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Record Information
Version3.6
Creation Date2009-07-25 00:03:56 UTC
Update Date2016-02-11 01:25:07 UTC
HMDB IDHMDB12611
Secondary Accession NumbersNone
Metabolite Identification
Common Name18R-HEPE
Description18R-HEPE which is the R form of 18(+/-)-HEPE, is produced by non-enzymatic oxidation of EPA.
Structure
Thumb
Synonyms
ValueSource
18(R)-Hydroxyeicosa-5Z,8Z,11E,14Z,16E-pentaenoateHMDB
18(R)-Hydroxyeicosa-5Z,8Z,11E,14Z,16E-pentaenoic acidHMDB
18-HEPEHMDB
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,11E,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid
Traditional Name(5Z,8Z,11E,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid
CAS Registry NumberNot Available
SMILES
CC[C@H](O)\C=C\C=C/C\C=C\C\C=C/C\C=C/CCCC(O)=O
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-/m0/s1
InChI KeyInChIKey=LRWYBGFSVUBWMO-NQZHIPPKSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0025 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m3·mol-1ChemAxon
Polarizability37.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000138 +/- 2.4E-5 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029149
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12611
Metagene LinkHMDB12611
METLIN IDNot Available
PubChem Compound53481496
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available