Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C73H131N3O31 |
Molecular Weight | 1546.8227 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 28 / 28 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]5(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@]([H])(O[C@H]2[C@@H](CO)O[C@@]([H])(O[C@@H]3[C@@H](CO)O[C@@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O[C@@]4(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O4)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H]1NC(C)=O)O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O
InChI
InChIKey=QPJBWNIQKHGLAU-IQZHVAEDSA-N
InChI=1S/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b33-31+/t44-,45+,46-,47+,48+,49+,50+,51+,53+,54+,55+,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66+,67+,68-,69+,70-,71-,73-/m0/s1
Molecular Formula | C73H131N3O31 |
Molecular Weight | 1546.8227 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 28 / 28 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Ganglioside GM1 is a monosialo-glycosphingolipid belonging to the gangliotetrahexosyl series that abundant in neurons of all animal species and plays important roles in many cell physiological processes, including differentiation, memory control, cell signaling, neuronal protection, neuronal recovery, and apoptosis. Ganglioside GM1 in neurons helps to transfer information from the exterior to the interior of the cell, through specific recognition and binding of biologically active molecules (membrane receptors and ion channels), and has specific functions in nerve conduction and/or synaptic transmission. The mechanisms underlying the effects of Ganglioside GM1 remain unclear in many cases, but it appears that these effects are often due to specific interactions between Ganglioside GM1 and proteins involved in signaling processes, within Ganglioside GM1-enriched lipid rafts in the plasma membrane. Ganglioside GM1 is a major component of total ganglioside mixtures from mammalian brains, from which it can be extracted and purified in large amounts. Ganglioside GM1 was widely used in the past as a therapeutic drug for a wide variety of neurological disorders. Further studies have shown that Ganglioside GM1 has immunogenic properties and led to the production of antibodies that promoted peripheral neuropathies such as Guillain–Barré syndrome.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27491214
Curator's Comment: Gangliosides are abundant in neurons of all animal species
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Further evidence that carbohydrates are the immunodeterminant structures of blood group M and N specificities. | 1981 |
|
GM1 ganglioside attenuates the behavioral deficits but not the granule cell damage produced by intradentate colchicine. | 1989 Jan 23 |
|
Molecular mimicry between GQ1b ganglioside and lipopolysaccharides of Campylobacter jejuni isolated from patients with Fisher's syndrome. | 1994 Nov |
|
Effects of monosialoganglioside GM1 on scopolamine-induced amnesia. | 1998 Jun 19 |
|
Is Campylobacter lipopolysaccharide bearing a GD3 epitope essential for the pathogenesis of Guillain-Barré syndrome? | 2000 Aug |
|
Guillain-Barré syndrome with IgM antibody to the ganglioside GalNAc-GD1a. | 2001 Feb 15 |
|
GM1 enhances dopaminergic markers in the brain of aged rats. | 2003 Oct |
|
Glucosamine induces cell-cycle arrest and hypertrophy of mesangial cells: implication of gangliosides. | 2005 Jun 1 |
|
Carbohydrate mimicry of Campylobacter jejuni lipooligosaccharide is critical for the induction of anti-GM1 antibody and neuropathy. | 2006 Feb |
|
Experimental axonopathy induced by immunization with Campylobacter jejuni lipopolysaccharide from a patient with Guillain-Barré syndrome. | 2006 May |
|
Neurochemical changes on oxidative stress in rat hippocampus during acute phase of pilocarpine-induced seizures. | 2010 Jan |
|
Gangliosides inhibit bee venom melittin cytotoxicity but not phospholipase A(2)-induced degranulation in mast cells. | 2011 May 1 |
|
Inhibitory effect of ganglioside on mastoparan-induced cytotoxicity and degranulation in lipid raft of connective tissue type mast cell. | 2011 May-Jun |
|
Neurophysiological and immunohistochemical studies of IgG anti-GM1 monoclonal antibody on neuromuscular transmission: effects in rat neuromuscular junctions. | 2014 Feb |
|
Methylmercury causes neuronal cell death through the suppression of the TrkA pathway: in vitro and in vivo effects of TrkA pathway activators. | 2015 Feb 1 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:52:24 GMT 2023
by
admin
on
Sat Dec 16 07:52:24 GMT 2023
|
Record UNII |
562413257Z
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000139313
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY | |||
|
562413257Z
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY | |||
|
61048
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY | |||
|
Ganglioside GM1
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY | |||
|
m5664
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY | Merck Index | ||
|
116950-37-9
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY | |||
|
9963963
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY | |||
|
SUB87146
Created by
admin on Sat Dec 16 07:52:24 GMT 2023 , Edited by admin on Sat Dec 16 07:52:24 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
|