Structure Database (LMSD)
Common Name
N-stearoyl dopamine
Systematic Name
N-[2-(3,4-dihydroxyphenyl)ethyl]-octadecanamide
Synonyms
LM ID
LMFA08020246
Formula
Exact Mass
Calculate m/z
419.339944
Sum Composition
Status
Curated
3D model of N-stearoyl dopamine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Stearda is an endogenous fatty acid amide composed of the catecholamine dopamine conjugated to the long-chain saturated fatty acid stearic acid .1 It is an inhibitor of 5-lipoxygenase (5-LO; IC50 = 16 nM). Stearda is cytotoxic to K562 chronic myeloid leukemia cells, HOS osteosarcoma fibroblasts, and IMR-32 neuroblastoma cells but not MCF-7 breast cancer cells (IC50s = 36.8, 15, 1.5, and >100 µM, respectively).2 It potentiates calcium influx induced by the arachidonoyl amino acid and cannabinoid 1 (CB1) receptor agonist N-arachidonoyl dopamine (NADA) in HEK293 cells expressing human transient receptor potential vanilloid 6 (TRPV6) when used at concentrations of 1 or 10 µM.3 In vivo, stearda (0.1 mg/ml per paw), in combination with NADA, decreases latency to paw withdrawal in the hot plate test in rats.
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
KOCSVLPLQCBIGW-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C26H45NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h18-19,22,28-29H,2-17,20-21H2,1H3,(H,27,30)
SMILES (Click to copy)
C(CCCCCCCCCCCCC)CCCC(=O)NCCC1=CC(O)=C(O)C=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
30
Rings
1
Aromatic Rings
1
Rotatable Bonds
19
Van der Waals Molecular Volume
461.91
Topological Polar Surface Area
69.56
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
7.30
Molar Refractivity
126.52
Admin
Created at
30th Jul 2019
Updated at
30th Jul 2019