LIPID MAPS

Structure Database (LMSD)

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Common Name

S-Geranylgeranyl-L-glutathione

Systematic Name

L-γ-glutamyl-S-(3,7,11,15-tetramethyl-2E,6E,10E,14-tetraen-1-yl)-L-cysteinylglycine

Synonyms

LM ID

LMPR0104010042

Formula

C₃₀H₄₉N₃O₆S

Exact Mass

Calculate m/z

579.334208

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

S-Geranylgeranyl-L-glutathione is a ligand of the orphan G protein-coupled receptor (GPCR) P2RY8.1 It selectively induces internalization of P2RY8 over sphingosine-1-phosphate receptor 2 (S1P2), GPR55, cysteinyl leukotriene receptor 1 (CysLT1 receptor), and CysLT2 receptor at 100 nM. S-Geranylgeranyl-L-glutathione (10 nM) inhibits the migration of P2RY8-expressing WEHI-231 B cell lymphoma cells and isolated human tonsil germinal center B cells induced by chemokine (C-X-C motif) ligand 12 (WEHI-231).

This information has been provided by Cayman Chemical

References

1. Lu, E., Wolfreys, F.D., Muppidi, J.R., et al. S-Geranylgeranyl-L-glutathione is a ligand for human B cell-confinement receptor P2RY8. Nature 567(7724), 244-248 (2019).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Mus musculus (#10090)

Mammalia (#40674)

S-Geranylgeranyl-L-glutathione is a ligand for human B cell-confinement receptor P2RY8.,
Nature, 2019

Pubmed ID: 30842656

String Representations

InChiKey (Click to copy)

BAJIBEVLRWVBAZ-DPRMOSMCSA-N

InChi (Click to copy)

InChI=1S/C30H49N3O6S/c1-21(2)9-6-10-22(3)11-7-12-23(4)13-8-14-24(5)17-18-40-20-26(29(37)32-19-28(35)36)33-27(34)16-15-25(31)30(38)39/h9,11,13,17,25-26H,6-8,10,12,14-16,18-20,31H2,1-5H3,(H,32,37)(H,33,34)(H,35,36)(H,38,39)/b22-11+,23-13+,24-17+/t25-,26-/m0/s1

SMILES (Click to copy)

C(/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/C)SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(O)=O