Human Metabolome Database Version 3.5

Showing metabocard for 8(S)-HPETE (HMDB04699)

Record Information
Version 3.5
Creation Date 2006-08-13 18:50:13 -0600
Update Date 2013-05-29 13:40:52 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name 8(S)-HPETE
Description 8S-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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  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 Formula C20H32O4
Average Molecular Weight 336.4657
Monoisotopic Molecular Weight 336.230059512
IUPAC Name (5Z,8S,9E,11Z,14Z)-8-hydroperoxyicosa-5,9,11,14-tetraenoic acid
Traditional IUPAC Name 8S-HpETE
CAS Registry Number Not Available
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroperoxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroperoxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
  • Acyclic Alkene
  • Carboxylic Acid
  • Hydroperoxide
Direct Parent Hydroperoxyeicosatetraenoic Acids
Status Expected and Not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0017 g/L ALOGPS
LogP 5.91 ALOGPS
LogP 5.81 ChemAxon
LogS -5.30 ALOGPS
pKa (strongest acidic) 4.39 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 102.82 ChemAxon
Polarizability 39.53 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023412
KNApSAcK ID Not Available
Chemspider ID 7827803 Link_out
KEGG Compound ID C14823 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04699 Link_out
Metagene Link HMDB04699 Link_out
METLIN ID Not Available
PubChem Compound 9548880 Link_out
PDB ID Not Available
ChEBI ID 34487 Link_out
Synthesis Reference Not 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. Pubmed: 16112079 Link_out

Name: Arachidonate 15-lipoxygenase B
Arachidonic acid + Oxygen unknown 8(S)-HPETE details
Gene Name: ALOX15B
Uniprot ID: O15296 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA