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Record Information
Version4.0
Creation Date2006-08-14 00:14:06 UTC
Update Date2017-09-25 09:31:55 UTC
HMDB IDHMDB0004679
Secondary Accession Numbers
  • HMDB04679
  • HMDB05080
StatusDetected and Quantified
Metabolite Identification
Common Name8-HETE
Description8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593 , 9113987 ).
Structure
Thumb
Synonyms
ValueSource
(5Z,8S,9E,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acidChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acidChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoic acidChEBI
(8S)-Hydroxy-(5Z),(9E),(11Z),(14Z)-eicosatetraenoic acidChEBI
(S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoic acidChEBI
8(S)-Hydroxyeicosatetraenoic acidChEBI
8S-HETEChEBI
(5Z,8S,9E,11Z,14Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoateGenerator
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyeicosa-5,9,11,14-tetraenoateGenerator
(5Z,9E,11Z,14Z)-(8S)-8-Hydroxyicosa-5,9,11,14-tetraenoateGenerator
(8S)-Hydroxy-(5Z),(9E),(11Z),(14Z)-eicosatetraenoateGenerator
(S)-(Z,e,Z,Z)-8-Hydroxyeicosa-5,9,11,14-tetraenoateGenerator
8(S)-HydroxyeicosatetraenoateGenerator
(5Z,8S,9E,11Z,14Z)-8-Hydroxyicosa-5,9,11,14-tetraenoateHMDB
(5Z,8S,9E,11Z,14Z)-8-Hydroxyicosa-5,9,11,14-tetraenoic acidHMDB
8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoateHMDB
8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoic acidHMDB
8S-Hydroxy-5Z,9E,11Z,14Z-eicosatetraenoateHMDB
8S-Hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acidHMDB
8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-isomerMeSH
8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomerMeSH
8-Hydroxyeicosatetraenoic acidMeSH
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid
Traditional Name8(S)-hete
CAS Registry Number98462-03-4
SMILES
CCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1
InChI KeyNLUNAYAEIJYXRB-VYOQERLCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic 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:
Source:
Subcellular:
Biofluid and excreta:
Process
Naturally occurring process:
Biological 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 Solubility0.0016 mg/mLALOGPS
logP5.87ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m3·mol-1ChemAxon
Polarizability37.71 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 41 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000749 +/- 3.3E-5 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00209 +/- 0.00016 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000512 +/- 0.000367 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000536 +/- 0.0004 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000055 +/- 0.000034 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
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 IDFDB023400
KNApSAcK IDNot Available
Chemspider ID4446278
KEGG Compound IDC14776
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0004679
METLIN IDNot Available
PubChem Compound5283154
PDB IDNot Available
ChEBI ID34486
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yu K, Bayona W, Kallen CB, Harding HP, Ravera CP, McMahon G, Brown M, Lazar MA: Differential activation of peroxisome proliferator-activated receptors by eicosanoids. J Biol Chem. 1995 Oct 13;270(41):23975-83. [PubMed:7592593 ]
  2. Kliewer SA, Sundseth SS, Jones SA, Brown PJ, Wisely GB, Koble CS, Devchand P, Wahli W, Willson TM, Lenhard JM, Lehmann JM: Fatty acids and eicosanoids regulate gene expression through direct interactions with peroxisome proliferator-activated receptors alpha and gamma. Proc Natl Acad Sci U S A. 1997 Apr 29;94(9):4318-23. [PubMed:9113987 ]