Structure Database (LMSD)

Common Name
Oleoyl Serotonin
Systematic Name
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-9Z-octadecanamide
Synonyms
  • OA-5HT
  • Oleoyl 5HT
LM ID
LMFA08020304
Formula
C28H44N2O2
Exact Mass
Calculate m/z
440.340278
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl amines [FA0802]

Biological Context

Oleoyl serotonin is a hybrid molecule patterned after arachidonoyl serotonin . Arachidonoyl serotonin is a dual antagonist of fatty acid amide hydrolase (FAAH) and the transient receptor potential vanilloid type 1 (TRPV1) channel, reducing both acute and chronic peripheral pain.1,2 Oleoyl Serotonin inhibits capsaicin-induced TRPV1 channel activation (IC50 = 2.57 μM) without blocking FAAH-mediated hydrolysis of arachidonoyl ethanolamine (IC50 > 50 μM).1

This information has been provided by Cayman Chemical

References

1. Ortar, G., Cascio, M.G., De Petrocellis, L., et al. New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain. J. Med. Chem. 50(26), 6554-6569 (2007).
2. Maione, S., De Petrocellis, L., de Novellis, V., et al. Analgesic actions of N-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors. Br. J. Pharmacol. 150(6), 766-781 (2007).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sus scrofa (#9823)
Mammalia (#40674)
Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators, in the intestinal tract.,
Biochim Biophys Acta, 2011
Pubmed ID: 21798367

String Representations

InChiKey (Click to copy)
LCQKHZYXPCLVBI-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C28H44N2O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(32)29-21-20-24-23-30-27-19-18-25(31)22-26(24)27/h9-10,18-19,22-23,30-31H,2-8,11-17,20-21H2,1H3,(H,29,32)/b10-9-
SMILES (Click to copy)
C(NCCC1=CNC2=CC=C(O)C=C12)(=O)CCCCCCC/C=C\CCCCCCCC

Other Databases

CHEBI ID
134064
PubChem CID
24749268
Cayman ID
9000629

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 2
Aromatic Rings 2
Rotatable Bonds 18
Van der Waals Molecular Volume 470.18
Topological Polar Surface Area 65.12
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 7.70
Molar Refractivity 136.55

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Created at
22nd Nov 2020
Updated at
23rd Nov 2020