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Showing metabocard for 8,9-Epoxyeicosatrienoic acid (BMDB0002232)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:59 UTC
Update Date2020-05-21 16:28:39 UTC
BMDB IDBMDB0002232
Secondary Accession Numbers
  • BMDB02232
Metabolite Identification
Common Name8,9-Epoxyeicosatrienoic acid
Description8,9-Epoxyeicosatrienoic acid, also known as (+/-)8,9-epetre or 8,9-eet, 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. Based on a literature review a significant number of articles have been published on 8,9-Epoxyeicosatrienoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+/-)8,9-epetreChEBI
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoic acidChEBI
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoic acidChEBI
8,9-Epoxy-5Z,11Z,14Z-eicosatrienoic acidChEBI
8,9-Epoxy-5Z,11Z,14Z-icosatrienoic acidChEBI
8,9-Epoxyicosatrienoic acidChEBI
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoateGenerator
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoateGenerator
8,9-Epoxy-5Z,11Z,14Z-eicosatrienoateGenerator
8,9-Epoxy-5Z,11Z,14Z-icosatrienoateGenerator
8,9-EpoxyicosatrienoateGenerator
8,9-EpoxyeicosatrienoateGenerator
8,9-EetHMDB
8,9-Epoxyeicosatrienoic acid, (2alpha(Z),3alpha(2Z,5Z))-isomerHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoic acid
Traditional Name8,9-epoxyeicosatrienoic acid
CAS Registry Number81246-85-7
SMILES
CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=O
InChI Identifier
InChI=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)/b7-6-,12-9-,13-10-
InChI KeyDBWQSCSXHFNTMO-TYAUOURKSA-N
Chemical Taxonomy
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 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
Polarizability38.55 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, Positivesplash10-000g-6980000000-07a990c3a66cfc7764e5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-002r-9553000000-120e27beab70feb84ed6View in MoNA
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-0229000000-4a7644f998116e5959aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0wn9-4921000000-727677e385ebbb995864View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015d-9500000000-903e4e69e6bda087561bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0219000000-80c9ec974d3aaabbc8b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-1539000000-c3f531539781dda28168View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9800000000-a8abb16134374c498d9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-4429000000-e15c713039784fb91bd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsi-9413000000-c06fd94936bbbdd11dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qc-9200000000-fd86608717f334cda9baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-5afdb8d651d23c147e45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0329000000-417e0056d0fd313e5a7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9311000000-bae1c492ade35c452642View in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002232
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022920
KNApSAcK IDNot Available
Chemspider ID4446324
KEGG Compound IDC14769
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283203
PDB IDNot Available
ChEBI ID34490
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 → 8,9-Epoxyeicosatrienoic 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
8,9-Epoxyeicosatrienoic acid + Water → 8,9-DiHETrEdetails