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Showing Compound 5,6-Epoxy-8,11,14-eicosatrienoic acid (FDB022895)

Record Information
Version1.0
Creation date2011-09-21 00:21:16 UTC
Update date2015-07-21 06:57:25 UTC
Primary IDFDB022895
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5,6-Epoxy-8,11,14-eicosatrienoic acid
Description5,6-Epoxy-8,11,14-eicosatrienoic acid is an Epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The 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. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113) [HMDB]
CAS Number81246-84-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Polarizability38.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O3
IUPAC name4-[3-(tetradeca-2,5,8-trien-1-yl)oxiran-2-yl]butanoic acid
InChI IdentifierInChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)
InChI KeyVBQNSZQZRAGRIX-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CCC=CCC=CCC1OC1CCCC(O)=O
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
Classification
Description Belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentEpoxy fatty acids
Alternative Parents
Substituents
  • Epoxy fatty acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5,6-Epoxy-8,11,14-eicosatrienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-9680000000-9277cd1ed0489c2f49f1Spectrum
Predicted GC-MS5,6-Epoxy-8,11,14-eicosatrienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,6-Epoxy-8,11,14-eicosatrienoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,6-Epoxy-8,11,14-eicosatrienoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-2229000000-4b640f08d264b586aba62021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-9323000000-7bf675ec327ad703f03b2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qc-9000000000-a13d0bb6e0fb21746a1d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-e9172f49e67d0b8f9e552021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-5009000000-64027d1612271f69287a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9210000000-fa7840477fde0f1ed0fc2021-10-12View Spectrum
NMRNot Available
ChemSpider ID4446323
ChEMBL IDCHEMBL1893588
KEGG Compound IDC14768
Pubchem Compound ID5283202
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02190
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference