Structure Database (LMSD)
Common Name
N-arachidonoyl alanine
Systematic Name
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl) alanine
Synonyms
LM ID
LMFA08020260
Formula
Exact Mass
Calculate m/z
375.277344
Sum Composition
Status
Curated
3D model of N-arachidonoyl alanine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Several different arachidonoyl amino acids, including N-arachidonoyl-L-alanine (NALA), have been isolated and characterized from bovine brain.1 The glycine congener (NAGly) was further characterized and found to suppress formalin-induced pain in rats. NALA may have activity at cannabinoid receptor and/or VR1, but has not been fully characterized to date.
This information has been provided by Cayman Chemical
References
1. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. The Journal of Biological Chemisty 276(46), 42639-42644 (2001).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Biosynthesis, degradation and pharmacological importance of the fatty acid amides.,
Drug Discov Today, 2008
Drug Discov Today, 2008
Pubmed ID:
18598910
Homo sapiens
(#9606)
Mammalia
(#40674)
Endocannabinoid Oxygenation by Cyclooxygenases, Lipoxygenases, and Cytochromes P450: Cross-Talk between the Eicosanoid and Endocannabinoid Signaling Pathways,
Chem Rev, 2011
Chem Rev, 2011
Pubmed ID:
21923193
DOI:
10.1021/cr2002799
String Representations
InChiKey (Click to copy)
ZECSOKFEQQDUCP-GDYZQIPQSA-N
InChi (Click to copy)
InChI=1S/C23H37NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22(25)24-21(2)23(26)27/h7-8,10-11,13-14,16-17,21H,3-6,9,12,15,18-20H2,1-2H3,(H,24,25)(H,26,27)/b8-7-,11-10-,14-13-,17-16-/t21-/m0/s1
SMILES (Click to copy)
C(=O)([C@H](C)NC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
0
Aromatic Rings
0
Rotatable Bonds
16
Van der Waals Molecular Volume
427.99
Topological Polar Surface Area
66.40
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
6.01
Molar Refractivity
114.16
Admin
Created at
1st Aug 2019
Updated at
19th Feb 2024