Showing Metabocard for N-(11,12-epoxy-5Z,8Z,14Z-eicosatrienoyl)-ethanolamine (BASm0008884)
| Common Name | N-(11,12-epoxy-5z,8z,14z-eicosatrienoyl)-ethanolamine |
|---|---|
| Description | (±)11(12)-EET ethanolamide is a potential cytochrome P450 (CYP450) metabolite of arachidonoyl ethanolamide (AEA; anandamide), although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism. AEA is an endogenous lipid neurotransmitter with cannibingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid CB2 receptors (PMID: 8395053 , 16078824 ). Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA (PMID: 12052036 ). Metabolism of AEA by cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented (PMID: 12052037 ). CYP450 metabolism of AEA may be particularly relevant under conditions of FAAH inhibition. Evidence for the formation of 11(12)-EET ethanolamide in vivo has not been documented. |
| Structure | |
| Molecular Formula | C22H37NO3 |
| Average Mass | 363.53410 |
| Monoisotopic Mass | 363.27734 |
| IUPAC Name | (5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide |
| Traditional Name | (5z,8z)-n-(2-hydroxyethyl)-10-{3-[(2z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide |
| CAS Registry Number | Not Available |
| SMILES | CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)NCCO |
| InChI Identifier | InChI=1S/C22H37NO3/c1-2-3-4-5-9-12-15-20-21(26-20)16-13-10-7-6-8-11-14-17-22(25)23-18-19-24/h6,8-10,12-13,20-21,24H,2-5,7,11,14-19H2,1H3,(H,23,25)/b8-6-,12-9-,13-10- |
| InChI Key | TYRRSRADDAROSO-KROJNAHFSA-N |
| CHEBI ID | CHEBI:136990 |
| HMDB ID | HMDB0013652 |
| State | Not Available |
| Water Solubility | 8.84e-04 g/l |
| logP | 5.43 |
| logS | -5.61 |
| pKa (Strongest Acidic) | 15.44 |
| pKa (Strongest Basic) | -0.34 |
| Hydrogen Acceptor Count | 3 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 61.86 Ų |
| Rotatable Bond Count | 16 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 111.37 m³·mol⁻¹ |
| Polarizability | 44.05 |