An official website of the United States government

Ganglioside GM2

PubChem CID
9898635
Structure
Ganglioside GM2_small.png
Molecular Formula
Synonyms
  • Ganglioside GM2
  • GM2 lipid
  • G(M2) GANGLIOSIDE
  • 127663-77-8
  • CHEBI:60327
Molecular Weight
1384.7 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-11
Description
Ganglioside GM2 (18:0) is a sialotriaosylceramide that is N-acetyl-beta-D-galactosaminyl-(1->4)-alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-acylsphingosine in which the acyl group on the sphingosine nitrogen is octadecanoyl. A constituent of natural ganglioside GM2. It has a role as an antigen. It is a N-acetyl-beta-D-galactosaminyl-(1->4)-alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-acylsphingosine and a sialotriaosylceramide. It is a conjugate acid of a ganglioside GM2 (18:0) (1-).
Ganglioside GM2 is a glycosphingolipid antigen expressed by a variety of human cancer cells. GM2 containing vaccines have been shown to elicit antibodies production in melanoma patients without deleterious effects associated with an immune response to GM2. Mutations in at least 1 of 3 recessive genes: HEXA, HEXB, and GM2A cause defects in GM2 catabolism, leading to lysosomal lipid storage disorders that manifest primarily as neurodegenerative diseases, including Tay-Sachs and Sandhoff Disease.
A glycosphingolipid that accumulates due to a deficiency of hexosaminidase A or B (BETA-N-ACETYLHEXOSAMINIDASES), or GM2 activator protein, resulting in GANGLIOSIDOSES, heredity metabolic disorders that include TAY-SACHS DISEASE and SANDHOFF DISEASE.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Ganglioside GM2.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C67H121N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-50(80)70-43(44(77)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-89-64-57(85)56(84)59(48(38-73)91-64)93-65-58(86)62(60(49(39-74)92-65)94-63-52(69-42(4)76)55(83)54(82)47(37-72)90-63)96-67(66(87)88)35-45(78)51(68-41(3)75)61(95-67)53(81)46(79)36-71/h31,33,43-49,51-65,71-74,77-79,81-86H,5-30,32,34-40H2,1-4H3,(H,68,75)(H,69,76)(H,70,80)(H,87,88)/b33-31+/t43-,44+,45-,46+,47+,48+,49+,51+,52+,53+,54-,55+,56+,57+,58+,59+,60-,61+,62+,63-,64+,65-,67-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

GIVLTTJNORAZON-HDBOBKCLSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)NC(=O)C)O[C@@]4(C[C@@H]([C@H]([C@@H](O4)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)[C@@H](/C=C/CCCCCCCCCCCCC)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C67H121N3O26
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 ChEBI ID

2.3.3 Lipid Maps ID (LM_ID)

2.3.4 NCI Thesaurus Code

2.3.5 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • G(M2) Ganglioside
  • Ganglioside GM2
  • Ganglioside, GM2
  • Ganglioside, Tay-Sachs Disease
  • GM2 Ganglioside
  • GM2, Ganglioside
  • Tay Sachs Disease Ganglioside
  • Tay-Sachs Disease Ganglioside

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
1384.7 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
5.6
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
17
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
26
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
49
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
1383.82383097 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
1383.82383097 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
461 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
96
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
2180
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
23
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

3.2 Chemical Classes

3.2.1 Lipids

Lipids -> Sphingolipids [SP] -> Acidic glycosphingolipids [SP06] -> Gangliosides [SP0601]

5 Chemical Vendors

6 Safety and Hazards

6.1 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Ganglioside GM2: Does not have an individual approval but may be used under an appropriate group standard

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 Chemical Co-Occurrences in Patents

8.3 Chemical-Disease Co-Occurrences in Patents

8.4 Chemical-Gene Co-Occurrences in Patents

9 Interactions and Pathways

9.1 Chemical-Target Interactions

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 LIPID MAPS Classification

10.4 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  3. ChEBI
  4. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  6. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  7. Wikidata
  8. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  9. PubChem
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS