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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:41:59 UTC
Update Date2022-03-07 03:17:52 UTC
HMDB IDHMDB0062294
Secondary Accession Numbers
  • HMDB62294
Metabolite Identification
Common Name15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
Description15(R)-HETE, also known as 15R-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, 15(R)-hete is considered to be an eicosanoid lipid molecule. 15(R)-HETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866292
Synonyms
ValueSource
15R-HETEChEBI
15R-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acidChEBI
15R-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoateGenerator
Chemical FormulaC20H32O3
Average Molecular Weight320.473
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,13E,15R)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
Traditional Name15R-hete
CAS Registry NumberNot Available
SMILES
[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C([H])=C([H])[C@]([H])(O)CCCCC
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m1/s1
InChI KeyJSFATNQSLKRBCI-UDQWCNDOSA-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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.002 g/lALOGPS
LogP5.82ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.82ALOGPS
logP5.36ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
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
Polarizability38.84 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]+189.63531661259
DarkChem[M-H]-188.69931661259
DeepCCS[M+H]+189.17830932474
DeepCCS[M-H]-187.35330932474
DeepCCS[M-2H]-220.59430932474
DeepCCS[M+Na]+194.78330932474
AllCCS[M+H]+186.832859911
AllCCS[M+H-H2O]+183.932859911
AllCCS[M+NH4]+189.532859911
AllCCS[M+Na]+190.332859911
AllCCS[M-H]-185.732859911
AllCCS[M+Na-2H]-187.532859911
AllCCS[M+HCOO]-189.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C([H])=C([H])[C@]([H])(O)CCCCC4104.4Standard polar33892256
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C([H])=C([H])[C@]([H])(O)CCCCC2368.8Standard non polar33892256
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid[H]\C(CCCC(O)=O)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C([H])=C([H])[C@]([H])(O)CCCCC2617.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid,1TMS,isomer #1CCCCC[C@@H](O)C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2634.4Semi standard non polar33892256
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid,1TMS,isomer #2CCCCC[C@H](C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2736.5Semi standard non polar33892256
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid,2TMS,isomer #1CCCCC[C@H](C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2711.7Semi standard non polar33892256
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid,1TBDMS,isomer #1CCCCC[C@@H](O)C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2876.5Semi standard non polar33892256
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid,1TBDMS,isomer #2CCCCC[C@H](C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2978.6Semi standard non polar33892256
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid,2TBDMS,isomer #1CCCCC[C@H](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)C3200.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbd-7392000000-c2dfffdfb7f66e1dfbeb2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9224200000-28bb287a1a8aa8319f912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 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 - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 10V, Positive-QTOFsplash10-0udi-0059000000-29d682672f6f76ce20142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 20V, Positive-QTOFsplash10-0r99-4393000000-fc93f4c0e6925dbe09be2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 40V, Positive-QTOFsplash10-0ab9-9730000000-908a873102b0d5ad22482017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 10V, Negative-QTOFsplash10-014i-0019000000-ebafac468e84ba5506122017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 20V, Negative-QTOFsplash10-0uxr-2059000000-351a2de26ec43cd0947c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 40V, Negative-QTOFsplash10-0a4l-9140000000-42f18def93db7669062a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 10V, Positive-QTOFsplash10-0udi-1249000000-43d1b8d94c8e551540212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 20V, Positive-QTOFsplash10-0fri-5593000000-ae2501633c7a9247872c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 40V, Positive-QTOFsplash10-067l-9810000000-ff4488e4ac71596deeb22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 10V, Negative-QTOFsplash10-014i-0019000000-d7f5ea0ce366341732692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 20V, Negative-QTOFsplash10-0gb9-1149000000-6b5173a9b24574c5af142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid 40V, Negative-QTOFsplash10-052f-9220000000-abb79fc4e0740be902ae2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283169
PDB IDNot Available
ChEBI ID63989
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.