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Showing Compound 5-HETE (FDB001434)

Record Information
Version1.0
Creation date2010-04-08 22:04:58 UTC
Update date2019-11-26 02:56:28 UTC
Primary IDFDB001434
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-HETE
Description5-Hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.; 5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in Arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then it is converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback. 5-HETE is found in corn.
CAS Number70608-72-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
5-HydroxyeicosatetraenoateKegg
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acidKegg
5-Hydroxyeicosatetraenoic acidGenerator
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoateGenerator
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidHMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidHMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acidHMDB
5(S)-Hydroxyeicosatetraenoic acidHMDB
5S-HETEHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateHMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateHMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoateHMDB
5(S)-HydroxyeicosatetraenoateHMDB
5(S)-HETEHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoateHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomerHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5S-Hydroxy-6,8,11,14-(e,Z,Z,Z)-eicosatetraenoic acidHMDB
FA(20:4(5-OH,6E,8Z,11Z,14Z))HMDB
FA(20:4(5S-OH,6E,8Z,11Z,14Z))HMDB
5-HETEHMDB
(5S,6e,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateGenerator
(5S,6e,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidChEBI
(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acidbiospider
(6e,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoateGenerator
(6e,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acidChEBI
5-Hydroxyarachidonic acidbiospider
6,8,11,14-Eicosatetraenoic acid, 5-hydroxy-, (S-(E,Z,Z,Z))-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP5.88ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O3
IUPAC name(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
InChI IdentifierInChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
InChI KeyKGIJOOYOSFUGPC-JGKLHWIESA-N
Isomeric SMILESCCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-HETE, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udr-7293000000-4000067abc9684c2e653Spectrum
Predicted GC-MS5-HETE, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056s-9117300000-40397121b4b937950f9dSpectrum
Predicted GC-MS5-HETE, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ldi-0079000000-52dac491931feca303a5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pvi-0196000000-b7a43328bfcf1b860873Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-1000-0293000000-6e834102b17e5bbec6fcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-1000-0390000000-61ebc99aa5f8333b07d2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-1930000000-b877c0d03861ddd2728dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0aor-9620000000-8cfab24155dae08cc2caSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0910000000-90f71c96ff730ececc7cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-08fr-4900000000-e0a2e06154c966bbfcc8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0a4i-9000000000-a54cdd357529bdc9f5e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0149000000-eb17d14c7966577fd391Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-4693000000-a850cad35b2bb6dbc176Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9880000000-8e15d5e341c49c793973Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-eb6fa786699adba566beSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ldi-2179000000-3bed63121486cd2b2630Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9150000000-29ad65a68f2ec87b590fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1549000000-24b83a60315e83b8c15bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl9-6943000000-d54f4d6e30d221259591Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o3-9400000000-745ec239ed811dee9dbdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-7a32e9e109204e833b16Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-4149000000-3bac989e03f14b200555Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k96-9432000000-25aaec361eff0ecf2d57Spectrum
NMRNot Available
ChemSpider ID4444314
ChEMBL IDCHEMBL164813
KEGG Compound IDC04805
Pubchem Compound ID5280733
Pubchem Substance IDNot Available
ChEBI ID28209
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11134
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000423
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID5-Hydroxyeicosatetraenoic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glutathione peroxidase 7GPX7Q96SL4
Epididymal secretory glutathione peroxidaseGPX5O75715
Glutathione peroxidase 6GPX6P59796
Glutathione peroxidase 1GPX1P07203
Phospholipid hydroperoxide glutathione peroxidase, mitochondrialGPX4P36969
Glutathione peroxidase 3GPX3P22352
Glutathione peroxidase 2GPX2P18283
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.