Human Metabolome Database Version 3.5

Showing metabocard for 11(R)-HETE (HMDB04682)

Record Information
Version 3.5
Creation Date 2006-08-13 18:20:18 -0600
Update Date 2013-05-29 13:40:45 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name 11(R)-HETE
Description 11(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 Link_out, 8555273 Link_out).
Structure Thumb
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Display: 2D Structure | 3D Structure
  1. 11-HETE
  2. 11-Hydroxy-arachidonic acid
  3. 11-Hydroxyeicosatetraenoate
  4. 11-Hydroxyeicosatetraenoic acid
  5. 11R-Hydroxy-5E,8Z,12Z,14Z-eicosatetraenoate
  6. 11R-Hydroxy-5E,8Z,12Z,14Z-eicosatetraenoic acid
Chemical Formula C20H32O3
Average Molecular Weight 320.4663
Monoisotopic Molecular Weight 320.23514489
IUPAC Name (5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid
Traditional IUPAC Name (5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid
CAS Registry Number 73347-43-0
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct Parent Hydroxyeicosatetraenoic Acids
Status Detected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 4.056 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0018 g/L ALOGPS
LogP 5.85 ALOGPS
LogP 5.36 ChemAxon
LogS -5.26 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -1.6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 101.47 ChemAxon
Polarizability 39.17 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.425 +/- 0.0095 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.00102 +/- 0.00125 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.401 +/- 0.36 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.000727 +/- 6E-5 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.000125 +/- 0.000077 uM Adult (>18 years old) Both Comment Normal
  • John W. Newm...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023402
KNApSAcK ID Not Available
Chemspider ID 4472406 Link_out
KEGG Compound ID C14780 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04682 Link_out
Metagene Link HMDB04682 Link_out
METLIN ID Not Available
PubChem Compound 5312981 Link_out
PDB ID Not Available
ChEBI ID 34126 Link_out
Synthesis Reference Not 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 Link_out
  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 Link_out