C\C=C\[C@@H](C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2770.1Semi standard non polar33892256
11R-HEPE,1TMS,isomer #2CC/C=C\C/C=C\C=C\[C@H](O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2642.4Semi standard non polar33892256
11R-HEPE,2TMS,isomer #1CC/C=C\C/C=C\C=C\[C@@H](C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2715.6Semi standard non polar33892256
11R-HEPE,1TBDMS,isomer #1CC/C=C\C/C=C\C=C\[C@@H](C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3011.3Semi standard non polar33892256
11R-HEPE,1TBDMS,isomer #2CC/C=C\C/C=C\C=C\[C@H](O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2881.1Semi standard non polar33892256
11R-HEPE,2TBDMS,isomer #1CC/C=C\C/C=C\C=C\[C@@H](C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3194.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11R-HEPE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-4952000000-cd3454cc64672f196c442017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11R-HEPE GC-MS (2 TMS) - 70eV, Positivesplash10-00g1-9135200000-f174d03ce68e3fc5eb3f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11R-HEPE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11R-HEPE 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 - 11R-HEPE 10V, Positive-QTOFsplash10-0udi-0149000000-318dc0e1ccc495f069e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 20V, Positive-QTOFsplash10-0pi0-5973000000-8056f87480f9d53ad5d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 40V, Positive-QTOFsplash10-0a4l-9730000000-2c7ee4f4a41fe1a2d5bd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 10V, Negative-QTOFsplash10-014i-0059000000-92858f17a43771aacc452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 20V, Negative-QTOFsplash10-00r2-1293000000-c7d63c90b921bb3164662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 40V, Negative-QTOFsplash10-0abc-9730000000-060ffc1abb20c45f69ac2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 10V, Negative-QTOFsplash10-014i-0019000000-c475af61b990b381eca52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 20V, Negative-QTOFsplash10-014j-0495000000-cb11bb0be17fb2f6002a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 40V, Negative-QTOFsplash10-052e-9680000000-9f737f2d3c6c8180b6342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 10V, Positive-QTOFsplash10-0udi-1549000000-1fc955f463e50f7819642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 20V, Positive-QTOFsplash10-0fza-2921000000-e098d6a463a3d56369492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11R-HEPE 40V, Positive-QTOFsplash10-014l-9410000000-89939f3bb975a49a29fe2021-09-22Wishart 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 IDFDB029114
KNApSAcK IDNot Available
Chemspider ID4446310
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283188
PDB IDNot Available
ChEBI ID91264
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Serhan CN, Clish CB, Brannon J, Colgan SP, Chiang N, Gronert K: Novel functional sets of lipid-derived mediators with antiinflammatory actions generated from omega-3 fatty acids via cyclooxygenase 2-nonsteroidal antiinflammatory drugs and transcellular processing. J Exp Med. 2000 Oct 16;192(8):1197-204. [PubMed:11034610 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.