LIPID MAPS

Structure Database (LMSD)

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Common Name

GM1(d18:1/18:0)

Systematic Name

Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glcβ-Cer(d18:1/18:0)

Synonyms

LM ID

LMSP0601AP02

Formula

C₇₃H₁₃₁N₃O₃₁

Exact Mass

Calculate m/z

1545.876664

Sum Composition

Hex(3)-HexNAc-NeuAc-Cer 36:1;O2

Status

Computationally Generated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Ganglioside GM1 is a monosialylated ganglioside and the prototypic ganglioside for those containing one sialic acid residue.^1,2 C18 Ganglioside GM1 is found in the brain, primarily in the piriform cortex, amygdala nucleus, striatum, and hippocampal CA1 region.³ The ratio of C18 ganglioside GM1 (d20:1/18:0) to C18 ganglioside GM1 (d18:1/18:0) is decreased in the outer molecular layer of the hippocampal dentate gyrus in postmortem tissue from patients with Alzheimer's disease.⁴ As this product is derived from a natural source, there may be variations in the sphingoid backbone.

This information has been provided by Cayman Chemical

References

1. Kolter, T. Ganglioside biochemistry. ISRN Biochem. 506160 (2012).

2. Mocchetti, I. Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins. Cell Mol. Life Sci. 62(19-20), 2283-2294 (2005).

3. Andres, A.D., Young, L.E.A., Gentry, M.S., et al. Spatial profiling of gangliosides in mouse brain by mass spectrometry imaging. J. Lipid Res. 61(12), 1537 (2020).

4. Hirano-Sakamaki, W., Sugiyama, E., Hayasaka, T., et al. Alzheimer’s disease is associated with disordered localization of ganglioside GM1 molecular species in the human dentate gyrus. FEBS Lett. 589(23), 3611-3616 (2015).

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String Representations

InChiKey (Click to copy)

QPJBWNIQKHGLAU-IQZHVAEDSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@](CO[C@@H]1O[C@H](CO)[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(=O)C)[C@H](O[C@]3(O[C@@]([H])([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C3)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)([H])(NC(CCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC