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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:06 UTC
Update Date2020-02-26 21:33:17 UTC
HMDB IDHMDB0010210
Secondary Accession Numbers
  • HMDB10210
Metabolite Identification
Common Name15-KETE
Description15-KETE, also known as 15-oxoete, 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. Thus, 15-KETE is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 15-KETE.
Structure
Data?1582752797
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
15-oxo-5,8,11-cis-13-trans-IcosatetraenoateKegg
(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-Icosatetraenoic acidGenerator
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 acidHMDB
15-KeteChEBI
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
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00089 g/LALOGPS
logP10(5.72) g/LALOGPS
logP10(5.77) g/LChemAxon
logS10(-5.6) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15-KETE,1TMS,#1CCCCCC(=O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2645.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
15-KETE,1TMS,#2CCCCC=C(/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2863.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
15-KETE,1TBDMS,#1CCCCCC(=O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2894.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
15-KETE,1TBDMS,#2CCCCC=C(/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3106.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15-KETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-7590000000-911599180505962308eb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-KETE GC-MS (1 TMS) - 70eV, Positivesplash10-01du-9352000000-e4e7da6939c625ad40712017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-KETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-01b9-0289000000-f17e51ccefc93bab69f12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-01b9-0594000000-565acf0178bd3b1196072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-01b9-0962000000-df808385b0725329323e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-014r-0920000000-c91bf031286952802dc92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-02ti-0900000000-13e1f7d679e949631c342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-01p9-1900000000-0bd5fa12d13347d415712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-03di-0900000000-a4d1e07ce34b877f81d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-000i-2900000000-fa594a5bbf49bdbbca132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-KETE LC-ESI-QIT , negative-QTOFsplash10-01p9-4900000000-75678f0b1f95bf4d2c542017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 10V, Negative-QTOFsplash10-014i-0049000000-fd00a2666d65f25e67e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 20V, Negative-QTOFsplash10-01ba-3093000000-20570498bc3216bb54ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 40V, Negative-QTOFsplash10-0a4l-9160000000-a4bec589c33555078f2a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 10V, Negative-QTOFsplash10-014i-0029000000-b380dd1484037b8efe892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 20V, Negative-QTOFsplash10-014j-2294000000-f636466abde0b65d00182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 40V, Negative-QTOFsplash10-052g-9440000000-3ddcfa01c42d0ce3e4aa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 10V, Positive-QTOFsplash10-0udi-0149000000-0252a1b64c8346b53a402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 20V, Positive-QTOFsplash10-0kmi-4492000000-8442c76e28e4e26e1c052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 40V, Positive-QTOFsplash10-05fu-9840000000-b64ec6a65a4d3257d80f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 10V, Positive-QTOFsplash10-0uxr-1469000000-7050713e316bbdd82f232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 20V, Positive-QTOFsplash10-0uei-5963000000-65c8d5270036e1727fab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-KETE 40V, Positive-QTOFsplash10-00l6-9800000000-11ff09d84e3e4009dde42021-09-24Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDM00393
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]