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CHEBI:60327 - ganglioside GM2 (18:0)

ChEBI IDCHEBI:60327
ChEBI Nameganglioside GM2 (18:0)
Stars
DefinitionA sialotriaosylceramide that is N-acetyl-β-D-galactosaminyl-(1→4)-α-N-acetylneuraminosyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucosyl-N-acylsphingosine in which the acyl group on the sphingosine nitrogen is octadecanoyl. A constituent of natural ganglioside GM2.
Last Modified12 May 2025
SubmitterSteve
DownloadsMolfile
FormulaC67H121N3O26
Net Charge0
Average Mass1384.700
Monoisotopic Mass1383.82383
SMILES[H][C@@]1([C@H](O)[C@H](O)CO)O[C@@](O[C@@H]2[C@@H](O)[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)/C=C/CCCCCCCCCCCCC)O[C@@H]3CO)O[C@H](CO)[C@@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2NC(C)=O)(C(=O)O)C[C@H](O)[C@H]1NC(C)=O
InChIInChI=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
InChIKeyGIVLTTJNORAZON-HDBOBKCLSA-N
Wikipedia
Roles Classification
Biological Roles:
antigen  Any substance that stimulates an immune response in the body, such as through antibody production or by presentation to a T-cell receptor after binding to a major histocompability complex (MHC).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
ChEBI Ontology
Outgoing Relation(s)
ganglioside GM2 (18:0) (CHEBI:60327) has role antigen (CHEBI:59132)
ganglioside GM2 (18:0) (CHEBI:60327) is a N-acetyl-β-D-galactosaminyl-(1→4)-α-N-acetylneuraminosyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucosyl-N-acylsphingosine (CHEBI:21509)
ganglioside GM2 (18:0) (CHEBI:60327) is a sialotriaosylceramide (CHEBI:36541)
ganglioside GM2 (18:0) (CHEBI:60327) is conjugate acid of ganglioside GM2 (18:0) (1−) (CHEBI:78485)
Incoming Relation(s)
ganglioside GM2 (18:0) (NeuAc-N-deacetyl) (CHEBI:141482) has functional parent ganglioside GM2 (18:0) (CHEBI:60327)
ganglioside GM2 (18:0) amide (CHEBI:141465) has functional parent ganglioside GM2 (18:0) (CHEBI:60327)
ganglioside GM2 (18:0) methyl ester (CHEBI:141471) has functional parent ganglioside GM2 (18:0) (CHEBI:60327)
ganglioside GM2 (18:0) methylamide (CHEBI:141470) has functional parent ganglioside GM2 (18:0) (CHEBI:60327)
ganglioside GM2 (18:0) NeuAc-C7-de(1,2,-dihydroxyethyl) (CHEBI:141481) has functional parent ganglioside GM2 (18:0) (CHEBI:60327)
tauro-GM2 (CHEBI:234281) has functional parent ganglioside GM2 (18:0) (CHEBI:60327)
ganglioside GM2 (natural compound) (CHEBI:141420) has part ganglioside GM2 (18:0) (CHEBI:60327)
ganglioside GM2 (18:0) (1−) (CHEBI:78485) is conjugate base of ganglioside GM2 (18:0) (CHEBI:60327)
IUPAC Name 
(2S,3R,4E)-3-hydroxy-2-(octadecanoylamino)octadec-4-en-1-yl 2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→4)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)]-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
Synonyms  Source
GM2 gangliosideChEBI
GM2 lipidChEBI
GM2ChEBI
β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→4)-β-D-Glc-(1↔1)-N-octadecanoylsphingosineChEBI
monosialoganglioside GM2ChEBI
monosialoganglioside GM2ChEBI
Manual XrefsDatabases
GM2_(ganglioside)Wikipedia
Citations