LIPID MAPS

Structure Database (LMSD)

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Common Name

Stearoyl Serotonin

Systematic Name

N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-octadecanamide

Synonyms

SA-5HT
Stearoyl 5HT

LM ID

LMFA08020303

Formula

C₂₈H₄₆N₂O₂

Exact Mass

Calculate m/z

442.355928

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Stearoyl 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 The effects of replacing the arachidonoyl portion with the saturated 18-carbon stearoyl moiety have not been studied. However, replacement of arachidonate with saturated 11- or 12-carbon fatty acids produces compounds that potently inhibit capsaicin-induced TRPV1 channel activation (IC50 = 0.76 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

DOI: 10.1016/j.bbalip.2011.07.008

Coffea arabica (#13443)

Magnoliopsida (#3398)

Liquid chromatographic analysis of N-.beta.)-alkanoyl-5-hydroxytryptamine (C-5-HT) in green coffee beans,
J Agric Food Chem, 1979

DOI: 10.1021/jf60221a031

String Representations

InChiKey (Click to copy)

FKWHKBXVLNKTGT-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C28H46N2O2/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/h18-19,22-23,30-31H,2-17,20-21H2,1H3,(H,29,32)

SMILES (Click to copy)

C(NCCC1=CNC2=CC=C(O)C=C12)(=O)CCCCCCCCCCCCCCCCC