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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 06:20:33 UTC
Update Date2022-03-07 03:18:00 UTC
HMDB IDHMDB0062798
Secondary Accession Numbers
  • HMDB62798
Metabolite Identification
Common Name5-hydroperoxy-15-HETE
Description(6E,8Z,11Z)-5-hydroperoxy-15-hydroxyicosa-6,8,11,13-tetraenoic acid belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds (6E,8Z,11Z)-5-hydroperoxy-15-hydroxyicosa-6,8,11,13-tetraenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866362
Synonyms
ValueSource
(6E,8Z,11Z)-5-Hydroperoxy-15-hydroxyicosa-6,8,11,13-tetraenoateGenerator
5-HP-15-HETEHMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.471
Monoisotopic Molecular Weight352.22497413
IUPAC Name(6E,8Z,11Z)-5-hydroperoxy-15-hydroxyicosa-6,8,11,13-tetraenoic acid
Traditional Name(6E,8Z,11Z)-5-hydroperoxy-15-hydroxyicosa-6,8,11,13-tetraenoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(C\C([H])=C(\[H])C([H])=C([H])C(CCCC(O)=O)OO)=C(/[H])C([H])=C([H])C(O)CCCCC
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-9-13-18(21)14-10-7-5-4-6-8-11-15-19(25-24)16-12-17-20(22)23/h5-8,10-11,14-15,18-19,21,24H,2-4,9,12-13,16-17H2,1H3,(H,22,23)/b7-5-,8-6-,14-10?,15-11+
InChI KeyAZHSPOPOMNJPFD-HRIRBLAHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroperoxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroperoxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Allylic hydroperoxide
  • Secondary alcohol
  • Hydroperoxide
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 Solubility0.015 g/lALOGPS
LogP4.86ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.86ALOGPS
logP4.57ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.39ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity104.34 m³·mol⁻¹ChemAxon
Polarizability40.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.66731661259
DarkChem[M-H]-195.82531661259
DeepCCS[M+H]+195.59130932474
DeepCCS[M-H]-193.69530932474
DeepCCS[M-2H]-226.93630932474
DeepCCS[M+Na]+201.36830932474
AllCCS[M+H]+194.132859911
AllCCS[M+H-H2O]+191.332859911
AllCCS[M+NH4]+196.632859911
AllCCS[M+Na]+197.332859911
AllCCS[M-H]-190.432859911
AllCCS[M+Na-2H]-192.332859911
AllCCS[M+HCOO]-194.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-hydroperoxy-15-HETE[H]\C(C\C([H])=C(\[H])C([H])=C([H])C(CCCC(O)=O)OO)=C(/[H])C([H])=C([H])C(O)CCCCC4463.3Standard polar33892256
5-hydroperoxy-15-HETE[H]\C(C\C([H])=C(\[H])C([H])=C([H])C(CCCC(O)=O)OO)=C(/[H])C([H])=C([H])C(O)CCCCC2490.0Standard non polar33892256
5-hydroperoxy-15-HETE[H]\C(C\C([H])=C(\[H])C([H])=C([H])C(CCCC(O)=O)OO)=C(/[H])C([H])=C([H])C(O)CCCCC2709.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-hydroperoxy-15-HETE,1TMS,isomer #1CCCCCC(O)C=C/C=C\C/C=C\C=CC(CCCC(=O)O[Si](C)(C)C)OO2987.7Semi standard non polar33892256
5-hydroperoxy-15-HETE,1TMS,isomer #2CCCCCC(C=C/C=C\C/C=C\C=CC(CCCC(=O)O)OO)O[Si](C)(C)C3084.2Semi standard non polar33892256
5-hydroperoxy-15-HETE,2TMS,isomer #1CCCCCC(C=C/C=C\C/C=C\C=CC(CCCC(=O)O[Si](C)(C)C)OO)O[Si](C)(C)C3026.7Semi standard non polar33892256
5-hydroperoxy-15-HETE,1TBDMS,isomer #1CCCCCC(O)C=C/C=C\C/C=C\C=CC(CCCC(=O)O[Si](C)(C)C(C)(C)C)OO3235.2Semi standard non polar33892256
5-hydroperoxy-15-HETE,1TBDMS,isomer #2CCCCCC(C=C/C=C\C/C=C\C=CC(CCCC(=O)O)OO)O[Si](C)(C)C(C)(C)C3330.1Semi standard non polar33892256
5-hydroperoxy-15-HETE,2TBDMS,isomer #1CCCCCC(C=C/C=C\C/C=C\C=CC(CCCC(=O)O[Si](C)(C)C(C)(C)C)OO)O[Si](C)(C)C(C)(C)C3496.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-hydroperoxy-15-HETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f77-9775000000-1790185f4501065499922017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-hydroperoxy-15-HETE GC-MS (2 TMS) - 70eV, Positivesplash10-05ei-9021500000-f9f622634fc1b304b2662017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-hydroperoxy-15-HETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-hydroperoxy-15-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 - 5-hydroperoxy-15-HETE 10V, Positive-QTOFsplash10-000i-0019000000-2dd31a8c017ea94191282017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 20V, Positive-QTOFsplash10-0k9i-4189000000-5157e0945f20583bfea22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 40V, Positive-QTOFsplash10-0006-9640000000-3658380f6bf4330f2ce42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 10V, Negative-QTOFsplash10-0udi-0009000000-16fc87e5801f4636a20f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 20V, Negative-QTOFsplash10-0f8i-3049000000-e2fa3722c5358d9d6dfa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 40V, Negative-QTOFsplash10-0a4l-9141000000-17b2ab6a1ef171bd48032017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 10V, Negative-QTOFsplash10-0udi-0009000000-2b50398ca1f93d438f1e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 20V, Negative-QTOFsplash10-0ldi-1149000000-b5b038bf10b80ae8e0132021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 40V, Negative-QTOFsplash10-052f-9170000000-a1697298679671e2a2302021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 10V, Positive-QTOFsplash10-0uy0-0039000000-7b2b60d981a4a2b71d2d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 20V, Positive-QTOFsplash10-0uy0-1197000000-2d877a073949db6ae09b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-hydroperoxy-15-HETE 40V, Positive-QTOFsplash10-0aor-4940000000-243d3f142d9f88a2e0da2021-09-25Wishart 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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.