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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2020-02-26 21:24:04 UTC
HMDB IDHMDB0002343
Secondary Accession Numbers
  • HMDB0004675
  • HMDB02343
  • HMDB04675
Metabolite Identification
Common Name5,6-DHET
Description5,6-DHET is an epoxide intermediate in the oxygenation of arachidonic acid by hepatic monooxygenases pathway. 5,6-DHET is the hydrolysis metabolite of cis-5(6)Epoxy-cis-8,11,14-eicosatrienoic acid by epoxide hydrolases. Many drugs, chemicals, and endogenous compounds are oxygenated in mammalian tissues and in some instances reactive and potentially toxic or carcinogenic epoxides are formed. Naturally occurring olefins may also be oxygenated by mammalian enzymes. The most well known are lipoxygenases and microsomal cytochrome P-450-linked monooxygenases. The epoxides may be chemically labile or may be enzymatically hydrolyzed. When arene or olefinic epoxides are formed by microsomal P-450-linked monooxygenases, they are often rapidly converted to less reactive trans-diols through the action of microsomal epoxide hydrolases. (PMID: 6801052 , 6548162 ).
Structure
Data?1582752244
Synonyms
ValueSource
(+/-)5,6-dihetreChEBI
(8Z,11Z,14Z)-5,6-Dihydroxyeicosa-8,11,14-trienoic acidChEBI
(8Z,11Z,14Z)-5,6-Dihydroxyicosa-8,11,14-trienoic acidChEBI
5,6-DiHETrEChEBI
5,6-Dihydroxy-8Z,11Z,14Z-eicosatrienoic acidChEBI
5,6-Dihydroxy-8Z,11Z,14Z-icosatrienoic acidChEBI
(8Z,11Z,14Z)-5,6-Dihydroxyeicosa-8,11,14-trienoateGenerator
(8Z,11Z,14Z)-5,6-Dihydroxyicosa-8,11,14-trienoateGenerator
5,6-Dihydroxy-8Z,11Z,14Z-eicosatrienoateGenerator
5,6-Dihydroxy-8Z,11Z,14Z-icosatrienoateGenerator
Chemical FormulaC20H34O4
Average Molecular Weight338.4816
Monoisotopic Molecular Weight338.245709576
IUPAC Name(8Z,11Z,14Z)-5,6-dihydroxyicosa-8,11,14-trienoic acid
Traditional Name5,6-DiHETrE
CAS Registry Number213382-49-1
SMILES
CCCCC\C=C/C\C=C/C\C=C/CC(O)C(O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-
InChI KeyGFNYAPAJUNPMGH-QNEBEIHSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.013 g/LALOGPS
logP5.42ALOGPS
logP4.49ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.87 m³·mol⁻¹ChemAxon
Polarizability39.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5893000000-644b265c8d0033c153a9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009l-9222440000-5ade17a2dea5f318127bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0119000000-f4202d6e168a885cfc7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9633000000-4bbc37276adca2cc7764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9630000000-158b1997b1c24dfab32bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-94be53b1436416a5170fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014u-5689000000-25170110627624a1f600Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9340000000-1bd1c79e4bc1b6ce57aaSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00061 +/- 0.000057 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000264 +/- 0.000025 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000438 +/- 0.000245 uMAdult (>18 years old)Not SpecifiedNormal
    • Oxygenated lipids...
details
BloodDetected and Quantified0.000189 +/- 0.000092 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022971
KNApSAcK IDNot Available
Chemspider ID4446266
KEGG Compound IDC14772
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283142
PDB IDNot Available
ChEBI ID63974
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Oliw EH, Guengerich FP, Oates JA: Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J Biol Chem. 1982 Apr 10;257(7):3771-81. [PubMed:6801052 ]
  2. Oliw EH: Biosynthesis of 5,6-dihydroxyprostaglandin E1 and F1 alpha from 5,6-dihydroxyeicosatrienoic acid by ram seminal vesicles. Biochim Biophys Acta. 1984 Sep 12;795(2):384-91. [PubMed:6548162 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
Gene Name:
EPHX2
Uniprot ID:
P34913
Molecular weight:
62615.22
Reactions
5,6-Epoxy-8,11,14-eicosatrienoic acid + Water → 5,6-DHETdetails