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Record Information
Version3.6
Creation Date2008-09-15 09:54:58 UTC
Update Date2016-02-11 01:16:23 UTC
HMDB IDHMDB10202
Secondary Accession NumbersNone
Metabolite Identification
Common Name12-HEPE
Description12-HEPE is hydroxy derivative of 12-lipoxygenase metabolites of Eicosapentaenoic acid (EPA). 12S-HEPE participates in platelet-neutrophil interactions in a manner similar to 12S-HETE. It can also compete with endogenous arachidonic acid for 5-lipoxygenation in stimulated human neutrophils. By providing competing substrates for neutrophil 5-lipoxygenase, platelets might contribute to the antiinflammatory potential of dietary n-3 fatty acids through platelet-neutrophil interaction. ( PMID: 2116491 ).
Structure
Thumb
Synonyms
ValueSource
(+-)-12-HEPEChEBI
(+-)-12-Hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoic acidChEBI
(5Z,8Z,10E,14Z,17Z)-12-Hydroxyeicosa-5,8,10,14,17-pentaenoic acidChEBI
12-Hydroxy-5Z,8Z,10E,14Z,17Z-icosapentaenoic acidChEBI
12-Hydroxyicosa-(5Z,8Z,10E,14Z,17Z)-pentaenoic acidChEBI
12-Hydroxy-5,8,10,14,17-eicosapentaenoateHMDB
12-Hydroxy-5,8,10,14,17-eicosapentaenoic acidHMDB
12-HydroxyeicosapentaenoateHMDB
12-Hydroxyeicosapentaenoic acidHMDB
12-Hydroxyicosa-(5Z,8Z,10E,14Z,17Z)-pentaenoateHMDB
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,10E,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoic acid
Traditional Name12-hepe
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/CC(O)\C=C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h3-4,7-11,13-14,17,19,21H,2,5-6,12,15-16,18H2,1H3,(H,22,23)/b4-3-,9-7-,11-8-,13-10-,17-14+
InChI KeyInChIKey=MCRJLMXYVFDXLS-QGQBRVLBSA-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
Biofunction
  • Signaling
Application
  • Not Available
Cellular locations
  • Membrane (predicted from logP)
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 Solubility0.0031 mg/mLALOGPS
logP5.54ALOGPS
logP4.99ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m3·mol-1ChemAxon
Polarizability37.18 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000517 +/- 0.000084 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00319 +/- 0.00035 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00492 +/- 0.00451 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.000195 +/- 0.00011 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 IDFDB027357
KNApSAcK IDNot Available
Chemspider ID8217157
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10202
Metagene LinkHMDB10202
METLIN IDNot Available
PubChem Compound10041593
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. von Schacky C, Marcus AJ, Safier LB, Ullman HL, Islam N, Broekman MJ, Fischer S: Platelet-neutrophil interactions. 12S,20- and 5S,12S-dihydroxyeicosapentaenoic acids: two novel neutrophil metabolites from platelet-derived 12S-hydroxyeicosapentaenoic acid. J Lipid Res. 1990 May;31(5):801-10. [2116491 ]