Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:13 UTC
Update Date2020-02-26 21:33:18 UTC
HMDB IDHMDB0010217
Secondary Accession Numbers
  • HMDB10217
Metabolite Identification
Common Name5-KETE
Description5-KETE, also known as 5-keto-ete or 5-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, 5-KETE is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 5-KETE.
Structure
Data?1582752798
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-ETEHMDB
5-oxo-6,8,11,14-Eicosatetraenoic acid, e,Z,Z,Z isomerHMDB
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
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.28430932474
DeepCCS[M-H]-188.92630932474
DeepCCS[M-2H]-221.81230932474
DeepCCS[M+Na]+197.37730932474
AllCCS[M+H]+185.232859911
AllCCS[M+H-H2O]+182.332859911
AllCCS[M+NH4]+187.932859911
AllCCS[M+Na]+188.732859911
AllCCS[M-H]-184.932859911
AllCCS[M+Na-2H]-186.632859911
AllCCS[M+HCOO]-188.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-KETECCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O4190.4Standard polar33892256
5-KETECCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O2348.1Standard non polar33892256
5-KETECCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O2642.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-KETE,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=O)CCCC(=O)O[Si](C)(C)C2654.6Semi standard non polar33892256
5-KETE,1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O)O[Si](C)(C)C2859.6Semi standard non polar33892256
5-KETE,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2800.1Semi standard non polar33892256
5-KETE,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2710.0Standard non polar33892256
5-KETE,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2848.1Standard polar33892256
5-KETE,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=O)CCCC(=O)O[Si](C)(C)C(C)(C)C2912.1Semi standard non polar33892256
5-KETE,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O)O[Si](C)(C)C(C)(C)C3102.9Semi standard non polar33892256
5-KETE,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3271.6Semi standard non polar33892256
5-KETE,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3098.3Standard non polar33892256
5-KETE,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2931.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-KETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-6490000000-f7442bdfafe15fcbd8be2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-KETE GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9334000000-c55c3efafdce8f7f48c82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-KETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-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 - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-014i-0019000000-cc3fc8fe0ef27f29f3fb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-014i-0019000000-73c8527e54e3481ad1a32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-014i-0039000000-0e2010fcd9ac17c6d0ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-014i-0189000000-5eba1c071b73ab1609062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-0v4j-0193000000-5251b2d0521f18bf6cdc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-0udi-0192000000-69bb1f0b8710630e34982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-0udi-0293000000-1ebf2792695803c02d992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-0udi-0493000000-6710e8cf7a82b74bf8e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOFsplash10-0ika-1890000000-3ca3507e7352ecaba4732017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 10V, Positive-QTOFsplash10-0udi-0139000000-56d3e500a2215f16ddba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 20V, Positive-QTOFsplash10-0ul9-7893000000-95b152324d0f205b491b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 40V, Positive-QTOFsplash10-0006-7960000000-b0a8aa3380cadece0d372017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 10V, Negative-QTOFsplash10-014i-0049000000-8a20eefad5150c79b6502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 20V, Negative-QTOFsplash10-00kb-1093000000-57fbe7ca052d52fe8cbb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 40V, Negative-QTOFsplash10-052f-8190000000-ad8a838b30e7500809fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 10V, Positive-QTOFsplash10-0uxr-1629000000-b0fafb9cc5aaed98cdc52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 20V, Positive-QTOFsplash10-0f89-5944000000-fd1af71047782189494e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 40V, Positive-QTOFsplash10-00lu-9700000000-cde9bfbce3fdd2d8c1b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 10V, Negative-QTOFsplash10-014i-0009000000-ac8d7382f0841f88fc4e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 20V, Negative-QTOFsplash10-014i-6297000000-81cdd06d01b88c7801f62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-KETE 40V, Negative-QTOFsplash10-052f-9580000000-e2e6654123cbfb72d9022021-09-24Wishart LabView Spectrum
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
FooDB IDFDB027371
KNApSAcK IDNot Available
Chemspider ID4446283
KEGG Compound IDC14732
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKETE
METLIN IDNot Available
PubChem Compound5283159
PDB IDNot Available
ChEBI ID52449
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]