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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:13 UTC
Update Date2019-07-23 05:54:08 UTC
HMDB IDHMDB0010217
Secondary Accession Numbers
  • HMDB10217
Metabolite Identification
Common Name5-KETE
Description5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE), 5-lipoxygenase product is a potent chemoattractant for neutrophils and eosinophils. Its actions are mediated by the oxoeicosanoid (OXE) receptor, a member of the G protein-coupled receptor family.(PMID:18292294 ).
Structure
Data?1563861248
Synonyms
ValueSource
(6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoic acidChEBI
5-keto-ETEChEBI
5-Ketoeicosatetraenoic acidChEBI
5-oxo, 6t,8C,11C,14C-20:4ChEBI
5-oxo-6(e),8(Z),11(Z),14(Z)-Eicosatetraenoic acidChEBI
5-oxo-6E,8Z,11Z,14Z-Eicosatetraenoic acidChEBI
5-oxo-Icosa-6,8,11,14-tetraenoic acidChEBI
5-Oxoeicosatetraenoic acidChEBI
5-OxoETEChEBI
5-Oxoicosatetraenoic acidChEBI
Eicosa-5,8,12,14-tetraenoic acidChEBI
(6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoateGenerator
5-KetoeicosatetraenoateGenerator
5-oxo-6(e),8(Z),11(Z),14(Z)-EicosatetraenoateGenerator
5-oxo-6E,8Z,11Z,14Z-EicosatetraenoateGenerator
5-oxo-Icosa-6,8,11,14-tetraenoateGenerator
5-OxoeicosatetraenoateGenerator
5-OxoicosatetraenoateGenerator
Eicosa-5,8,12,14-tetraenoateGenerator
5-keto-6,8,11,14-EicosatetraenoateHMDB
5-keto-6,8,11,14-Eicosatetraenoic acidHMDB
5-oxo-6,8,11,14-EicosatetraenoateHMDB
5-oxo-6,8,11,14-Eicosatetraenoic acidHMDB
5-oxo-EicosatetraenoateHMDB
5-oxo-Eicosatetraenoic acidHMDB
5-oxo-6,8,11,14-ETEMeSH
5-oxo-6,8,11,14-Eicosatetraenoic acid, e,Z,Z,Z isomerMeSH
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoic acid
Traditional Name5-Oxo-ETE
CAS Registry Number126432-17-5
SMILES
CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+
InChI KeyMEASLHGILYBXFO-XTDASVJISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

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 Solubility0.00062 g/LALOGPS
logP5.85ALOGPS
logP5.77ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.43ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity100.57 m³·mol⁻¹ChemAxon
Polarizability37.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-6490000000-f7442bdfafe15fcbd8beJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9334000000-c55c3efafdce8f7f48c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0019000000-cc3fc8fe0ef27f29f3fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0019000000-73c8527e54e3481ad1a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0039000000-0e2010fcd9ac17c6d0eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0189000000-5eba1c071b73ab160906JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0v4j-0193000000-5251b2d0521f18bf6cdcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0192000000-69bb1f0b8710630e3498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0293000000-1ebf2792695803c02d99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0493000000-6710e8cf7a82b74bf8e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ika-1890000000-3ca3507e7352ecaba473JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0139000000-56d3e500a2215f16ddbaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul9-7893000000-95b152324d0f205b491bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-7960000000-b0a8aa3380cadece0d37JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0049000000-8a20eefad5150c79b650JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-1093000000-57fbe7ca052d52fe8cbbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-8190000000-ad8a838b30e7500809faJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000136 +/- 0.000018 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000145 +/- 0.00012 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000136 +/- 0.000018 ) uMAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027371
KNApSAcK IDNot Available
Chemspider ID4446283
KEGG Compound IDC14732
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283159
PDB IDNot Available
ChEBI ID52449
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Patel P, Cossette C, Anumolu JR, Gravel S, Lesimple A, Mamer OA, Rokach J, Powell WS: Structural requirements for activation of the 5-oxo-6E,8Z, 11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) receptor: identification of a mead acid metabolite with potent agonist activity. J Pharmacol Exp Ther. 2008 May;325(2):698-707. doi: 10.1124/jpet.107.134908. Epub 2008 Feb 21. [PubMed:18292294 ]