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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-29 12:41:53 UTC
Update Date2022-03-07 02:51:03 UTC
HMDB IDHMDB0011135
Secondary Accession Numbers
  • HMDB11135
Metabolite Identification
Common Name5-HPETE
Description5-HPETE, also known as 5(S)-hpete, 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. Thus, 5-HPETE is considered to be an eicosanoid lipid molecule. 5-HPETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752871
Synonyms
ValueSource
(6E,8Z,11Z,14Z)-5-Hydroperoxyicosatetraenoic acidHMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acidHMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoic acidHMDB
6,8,11,14-Eicosatetraenoic acid 5-hydroperoxideHMDB
Arachidonic acid 5-hydroperoxideHMDB
(6E,8Z,11Z,14Z)-5-HydroperoxyicosatetraenoateHMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateHMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoateHMDB
6,8,11,14-Eicosatetraenoate 5-hydroperoxideHMDB
Arachidonate 5-hydroperoxideHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoateHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acidHMDB
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoateHMDB
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acidHMDB
5(S)-HPETEHMDB
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoateHMDB
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acidHMDB
5-Hydroperoxy-6,8,11,14-eicosatetraenoic acidHMDB
cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
Traditional Name(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
CAS Registry Number74581-83-2
SMILES
CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+
InChI KeyJNUUNUQHXIOFDA-XTDASVJISA-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
  • Fatty acid
  • Unsaturated fatty acid
  • Allylic hydroperoxide
  • Hydroperoxide
  • Carboxylic acid derivative
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot 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
logP5.92ALOGPS
logP5.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.39ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.82 m³·mol⁻¹ChemAxon
Polarizability39.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.45331661259
DarkChem[M-H]-192.22731661259
DeepCCS[M+H]+189.13430932474
DeepCCS[M-H]-186.77630932474
DeepCCS[M-2H]-219.66230932474
DeepCCS[M+Na]+195.22730932474
AllCCS[M+H]+190.632859911
AllCCS[M+H-H2O]+187.732859911
AllCCS[M+NH4]+193.232859911
AllCCS[M+Na]+193.932859911
AllCCS[M-H]-188.132859911
AllCCS[M+Na-2H]-190.032859911
AllCCS[M+HCOO]-192.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HPETECCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO4170.8Standard polar33892256
5-HPETECCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO2397.0Standard non polar33892256
5-HPETECCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO2644.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-HPETE,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C)OO2757.3Semi standard non polar33892256
5-HPETE,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C(C)(C)C)OO2999.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-HPETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufv-7293000000-1f097659cf0dcff9bef92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-HPETE GC-MS (1 TMS) - 70eV, Positivesplash10-00bl-9145000000-04747e5703a025ef8f4f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-HPETE 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-HPETE 10V, Positive-QTOFsplash10-014i-0129000000-4500aedb60e4f301fc492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 20V, Positive-QTOFsplash10-000l-5895000000-d22ccb32f3d2e86a7abe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 40V, Positive-QTOFsplash10-0f6x-7960000000-eeee1d1eae1b6538345d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 10V, Negative-QTOFsplash10-000i-0029000000-5771c8b8f884a5a6e7922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 20V, Negative-QTOFsplash10-00kr-3189000000-2e7fb2d06fbec5bc69002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 40V, Negative-QTOFsplash10-0pbc-9160000000-f9cca7f9dfab4a0ee1212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 10V, Positive-QTOFsplash10-000i-1369000000-fdc7ed645955c857b4f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 20V, Positive-QTOFsplash10-00li-6924000000-769a1698f7fc3038abd92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 40V, Positive-QTOFsplash10-05nf-9300000000-13e0c97d67ef1cdf5fc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 10V, Negative-QTOFsplash10-000i-0009000000-4313d8567d98daeec5be2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 20V, Negative-QTOFsplash10-0k9i-2069000000-56e8fbe6c944c99016642021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-HPETE 40V, Negative-QTOFsplash10-052f-9330000000-a6266812ce67a6e4e4f62021-09-23Wishart 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 IDFDB027913
KNApSAcK IDNot Available
Chemspider ID4446295
KEGG Compound IDC05356
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArachidonic acid 5-hydroperoxide
METLIN IDNot Available
PubChem Compound5283171
PDB IDNot Available
ChEBI ID91268
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. Winkler JD, Sung CM, Hubbard WC, Chilton FH: Influence of arachidonic acid on indices of phospholipase A2 activity in the human neutrophil. Biochem J. 1993 May 1;291 ( Pt 3):825-31. [PubMed:8387780 ]
  2. Seya A, Terano T, Tamura Y, Yoshida S: The role of 5-hydroperoxyeicosatetraenoic acid in neutrophil activation. Agents Actions. 1992 Sep;37(1-2):121-6. [PubMed:1456173 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in glutathione peroxidase activity
Specific function:
It protects esophageal epithelia from hydrogen peroxide-induced oxidative stress. It suppresses acidic bile acid-induced reactive oxigen species (ROS) and protects against oxidative DNA damage and double-strand breaks.
Gene Name:
GPX7
Uniprot ID:
Q96SL4
Molecular weight:
20995.88
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione. May constitute a glutathione peroxidase-like protective system against peroxide damage in sperm membrane lipids.
Gene Name:
GPX5
Uniprot ID:
O75715
Molecular weight:
25202.14
General function:
Involved in glutathione peroxidase activity
Specific function:
Not Available
Gene Name:
GPX6
Uniprot ID:
P59796
Molecular weight:
24970.46
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:
GPX1
Uniprot ID:
P07203
Molecular weight:
22087.94
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells against membrane lipid peroxidation and cell death. Required for normal sperm development and male fertility. Could play a major role in protecting mammals from the toxicity of ingested lipid hydroperoxides. Essential for embryonic development. Protects from radiation and oxidative damage (By similarity).
Gene Name:
GPX4
Uniprot ID:
P36969
Molecular weight:
25046.57
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione.
Gene Name:
GPX3
Uniprot ID:
P22352
Molecular weight:
25552.185
General function:
Involved in glutathione peroxidase activity
Specific function:
Could play a major role in protecting mammals from the toxicity of ingested organic hydroperoxides. Tert-butyl hydroperoxide, cumene hydroperoxide and linoleic acid hydroperoxide but not phosphatidycholine hydroperoxide, can act as acceptors.
Gene Name:
GPX2
Uniprot ID:
P18283
Molecular weight:
21953.835
General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595