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

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

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
-