You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-14 00:14:06 UTC
Update Date2017-10-23 19:04:12 UTC
HMDB IDHMDB0004679
Secondary Accession Numbers
  • HMDB04679
  • 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,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:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability37.71 ųChemAxon
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-MS (Non-derivatized) - 70eV, Positivesplash10-0gvp-9873000000-8211b99c90a885b091c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004j-9124200000-30e0b0a2d30ec66fb8f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0149000000-1b14f944e91c989f99f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zia-5984000000-8f3d10aef9fa823312e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9530000000-05fe7e1e9e477bb82828View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-5d3b737e28bd5ef8e694View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1249000000-8e5d74e8305ef73a6b16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9630000000-949f0536427c39b9dddfView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Rofecoxib PathwayPw000132Pw000132 greyscalePw000132 simpleNot Available
Salicylate-sodium Action PathwayPw000685Pw000685 greyscalePw000685 simpleNot Available
Salicylic Acid Action PathwayPw000686Pw000686 greyscalePw000686 simpleNot Available
Salsalate Action PathwayPw000684Pw000684 greyscalePw000684 simpleNot Available
Sulindac PathwayPw000136Pw000136 greyscalePw000136 simpleNot Available
Displaying entries 31 - 35 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
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 ]