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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2021-09-14 14:59:08 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

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP10(5.42) g/LALOGPS
logP10(4.49) g/LChemAxon
logS10(-4.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.00531661259
DarkChem[M-H]-190.53131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-DHETCCCCC\C=C/C\C=C/C\C=C/CC(O)C(O)CCCC(O)=O4196.7Standard polar33892256
5,6-DHETCCCCC\C=C/C\C=C/C\C=C/CC(O)C(O)CCCC(O)=O2400.1Standard non polar33892256
5,6-DHETCCCCC\C=C/C\C=C/C\C=C/CC(O)C(O)CCCC(O)=O2612.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,6-DHET,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C)C(O)CCCC(=O)O2824.5Semi standard non polar33892256
5,6-DHET,1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CC(O)C(CCCC(=O)O)O[Si](C)(C)C2815.5Semi standard non polar33892256
5,6-DHET,1TMS,isomer #3CCCCC/C=C\C/C=C\C/C=C\CC(O)C(O)CCCC(=O)O[Si](C)(C)C2736.1Semi standard non polar33892256
5,6-DHET,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C)C(CCCC(=O)O)O[Si](C)(C)C2803.9Semi standard non polar33892256
5,6-DHET,2TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C)C(O)CCCC(=O)O[Si](C)(C)C2762.6Semi standard non polar33892256
5,6-DHET,2TMS,isomer #3CCCCC/C=C\C/C=C\C/C=C\CC(O)C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2750.9Semi standard non polar33892256
5,6-DHET,3TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C)C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2739.1Semi standard non polar33892256
5,6-DHET,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)CCCC(=O)O3076.0Semi standard non polar33892256
5,6-DHET,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CC(O)C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C3071.3Semi standard non polar33892256
5,6-DHET,1TBDMS,isomer #3CCCCC/C=C\C/C=C\C/C=C\CC(O)C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C2980.0Semi standard non polar33892256
5,6-DHET,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C3255.4Semi standard non polar33892256
5,6-DHET,2TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C3234.5Semi standard non polar33892256
5,6-DHET,2TBDMS,isomer #3CCCCC/C=C\C/C=C\C/C=C\CC(O)C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3223.5Semi standard non polar33892256
5,6-DHET,3TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3431.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-DHET GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5893000000-644b265c8d0033c153a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-DHET GC-MS (3 TMS) - 70eV, Positivesplash10-009l-9222440000-5ade17a2dea5f318127b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-DHET GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 10V, Positive-QTOFsplash10-00di-0119000000-f4202d6e168a885cfc7a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 20V, Positive-QTOFsplash10-0006-9633000000-4bbc37276adca2cc77642017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 40V, Positive-QTOFsplash10-0006-9630000000-158b1997b1c24dfab32b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 10V, Negative-QTOFsplash10-000i-0019000000-94be53b1436416a5170f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 20V, Negative-QTOFsplash10-014u-5689000000-25170110627624a1f6002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 40V, Negative-QTOFsplash10-0a4i-9340000000-1bd1c79e4bc1b6ce57aa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 10V, Negative-QTOFsplash10-000i-0009000000-945cd3bf83aabf5d06732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 20V, Negative-QTOFsplash10-014s-7649000000-6b70b3117d96d37e7df32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 40V, Negative-QTOFsplash10-05mn-9200000000-e6d9c0d22c30c01eb8f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 10V, Positive-QTOFsplash10-0fk9-2209000000-a0f3d1a2de3540d03cfc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 20V, Positive-QTOFsplash10-00e9-9703000000-9a45a450e1c54e75f5642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-DHET 40V, Positive-QTOFsplash10-05nf-9200000000-357fecf17a9ed28b52d62021-09-24Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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