Structure Database (LMSD)
Common Name
N-(2-fluoro-ethyl) arachidonoyl amine
Systematic Name
N-(2-fluoro-ethyl)-5Z,8Z,11Z,14Z-eicosatetraenoyl amine
Synonyms
- N-(2-fluoro-ethyl)arachidonoylamide
- arachidonoyl-(2'-fluoroethyl)amide
3D model of N-(2-fluoro-ethyl) arachidonoyl amine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Arachidonoyl-2'-fluoroethylamide (2-fluoro AEA) is an analog of anandamide in which the alcohol of the ethanolamide group has been removed and replaced with a fluorine atom. This substitution adds considerably increased binding affinity for the CB1 receptor (Kis = 26.7 and 908 nM for CB1 and CB2, respectively). It also contributes additional selectivity, in that binding to CB2 is decreased relative to AEA.1 However, the in vivo activity of 2-fluoro AEA is enhanced much less than the binding affinity, because the analog remains a good substrate for FAAH and is rapidly hydrolyzed by this enzyme.
This information has been provided by Cayman Chemical
References
1. Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. J. Med. Chem. 41(27), 5353-5361 (1998).
References
String Representations
InChiKey (Click to copy)
DOGHEWWVBBVYEY-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C22H36FNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)NCCF
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
0
Aromatic Rings
0
Rotatable Bonds
16
Van der Waals Molecular Volume
401.82
Topological Polar Surface Area
29.10
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
6.79
Molar Refractivity
108.37
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Created at
-
Updated at
9th Apr 2021