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 Date2006-08-14 00:50:13 UTC
Update Date2013-05-29 19:40:52 UTC
HMDB IDHMDB04699
Secondary Accession NumbersNone
Metabolite Identification
Common Name8(S)-HPETE
Description8S-HPETE is metabolized from arachidonic acid by the enzyme 8S-lipoxygenase (8-LOX in mouse, ALOX15 and ALOX15B in human). 8S-HPETE will be readily reduced under physiological circumstances to 8S-hydroxyeicosatetraenoic acid (8S-HETE), a natural agonist of peroxisome proliferator-activated receptor alpha (PPAR alpha). (PMID: 16112079 ).
Structure
Thumb
Synonyms
  1. 8-Peroxy-5Z,9E,11Z,14Z-eicosatetraenoate
  2. 8-Peroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid
  3. 8S-HpETE
  4. 8S-Hydoperoxy-5Z,9E,11Z,14Z-eicosatetraenoate
  5. 8S-Hydoperoxy-5Z,9E,11Z,14Z-eicosatetraenoic acid
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8S,9E,11Z,14Z)-8-hydroperoxyicosa-5,9,11,14-tetraenoic acid
Traditional Name8S-HpETE
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C=C/[C@H](C\C=C/CCCC(O)=O)OO
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-13-16-19(24-23)17-14-11-12-15-18-20(21)22/h6-7,9-11,13-14,16,19,23H,2-5,8,12,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1
InChI KeyQQUFCXFFOZDXLA-VYOQERLCSA-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
  • 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 Solubility0.0017 mg/mLALOGPS
logP5.91ALOGPS
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
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
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 IDFDB023412
KNApSAcK IDNot Available
Chemspider ID7827803
KEGG Compound IDC14823
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04699
Metagene LinkHMDB04699
METLIN IDNot Available
PubChem Compound9548880
PDB IDNot Available
ChEBI ID34487
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jisaka M, Iwanaga C, Takahashi N, Goto T, Kawada T, Yamamoto T, Ikeda I, Nishimura K, Nagaya T, Fushiki T, Yokota K: Double dioxygenation by mouse 8S-lipoxygenase: specific formation of a potent peroxisome proliferator-activated receptor alpha agonist. Biochem Biophys Res Commun. 2005 Dec 9;338(1):136-43. Epub 2005 Aug 15. [16112079 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid exclusively to 15S-hydroperoxyeicosatetraenoic acid, while linoleic acid is less well metabolized.
Gene Name:
ALOX15B
Uniprot ID:
O15296
Molecular weight:
72522.25
Reactions
Arachidonic acid + Oxygen → 8(S)-HPETEdetails