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Showing metabocard for 15-KETE (HMDB0010210)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
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 lipid molecule. 15-KETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752797
MOLSDFPDBSMILESInChI
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

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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-7590000000-911599180505962308ebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01du-9352000000-e4e7da6939c625ad4071Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01b9-0289000000-f17e51ccefc93bab69f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01b9-0594000000-565acf0178bd3b119607Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01b9-0962000000-df808385b0725329323eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014r-0920000000-c91bf031286952802dc9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-02ti-0900000000-13e1f7d679e949631c34Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01p9-1900000000-0bd5fa12d13347d41571Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-0900000000-a4d1e07ce34b877f81d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-2900000000-fa594a5bbf49bdbbca13Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01p9-4900000000-75678f0b1f95bf4d2c54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0149000000-0252a1b64c8346b53a40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-4492000000-8442c76e28e4e26e1c05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9840000000-b64ec6a65a4d3257d80fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0049000000-fd00a2666d65f25e67e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-3093000000-20570498bc3216bb54ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9160000000-a4bec589c33555078f2aSpectrum
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
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 ]