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Showing metabocard for 5,6-Epoxy-8,11,14-eicosatrienoic acid (BMDB0002190)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:20 UTC
Update Date2020-05-21 16:28:40 UTC
BMDB IDBMDB0002190
Secondary Accession Numbers
  • BMDB02190
Metabolite Identification
Common Name5,6-Epoxy-8,11,14-eicosatrienoic acid
Description5,6-Epoxy-8,11,14-eicosatrienoic acid, also known as (+/-)5,6-epetre or 5,6-eet, 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. Based on a literature review very few articles have been published on 5,6-Epoxy-8,11,14-eicosatrienoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+/-)5,6-epetreChEBI
(8Z,11Z,14Z)-5,6-Epoxyeicosa-8,11,14-trienoic acidChEBI
(8Z,11Z,14Z)-5,6-Epoxyicosa-8,11,14-trienoic acidChEBI
5,6-EpETrEChEBI
5,6-Epoxy-8,11,14-icosatrienoic acidChEBI
5,6-Epoxy-8Z,11Z,14Z-eicosatrienoic acidChEBI
5,6-Epoxy-8Z,11Z,14Z-icosatrienoic acidChEBI
(8Z,11Z,14Z)-5,6-Epoxyeicosa-8,11,14-trienoateGenerator
(8Z,11Z,14Z)-5,6-Epoxyicosa-8,11,14-trienoateGenerator
5,6-Epoxy-8,11,14-icosatrienoateGenerator
5,6-Epoxy-8Z,11Z,14Z-eicosatrienoateGenerator
5,6-Epoxy-8Z,11Z,14Z-icosatrienoateGenerator
5,6-Epoxy-8,11,14-eicosatrienoateGenerator
5,6-EetHMDB
5(6)-Oxido-8,11,14-eicosatrienoic acidHMDB
5(6)-Oxidoeicosatrienoic acidHMDB
5(6)Epoxyeicosatrienoic acidHMDB
5,6-Epoxy-8,11,14-eicosatrienoic acid, (2alpha,3alpha(2Z,5Z,8Z))-isomerHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoic acid
Traditional Name5(6)epoxyeicosatrienoic acid
CAS Registry Number81246-84-6
SMILES
CCCCC\C=C/C\C=C/C\C=C/CC1OC1CCCC(O)=O
InChI Identifier
InChI=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)/b7-6-,10-9-,13-12-
InChI KeyVBQNSZQZRAGRIX-QNEBEIHSSA-N
Chemical Taxonomy
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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability39.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9680000000-9277cd1ed0489c2f49f1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-9343000000-8ebbc6b83f90c4773092View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1039000000-61ea0b5e6095e5a712d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-9452000000-e56fa17dede58805db86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9420000000-4b7097444d03a2a2aa7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-4e96728f18c66da2e4e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v00-3069000000-4536562ff67ce028e249View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9130000000-60d70cad2f9296348221View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-e9172f49e67d0b8f9e55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-5119000000-d0ab8275ed285438b566View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9210000000-fa7840477fde0f1ed0fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-3329000000-2299a698c0d69c27f7f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-9323000000-7bf675ec327ad703f03bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qc-9000000000-a13d0bb6e0fb21746a1dView in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002190
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022895
KNApSAcK IDNot Available
Chemspider ID4446323
KEGG Compound IDC14768
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283202
PDB IDNot Available
ChEBI ID34450
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 2E1
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids. May be involved in the oxidative metabolism of xenobiotics.
Gene Name:
CYP2E1
Uniprot ID:
O18963
Molecular weight:
56827.0
Reactions
Arachidonic acid + Oxygen → 5,6-Epoxy-8,11,14-eicosatrienoic acid + Waterdetails
Enzyme Details
2. Epoxide hydrolase 2, cytoplasmic
General function:
Not Available
Specific function:
Not Available
Gene Name:
EPHX2
Uniprot ID:
Q17QK4
Molecular weight:
62691.0
Reactions
5,6-Epoxy-8,11,14-eicosatrienoic acid + Water → 5,6-DHETdetails