You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:59 UTC
HMDB IDHMDB01193
Secondary Accession NumbersNone
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
Thumb
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
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
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 KeyInChIKey=JNUUNUQHXIOFDA-JGKLHWIESA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroperoxide
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
  • Cytoplasm
  • 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0119000000-5146d59d15dbfb1648acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-5895000000-636edd63bf1c315085fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-7970000000-59e419db47612aac9e21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029000000-27b34dc78df443e7b2e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fri-4189000000-4d5ecf358e00eaff1450View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9160000000-7865a2863663a5eb39abView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 IDFDB022480
KNApSAcK IDNot Available
Chemspider ID4444340
KEGG Compound IDC05356
BioCyc ID6E8Z11Z14Z-5S-5-HYDROPEROXYCOSA-6
BiGG ID45650
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01193
Metagene LinkHMDB01193
METLIN ID6070
PubChem Compound5280778
PDB IDNot Available
ChEBI ID15632
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. [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. [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