Showing metabocard for 12-HEPE (BMDB0010202)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:01:19 UTC
Update Date2020-04-22 15:39:23 UTC
BMDB IDBMDB0010202
Secondary Accession Numbers
  • BMDB10202
Metabolite Identification
Common Name12-HEPE
Description12-HEPE, also known as (+-)-12-hepe, 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. Thus, 12-HEPE is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 12-HEPE.
Structure
Thumb
MOLSDFPDBSMILESInChI
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)-isomerHMDB
12-HEPHMDB
12-Hydroxy-5,8,10,14,17-eicospentaenoic acidHMDB
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
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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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
BioavailabilityYesChemAxon
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1439000000-1ad5c3c69b385dbd8aa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zni-3921000000-e715df1e8281d220feeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9600000000-7c0ab94ee5781a6d90eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-45e47974262e9d7f8109View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0696000000-f039341bf46bc4fcdff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abd-8590000000-793ec53939b4437ef22aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0010202
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 ID72645
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available