Showing metabocard for 5(S)-Hydroperoxyeicosatetraenoic acid (BMDB0001193)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:42:23 UTC
Update Date2020-04-22 15:07:04 UTC
BMDB IDBMDB0001193
Secondary Accession Numbers
  • BMDB01193
Metabolite Identification
Common Name5(S)-Hydroperoxyeicosatetraenoic acid
Description5(S)-Hydroperoxyeicosatetraenoic acid, also known as (S)-5-hpete or 5S-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. 5(S)-Hydroperoxyeicosatetraenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufv-7293000000-1f097659cf0dcff9bef9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bl-9145000000-04747e5703a025ef8f4fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-4313d8567d98daeec5beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9i-2069000000-56e8fbe6c944c9901664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9330000000-a6266812ce67a6e4e4f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1369000000-fdc7ed645955c857b4f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-6924000000-769a1698f7fc3038abd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nf-9300000000-13e0c97d67ef1cdf5fc0View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001193
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
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 ReferencesNot Available