Structure Database (LMSD)

Common Name
N-lignoceroyl taurine
Systematic Name
N-tetracosanoyl taurine
Synonyms
  • lignoceroyltaurine
LM ID
LMFA08020252
Formula
C26H53NO4S
Exact Mass
Calculate m/z
475.369531
Sum Composition
NAT 24:0
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-lignoceroyl 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-lignoceroyl taurine were elevated 23-26 fold in FAAH-/- mice compared to wild-type mice, indicating that FAAH utilizes N-lignoceroyl taurine as a substrate. However, in vitro experiments with purified FAAH indicate N-lignoceroyl taurine is hydrolyzed 2,000 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).

References

Reference
Biosynthesis, degradation and pharmacological importance of the fatty acid amides. Emma K.Farrell and David J.Merkler. Drug Discovery Today. Volume 13, Issues 13–14, 2008, pp. 558-568. doi.org/10.1016/j.drudis.2008.02.006

https://www.sciencedirect.com/science/article/pii/S1359644608000482?via%3Dihub#bib118

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Assignment of endogenous substrates to enzymes by global metabolite profiling.,
Biochemistry, 2004
Pubmed ID: 15533037

String Representations

InChiKey (Click to copy)
DDCFSFYOVZMRHL-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C26H53NO4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-26(28)27-24-25-32(29,30)31/h2-25H2,1H3,(H,27,28)(H,29,30,31)
SMILES (Click to copy)
C(CNC(CCCCCCCCCCCCCCCCCCCCCCC)=O)S(O)(=O)=O

Other Databases

CHEBI ID
132505
PubChem CID
53442599
Cayman ID
10007286

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 0
Aromatic Rings 0
Rotatable Bonds 25
Van der Waals Molecular Volume 520.39
Topological Polar Surface Area 83.47
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 9.41
Molar Refractivity 137.56

Admin

Created at
1st Aug 2019
Updated at
16th Feb 2024