Structure Database (LMSD)
Common Name
N-arachidonoyl dopamine
Systematic Name
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-dopamine
Synonyms
- NADA
LM ID
LMFA08020084
Formula
Exact Mass
Calculate m/z
439.308644
Sum Composition
Status
Curated
3D model of N-arachidonoyl dopamine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
N-Arachidonoyl dopamine (NADA) is an arachidonoyl amino acid and cannabinoid (CB) receptor 1 agonist (Ki = 250 nM in rat brain membranes, which highly express CB1 receptors).1 It is selective for CB1 over CB2 receptors (Ki = 12,000 nM in rat spleen membranes, which highly express CB2 receptors). NADA induces intracellular calcium mobilization in N18TG2 neuroblastoma cells (EC50 = 0.7 µM). It inhibits the proliferation of MCF-7 breast cancer cells (IC50 = 0.25 µM), an effect that can be reversed by the CB1 receptor antagonist SR141716A (rimonabant). NADA (10 mg/kg) induces hypothermia, catalepsy, hypolocomotion, and analgesia in mice.
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
MVVPIAAVGAWJNQ-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C28H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(32)29-23-22-25-20-21-26(30)27(31)24-25/h6-7,9-10,12-13,15-16,20-21,24,30-31H,2-5,8,11,14,17-19,22-23H2,1H3,(H,29,32)/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(NCCC1C=C(O)C(O)=CC=1)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
32
Rings
1
Aromatic Rings
1
Rotatable Bonds
17
Van der Waals Molecular Volume
485.95
Topological Polar Surface Area
69.56
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
3
logP
7.19
Molar Refractivity
135.38
Admin
Created at
-
Updated at
-