Record Information
Version3.6
Creation Date2006-10-19 12:44:39 UTC
Update Date2013-02-09 00:13:51 UTC
HMDB IDHMDB05050
Secondary Accession Numbers
  • HMDB04683
Metabolite Identification
Common Name15H-11,12-EETA
Description15H-11,12-EETA is an epoxyeicosatrienoic acid (EET). The role of EETs in regulation of the cerebral circulation has become more important, since it was realized that EETs are produced in another specialized cell type of the brain, the astrocytes. It has become evident that EETs released from astrocytes may mediate cerebral functional hyperemia. Molecular and pharmacological evidence hve shown that neurotransmitter release and spillover onto astrocytes can generate EETs. Since these EETs may reach the vasculature via astrocyte foot-processes, they have the same potential as their endothelial counterparts to hyperpolarize and dilate cerebral vessels. P450 enzymes contain heme in their catalytic domain and nitric oxide (NO) appears to bind to these heme moieties and block formation of P450 products, including EETs. Thus, there appears to be crosstalk between P450 enzymes and NO/NO synthase. The role of fatty acid metabolites and cerebral blood flow becomes even more complex in light of data demonstrating that cyclooxygenase products can act as substrates for P450 enzymes. (PMID: 17494091 , 17468203 , 17434916 , 17406062 , 17361113 , 15581597 , 11413051 , 10519554 , 11893556 ).
Structure
Thumb
Synonyms
  1. (+/-)11,12-Ep-15(S)-hetre
  2. (5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoate
  3. (5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoic acid
  4. (5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoate
  5. (5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoic acid
  6. 11,12-Epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoate
  7. 11,12-Epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoic acid
  8. 15-Hydroxy-11,12-epoxyeicosatrienoate
  9. 15-Hydroxy-11,12-epoxyeicosatrienoic acid
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
Traditional IUPAC Name(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
CAS Registry Number877878-78-9
SMILES
CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-9-12-17(21)15-16-19-18(24-19)13-10-7-5-4-6-8-11-14-20(22)23/h4,6-7,10,15-19,21H,2-3,5,8-9,11-14H2,1H3,(H,22,23)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1
InChI KeyGELFSVXLSDZDHE-YZSNCDGGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassHeterocyclic Fatty Acids
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Dialkyl Ether
  • Oxirane
  • Secondary Alcohol
Direct ParentEpoxy Fatty Acids
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
water solubility0.011 g/LALOGPS
logP5.35ALOGPS
logP4.57ChemAxon
logS-4.5ALOGPS
pKa (strongest acidic)4.82ChemAxon
pKa (strongest basic)-2.8ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area70.06ChemAxon
rotatable bond count14ChemAxon
refractivity99.72ChemAxon
polarizability39.47ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023612
KNApSAcK IDNot Available
Chemspider ID10128337
KEGG Compound IDC14781
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05050
Metagene LinkHMDB05050
METLIN IDNot Available
PubChem Compound11954042
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lipid Maps (LMFA03080007)

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Gene Name:
CYP2C18
Uniprot ID:
P33260
Gene Name:
CYP2F1
Uniprot ID:
P24903
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Gene Name:
CYP2B6
Uniprot ID:
P20813
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Gene Name:
CYP3A7
Uniprot ID:
P24462
Gene Name:
CYP4B1
Uniprot ID:
P13584
Gene Name:
CYP4Z1
Uniprot ID:
Q86W10
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
CYP19A1
Uniprot ID:
P11511
Gene Name:
CYP2C8
Uniprot ID:
P10632
Gene Name:
CYP2S1
Uniprot ID:
Q96SQ9
Gene Name:
CYP2J2
Uniprot ID:
P51589
Gene Name:
CYP2A7
Uniprot ID:
P20853
Gene Name:
CYP2A6
Uniprot ID:
P11509
Gene Name:
CYP2D6
Uniprot ID:
Q6NWU0