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

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

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
Pubmed ID: 18598910

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

CHEBI ID
PubChem CID
Cayman ID

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

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Created at
30th Jul 2019
Updated at
30th Jul 2019