Hmdb loader
Survey
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
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:01:58 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012508
Secondary Accession Numbers
  • HMDB12508
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
Data?1582753062
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-10-Hydroxyicosatetraenoic acidChEBI
10-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateChEBI
10-Hydroxy-(5Z,8Z,11Z,14Z)-icosatetraenoateChEBI
10-Hydroxyarachidonic acidChEBI
(5Z,8Z,11Z,14Z)-10-HydroxyicosatetraenoateGenerator
10-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acidGenerator
10-Hydroxy-(5Z,8Z,11Z,14Z)-icosatetraenoic acidGenerator
10-HydroxyarachidonateGenerator
10-Hydroxyeicosatetraenoic acidMeSH
10-Hydroxyeicosatetraenoic acid, (S)-(all-Z)-isomerMeSH
10-Hydroxyeicosa-all-cis-5,8,11,14-tetraenoateHMDB
10-Hydroxyeicosa-all-cis-5,8,11,14-tetraenoic acidHMDB
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
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 DescriptorsNot Available
Ontology
Not AvailableNot Available
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
logP5.84ALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.32 m³·mol⁻¹ChemAxon
Polarizability37.98 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]+188.09531661259
DarkChem[M-H]-189.46631661259
DeepCCS[M+H]+191.46630932474
DeepCCS[M-H]-189.10830932474
DeepCCS[M-2H]-221.99430932474
DeepCCS[M+Na]+197.55930932474
AllCCS[M+H]+187.032859911
AllCCS[M+H-H2O]+184.132859911
AllCCS[M+NH4]+189.732859911
AllCCS[M+Na]+190.532859911
AllCCS[M-H]-185.632859911
AllCCS[M+Na-2H]-187.432859911
AllCCS[M+HCOO]-189.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
10-HETECCCCC\C=C/C\C=C/C(O)\C=C/C\C=C/CCCC(O)=O4035.2Standard polar33892256
10-HETECCCCC\C=C/C\C=C/C(O)\C=C/C\C=C/CCCC(O)=O2301.5Standard non polar33892256
10-HETECCCCC\C=C/C\C=C/C(O)\C=C/C\C=C/CCCC(O)=O2507.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
10-HETE,1TMS,isomer #1CCCCC/C=C\C/C=C\C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2698.3Semi standard non polar33892256
10-HETE,1TMS,isomer #2CCCCC/C=C\C/C=C\C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2561.6Semi standard non polar33892256
10-HETE,2TMS,isomer #1CCCCC/C=C\C/C=C\C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2618.6Semi standard non polar33892256
10-HETE,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2927.3Semi standard non polar33892256
10-HETE,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2812.5Semi standard non polar33892256
10-HETE,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3107.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 10-HETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udv-8793000000-47fc624b790ad674a71c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10-HETE GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9115300000-d8f77e62dc7e863edb072017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10-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 - 10-HETE 10V, Positive-QTOFsplash10-0udi-0149000000-45b562d03702e99e10d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 20V, Positive-QTOFsplash10-0kp0-5974000000-7f596198d33bcc0df0e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 40V, Positive-QTOFsplash10-052f-9530000000-e9af6804eec8404e62102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 10V, Negative-QTOFsplash10-014i-0019000000-dd216c4c735cd22bb2012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 20V, Negative-QTOFsplash10-0uxr-1349000000-17cb2a2e5823d60f4c342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 40V, Negative-QTOFsplash10-0a4l-9820000000-8f5fa6787972a8dcf2802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 10V, Positive-QTOFsplash10-0udi-1349000000-0fabd76f4aa55905bfd72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 20V, Positive-QTOFsplash10-0f8i-5942000000-59330d98c96eab8b87c32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 40V, Positive-QTOFsplash10-00nf-9310000000-cd593a1ecc8e5f0d15ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 10V, Negative-QTOFsplash10-014i-0009000000-777fdb814292c66079c92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 20V, Negative-QTOFsplash10-0gb9-1319000000-81951b28eb51a860055d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-HETE 40V, Negative-QTOFsplash10-052p-8981000000-99b14680fdab38d83bd72021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029107
KNApSAcK IDNot Available
Chemspider ID35032538
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481450
PDB IDNot Available
ChEBI ID134453
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. 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 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.