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Record Information
Version3.6
Creation Date2008-10-29 12:41:53 UTC
Update Date2017-09-21 23:20:11 UTC
HMDB IDHMDB0011135
Secondary Accession Numbers
  • HMDB11135
Metabolite Identification
Common Name5-HPETE
DescriptionArachidonic acid 5-hydroperoxide (5-hydroperoxyeicosatetraenoic acid, 5-HPETE) is an intermediate in the production of leukotriene A4 from arachidonic acid.
Structure
Thumb
Synonyms
ValueSource
(6E,8Z,11Z,14Z)-5-Hydroperoxyicosatetraenoic acidChEBI
5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acidChEBI
5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoic acidChEBI
6,8,11,14-Eicosatetraenoic acid 5-hydroperoxideChEBI
Arachidonic acid 5-hydroperoxideChEBI
(6E,8Z,11Z,14Z)-5-HydroperoxyicosatetraenoateGenerator
5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateGenerator
5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoateGenerator
6,8,11,14-Eicosatetraenoate 5-hydroperoxideGenerator
Arachidonate 5-hydroperoxideGenerator
(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 acidMeSH
cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acidMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.82 m3·mol-1ChemAxon
Polarizability39.53 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 41 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027913
KNApSAcK IDNot Available
Chemspider ID4446295
KEGG Compound IDC05356
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0011135
METLIN IDNot Available
PubChem Compound5283171
PDB IDNot Available
ChEBI 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 ]

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