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Showing metabocard for 9-HETE (HMDB10222)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version3.6
Creation Date2008-09-15 09:55:18 UTC
Update Date2013-05-29 19:45:53 UTC
HMDB IDHMDB10222
Secondary Accession NumbersNone
Metabolite Identification
Common Name9-HETE
Description9-HETE, which is a product of free radical-mediated arachidonic acid oxidation, is significantly elevated in patients with angiographically defined CAD. (PMID: 17145556 ). 9-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid.
Structure
Thumb
ZoomMOLSDFPDBSMILESInChIView Structure
Synonyms
  1. ()-9-HETE
  2. ()-9-Hydroxy-(5Z,7E,11Z,14Z)-eicosatetraenoate
  3. ()-9-Hydroxy-(5Z,7E,11Z,14Z)-eicosatetraenoic acid
  4. 9-Hydroxy-5Z,7E,11Z,14Z-eicosatetraenoate
  5. 9-Hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5E,7Z,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoic acid
Traditional IUPAC Name9-hete
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CC(O)\C=C/C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9+,13-10-,17-14-
InChI KeyKATOYYZUTNAWSA-DLJQHUEDSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHydroxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct ParentHydroxyeicosatetraenoic Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Signaling
Application
  • Not Available
Cellular locations
  • Membrane (predicted from logP)
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 solubility0.0016 g/LALOGPS
logP5.88ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
pKa (strongest acidic)4.49ChemAxon
pKa (strongest basic)-1.6ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area57.53ChemAxon
rotatable bond count14ChemAxon
refractivity101.47ChemAxon
polarizability38.31ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.001704 +/- 8.1E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.304 +/- 0.072 uMAdult (>18 years old)Not Specified
Normal		 details
BloodDetected and Quantified0.166 +/- 0.16 uMAdult (>18 years old)Not Specified
Normal		 details
BloodDetected and Quantified0.001495 +/-0.000875 uMAdult (>18 years old)Both
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00014 +/- 0.00006 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027375
KNApSAcK IDNot Available
Chemspider ID4472403
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10222
Metagene LinkHMDB10222
METLIN IDNot Available
PubChem Compound5312978
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shishehbor MH, Zhang R, Medina H, Brennan ML, Brennan DM, Ellis SG, Topol EJ, Hazen SL: Systemic elevations of free radical oxidation products of arachidonic acid are associated with angiographic evidence of coronary artery disease. Free Radic Biol Med. 2006 Dec 1;41(11):1678-83. Epub 2006 Sep 8. Pubmed: 17145556