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Human Metabolome Database Version 2.5
Showing metabocard for (±)8(9)-EET Ethanolamide (HMDB13659)
Legend: enzyme field
| Version | 2.5 | ||||||||||||||||||
| Creation Date | 2011-07-12 11:28:56 | ||||||||||||||||||
| Update Date | 2011-07-12 11:38:14 | ||||||||||||||||||
| Accession Number | HMDB13659 | ||||||||||||||||||
| Secondary Accession Numbers | Not Available | ||||||||||||||||||
| Common Name | (±)8(9)-EET Ethanolamide | ||||||||||||||||||
| Description | Arachidonoyl ethanolamide (AEA) is an endogenous lipid neurotransmitter with cannabingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors.1,2 Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA.3 Metabolism of AEA by COX-2, lipoxygenases, and CYP450 enzymes has also been documented.4,5 (±)8(9)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism.5 Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner.5 (±)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction.6 The physiological actions of (±)8(9)-EET ethanolamide have not been examined. | ||||||||||||||||||
| Synonyms |
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| Chemical IUPAC Name | N-(2-hydroxyethyl)-(±)8(9)-epoxy-5Z,11Z,14Z-eicosatrienoic amide | ||||||||||||||||||
| Chemical Formula | C22H37NO3 | ||||||||||||||||||
| Chemical Structure |  |
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| Chemical Taxonomy |
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| Average Molecular Weight | 363.534 | ||||||||||||||||||
| Monoisotopic Molecular Weight | 363.277344 | ||||||||||||||||||
| Isomeric SMILES | CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO | ||||||||||||||||||
| Canonical SMILES | CCCCCC=CCC=CCC1OC1CC=CCCCC(=O)NCCO | ||||||||||||||||||
| KEGG Compound ID | Not Available | ||||||||||||||||||
| BioCyc ID | Not Available | ||||||||||||||||||
| BiGG ID | Not Available | ||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||
| NuGOwiki Link | HMDB13659  |
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| Metagene Link | HMDB13659 |
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| METLIN ID | Not Available | ||||||||||||||||||
| PubChem Compound | Not Available | ||||||||||||||||||
| PubChem Substance | Not Available | ||||||||||||||||||
| ChEBI ID | Not Available | ||||||||||||||||||
| CAS Registry Number | Not Available | ||||||||||||||||||
| InChI Identifier | InChI=1/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10- | ||||||||||||||||||
| Synthesis Reference | Not Available | ||||||||||||||||||
| Melting Point (Experimental) | Not Available | ||||||||||||||||||
| Experimental Water Solubility | Not Available Source: PhysProp | ||||||||||||||||||
| Predicted Water Solubility | Not Available Calculated using ALOGPS | ||||||||||||||||||
| Physiological Charge | 0 | ||||||||||||||||||
| State | Solid | ||||||||||||||||||
| Experimental LogP/Hydrophobicity | Not Available Source: PhysProp | ||||||||||||||||||
| Predicted LogP/Hydrophobicity | Not Available Calculated using ALOGPS | ||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||
| MOL File | Show |
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| SDF File | Show |
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| PDB File | Show |
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| 2D Structure | |||||||||||||||||||
| 3D Structure | |||||||||||||||||||
| Experimental PDB ID | Not Available | ||||||||||||||||||
| Experimental 1H NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C HSQC Spectrum | Not Available | ||||||||||||||||||
| Predicted 1H NMR Spectrum |
Not Available Not Available |
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| Predicted 13C NMR Spectrum |
Not Available Not Available |
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| Mass Spectrum | Not Available | ||||||||||||||||||
| Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||
| BMRB Spectrum | Not Available | ||||||||||||||||||
| Cellular Location | Not Available | ||||||||||||||||||
| Biofluid Location | Not Available | ||||||||||||||||||
| Tissue Location | Not Available | ||||||||||||||||||
| Concentrations (Normal) | Not Available | ||||||||||||||||||
| Concentrations (Abnormal) | Not Available | ||||||||||||||||||
| Associated Disorders | Not Available | ||||||||||||||||||
| OMIM ID | Not Available | ||||||||||||||||||
| Pathways | Not Available | ||||||||||||||||||
| General References | Not Available |
