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Record Information
Version3.6
Creation Date2006-08-14 00:14:06 UTC
Update Date2016-02-11 01:06:46 UTC
HMDB IDHMDB04679
Secondary Accession Numbers
  • HMDB05080
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,8S,9E,11Z,14Z)-8-Hydroxyicosa-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
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
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 KeyInChIKey=NLUNAYAEIJYXRB-VYOQERLCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
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
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Acetaminophen Action PathwaySMP00710Not Available
Acetylsalicylic Acid PathwaySMP00083Not Available
Antipyrine Action PathwaySMP00692Not Available
Antrafenine Action PathwaySMP00693Not Available
Arachidonic Acid MetabolismSMP00075map00590
Bromfenac PathwaySMP00102Not Available
Carprofen Action PathwaySMP00694Not Available
Celecoxib PathwaySMP00096Not Available
Diclofenac PathwaySMP00093Not Available
Diflunisal PathwaySMP00289Not Available
Etodolac PathwaySMP00084Not Available
Etoricoxib Action PathwaySMP00695Not Available
Fenoprofen Action PathwaySMP00696Not Available
Flurbiprofen Action PathwaySMP00697Not Available
Ibuprofen PathwaySMP00086Not Available
Indomethacin PathwaySMP00104Not Available
Ketoprofen PathwaySMP00085Not Available
Ketorolac PathwaySMP00098Not Available
Leukotriene C4 Synthesis DeficiencySMP00353Not Available
Lornoxicam Action PathwaySMP00700Not Available
Lumiracoxib Action PathwaySMP00699Not Available
Magnesium salicylate Action PathwaySMP00698Not Available
Mefanamic Acid PathwaySMP00109Not Available
Meloxicam PathwaySMP00106Not Available
Nabumetone PathwaySMP00114Not Available
Naproxen PathwaySMP00120Not Available
Nepafenac Action PathwaySMP00702Not Available
Oxaprozin PathwaySMP00113Not Available
Phenylbutazone Action PathwaySMP00701Not Available
Piroxicam PathwaySMP00077Not Available
Rofecoxib PathwaySMP00087Not Available
Salicylate-sodium Action PathwaySMP00708Not Available
Salicylic Acid Action PathwaySMP00709Not Available
Salsalate Action PathwaySMP00707Not Available
Sulindac PathwaySMP00094Not Available
Suprofen PathwaySMP00101Not Available
Tenoxicam Action PathwaySMP00706Not Available
Tiaprofenic Acid Action PathwaySMP00705Not Available
Tolmetin Action PathwaySMP00704Not Available
Trisalicylate-choline Action PathwaySMP00703Not Available
Valdecoxib PathwaySMP00116Not Available
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 LinkHMDB04679
Metagene LinkHMDB04679
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. [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. [9113987 ]