Structure Database (LMSD)

Common Name
N-docosanoyl taurine
Systematic Name
N-docosanoyl-taurine
Synonyms
LM ID
LMFA08020083
Formula
C24H49NO4S
Exact Mass
Calculate m/z
447.338231
Sum Composition
NAT 22:0
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

Several different arachidonoyl amino acid conjugates, including N-arachidonoyl dopamine and N-arachidonoyl-L-serine, have been isolated and characterized from bovine brain.1 N-Docosanoyl taurine is one of several novel taurine-conjugated fatty acids discovered during mass spectrometry lipidomic analysis of brain and spinal cord from wild-type and fatty acid amide hydrolase (FAAH) knockout mice.2 The levels of N-docosanoyl taurine were elevated ~12 fold in FAAH-/- mice compared to wild-type mice, indicating that FAAH utilizes N-docosanoyl taurine as a substrate. However, in vitro experiments with purified FAAH indicate that related N-fatty acyl taurines and ethanolamines of similar chain length are hydrolyzed 2,000-50,000 times more slowly by FAAH compared to oleoyl ethanolamide.2 N-acyl taurines bearing polyunsaturated acyl chains can activate members of the transient receptor potential (TRP) family of calcium channels, including TRPV1 and TRPV4.3

This information has been provided by Cayman Chemical

References

1. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. The Journal of Biological Chemisty 276(46), 42639-42644 (2001).
2. Saghatelian, A., Trauger, S.A., Want, E.J., et al. Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochemistry 43(45), 14332-14339 (2004).
3. Saghatelian, A., McKinney, M.K., Bandell, M., et al. A FAAH-regulated class of N-acyl taurines that activates TRP ion channels. Biochemistry 45(30), 9007-9015 (2006).

String Representations

InChiKey (Click to copy)
SAIMYQVCHHQQMU-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C24H49NO4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)25-22-23-30(27,28)29/h2-23H2,1H3,(H,25,26)(H,27,28,29)
SMILES (Click to copy)
C(CNC(CCCCCCCCCCCCCCCCCCCCC)=O)S(O)(=O)=O

Other Databases

CHEBI ID
156045
PubChem CID
42607333
Cayman ID
10007288

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 0
Aromatic Rings 0
Rotatable Bonds 23
Van der Waals Molecular Volume 485.79
Topological Polar Surface Area 83.47
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 8.63
Molar Refractivity 128.33

Admin

Created at
-
Updated at
-