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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001193
Secondary Accession Numbers
  • HMDB01193
Metabolite Identification
Common Name5(S)-Hydroperoxyeicosatetraenoic acid
Description5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. These DNA modifications are proposed to be involved in the etiology of cancer, cardiovascular disease, and neurodegeneration. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. Studies have implicated the 5-LOX pathway as an important mediator in the pathology of atherosclerosis. (PMID: 15777099 ). Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. Thus, the arachidonic acid moiety is preferentially converted to LTA4 in a concerted reaction without dissociation of a 5-HPETE intermediate. (PMID: 3036580 ).
Structure
Data?1582752183
Synonyms
ValueSource
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acidChEBI
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoateChEBI
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoateChEBI
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acidChEBI
(S)-5-HPETEChEBI
5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acidChEBI
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acidChEBI
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acidChEBI
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoic acidChEBI
5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoateChEBI
5S-HpETEChEBI
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoateGenerator
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acidGenerator
5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoateGenerator
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoateGenerator
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoateGenerator
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoateGenerator
5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acidGenerator
5(S)-HydroperoxyeicosatetraenoateGenerator
5-HPETEHMDB
5-Hydroperoxy-6,8,11,14-eicosatetraenoic acidHMDB
6,8,11,14-Eicosatetraenoic acid 5-hydroperoxideHMDB
Arachidonic acid 5-hydroperoxideHMDB
cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
Traditional Name5-HpETE
CAS Registry Number71774-08-8
SMILES
CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](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+/t19-/m1/s1
InChI KeyJNUUNUQHXIOFDA-JGKLHWIESA-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
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]+194.63431661259
DarkChem[M-H]-190.76731661259
AllCCS[M+H]+190.55132859911
AllCCS[M-H]-188.1432859911
DeepCCS[M+H]+190.02430932474
DeepCCS[M-H]-187.66630932474
DeepCCS[M-2H]-221.07630932474
DeepCCS[M+Na]+196.35330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5(S)-Hydroperoxyeicosatetraenoic acidCCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO4173.3Standard polar33892256
5(S)-Hydroperoxyeicosatetraenoic acidCCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO2413.6Standard non polar33892256
5(S)-Hydroperoxyeicosatetraenoic acidCCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO2675.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5(S)-Hydroperoxyeicosatetraenoic acid,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)OO2761.3Semi standard non polar33892256
5(S)-Hydroperoxyeicosatetraenoic acid,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)OO3004.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufv-7293000000-1f097659cf0dcff9bef92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00bl-9145000000-04747e5703a025ef8f4f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic 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 - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Positive-QTOFsplash10-014i-0119000000-5146d59d15dbfb1648ac2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Positive-QTOFsplash10-000l-5895000000-636edd63bf1c315085fb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Positive-QTOFsplash10-0f96-7970000000-59e419db47612aac9e212015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Negative-QTOFsplash10-000i-0029000000-27b34dc78df443e7b2e72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Negative-QTOFsplash10-0fri-4189000000-4d5ecf358e00eaff14502015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Negative-QTOFsplash10-0a4l-9160000000-7865a2863663a5eb39ab2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Negative-QTOFsplash10-000i-0009000000-4313d8567d98daeec5be2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Negative-QTOFsplash10-0k9i-2069000000-56e8fbe6c944c99016642021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Negative-QTOFsplash10-052f-9330000000-a6266812ce67a6e4e4f62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Positive-QTOFsplash10-000i-1369000000-fdc7ed645955c857b4f62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Positive-QTOFsplash10-00li-6924000000-769a1698f7fc3038abd92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Positive-QTOFsplash10-05nf-9300000000-13e0c97d67ef1cdf5fc02021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB022480
KNApSAcK IDNot Available
Chemspider ID4444340
KEGG Compound IDC05356
BioCyc IDNot Available
BiGG ID45650
Wikipedia LinkNot Available
METLIN ID6070
PubChem Compound5280778
PDB IDNot Available
ChEBI ID15632
Food Biomarker OntologyNot Available
VMH ID5HPET
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDussault, Patrick; Lee, In Quen. A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE. Journal of Organic Chemistry (1995), 60(1), 218-26.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jian W, Lee SH, Arora JS, Silva Elipe MV, Blair IA: Unexpected formation of etheno-2'-deoxyguanosine adducts from 5(S)-hydroperoxyeicosatetraenoic acid: evidence for a bis-hydroperoxide intermediate. Chem Res Toxicol. 2005 Mar;18(3):599-610. [PubMed:15777099 ]
  2. Puustinen T, Scheffer MM, Samuelsson B: Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. FEBS Lett. 1987 Jun 15;217(2):265-8. [PubMed:3036580 ]

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
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
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
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
General function:
Involved in glutathione peroxidase activity
Specific function:
Not Available
Gene Name:
GPX6
Uniprot ID:
P59796
Molecular weight:
24970.46
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
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
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
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
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
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
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
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
Reactions
Arachidonic acid + Oxygen → 5(S)-Hydroperoxyeicosatetraenoic aciddetails
5(S)-Hydroperoxyeicosatetraenoic acid → Leukotriene A4 + Waterdetails