Structure Database (LMSD)

Common Name
N-nervonoyl taurine
Systematic Name
N-(15Z-tetracosenoyl) taurine
Synonyms
LM ID
LMFA08020257
Formula
Exact Mass
Calculate m/z
473.353881
Sum Composition
Status
Curated

Classification

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-Nervonyl 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-nervonyl taurine were elevated ~25 fold in FAAH-/- mice compared to wild-type mice, indicating that FAAH utilizes N-nervonyl 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 The biological function of the taurine fatty acids class of molecules, as well as their relevance to endocannabinoid signaling, remains to be determined. 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).

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)
QIEYQUYASMRRHE-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C26H51NO4S/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/h9-10H,2-8,11-25H2,1H3,(H,27,28)(H,29,30,31)/b10-9-
SMILES (Click to copy)
C(CNC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)S(O)(=O)=O

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 0
Aromatic Rings 0
Rotatable Bonds 24
Van der Waals Molecular Volume 517.75
Topological Polar Surface Area 83.47
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 9.19
Molar Refractivity 137.47

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