Human Metabolome Database Version 3.5

Showing metabocard for 15H-11,12-EETA (HMDB05050)

Record Information
Version 3.5
Creation Date 2006-10-19 06:44:39 -0600
Update Date 2013-02-08 17:13:51 -0700
HMDB ID HMDB05050
Secondary Accession Numbers
  • HMDB04683
Metabolite Identification
Common Name 15H-11,12-EETA
Description 15H-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 Link_out, 17468203 Link_out, 17434916 Link_out, 17406062 Link_out, 17361113 Link_out, 15581597 Link_out, 11413051 Link_out, 10519554 Link_out, 11893556 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C20H32O4
Average Molecular Weight 336.4657
Monoisotopic Molecular Weight 336.230059512
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 Number 877878-78-9
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 Key GELFSVXLSDZDHE-YZSNCDGGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Heterocyclic Fatty Acids
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Dialkyl Ether
  • Oxirane
  • Secondary Alcohol
Direct Parent Epoxy Fatty Acids
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.011 g/L ALOGPS
LogP 5.35 ALOGPS
LogP 4.57 ChemAxon
LogS -4.47 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 70.06 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 99.72 ChemAxon
Polarizability 39.47 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023612
KNApSAcK ID Not Available
Chemspider ID 10128337 Link_out
KEGG Compound ID C14781 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05050 Link_out
Metagene Link HMDB05050 Link_out
METLIN ID Not Available
PubChem Compound 11954042 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Lipid Maps (LMFA03080007) Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A43
Reactions: Not Available
Gene Name: CYP3A43
Uniprot ID: Q9HB55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions: Not Available
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C18
Reactions: Not Available
Gene Name: CYP2C18
Uniprot ID: P33260 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2F1
Reactions: Not Available
Gene Name: CYP2F1
Uniprot ID: P24903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4X1
Reactions: Not Available
Gene Name: CYP4X1
Uniprot ID: Q8N118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions: Not Available
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A13
Reactions: Not Available
Gene Name: CYP2A13
Uniprot ID: Q16696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4B1
Reactions: Not Available
Gene Name: CYP4B1
Uniprot ID: P13584 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4Z1
Reactions: Not Available
Gene Name: CYP4Z1
Uniprot ID: Q86W10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions: Not Available
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2S1
Reactions: Not Available
Gene Name: CYP2S1
Uniprot ID: Q96SQ9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2J2
Reactions: Not Available
Gene Name: CYP2J2
Uniprot ID: P51589 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A7
Reactions: Not Available
Gene Name: CYP2A7
Uniprot ID: P20853 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A6
Reactions: Not Available
Gene Name: CYP2A6
Uniprot ID: P11509 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 1, subfamily A, polypeptide 1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: A0N0X8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: Q6NWU0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA