13-HETE (CHEM040954)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:05:36 UTC
Update Date2016-11-09 01:22:22 UTC
Accession NumberCHEM040954
Identification
Common Name13-HETE
ClassSmall Molecule
DescriptionA HETE that is arachidonic acid carrying a hydroxy substituent at position 13.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-13-Hydroxyicosatetraenoic acidChEBI
13-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acidChEBI
13-Hydroxy-(5Z,8Z,11Z,14Z)-icosatetraenoic acidChEBI
13-Hydroxyeicosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-13-HydroxyicosatetraenoateGenerator
13-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateGenerator
13-Hydroxy-(5Z,8Z,11Z,14Z)-icosatetraenoateGenerator
13-HydroxyeicosatetraenoateGenerator
13-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoateHMDB
13-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidHMDB
13-Hydroxyeicosatetraenoic acid, (S)-(all-Z)-isomerMeSH, HMDB
Chemical FormulaC20H32O3
Average Molecular Mass320.466 g/mol
Monoisotopic Mass320.235 g/mol
CAS Registry Number151910-72-4
IUPAC Name(5Z,8Z,11Z,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name(5Z,8Z,11Z,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid
SMILESCCCCC\C=C/C(O)\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI IdentifierInChI=1S/C20H32O3/c1-2-3-4-10-13-16-19(21)17-14-11-8-6-5-7-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b8-6-,9-7-,16-13-,17-14-
InChI KeySAKQICHVWOJSNI-BWWNDVLWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP5.82ALOGPS
logP5.51ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.32 m³·mol⁻¹ChemAxon
Polarizability38.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udm-9573000000-fd1ef654a114fbdce8f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004j-9225300000-d57a6b96d837ca425c07Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0049000000-33aab7be1c53ffedfa68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zj0-7694000000-b0537b8d894c47d11dedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9730000000-89f61926136ab6394c48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-907ce78259323183429eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-2149000000-b29439c6107511b4f9e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9430000000-f999fd58d02e9da56145Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1349000000-82fcf33dd08cfc69ca34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udv-9864000000-93e04762b76a59d719c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9610000000-18b551ab2467c2b0b627Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-db4700af17a6033433d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1239000000-5462bef50ee96ca03f6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kfx-9241000000-28671b487cbe8094a2e3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012567
FooDB IDFDB029131
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35032542
ChEBI ID137345
PubChem Compound ID53481471
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=7646075
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8424677
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8443245
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8806734
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=9435160
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. 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.
8. 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.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. Oliw EH: bis-Allylic hydroxylation of linoleic acid and arachidonic acid by human hepatic monooxygenases. Biochim Biophys Acta. 1993 Feb 24;1166(2-3):258-63.
11. Hornsten L, Bylund J, Oliw EH: Dexamethasone induces bisallylic hydroxylation of polyunsaturated fatty acids by rat liver microsomes. Arch Biochem Biophys. 1996 Aug 15;332(2):261-8.
12. Bylund J, Kunz T, Valmsen K, Oliw EH: Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes. J Pharmacol Exp Ther. 1998 Jan;284(1):51-60.
13. The lipid handbook with CD-ROM