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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2010-06-14 15:13:00 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0013633
Secondary Accession Numbers
  • HMDB13633
Metabolite Identification
Common Name12-KETE
Description12-keto-eicosatetraenoic acid is a biologically active eicosanoid in the nervous system of Aplysia.It is a metabolite of 12-HPETE formed by Aplysia nervous tissue. 12-KETE was identified in incubations of the tissue with arachidonic acid using HPLC, UV spectrometry, and gas-chromatography/mass spectrometry. [3H]12-KETE is formed from endogenous lipid stores in nervous tissue, labeled with [3H]arachidonic acid upon stimulation by application of histamine. In L14 and L10 cells, identified neurons in the abdominal ganglion, applications of 12-KETE elicit changes in membrane potential similar to those evoked by histamine.[PMID:2774398 ].
Structure
Thumb
Synonyms
ValueSource
(5Z,8Z,10E,14Z)-12-Oxoeicosa-5,8,10,14-tetraenoic acidChEBI
(5Z,8Z,10E,14Z)-12-Oxoicosa-5,8,10,14-tetraenoic acidChEBI
12-Keto-eteChEBI
12-Ketoeicosatetraenoic acidChEBI
12-oxo, 5C,8C,10t,14C-20:4ChEBI
12-OxoETEChEBI
(5Z,8Z,10E,14Z)-12-Oxoeicosa-5,8,10,14-tetraenoateGenerator
(5Z,8Z,10E,14Z)-12-Oxoicosa-5,8,10,14-tetraenoateGenerator
12-KetoeicosatetraenoateGenerator
12-oxo-ETEHMDB
12-keto-5,8,11,13-Eicosatetraenoic acidMeSH, HMDB
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,10E,14Z)-12-oxoicosa-5,8,10,14-tetraenoic acid
Traditional Name12-oxo-ETE
CAS Registry Number108437-64-5
SMILES
CCCCC\C=C/CC(=O)\C=C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+
InChI KeyGURBRQGDZZKITB-VXBMJZGYSA-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
Physiological effectNot Available
Disposition
Process
Naturally occurring process
Role
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029609
KNApSAcK IDNot Available
Chemspider ID4446286
KEGG Compound IDC14807
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283162
PDB IDNot Available
ChEBI ID34151
Food Biomarker OntologyNot Available
VMH IDM00334
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Piomelli D, Feinmark SJ, Shapiro E, Schwartz JH: 12-keto-eicosatetraenoic acid. A biologically active eicosanoid in the nervous system of Aplysia. Ann N Y Acad Sci. 1989;559:208-18. [PubMed:2774398 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.