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Record Information
Version3.6
Creation Date2008-09-15 09:55:12 UTC
Update Date2016-02-11 01:16:25 UTC
HMDB IDHMDB10216
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,15-DiHETE
Description5,15-DiHETE or 5,15-dihydroxyeicosatetraenoic acid is a double oxidation product of arachadonic acid. (PMID: 6817003 ). It is produced by the action of lipoxygenases (specifically 5-lipoxygenase and 15 lipoxygenase) in the liver and in neutrophils.
Structure
Thumb
Synonyms
ValueSource
5(S),15(S)-DiHETEHMDB
5,15-Dihydroxy-6,8,11,13-eicosatetraenoateHMDB
5,15-Dihydroxy-6,8,11,13-eicosatetraenoic acidHMDB
5,15-DihydroxyeicosatetraenoateHMDB
5,15-Dihydroxyeicosatetraenoic acidHMDB
5S,15S-DiHETEHMDB
5S,15S-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoateHMDB
5S,15S-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6E,8Z,11Z,13E,15S)-5,15-dihydroxyicosa-6,8,11,13-tetraenoic acid
Traditional Name5S,15S-DiHETE
CAS Registry Number82200-87-1
SMILES
CCCCC[C@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-9-13-18(21)14-10-7-5-4-6-8-11-15-19(22)16-12-17-20(23)24/h5-8,10-11,14-15,18-19,21-22H,2-4,9,12-13,16-17H2,1H3,(H,23,24)/b7-5-,8-6-,14-10+,15-11+/t18-,19+/m0/s1
InChI KeyInChIKey=UXGXCGPWGSUMNI-BVHTXILBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Signaling
Application
  • Not Available
Cellular locations
  • Membrane (predicted from logP)
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 Solubility0.016 mg/mLALOGPS
logP5.33ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m3·mol-1ChemAxon
Polarizability39.52 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000527 +/- 1.7E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000247 +/- 0.00002 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.00007 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000247 +/- 0.0000200 uMAdult (>18 years old)Not Specified
Normal
details
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 IDFDB027370
KNApSAcK IDNot Available
Chemspider ID4446282
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10216
Metagene LinkHMDB10216
METLIN IDNot Available
PubChem Compound5283158
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Borgeat P, Picard S, Drapeau J, Vallerand P: Metabolism of arachidonic acid in leukocytes: isolation of a 5,15-dihydroxy-eicosatetraenoic acid. Lipids. 1982 Oct;17(10):676-81. [6817003 ]