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Record Information
Version3.6
Creation Date2006-10-25 10:38:58 UTC
Update Date2016-02-11 01:07:04 UTC
HMDB IDHMDB05081
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-HEPE
Description5-HEPE is a major eicosanoid formed from eicosapentaenoic acid (EPA). 5-HEPE is produced in human neutrophils. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. (PMID: 8847485 , 15896193 ).
Structure
Thumb
Synonyms
ValueSource
(+-)-5-HEPEChEBI
(+-)-5-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acidChEBI
(+/-)-5-hepeHMDB
(+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoateHMDB
(+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acidHMDB
5-Hydroxy-6,8,11,14,17-eicosapentaenoateHMDB
5-Hydroxy-6,8,11,14,17-eicosapentaenoic acidHMDB
5-HydroxyeicosapentaenoateHMDB
5-Hydroxyeicosapentaenoic acidHMDB
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid
Traditional Name5-hydroxyeicosapentaenoic acid
CAS Registry Number92008-51-0
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+
InChI KeyInChIKey=FTAGQROYQYQRHF-FCWZHQICSA-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 Solubility0.0029 mg/mLALOGPS
logP5.54ALOGPS
logP4.99ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m3·mol-1ChemAxon
Polarizability37.17 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 Quantified0.00067 +/- 0.000121 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000863 +/- 0.000404 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.00115 +/- 0.00014 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000228 +/- 0.000091 uMAdult (>18 years old)Both
Normal
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 IDFDB023620
KNApSAcK IDNot Available
Chemspider ID4944072
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05081
Metagene LinkHMDB05081
METLIN IDNot Available
PubChem Compound6439678
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Powell WS, Gravel S, Gravelle F: Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. J Lipid Res. 1995 Dec;36(12):2590-8. [8847485 ]
  2. Charbeneau RP, Peters-Golden M: Eicosanoids: mediators and therapeutic targets in fibrotic lung disease. Clin Sci (Lond). 2005 Jun;108(6):479-91. [15896193 ]
  3. Lipid Maps (LMFA03070010) [Link]