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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:18 UTC
Update Date2021-09-14 14:58:06 UTC
HMDB IDHMDB0010222
Secondary Accession Numbers
  • HMDB10222
Metabolite Identification
Common Name9-HETE
Description9-HETE, also known as ()-9-hete, 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. Thus, 9-HETE is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 9-HETE.
Structure
Data?1582752798
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
9-Hydroxy-5E,7Z,11Z,14Z-eicosatetraenoateHMDB
9-HETEChEBI
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
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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.02931661259
DarkChem[M-H]-187.51931661259
DeepCCS[M+H]+189.98430932474
DeepCCS[M-H]-187.62630932474
DeepCCS[M-2H]-220.51230932474
DeepCCS[M+Na]+196.07730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9-HETECCCCC\C=C/C\C=C/CC(O)\C=C/C=C/CCCC(O)=O4181.4Standard polar33892256
9-HETECCCCC\C=C/C\C=C/CC(O)\C=C/C=C/CCCC(O)=O2409.9Standard non polar33892256
9-HETECCCCC\C=C/C\C=C/CC(O)\C=C/C=C/CCCC(O)=O2554.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9-HETE,1TMS,isomer #1CCCCC/C=C\C/C=C\CC(/C=C\C=C\CCCC(=O)O)O[Si](C)(C)C2756.0Semi standard non polar33892256
9-HETE,1TMS,isomer #2CCCCC/C=C\C/C=C\CC(O)/C=C\C=C\CCCC(=O)O[Si](C)(C)C2642.3Semi standard non polar33892256
9-HETE,2TMS,isomer #1CCCCC/C=C\C/C=C\CC(/C=C\C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2697.2Semi standard non polar33892256
9-HETE,1TBDMS,isomer #1CCCCC/C=C\C/C=C\CC(/C=C\C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2990.2Semi standard non polar33892256
9-HETE,1TBDMS,isomer #2CCCCC/C=C\C/C=C\CC(O)/C=C\C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2883.5Semi standard non polar33892256
9-HETE,2TBDMS,isomer #1CCCCC/C=C\C/C=C\CC(/C=C\C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3184.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9-HETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-6953000000-5a3158ff1d66735e44a62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-HETE GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9104200000-0e86a645fd8c8714847b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-HETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-HETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 10V, Positive-QTOFsplash10-0udi-0149000000-656a91eb8e4bcede52132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 20V, Positive-QTOFsplash10-0udr-5984000000-01f0f25f8c5427ee57dc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 40V, Positive-QTOFsplash10-0006-9530000000-a0b7ef17e2ae4114c0212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 10V, Negative-QTOFsplash10-014i-0019000000-c3fe798916131b3366db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 20V, Negative-QTOFsplash10-0uxr-1249000000-af3fee44e98a23017d832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 40V, Negative-QTOFsplash10-0a4l-9620000000-49f685fb629bf144b2982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 10V, Negative-QTOFsplash10-014i-0019000000-ea61b7291cb1b7a3a7202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 20V, Negative-QTOFsplash10-0gb9-0539000000-c6fbb89fafc8023a8f4b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 40V, Negative-QTOFsplash10-066u-6790000000-d34f2cb66ec714f8a3832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 10V, Positive-QTOFsplash10-0udi-1249000000-6646144cf2ca9b3d26242021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 20V, Positive-QTOFsplash10-0fav-9542000000-0462d14dd9797253a4f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-HETE 40V, Positive-QTOFsplash10-05po-9210000000-3cff61b6d6b599009dfc2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
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
FooDB IDFDB027375
KNApSAcK IDNot Available
Chemspider ID4472403
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHETE
METLIN IDNot Available
PubChem Compound5312978
PDB IDNot Available
ChEBI ID72785
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. 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 ]