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Showing Compound 15H-11,12-EETA (FDB023612)

Record Information
Version1.0
Creation date2011-09-21 00:32:24 UTC
Update date2015-07-21 06:57:47 UTC
Primary IDFDB023612
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number877878-78-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(+/-)11,12-Ep-15(S)-hetrehmdb
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoatehmdb
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoic acidhmdb
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoatehmdb
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoic acidhmdb
11,12-epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoatehmdb
11,12-epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoic acidhmdb
15-Hydroxy-11,12-epoxyeicosatrienoatehmdb
15-Hydroxy-11,12-epoxyeicosatrienoic acidhmdb
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 Area70.06 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.72 m³·mol⁻¹ChemAxon
Polarizability39.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O4
IUPAC name10-{3-[(3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
InChI IdentifierInChI=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)/t17-,18?,19?/m0/s1
InChI KeyGELFSVXLSDZDHE-VIQWUECVSA-N
Isomeric SMILES[H][C@](O)(CCCCC)C=CC1OC1CC=CCC=CCCCC(O)=O
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
Classification
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Heterocyclic fatty acid
  • Epoxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • 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
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID10128337
ChEMBL IDNot Available
KEGG Compound IDC14781
Pubchem Compound ID11954042
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05050
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference