Structure Database (LMSD)
Common Name
N-(1R-methyl-2-hydroxy-ethyl) arachidonoyl amine
Systematic Name
N-(1R-methyl-2-hydroxy-ethyl)-5Z,8Z,11Z,14Z-eicosatetraenoyl amine
Synonyms
- N-(1R-methyl-2-hydroxy-ethyl)arachidonoylamide
3D model of N-(1R-methyl-2-hydroxy-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
R-1 methanandamide is a potent cannabinoid (CB) receptor 1 agonist in the methanandamide series. It is selective for CB1 over CB2 receptors with Ki values ranging from 17.9 to 28.3 and 815 to 868 nM, respectively.1,2 R-1 methanandamide is more potent than arachidonoyl ethanolamide (AEA). In addition, R-1 methanandamide is more resistant than AEA to hydrolytic inactivation by fatty acid amide hydrolase (FAAH).3
This information has been provided by Cayman Chemical
References
1. Abadji, V., Lin, S., Taha, G., et al. (R)-Methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability. J. Med. Chem. 37(12), 1889-1893 (1994).
2. Pertwee, R.G. Pharmacology of cannabinoid receptor ligands. Curr. Med. Chem. 6(8), 635-664 (1999).
References
String Representations
InChiKey (Click to copy)
SQKRUBZPTNJQEM-FQPARAGTSA-N
InChi (Click to copy)
InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m1/s1
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)N[C@H](C)CO
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
0
Aromatic Rings
0
Rotatable Bonds
16
Van der Waals Molecular Volume
421.84
Topological Polar Surface Area
49.33
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
6.20
Molar Refractivity
114.10
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Created at
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Updated at
18th Oct 2021