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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:54:58 UTC
Update Date2017-12-07 02:24:35 UTC
HMDB IDHMDB0010202
Secondary Accession Numbers
  • HMDB10202
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-5Z,8Z,10E,14Z,17Z-eicosapentaenoateGenerator
(5Z,8Z,10E,14Z,17Z)-12-Hydroxyeicosa-5,8,10,14,17-pentaenoateGenerator
12-Hydroxy-5Z,8Z,10E,14Z,17Z-icosapentaenoateGenerator
12-Hydroxyicosa-(5Z,8Z,10E,14Z,17Z)-pentaenoateGenerator
12-Hydroxy-5,8,10,14,17-eicosapentaenoateHMDB
12-Hydroxy-5,8,10,14,17-eicosapentaenoic acidHMDB
12-HydroxyeicosapentaenoateHMDB
12-Hydroxyeicosapentaenoic acidHMDB
12-Hydroxy-5,8,10,14,17-eicospentaenoic acid, (e,Z,Z,Z,Z)-isomerMeSH
12-HEPMeSH
12-Hydroxy-5,8,10,14,17-eicospentaenoic acidMeSH
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 KeyMCRJLMXYVFDXLS-QGQBRVLBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Cellular process:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability37.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k97-4983000000-918f0c66f2bc78257380View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-9326300000-3e49ae1891d17fe7385cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0149000000-c04096243bd40699c2e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pir-5984000000-33653a61aea10493adc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apu-9830000000-2b1f35ccf8272f1b2ff0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0059000000-0e3ce234470c380d8d9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mk-1293000000-c1089383b2f8453850b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9730000000-915554f514d5f25d5fffView in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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. [PubMed:2116491 ]