Showing metabocard for 11,12-Epoxyeicosatrienoic acid (BMDB0004673)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:10:08 UTC
Update Date2020-05-21 16:28:39 UTC
BMDB IDBMDB0004673
Secondary Accession Numbers
  • BMDB04673
Metabolite Identification
Common Name11,12-Epoxyeicosatrienoic acid
Description11,12-Epoxyeicosatrienoic acid, also known as (11S,12R)-epetre or 11,12-eet, belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain. 11,12-Epoxyeicosatrienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(11S,12R)-EpETrEChEBI
(11S,12R)-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acidChEBI
(11S,12R)-Epoxy-(5Z,8Z,14Z)-icosatrienoic acidChEBI
11(S),12(R)-EETChEBI
11(S),12(R)-EpETrEChEBI
11S,12R-EETChEBI
11S,12R-EpETrEChEBI
11S,12R-Epoxy-5Z,8Z,14Z-eicosatrienoic acidChEBI
(11S,12R)-Epoxy-(5Z,8Z,14Z)-eicosatrienoateGenerator
(11S,12R)-Epoxy-(5Z,8Z,14Z)-icosatrienoateGenerator
11S,12R-Epoxy-5Z,8Z,14Z-eicosatrienoateGenerator
11,12-EpoxyeicosatrienoateGenerator
11,12-Epoxy-5,8,14-eicosatrienoic acid, (2alpha(5Z,8Z),3alpha(Z))-isomerHMDB
11,12-Oxido-5,8,14-eicosatrienoic acidHMDB
11(12)-Epoxy-5Z,8Z,14Z-eicosatrienoic acidHMDB
11,12-EETHMDB
11,12-Epoxy-5,8,14-eicosatrienoic acidHMDB
(11S,12R)-Oxidoarachidonic acidHMDB
(5Z,8Z)-10-[(2S,3R)-3-(2Z)-2-Octen-1-yl-2-oxiranyl]-5,8-decadienoic acidHMDB
(5Z,8Z)-10-[3-(2Z)-2-Octen-1-yl-2-oxiranyl]-5,8-decadienoic acidHMDB
10-[3-(2-Octen-1-yl)-2-oxiranyl]-5,8-decadienoic acidHMDB
10-[3-(2-Octenyl)oxiranyl]-5,8-decadienoic acidHMDB
11(12)-EETHMDB
11(12)-EpETrEHMDB
11,12-Epoxyeicosa-5,8,14-trienoic acidHMDB
cis-11(12)-EpEtrEHMDB
11,12-Epoxyeicosatrienoic acidHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.473
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid
Traditional Name(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid
CAS Registry Number81276-02-0
SMILES
CCCCC\C=C/C[C@H]1O[C@H]1C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6-,12-9-,13-10-/t18-,19+/m1/s1
InChI KeyDXOYQVHGIODESM-LZXKBWHHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHepoxilins
Alternative Parents
Substituents
  • Hepoxilin
  • Medium-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • 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
  • 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)4.82ChemAxon
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
Polarizability38.65 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, 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, Negativesplash10-014i-0009000000-8a30f962c830a060bbaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0419000000-e44cb44d1b9170384b12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9761000000-d3c981434cabe5877633View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uki-2339000000-dbc9012403da685e17bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udu-9645000000-0a0c6b80e626735811c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-9200000000-27dc327d0927da0eb208View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004673
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027560
KNApSAcK IDNot Available
Chemspider ID23208913
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound40490664
PDB IDNot Available
ChEBI ID132276
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 → 11,12-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
11,12-Epoxyeicosatrienoic acid + Water → 11,12-DiHETrEdetails