R-(+)-methanandamide   

GtoPdb Ligand ID: 2506

Synonyms: (R)-methanandamide | AM-356 | methanandamide
Compound class: Synthetic organic
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 49.33
Molecular weight 361.3
XLogP 7.89
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CO)C
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@@H](CO)C
InChI 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
InChI Key SQKRUBZPTNJQEM-FQPARAGTSA-N
References
1. Khanolkar AD, Abadji V, Lin S, Hill WA, Taha G, Abouzid K, Meng Z, Fan P, Makriyannis A. (1996)
Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand.
J. Med. Chem., 39 (22): 4515-9. [PMID:8893848]
2. Maingret F, Patel AJ, Lazdunski M, Honoré E. (2001)
The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1.
EMBO J., 20 (1-2): 47-54. [PMID:11226154]
3. Rajan S, Wischmeyer E, Xin Liu G, Preisig-Müller R, Daut J, Karschin A, Derst C. (2000)
TASK-3, a novel tandem pore domain acid-sensitive K+ channel. An extracellular histiding as pH sensor.
J. Biol. Chem., 275 (22): 16650-7. [PMID:10747866]