anandamide   

GtoPdb Ligand ID: 2364

Synonyms: AEA | arachidonoyl ethanolamide | N-arachidonoylethanolamine
Comment: Anandamide is an endogenous cannabinoid neurotransmitter found in animal and human organs, especially in the brain. It activates the cannabinoid receptors CB1 and CB2. Anandamide is also known to be an endogenous activator of the TRPV1 cation channel [3,12], which is involved in regulation of body temperature and nociception.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 49.33
Molecular weight 347.28
XLogP 7.43
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChI InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-
InChI Key LGEQQWMQCRIYKG-DOFZRALJSA-N
Classification
Compound class Metabolite or derivative
IUPAC Name
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Synonyms
AEA | arachidonoyl ethanolamide | N-arachidonoylethanolamine
Database Links
BindingDB Ligand 22988
CAS Registry No. 94421-68-8 (source: ChEBI)
ChEBI CHEBI:2700
ChEMBL Ligand CHEMBL15848
GtoPdb PubChem SID 135651438
PubChem CID 5281969
RCSB PDB Ligand E7Y
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Wikipedia Anandamide

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Tocris
Anandamide
Cat. No. 1339