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Showing metabocard for 9-HETE (HMDB0010222)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:18 UTC
Update Date2018-01-05 00:27:01 UTC
HMDB IDHMDB0010222
Secondary Accession Numbers
  • HMDB10222
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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
()-9-HETEHMDB
()-9-Hydroxy-(5Z,7E,11Z,14Z)-eicosatetraenoateHMDB
()-9-Hydroxy-(5Z,7E,11Z,14Z)-eicosatetraenoic acidHMDB
9-Hydroxy-5Z,7E,11Z,14Z-eicosatetraenoateHMDB
9-Hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acidHMDB
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 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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.31 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-6953000000-5a3158ff1d66735e44a6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9104200000-0e86a645fd8c8714847bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0149000000-656a91eb8e4bcede5213View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-5984000000-01f0f25f8c5427ee57dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9530000000-a0b7ef17e2ae4114c021View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-c3fe798916131b3366dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1249000000-af3fee44e98a23017d83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9620000000-49f685fb629bf144b298View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.001704 +/- 0.000081 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000304 +/- 0.000072 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified0.000166 +/- 0.00016 uMAdult (>18 years old)Both
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
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027375
KNApSAcK IDNot Available
Chemspider ID4472403
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312978
PDB IDNot Available
ChEBI ID72785
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 ]