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Record Information
Version4.0
Creation Date2008-09-15 09:55:13 UTC
Update Date2017-09-27 08:26:09 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
Thumb
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 chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0019000000-cc3fc8fe0ef27f29f3fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0019000000-73c8527e54e3481ad1a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0039000000-0e2010fcd9ac17c6d0eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0189000000-5eba1c071b73ab160906View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0v4j-0193000000-5251b2d0521f18bf6cdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0192000000-69bb1f0b8710630e3498View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0293000000-1ebf2792695803c02d99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0493000000-6710e8cf7a82b74bf8e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ika-1890000000-3ca3507e7352ecaba473View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0139000000-56d3e500a2215f16ddbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul9-7893000000-95b152324d0f205b491bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-7960000000-b0a8aa3380cadece0d37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0049000000-8a20eefad5150c79b650View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-1093000000-57fbe7ca052d52fe8cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-8190000000-ad8a838b30e7500809faView in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 41 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite 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 ]