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
3D model of N-nervonoyl taurine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
https://www.sciencedirect.com/science/article/pii/S1359644608000482?via%3Dihub#bib118
Taxonomy Information
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
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
Admin
Created at
1st Aug 2019
Updated at
16th Feb 2024