Structure Database (LMSD)

Common Name
Arachidonoyl Serotonin
Systematic Name
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
Synonyms
  • AA-5HT
  • Arachinonoyl 5HT
LM ID
LMFA08020141
Formula
C30H42N2O2
Exact Mass
Calculate m/z
462.324628
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]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]
Carbocyclic fatty acids [FA0114]

Biological Context

Arachidonoyl serotonin is an inhibitor of fatty acid amide hydrolase (FAAH), the enzyme responsible for inactivation of anandamide and other endogenous cannabinoids. It inhibits the FAAH activity isolated from mouse neuroblastoma cells with an IC50 value of 12 µM. Both the Km and the Vmax of the enzyme are affected, indicating the Arachidonoyl serotonin is a very tight binding, competitive inhibitor of FAAH. Arachidonoyl serotonin does not inhibit cPLA2 and is essentially devoid of cannabimimetic activity.1

This information has been provided by Cayman Chemical

References

1. Bisogno, T., Melck, D., De Petrocellis, L., et al. Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase. Biochem. Biophys. Res. Commun. 248(3), 515-522 (1998).

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
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

String Representations

InChiKey (Click to copy)
QJDNHGXNNRLIGA-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C30H42N2O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(34)31-23-22-26-25-32-29-21-20-27(33)24-28(26)29/h6-7,9-10,12-13,15-16,20-21,24-25,32-33H,2-5,8,11,14,17-19,22-23H2,1H3,(H,31,34)/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(NCCC1=CNC2=CC=C(O)C=C12)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC

Other Databases

CHEBI ID
132255
PubChem CID
10027372
Cayman ID
70665

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 2
Aromatic Rings 2
Rotatable Bonds 17
Van der Waals Molecular Volume 496.86
Topological Polar Surface Area 65.12
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 7.81
Molar Refractivity 145.50

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Created at
-
Updated at
4th May 2022