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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:06 UTC
Update Date2019-07-23 05:54:07 UTC
HMDB IDHMDB0010210
Secondary Accession Numbers
  • HMDB10210
Metabolite Identification
Common Name15-KETE
Description15-OxoETE or 15-KETE is a keto-containing leukotriene derivative produced by oxidation of the 15-hydroxyl of 15-HETE.
Structure
Data?1563861247
Synonyms
ValueSource
(5Z,8Z,11Z,13E)-15-Ketoeicosa-5,8,11,13-tetraenoic acidChEBI
(5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-Eicosatetraenoic acidChEBI
(5Z,8Z,11Z,13E)-15-Oxoeicosa-5,8,11,13-tetraenoic acidChEBI
(5Z,8Z,11Z,13E)-15-Oxoicosa-5,8,11,13-tetraenoic acidChEBI
15-oxo-5,8,11-cis-13-trans-EicosatetraenoateChEBI
15-OxoETEChEBI
(5Z,8Z,11Z,13E)-15-Ketoeicosa-5,8,11,13-tetraenoateGenerator
(5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-EicosatetraenoateGenerator
(5Z,8Z,11Z,13E)-15-Oxoeicosa-5,8,11,13-tetraenoateGenerator
(5Z,8Z,11Z,13E)-15-Oxoicosa-5,8,11,13-tetraenoateGenerator
15-oxo-5,8,11-cis-13-trans-Eicosatetraenoic acidGenerator
15-oxo-5,8,11-cis-13-trans-IcosatetraenoateHMDB
15-oxo-5,8,11-cis-13-trans-Icosatetraenoic acidHMDB
15-oxo-5Z,8Z,11Z,13E-EicosatetraenoateHMDB
15-oxo-5Z,8Z,11Z,13E-Eicosatetraenoic acidHMDB
15-oxo-ETEHMDB
15-keto-5,8,11,13-Eicosatetraenoic acidMeSH
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoic acid
Traditional Name15-Oxo-ETE
CAS Registry Number81416-72-0
SMILES
CCCCCC(=O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+
InChI KeyYGJTUEISKATQSM-USWFWKISSA-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 Solubility0.00089 g/LALOGPS
logP5.72ALOGPS
logP5.77ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
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
Polarizability37.58 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, Positivesplash10-00kg-7590000000-911599180505962308ebJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01du-9352000000-e4e7da6939c625ad4071JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01b9-0289000000-f17e51ccefc93bab69f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01b9-0594000000-565acf0178bd3b119607JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01b9-0962000000-df808385b0725329323eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014r-0920000000-c91bf031286952802dc9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-02ti-0900000000-13e1f7d679e949631c34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01p9-1900000000-0bd5fa12d13347d41571JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-0900000000-a4d1e07ce34b877f81d3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-2900000000-fa594a5bbf49bdbbca13JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01p9-4900000000-75678f0b1f95bf4d2c54JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0149000000-0252a1b64c8346b53a40JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-4492000000-8442c76e28e4e26e1c05JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9840000000-b64ec6a65a4d3257d80fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0049000000-fd00a2666d65f25e67e5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-3093000000-20570498bc3216bb54ffJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9160000000-a4bec589c33555078f2aJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000069 +/- 0.000033 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000749 +/- 0.00008 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000682 +/- 0.00076 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000749 +/- 0.000080 uMAdult (>18 years old)Not SpecifiedNormal
    • Oxygenated lipids...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00002 +/- 0.00004 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
FoodDB IDFDB027365
KNApSAcK IDNot Available
Chemspider ID4444287
KEGG Compound IDC04577
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280701
PDB IDNot Available
ChEBI ID15559
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yeh HC, Tsai AL, Wang LH: Reaction mechanisms of 15-hydroperoxyeicosatetraenoic acid catalyzed by human prostacyclin and thromboxane synthases. Arch Biochem Biophys. 2007 May 15;461(2):159-68. Epub 2007 Apr 11. [PubMed:17459323 ]
  2. Wei C, Zhu P, Shah SJ, Blair IA: 15-oxo-Eicosatetraenoic acid, a metabolite of macrophage 15-hydroxyprostaglandin dehydrogenase that inhibits endothelial cell proliferation. Mol Pharmacol. 2009 Sep;76(3):516-25. doi: 10.1124/mol.109.057489. Epub 2009 Jun 17. [PubMed:19535459 ]
  3. Snyder NW, Revello SD, Liu X, Zhang S, Blair IA: Cellular uptake and antiproliferative effects of 11-oxo-eicosatetraenoic acid. J Lipid Res. 2013 Nov;54(11):3070-7. doi: 10.1194/jlr.M040741. Epub 2013 Aug 14. [PubMed:23945567 ]