You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2009-07-25 00:01:58 UTC
Update Date2013-05-29 19:48:08 UTC
HMDB IDHMDB12508
Secondary Accession NumbersNone
Metabolite Identification
Common Name10-HETE
Description10-HETE is a HETE(Hydroxyeicosatetraenoic acid)with the hydroxy group located in C-10 position. The HETE metabolites are identified as omega-hydroxy derivatives and 10-HETE is one of the major products of NADPH-dependent arachidonic acid metabolism in rat liver microsomes. The conversion of arachidonic acid to HETE can be catalyzed via lipoxygenase ,cyclooxygenase or P-450 dependent route. [PMID: 7646075 ].
Structure
Thumb
Synonyms
  1. 10-Hydroxyeicosa-all-cis-5,8,11,14-tetraenoate
  2. 10-Hydroxyeicosa-all-cis-5,8,11,14-tetraenoic acid
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name(5Z,8Z,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoic acid
CAS Registry Number167697-52-1
SMILES
CCCCC\C=C/C\C=C/C(O)\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-10-13-16-19(21)17-14-11-8-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b7-6-,9-8-,16-13-,17-14-
InChI KeyZUOCVLADVGGUGH-OVMCANAPSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassOther Hydroxyeicosapolyenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid Salt
  • Fatty Alcohol
  • Secondary Alcohol
Direct ParentOther Hydroxyeicosapolyenoic Acids
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016ALOGPS
logP5.84ALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.32 m3·mol-1ChemAxon
Polarizability37.98 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029107
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12508
Metagene LinkHMDB12508
METLIN IDNot Available
PubChem Compound53481450
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brash AR, Boeglin WE, Capdevila JH, Yeola S, Blair IA: 7-HETE, 10-HETE, and 13-HETE are major products of NADPH-dependent arachidonic acid metabolism in rat liver microsomes: analysis of their stereochemistry, and the stereochemistry of their acid-catalyzed rearrangement. Arch Biochem Biophys. 1995 Aug 20;321(2):485-92. Pubmed: 7646075