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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:05 UTC
Update Date2017-12-07 02:24:37 UTC
HMDB IDHMDB0010209
Secondary Accession Numbers
  • HMDB10209
Metabolite Identification
Common Name15-HEPE
Description15-HEPE has been identified as a possible anti-inflammatory metabolite, and its elevated presence in the epidermis of animals fed oils rich in 20:5(n-3) or 18:3(n-6) may provide a mechanism for the beneficial effects of these oils on inflammatory conditions. 15-HEPE is a metabolite of eicosapentaenoic acid (EPA) which has anti-inflammatory properties and plays an important role in the resolution phase of inflammation. 15-HEPE is deposited in the epidermis, particularly in the metabolically active basal layer. This is considered advantageous in psoriasis therapy. (PMID: 17540633 , 2106017 ).
Structure
Thumb
Synonyms
ValueSource
(15R)-15-Hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoateHMDB
(15R)-15-Hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acidHMDB
(15S)-15-Hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoateHMDB
(15S)-15-Hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acidHMDB
15(R)-HEPEHMDB
15(S)-HEPEHMDB
15-Hydroxy-5,8,11,13,17-eicosapentaenoateHMDB
15-Hydroxy-5,8,11,13,17-eicosapentaenoic acidHMDB
15-HydroxyeicosapentaenoateHMDB
15-Hydroxyeicosapentaenoic acidHMDB
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,11Z,13E,17Z)-16-hydroxyicosa-5,8,11,13,17-pentaenoic acid
Traditional Name(5Z,8Z,11Z,13E,17Z)-16-hydroxyicosa-5,8,11,13,17-pentaenoic acid
CAS Registry Number97850-14-1
SMILES
CC\C=C/C(O)C\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h3-5,8-12,14,16,19,21H,2,6-7,13,15,17-18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,14-12+,16-3-
InChI KeyUDXLGBLAJBYLSZ-XBCQTNLFSA-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 DescriptorsNot Available
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 Solubility0.003 g/LALOGPS
logP5.55ALOGPS
logP4.99ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
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
Polarizability38.01 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, Positivesplash10-0f6x-9182000000-ceafb87ef7f18bc914d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05i1-9326300000-3419bfcd6eb3a12958b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0059000000-8dc15ca069de44682ca9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0piu-5393000000-745f15890cf2792b4b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g3-9830000000-9e574ad248ec3d50dc13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0059000000-34299018bad23c98aff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mk-2093000000-8a92b0e27bb95dea96ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9040000000-b5e113a59ae2eb53aee4View 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 Quantified0.000197 +/- 1.9E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00028 +/- 0.000042 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00163 +/- 0.0016 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000287 +/- 0.000066 uMAdult (>18 years old)Not Specified
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 IDFDB027364
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480357
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zulfakar MH, Edwards M, Heard CM: Is there a role for topically delivered eicosapentaenoic acid in the treatment of psoriasis? Eur J Dermatol. 2007 Jul-Aug;17(4):284-91. Epub 2007 Jun 1. [PubMed:17540633 ]
  2. Miller CC, Ziboh VA, Wong T, Fletcher MP: Dietary supplementation with oils rich in (n-3) and (n-6) fatty acids influences in vivo levels of epidermal lipoxygenase products in guinea pigs. J Nutr. 1990 Jan;120(1):36-44. [PubMed:2106017 ]