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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-25 10:38:58 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005081
Secondary Accession Numbers
  • HMDB05081
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
Data?1582752344
Synonyms
ValueSource
(+-)-5-HEPEChEBI
(+-)-5-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acidChEBI
(+-)-5-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoateGenerator
(+/-)-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
5-HEPEMeSH
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 KeyFTAGQROYQYQRHF-FCWZHQICSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability37.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.18131661259
DarkChem[M-H]-187.02731661259
DeepCCS[M+H]+184.31230932474
DeepCCS[M-H]-181.95430932474
DeepCCS[M-2H]-214.84130932474
DeepCCS[M+Na]+190.40530932474
AllCCS[M+H]+185.632859911
AllCCS[M+H-H2O]+182.632859911
AllCCS[M+NH4]+188.432859911
AllCCS[M+Na]+189.232859911
AllCCS[M-H]-183.632859911
AllCCS[M+Na-2H]-185.332859911
AllCCS[M+HCOO]-187.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HEPECC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O4339.3Standard polar33892256
5-HEPECC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O2377.1Standard non polar33892256
5-HEPECC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O2567.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-HEPE,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O)O[Si](C)(C)C2805.4Semi standard non polar33892256
5-HEPE,1TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(O)CCCC(=O)O[Si](C)(C)C2643.5Semi standard non polar33892256
5-HEPE,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2709.7Semi standard non polar33892256
5-HEPE,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C3040.8Semi standard non polar33892256
5-HEPE,1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C2889.7Semi standard non polar33892256
5-HEPE,2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3188.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-HEPE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-5394000000-3c896430e353b0ced0db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-HEPE GC-MS (2 TMS) - 70eV, Positivesplash10-0umj-8209200000-58c4694ad173b557f3c52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-HEPE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 10V, Positive-QTOFsplash10-0udi-0149000000-dfe33b6babf270b347522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 20V, Positive-QTOFsplash10-0udu-5693000000-fb5c896d30ace0c553d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 40V, Positive-QTOFsplash10-000l-9880000000-5d7665b416fe42c2c3712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 10V, Negative-QTOFsplash10-014i-0069000000-023fef6c61163c7bc8172017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 20V, Negative-QTOFsplash10-00kb-2093000000-e62551450dc40c949d522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 40V, Negative-QTOFsplash10-0a4l-9160000000-b435064b3bb6876f2d7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 10V, Negative-QTOFsplash10-014i-0019000000-816e1c2de0c22c09572d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 20V, Negative-QTOFsplash10-066r-5298000000-38dbc1cf2b56e0e1e6ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 40V, Negative-QTOFsplash10-052g-9650000000-5f5552a443dffc55be3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 10V, Positive-QTOFsplash10-0ue9-1549000000-3a0bdd92ab4130f1a2cf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 20V, Positive-QTOFsplash10-001i-4932000000-a4abea64aa118c0599d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HEPE 40V, Positive-QTOFsplash10-003u-9500000000-f8f2e81a65d2e71229cf2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB023620
KNApSAcK IDNot Available
Chemspider ID4944072
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6439678
PDB IDNot Available
ChEBI ID72801
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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. [PubMed: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. [PubMed:15896193 ]
  3. Lipid Maps (LMFA03070010) [Link]