Record Information
Version2.0
Creation Date2012-05-31 13:47:16 -0600
Update Date2015-06-03 15:53:50 -0600
Secondary Accession Numbers
  • ECMDB01193
Identification
Name:5(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. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. (PMID: 15777099)
Structure
Thumb
Synonyms:
  • (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
  • (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoic acid
  • 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate
  • 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid
  • 5(S)-Hydroperoxyeicosatetraenoate
  • 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate
  • 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid
Chemical Formula:C20H32O4
Weight:Average: 336.4657
Monoisotopic: 336.230059512
InChI Key:JNUUNUQHXIOFDA-JGKLHWIESA-N
InChI: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
CAS number:71774-08-8
IUPAC Name:(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
Traditional IUPAC Name:5-HpETE
SMILES:CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO
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
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted 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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Arachidonic acid metabolismPW000759 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
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 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
References
References:
  • Jian, W., Lee, S. H., Arora, J. S., Silva Elipe, M. V., Blair, I. A. (2005). "Unexpected formation of etheno-2'-deoxyguanosine adducts from 5(S)-hydroperoxyeicosatetraenoic acid: evidence for a bis-hydroperoxide intermediate." Chem Res Toxicol 18:599-610. Pubmed: 15777099
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
Synthesis Reference:Dussault, 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
External Links:
ResourceLink
CHEBI ID15632
HMDB IDHMDB01193
Pubchem Compound ID5280778
Kegg IDC05356
ChemSpider ID4444340
Wikipedia IDNot Available
BioCyc ID6E8Z11Z14Z-5S-5-HYDROPEROXYCOSA-6
EcoCyc ID6E8Z11Z14Z-5S-5-HYDROPEROXYCOSA-6

Enzymes

General function:
Involved in glutathione peroxidase activity
Specific function:
Not essential for B12 transport; however, it is an auxiliary component of the transport system
Gene Name:
btuE
Uniprot ID:
P06610
Molecular weight:
20469