LIPID MAPS

Structure Database (LMSD)

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Common Name

N-arachidonoyl taurine

Systematic Name

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-taurine

Synonyms

LM ID

LMFA08020075

Formula

C₂₂H₃₇NO₄S

Exact Mass

Calculate m/z

411.244331

Sum Composition

NAT 20:4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

N-Arachidonoyl taurine is an arachidonoyl amino acid.¹ It is oxygenated by 12(S)- and 15(S)-lipoxygenase and is converted to 12-HETE-taurine (12-HETE-T) in murine resident peritoneal macrophages.² N-Arachidonoyl taurine is an activator of the transient receptor potential vanilloid (TRPV) channels TRPV1 and TRPV4 (EC50s = 28 and 21 µM, respectively).¹ It increases calcium flux in HIT-T15 pancreatic β-cells and INS-1 rat islet cells when used at a concentration of 10 µM and increases insulin secretion from 832/13 INS-1 pancreatic β-cells.³ The levels of N-arachidonoyl taurine are changed in mouse brain following administration of Δ9-tetrahydrocannabinol (Δ9-THC).⁴

This information has been provided by Cayman Chemical

References

1. 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).

2. Turman, M.V., Kingsley, P.J., Rouzer, C.A., et al. Oxidative metabolism of a fatty acid amide hydrolase-regulated lipid, arachidonoyltaurine. Biochemistry 47(12), 3917-3925 (2008).

3. Waluk, D.P., Vielfort, K., Derakhshan, S., et al. N-Acyl taurines trigger insulin secretion by increasing calcium flux in pancreatic β-cells. Biochem. Biophys. Res. Commun. 430(1), 54-59 (2013).

4. Leishman, E., Murphy, M., Mackie, K., et al. Δ9-Tetrahydrocannabinol changes the brain lipidome and transcriptome differentially in the adolescent and the adult. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1863(5), 479-492 (2018).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Mus musculus (#10090)

Mammalia (#40674)

A FAAH-regulated class of N-acyl taurines that activates TRP ion channels.,
Biochemistry, 2006

Pubmed ID: 16866345

String Representations

InChiKey (Click to copy)

YUNYSWCRLRYOPO-DOFZRALJSA-N

InChi (Click to copy)

InChI=1S/C22H37NO4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)23-20-21-28(25,26)27/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)(H,25,26,27)/b7-6-,10-9-,13-12-,16-15-

SMILES (Click to copy)

C(CNC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)S(O)(=O)=O