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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2021-09-14 14:58:12 UTC
HMDB IDHMDB0002311
Secondary Accession Numbers
  • HMDB0002351
  • HMDB0004676
  • HMDB02311
  • HMDB02351
  • HMDB04676
Metabolite Identification
Common Name8,9-DiHETrE
Description8,9-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid (AA) metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. P450converts AA to 8,9- dihydroxyeicosatrienoic acid. This enzymatic pathway was first described in liver; however, it is now clear that AA can be metabolized by P450 in many tissues including the pituitary gland, eye, kidney, adrenal gland, and blood vessels. (PMID: 17431031 , 11700990 ).
Structure
Data?1582752243
Synonyms
ValueSource
(5Z,11Z,14Z)-8,9-Dihydroxyeicosa-5,11,14-trienoic acidChEBI
(5Z,11Z,14Z)-8,9-Dihydroxyicosa-5,11,14-trienoic acidChEBI
8,9-DHETChEBI
8,9-Dihydroxy-5Z,11Z,14Z-eicosatrienoic acidChEBI
8,9-Dihydroxy-5Z,11Z,14Z-icosatrienoic acidChEBI
8,9-Dihydroxyeicosatrienoic acidChEBI
(5Z,11Z,14Z)-8,9-Dihydroxyeicosa-5,11,14-trienoateGenerator
(5Z,11Z,14Z)-8,9-Dihydroxyicosa-5,11,14-trienoateGenerator
8,9-Dihydroxy-5Z,11Z,14Z-eicosatrienoateGenerator
8,9-Dihydroxy-5Z,11Z,14Z-icosatrienoateGenerator
8,9-DihydroxyeicosatrienoateGenerator
(+/-)8,9-dihetreHMDB
Chemical FormulaC20H34O4
Average Molecular Weight338.4816
Monoisotopic Molecular Weight338.245709576
IUPAC Name(5Z,11Z,14Z)-8,9-dihydroxyicosa-5,11,14-trienoic acid
Traditional Name8,9-DiHETrE
CAS Registry Number192461-96-4
SMILES
CCCCC\C=C/C\C=C/CC(O)C(O)C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,12-9-,13-10-
InChI KeyDCJBINATHQHPKO-TYAUOURKSA-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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP10(5.45) g/LALOGPS
logP10(4.49) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity101.87 m³·mol⁻¹ChemAxon
Polarizability39.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.20831661259
DarkChem[M-H]-189.24931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8,9-DiHETrE,1TMS,#1CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\CCCC(=O)O2796.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,1TMS,#2CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C2795.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,1TMS,#3CCCCC/C=C\C/C=C\CC(O)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C2719.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,2TMS,#1CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C2797.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,2TMS,#2CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C2739.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,2TMS,#3CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2740.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,3TMS,#1CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2726.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,1TBDMS,#1CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\CCCC(=O)O3049.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,1TBDMS,#2CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3050.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,1TBDMS,#3CCCCC/C=C\C/C=C\CC(O)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2970.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,2TBDMS,#1CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3232.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,2TBDMS,#2CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3211.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,2TBDMS,#3CCCCC/C=C\C/C=C\CC(O)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3213.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
8,9-DiHETrE,3TBDMS,#1CCCCC/C=C\C/C=C\CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3423.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-DiHETrE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kpi-3931000000-9660c7e0c24b66a145632017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-DiHETrE GC-MS (3 TMS) - 70eV, Positivesplash10-0f9i-9212430000-caddc47ca14076a600eb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-DiHETrE 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 - 8,9-DiHETrE 10V, Positive-QTOFsplash10-00di-0119000000-0276473f3dd77d612b5f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Positive-QTOFsplash10-0ue9-5913000000-4d67f2c146851cdb48db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Positive-QTOFsplash10-0hgx-9400000000-998c31cc7528c1659a1b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 10V, Negative-QTOFsplash10-000i-0019000000-092edd96d90bb2988b322017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Negative-QTOFsplash10-0699-1925000000-106e392714fab8f93cd62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Negative-QTOFsplash10-0a4i-7910000000-487e4a96aea86a79fbf32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 10V, Positive-QTOFsplash10-0fk9-1209000000-f00de6b9bdba3d80e2a82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Positive-QTOFsplash10-00ai-9502000000-387b760f173f7802c2d42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Positive-QTOFsplash10-069u-9200000000-1f79a95ef141e773e52a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 10V, Negative-QTOFsplash10-000i-0109000000-d7cf9ea53b7adcdc367d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 20V, Negative-QTOFsplash10-000i-3839000000-aff175e8d9191e9e8d4e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-DiHETrE 40V, Negative-QTOFsplash10-052f-9620000000-2a240acda50a554859122021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00051 +/- 0.000066 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000294 +/- 0.000056 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000400 +/- 0.000151 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000244 +/- 0.000078 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00013 +/- 0.00003 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022960
KNApSAcK IDNot Available
Chemspider ID4446268
KEGG Compound IDC14773
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283144
PDB IDNot Available
ChEBI ID63970
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. Ng VY, Huang Y, Reddy LM, Falck JR, Lin ET, Kroetz DL: Cytochrome P450 eicosanoids are activators of peroxisome proliferator-activated receptor alpha. Drug Metab Dispos. 2007 Jul;35(7):1126-34. Epub 2007 Apr 12. [PubMed:17431031 ]
  2. Nithipatikom K, Grall AJ, Holmes BB, Harder DR, Falck JR, Campbell WB: Liquid chromatographic-electrospray ionization-mass spectrometric analysis of cytochrome P450 metabolites of arachidonic acid. Anal Biochem. 2001 Nov 15;298(2):327-36. [PubMed:11700990 ]

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
8,9-Epoxyeicosatrienoic acid + Water → 8,9-DiHETrEdetails