Record Information
Version1.0
Creation date2011-09-21 01:23:12 UTC
Update date2017-04-03 05:02:17 UTC
Primary IDFDB027357
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number402-45-9
Structure
Thumb
Synonyms
SynonymSource
12-HEPMeSH
12-Hydroxy-5,8,10,14,17-eicospentaenoic acidMeSH
12-Hydroxyeicosapentaenoic acidMeSH
12-Hydroxy-5,8,10,14,17-eicospentaenoic acid, (e,Z,Z,Z,Z)-isomerMeSH
(+-)-12-HEPEChEBI
(+-)-12-Hydroxy-5Z,8Z,10e,14Z,17Z-eicosapentaenoateGenerator
(+-)-12-Hydroxy-5Z,8Z,10e,14Z,17Z-eicosapentaenoic acidChEBI
(5Z,8Z,10e,14Z,17Z)-12-Hydroxyeicosa-5,8,10,14,17-pentaenoateGenerator
(5Z,8Z,10e,14Z,17Z)-12-Hydroxyeicosa-5,8,10,14,17-pentaenoic acidChEBI
12-Hydroxy-5,8,10,14,17-eicosapentaenoatehmdb
12-Hydroxy-5,8,10,14,17-eicosapentaenoic acidhmdb
12-Hydroxy-5Z,8Z,10e,14Z,17Z-icosapentaenoateGenerator
12-Hydroxy-5Z,8Z,10e,14Z,17Z-icosapentaenoic acidChEBI
12-Hydroxyeicosapentaenoatehmdb
12-hydroxyicosa-(5Z,8Z,10E,14Z,17Z)-pentaenoatehmdb
12-hydroxyicosa-(5Z,8Z,10E,14Z,17Z)-pentaenoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.003 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
Polarizability38.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O3
IUPAC name12-hydroxyicosa-5,8,10,14,17-pentaenoic acid
InChI IdentifierInChI=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)
InChI KeyMCRJLMXYVFDXLS-UHFFFAOYSA-N
Isomeric SMILESCCC=CCC=CCC(O)C=CC=CCC=CCCCC(O)=O
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS12-HEPE, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0k97-4983000000-918f0c66f2bc78257380Spectrum
Predicted GC-MS12-HEPE, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HEPE, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HEPE, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HEPE, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HEPE, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HEPE, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HEPE, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1339000000-8e216b71745a4b202d002021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zni-3921000000-e715df1e8281d220feea2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9600000000-7c0ab94ee5781a6d90ee2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-45e47974262e9d7f81092021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0696000000-d277c67355dc99ac63522021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abd-8590000000-793ec53939b4437ef22a2021-10-12View Spectrum
NMRNot Available
ChemSpider ID8217157
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10041593
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10202
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference