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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-14 00:20:18 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004682
Secondary Accession Numbers
  • HMDB04682
Metabolite Identification
Common Name11(R)-HETE
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 ).
Structure
Thumb
Synonyms
ValueSource
11R-Hydroxy-5E,8Z,12Z,14Z-eicosatetraenoateHMDB
11-HETEHMDB
11-Hydroxy-5,8,12,14-eicosatetraenoic acidHMDB
11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (R)-(e,Z,Z,Z)-isomerHMDB
11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomerHMDB
11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerHMDB
11-Hydroxy-arachidonic acidHMDB
11-HydroxyeicosatetraenoateHMDB
11-Hydroxyeicosatetraenoic acidHMDB
11R-Hydroxy-5E,8Z,12Z,14Z-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid
Traditional Name(5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid
CAS Registry Number73347-43-0
SMILES
CCCCC\C=C/C=C\[C@H](O)C\C=C/C\C=C\CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6+,10-7-,14-11-,16-13-/t19-/m0/s1
InChI KeyGCZRCCHPLVMMJE-RSPKXIRXSA-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.056Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000425 +/- 0.0000095 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00102 +/- 0.00125 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000401 +/- 0.00036 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000727 +/- 0.00006 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000125 +/- 0.000077 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 IDFDB023402
KNApSAcK IDNot Available
Chemspider ID4472406
KEGG Compound IDC14780
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312981
PDB IDNot Available
ChEBI ID34126
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. 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. [PubMed:15964853 ]
  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. [PubMed:8555273 ]