SML3689

S-Geranylgeranyl-L-glutathione

≥98% (HPLC)

• Synonym(s): (S)-2-Amino-5-((R)-1-(carboxymethylamino)-1-oxo-3-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenylthio)propan-2-ylamino)-5-oxopentanoic acid, GGG
• Empirical Formula (Hill Notation): C₃₀H₄₉N₃O₆S
• CAS Number: 2364639-42-7
• Molecular Weight: 579.79
• UNSPSC Code: 12352200
• NACRES: NA.21
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear (Warmed)
• storage temp.: 2-8°C
• SMILES string: OC([C@@H](N)CCC(N[C@H](C(NCC(O)=O)=O)CSC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=O)=O
• 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
• InChI key: BAJIBEVLRWVBAZ-DPRMOSMCSA-N

Description

Biochem/physiol Actions

Potent and selective ligand for P2RY8

The metabolite S-Geranylgeranyl-L-glutathione (GGG) is a potent and selective ligand for P2RY8, a Gα13-coupled receptor. GGG promotes internalization of P2RY8 and inhibits the migration of P2RY8-expressing cells (10 – 100 nM range in WEHI-231 cells). Extracellular GGG is shown to be actively transported by ABCC1 (ATP-binding cassette subfamily C member 1) and catabolized by GGT5 (gamma-glutamyltransferase-5) to S-geranylgeranyl-L-Cys-Gly plus glutathione.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable