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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:34:05 UTC
Update Date2019-07-23 07:18:02 UTC
HMDB IDHMDB0062222
Secondary Accession Numbers
  • HMDB62222
Metabolite Identification
Common Name18R-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid
Description18R-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid, also known as (5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosapentaenoic acid or 18(R)-hydroxyeicosa-5Z,8Z,11E,14Z,16E-pentaenoic acid, 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. 18R-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866282
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,16E,18R)-18-Hydroxyicosapentaenoic acidChEBI
18(R)-Hydroxyeicosa-5Z,8Z,11E,14Z,16E-pentaenoic acidChEBI
18-HEPEChEBI
18R-HEPEChEBI
(5Z,8Z,11Z,14Z,16E,18R)-18-HydroxyicosapentaenoateGenerator
18(R)-Hydroxyeicosa-5Z,8Z,11E,14Z,16E-pentaenoateGenerator
18R-Hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoateGenerator
Chemical FormulaC20H30O3
Average Molecular Weight318.457
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid
Traditional Name18R-hepe
CAS Registry NumberNot Available
SMILES
[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@]([H])(O)CC
InChI Identifier
InChI=1S/C20H30O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,15,17,19,21H,2-3,8-9,14,16,18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-,17-15+/t19-/m1/s1
InChI KeyLRWYBGFSVUBWMO-UAAZXLHOSA-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 Solubility0.0025 g/lALOGPS
LogP5.60ALOGPS
Predicted Properties
PropertyValueSource
logP5.6ALOGPS
logP4.99ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability38.34 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, Positivesplash10-0f96-5292000000-3370793b5217e6cb312bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g1-9224300000-24d4fa79f8cba47eee85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0059000000-37e8d5e0a2b3f027af2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pir-1292000000-fe985e0055513c0581a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hft-8890000000-5024358c97ee6797a470Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0059000000-8facefa2fa633323c577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-1093000000-c454f7dea34532f16c59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9030000000-272f1a04adc1325d8e6cSpectrum
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 IDC18177
BioCyc IDCPD66-68
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061126
PDB IDNot Available
ChEBI ID81563
Food Biomarker OntologyNot Available
VMH 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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.