Record Information
Version1.0
Creation date2011-09-21 00:21:44 UTC
Update date2015-07-21 06:57:25 UTC
Primary IDFDB022920
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8,9-Epoxyeicosatrienoic acid
Description8,9-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid eicosanoid, a metabolite of arachidonic acid. The P450 epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597) [HMDB]
CAS Number81246-85-7
Structure
Thumb
Synonyms
SynonymSource
(Z)-7-((2S,3R)-3-((2Z,5Z)-Undeca-2,5-dienyl)oxiran-2-yl)hept-5-enoateGenerator
8,9-EpoxyeicosatrienoateHMDB
8,9-EETMeSH
8,9-Epoxyeicosatrienoic acid, (2alpha(Z),3alpha(2Z,5Z))-isomerMeSH
(+/-)8,9-EpETrEhmdb
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoatehmdb
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoic acidhmdb
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoatehmdb
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoic acidhmdb
8,9-Eethmdb
8,9-epoxy-5Z,11Z,14Z-eicosatrienoatehmdb
8,9-epoxy-5Z,11Z,14Z-eicosatrienoic acidhmdb
8,9-Epoxy-5Z,11Z,14Z-icosatrienoateGenerator
8,9-Epoxy-5Z,11Z,14Z-icosatrienoic acidChEBI
8,9-Epoxyeicosatrienoic acidhmdb
8,9-EpoxyicosatrienoateGenerator
8,9-Epoxyicosatrienoic acidChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP6.25ALOGPS
logP5.65ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity98.36 m³·mol⁻¹ChemAxon
Polarizability38.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O3
IUPAC name7-[3-(undeca-2,5-dien-1-yl)oxiran-2-yl]hept-5-enoic acid
InChI IdentifierInChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)
InChI KeyDBWQSCSXHFNTMO-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CCC=CCC1OC1CC=CCCCC(O)=O
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
Classification
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8,9-Epoxyeicosatrienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000g-6980000000-07a990c3a66cfc7764e5Spectrum
Predicted GC-MS8,9-Epoxyeicosatrienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8,9-Epoxyeicosatrienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-4319000000-c8927cc0e7aad6378c20Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsi-9413000000-c06fd94936bbbdd11dd3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qc-9200000000-fd86608717f334cda9baSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-5afdb8d651d23c147e45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0219000000-d59a22402225083aed54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9311000000-bae1c492ade35c452642Spectrum
NMRNot Available
ChemSpider ID4446324
ChEMBL IDCHEMBL1437769
KEGG Compound IDC14769
Pubchem Compound ID5283203
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02232
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference