Structure Database (LMSD)

Common Name
alpha,alpha-dimethyl anandamide
Systematic Name
N-(2,2-dimethy-5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine
Synonyms
  • 2,2-dimethyl-arachidonoyl-EA
  • 2,2-dimethyl-arachidonoyl ethanolamide
LM ID
LMFA08040017
Formula
C24H41NO2
Exact Mass
Calculate m/z
375.313729
Sum Composition
NAE 22:4
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl ethanolamines (endocannabinoids) [FA0804]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Branched fatty acids [FA0102]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.,
J Med Chem, 1997
Pubmed ID: 9057852

String Representations

InChiKey (Click to copy)
GATFOXMZJHQECQ-GKFVBPDJSA-N
InChi (Click to copy)
InChI=1S/C24H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24(2,3)23(27)25-21-22-26/h8-9,11-12,14-15,17-18,26H,4-7,10,13,16,19-22H2,1-3H3,(H,25,27)/b9-8-,12-11-,15-14-,18-17-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCC(C)(C)C(=O)NCCO

Other Databases

LIPIDBANK ID
XPR7046
PubChem CID
5283456

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 439.14
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.45
Molar Refractivity 118.64

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Created at
-
Updated at
7th Feb 2024