11R-HEPE (CHEM040937)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:05:14 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040937
Identification
Common Name11R-HEPE
ClassSmall Molecule
DescriptionAn 11-HEPE that consists of (5Z,8Z,12E,14Z,17Z)-icosapentaenoic acid in which the hydroxy group is located at the 11R-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass318.450 g/mol
Monoisotopic Mass318.219 g/mol
CAS Registry NumberNot Available
IUPAC Name(5Z,8Z,11R,12E,14Z,17Z)-11-hydroxyicosa-5,8,12,14,17-pentaenoic acid
Traditional Name11R-hepe
SMILESCC\C=C/C\C=C/C=C/[C@H](O)C\C=C/C\C=C/CCCC(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-4952000000-cd3454cc64672f196c44Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g1-9135200000-f174d03ce68e3fc5eb3fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0149000000-318dc0e1ccc495f069e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-5973000000-8056f87480f9d53ad5d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9730000000-2c7ee4f4a41fe1a2d5bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0059000000-92858f17a43771aacc45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r2-1293000000-c7d63c90b921bb316466Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9730000000-060ffc1abb20c45f69acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-c475af61b990b381eca5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0495000000-cb11bb0be17fb2f6002aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9680000000-9f737f2d3c6c8180b634Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1549000000-1fc955f463e50f781964Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fza-2921000000-e098d6a463a3d5636949Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9410000000-89939f3bb975a49a29feSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012534
FooDB IDFDB029114
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446310
ChEBI ID91264
PubChem Compound ID5283188
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11034610
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16386769
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. 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.
5. 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.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. 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.
8. The lipid handbook with CD-ROM