For research use only. Not for therapeutic Use.
Ganglioside GM3 is a precursor of a-, b-, and c-series gangliosides, interacts with transmembrane receptors such as the epidermal growth factor and insulin receptors, and regulates receptor functions by creating a specialized lipid environment. Ganglioside GM3 is synthesized by GM3 synthase and can be used for the research of hypercholesterolemia[1].
Ganglioside GM3, produced by addition of sialic acid to LacCer, is expressed mainly in adipose tissue and muscle in humans and mice, and liver and serum in humans. GM3 expression in adipocytes is induced by stimulation of the inflammatory cytokines TNF-α and IL-1β, derived from tissue macrophages[2].
| Catalog Number | I042672 |
| CAS Number | 124579-05-1 |
| Synonyms | (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
| Molecular Formula | C59H108N2O21 |
| Purity | ≥95% |
| InChI | InChI=1S/C59H108N2O21/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(69)61-40(41(66)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-77-56-51(73)50(72)53(45(37-64)79-56)80-57-52(74)55(49(71)44(36-63)78-57)82-59(58(75)76)34-42(67)47(60-39(3)65)54(81-59)48(70)43(68)35-62/h30,32,40-45,47-57,62-64,66-68,70-74H,4-29,31,33-38H2,1-3H3,(H,60,65)(H,61,69)(H,75,76)/b32-30+/t40-,41+,42-,43+,44+,45+,47+,48+,49-,50+,51+,52+,53+,54+,55-,56+,57-,59-/m0/s1 |
| InChIKey | UIKPUUZBQYTDRX-YRRBDHRDSA-N |
| SMILES | CCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)OC3(CC(C(C(O3)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)C(C=CCCCCCCCCCCCCC)O |
| Reference | [1]. Nihei W, et al. NPC1L1-dependent intestinal cholesterol absorption requires ganglioside GM3 in membrane microdomains. J Lipid Res. 2018 Nov;59(11):2181-2187. [2]. Inokuchi JI, et al. Pathophysiological Significance of GM3 Ganglioside Molecular Species With a Particular Attention to the Metabolic Syndrome Focusing on Toll-Like Receptor 4 Binding. Front Mol Biosci. 2022 May 30;9:918346. |
