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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-14 00:14:06 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004679
Secondary Accession Numbers
  • HMDB0005080
  • 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
Data?1582752311
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
8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomerHMDB
8-Hydroxyeicosatetraenoic acidHMDB
8-Hydroxyeicosatetraenoic acid, (e,Z,Z,Z)-isomerHMDB
(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
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
Description 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
  • 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

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available185.067http://allccs.zhulab.cn/database/detail?ID=AllCCS00001864
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.44331661259
DarkChem[M-H]-188.35631661259
DeepCCS[M+H]+194.3330932474
DeepCCS[M-H]-191.97230932474
DeepCCS[M-2H]-224.85830932474
DeepCCS[M+Na]+200.42330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-HETECCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=O4156.8Standard polar33892256
8-HETECCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=O2419.9Standard non polar33892256
8-HETECCCCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCC(O)=O2593.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-HETE,1TMS,isomer #1CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O)O[Si](C)(C)C2735.1Semi standard non polar33892256
8-HETE,1TMS,isomer #2CCCCC/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CCCC(=O)O[Si](C)(C)C2630.7Semi standard non polar33892256
8-HETE,2TMS,isomer #1CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2705.9Semi standard non polar33892256
8-HETE,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2981.6Semi standard non polar33892256
8-HETE,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C=C\[C@@H](O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2872.6Semi standard non polar33892256
8-HETE,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3192.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-HETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gvp-9873000000-8211b99c90a885b091c92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-HETE GC-MS (2 TMS) - 70eV, Positivesplash10-004j-9124200000-30e0b0a2d30ec66fb8f62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-HETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-HETE 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 - 8-HETE 10V, Positive-QTOFsplash10-0udi-0149000000-1b14f944e91c989f99f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 20V, Positive-QTOFsplash10-0zia-5984000000-8f3d10aef9fa823312e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 40V, Positive-QTOFsplash10-014l-9530000000-05fe7e1e9e477bb828282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 10V, Negative-QTOFsplash10-014i-0019000000-5d3b737e28bd5ef8e6942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 20V, Negative-QTOFsplash10-0uxr-1249000000-8e5d74e8305ef73a6b162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 40V, Negative-QTOFsplash10-0a4l-9630000000-949f0536427c39b9dddf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 10V, Negative-QTOFsplash10-014i-0009000000-26408992e4d02820d7db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 20V, Negative-QTOFsplash10-0gb9-1349000000-c600b24f75f55f01a3742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 40V, Negative-QTOFsplash10-0ac3-9761000000-bbaf759d3a09618e7f952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 10V, Positive-QTOFsplash10-0udi-1449000000-77497dbdc78a478cb0172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 20V, Positive-QTOFsplash10-0fl9-5922000000-9b495b5a9ffb5dbf51282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-HETE 40V, Positive-QTOFsplash10-052f-9200000000-d2a456a18db9ecb165762021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000749 +/- 0.000033 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
Phenol Explorer Compound IDNot Available
FooDB IDFDB023400
KNApSAcK IDNot Available
Chemspider ID4446278
KEGG Compound IDC14776
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVâlcele, Covasna
METLIN IDNot Available
PubChem Compound5283154
PDB IDNot Available
ChEBI ID34486
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]