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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:12 UTC
Update Date2017-12-07 02:24:38 UTC
HMDB IDHMDB0010216
Secondary Accession Numbers
  • HMDB10216
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
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoic acidChEBI
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-icosatetraenoic acidChEBI
(5S,6E,8Z,11Z,13E,15S)-5,15-Dihydroxyicosatetraenoic acidChEBI
5(S),15(S)-Dihydroxy-6,13-trans-8,11-cis-eicosatetraenoic acidChEBI
5,15-Dihydroxy-6,8,11,13-eicosatetraenoic acidChEBI
5,15-Dihydroxyeicosatetraenoic acidChEBI
5S,15S-DiHETEChEBI
5S,15S-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acidChEBI
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateGenerator
(5S,15S)-Dihydroxy-(6E,8Z,11Z,13E)-icosatetraenoateGenerator
(5S,6E,8Z,11Z,13E,15S)-5,15-DihydroxyicosatetraenoateGenerator
5(S),15(S)-Dihydroxy-6,13-trans-8,11-cis-eicosatetraenoateGenerator
5,15-Dihydroxy-6,8,11,13-eicosatetraenoateGenerator
5,15-DihydroxyeicosatetraenoateGenerator
5S,15S-Dihydroxy-6E,8Z,11Z,13E-eicosatetraenoateGenerator
5(S),15(S)-DiHETEHMDB
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 KeyUXGXCGPWGSUMNI-BVHTXILBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Cellular process:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability39.52 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kk-6492000000-3c2ee47ee6c0da2b1c18View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-002u-9013440000-ef35dbcf7f2fcff2741eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-f48b85306f04941fd350View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-106r-4196000000-2bead0468d6c53e9925eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9460000000-5fbe33b7844341ee0d01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0029000000-d8e68d87d5e32a76be4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bi-3069000000-b36c2c202ba716d4d1b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9040000000-45f4070691efc333f188View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
METLIN IDNot Available
PubChem Compound5283158
PDB IDNot Available
ChEBI ID91286
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. [PubMed:6817003 ]