GM1

GM1
Names
	IUPAC name (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[(E,2R,3S)-3-hydroxy-2-(icosanoylamino)icos-4-enoxy]-2-(hydroxymethyl)oxan-3-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
	Other names Monosialotetrahexosylganglioside
Identifiers
CAS Number	37758-47-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	4593688 ;
MeSH	G(M1)+Ganglioside
PubChem CID	5497107;
UNII	A763JQ77KX ;
	InChI 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 Key: QPJBWNIQKHGLAU-BVLUPYCXSA-N ; InChI=1/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 Key: QPJBWNIQKHGLAU-BVLUPYCXBP;
	SMILES O[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O[C@@]5(C(O)=O)O[C@@]([H])([C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C5)[C@H]2O)[C@@H](CO)O[C@@H](OC[C@@H]([C@@H](O)/C=C/CCCCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCCCC)=O)[C@@H]1O;
Properties
Chemical formula	C77H139N3O31
Molar mass	1602.949 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

GM1 (monosialotetrahexosylganglioside) the "prototype" ganglioside, is a member of the ganglio series of gangliosides which contain one sialic acid residue. GM1 has important physiological properties and impacts neuronal plasticity and repair mechanisms, and the release of neurotrophins in the brain. Besides its function in the physiology of the brain, GM1 acts as the site of binding for both cholera toxin and E. coli heat-labile enterotoxin (Traveller's diarrhea).^[1]^[2]

^ Mocchetti I (2005). "Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins". Cell. Mol. Life Sci. 62 (19–20): 2283–94. doi:10.1007/s00018-005-5188-y. PMC 11139125. PMID 16158191.
^ Chen JC, Chang YS, Wu SL, et al. (September 2007). "Inhibition of Escherichia coli heat-labile enterotoxin-induced diarrhea by Chaenomeles speciosa". J Ethnopharmacol. 113 (2): 233–9. doi:10.1016/j.jep.2007.05.031. PMID 17624704.

[pmid16158191-1] Mocchetti I (2005). "Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins". Cell. Mol. Life Sci. 62 (19–20): 2283–94. doi:10.1007/s00018-005-5188-y. PMC 11139125. PMID 16158191.

[2] Chen JC, Chang YS, Wu SL, et al. (September 2007). "Inhibition of Escherichia coli heat-labile enterotoxin-induced diarrhea by Chaenomeles speciosa". J Ethnopharmacol. 113 (2): 233–9. doi:10.1016/j.jep.2007.05.031. PMID 17624704.

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