Structure database (LMSD)
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LM IDLMFA08040001
Common NameAnandamide (20:4, n-6) (W)
Systematic NameN-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine
SynonymsAnandamide; Anandamide(20:4, n-6); N-arachidonoyl ethanolamine;
arachidonoylethanolamide; Arachidonoyl-EA; Arachidonoyl ethanolamide; AEA
Exact Mass
347.2824 (neutral)    Calculate m/z:
FormulaC22H37NO2
CategoryFatty Acyls [FA]
Main ClassFatty amides [FA08]
Sub ClassN-acyl ethanolamines (endocannabinoids) [FA0804]
Alternative ClassesUnsaturated fatty acids[FA0103], Hydroxy fatty acids[FA0105]
AbbrevNAE 20:4
LIPIDBANK IDXPR7001
PubChem CID5281969
KEGG IDC11695
HMDB IDHMDB0004080
CHEBI ID2700
SWISSLIPIDS IDSLM:000000294
CAYMAN ID10007270
InChIKeyLGEQQWMQCRIYKG-DOFZRALJSA-N  Show lipids differing only in stereochemistry/bond geometry
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-
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SMILES
C(NCCO)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
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MS SpectraView MoNA MS spectra     
MS StandardView lipid standard
StatusActive
ReferencesIsolation and structure of a brain constituent that binds to the cannabinoid receptor
Science, 1992
DOI: 10.1126/science.1470919
PMID 1470919
Calculated physicochemical properties (?):
 Heavy Atoms25Rings0Aromatic Rings0Rotatable Bonds16
 van der Waals
Molecular Volume		404.54Topological Polar
Surface Area		49.33Hydrogen
Bond Donors		2Hydrogen
Bond Acceptors		3
 logP5.81Molar
Refractivity		109.48