11-Hydroxyeicosatetraenoate glyceryl ester (CHEM040935)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:05:11 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040935
Identification
Common Name11-Hydroxyeicosatetraenoate glyceryl ester
ClassSmall Molecule
Description11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853, 8555273).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11-Hydroxyeicosatetraenoic acid glyceryl esterGenerator
(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl-2-glyceryl esterHMDB
(5Z,8Z,12E,14Z)-11S-Hydroxyeicosatetraenoyl-2-glyceryl esterHMDB
11-HETE-gHMDB
2-[(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-glycerolHMDB
1,3-Dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acidGenerator
Chemical FormulaC23H38O5
Average Molecular Mass394.545 g/mol
Monoisotopic Mass394.272 g/mol
CAS Registry NumberNot Available
IUPAC Name1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate
Traditional Name1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate
SMILESCCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO
InChI IdentifierInChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1
InChI KeySSHLWLAPLZCWOT-XYOZOUKRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassEndocannabinoids
Sub ClassNot Available
Direct ParentEndocannabinoids
Alternative Parents
Substituents
  • 2-arachidonoylglycerol-skeleton
  • Hydroxyeicosapolyenoic acid
  • Eicosanoid
  • Fatty alcohol
  • 2-acyl-sn-glycerol
  • Monoradylglycerol
  • Monoacylglycerol
  • Glycerolipid
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Solubility0.0099 g/LALOGPS
logP4.62ALOGPS
logP4.18ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.28ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity118.49 m³·mol⁻¹ChemAxon
Polarizability45.89 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-016s-7296050000-011e66dfb552a34df54aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-c575869144f9867bdc65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03do-0009900000-83bfe115c75e35557114Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e6-0009400000-dee91ea16fe16cc8f25cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-9f51d2ac31733f26a5d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0009600000-63e6fe070d3a08dec7f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000o-0009000000-0b37b0af2169a49a2409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k96-9007000000-c2b31f587c794f278584Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9118000000-c387f63afba105336f30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1003-6389000000-6b0c63033b2863336dabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-7af95ca2b5f90947ec62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dk-0009000000-74867a444b209a7ff6d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i0-0009000000-2eb3c3d4cfdf9069509eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-f48df2712a778cf5e692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000900000-f48df2712a778cf5e692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aox-0009300000-2fa39b4f929308f6a25eSpectrum
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 IDHMDB0012530
FooDB IDFDB029112
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776620
ChEBI ID171687
PubChem Compound ID53481455
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. Epub 2005 Jun 17.
2. Rosolowsky M, Campbell WB: Synthesis of hydroxyeicosatetraenoic (HETEs) and epoxyeicosatrienoic acids (EETs) by cultured bovine coronary artery endothelial cells. Biochim Biophys Acta. 1996 Jan 19;1299(2):267-77.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. 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.
5. 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.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. The lipid handbook with CD-ROM