Human Metabolome Database Version 3.5

Showing metabocard for 13-HETE (HMDB12567)

Record Information
Version 3.5
Creation Date 2009-07-24 18:03:04 -0600
Update Date 2013-02-08 17:29:20 -0700
HMDB ID HMDB12567
Secondary Accession Numbers None
Metabolite Identification
Common Name 13-HETE
Description 13-Hydroxyeicosatetraenoic acid is one of the main metabolites of 15-lipoxygenases (15-LOXs), are endogenous ligands of PPARr. It can inhibit cell proliferation and induce apoptosis in several types of human cancer. 13-HETE is an arachidonic acid metabolite in rat liver microsomes, and is a metabolite of red algae.Hydroxyeicosatetraenoic acids (HETEs) are formed in numerous cell types by enzymatically-mediated hydroxylation of arachidonic acid. There are three distinct enzymes involved in HETE biosynthesis:lipoxygenase (LOX), prostaglandin H (PGH) synthase, and cytochrome P-450. LOX- and PGH-synthase-mediated arachidonic acid metabolism is normally highly stereoselective.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 13-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate
  2. 13-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
Chemical Formula C20H32O3
Average Molecular Weight 320.4663
Monoisotopic Molecular Weight 320.23514489
IUPAC Name (5Z,8Z,11Z,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional IUPAC Name (5Z,8Z,11Z,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid
CAS Registry Number 151910-72-4
SMILES CCCCC\C=C/C(O)\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier InChI=1S/C20H32O3/c1-2-3-4-10-13-16-19(21)17-14-11-8-6-5-7-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b8-6-,9-7-,16-13-,17-14-
InChI Key SAKQICHVWOJSNI-BWWNDVLWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Other Hydroxyeicosapolyenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid Salt
  • Fatty Alcohol
  • Secondary Alcohol
Direct Parent Other Hydroxyeicosapolyenoic Acids
Ontology
Status Expected and 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
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 0.0016 g/L ALOGPS
LogP 5.82 ALOGPS
LogP 5.51 ChemAxon
LogS -5.29 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -1.9 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 101.32 ChemAxon
Polarizability 38.02 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
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 FDB029131
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12567 Link_out
Metagene Link HMDB12567 Link_out
METLIN ID Not Available
PubChem Compound 53481471 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA