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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:42:04 UTC
Update Date2019-07-23 07:18:12 UTC
HMDB IDHMDB0062296
Secondary Accession Numbers
  • HMDB62296
Metabolite Identification
Common Name15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
Description15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid, also known as 15S-HEPE, is classified as a member of the Hydroxyeicosapentaenoic acids. Hydroxyeicosapentaenoic acids are eicosanoic acids with an attached hydroxyl group and five CC double bonds. 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid is considered to be practically insoluble (in water) and acidic. 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid is an eicosanoid lipid molecule
Structure
Data?1563866292
Synonyms
ValueSource
(5Z,8Z,11Z,13E,15S,17Z)-15-Hydroxyicosapentaenoic acidChEBI
15S-HEPEChEBI
15S-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acidChEBI
(5Z,8Z,11Z,13E,15S,17Z)-15-HydroxyicosapentaenoateGenerator
15S-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoateGenerator
Chemical FormulaC20H30O3
Average Molecular Weight318.457
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,11Z,13E,15S,17Z)-15-hydroxyicosa-5,8,11,13,17-pentaenoic acid
Traditional Name15S-hepe
CAS Registry NumberNot Available
SMILES
[H]\C(CC)=C(/[H])C[C@]([H])(O)C(\[H])=C(/[H])\C(\[H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h3-5,8-11,13-14,17,19,21H,2,6-7,12,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,13-3-,17-14+/t19-/m0/s1
InChI KeyWLKCSMCLEKGITB-DBVSHIMFSA-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0031 g/lALOGPS
LogP5.55ALOGPS
Predicted Properties
PropertyValueSource
logP5.55ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-7192000000-80fb061f4893b98fc916Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9325200000-ec091e75ea7bdf1c7e32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0059000000-b14d85c391199749293dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0q29-5393000000-269d667b30487e873a45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9830000000-4d9c3662da6e7214994bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0059000000-bc25dd9d7efaf3a01d90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2093000000-a57de046f7134e151174Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-2893e6a7c9d14d19668dSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283192
PDB IDNot Available
ChEBI ID88347
Food Biomarker OntologyNot Available
VMH IDCE7082
MarkerDB ID
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.