Structure Database (LMSD)
Common Name
N-(2-methyl-2S-hydroxy-ethyl) arachidonoyl amine
Systematic Name
N-(2-hydroxy-2S-methyl-ethyl)-5Z,8Z,11Z,14Z-eicosatetraenoyl amine
Synonyms
- N-(2-methyl-2S-hydroxy-ethyl)arachidonoylamide
3D model of N-(2-methyl-2S-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
S-2 methanandamide is the second most potent CB1 receptor agonist in the methanandamide series. It has a Ki value of 26 nM for the CB1 receptor.1 S-2 methanandamide is also less prone to FAAH inactivation and inhibits the murine vas deferens twitch response with an IC50 value of 47 nM.1
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).
References
String Representations
InChiKey (Click to copy)
HTNMZCWZEMNFCR-AQNSPSBUSA-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)24-21-22(2)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-/m0/s1
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)NC[C@H](C)O
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