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CHEBI:63532 - GM3 lactam

ChEBI IDCHEBI:63532
ChEBI NameGM3 lactam
Stars
DefinitionA lactam obtained via formal condensation of the carboxy group of an N-acetylneuraminyl residue and the amino group of the adjacent galactosamine residue in the ganglioside (2S,3R,4E)-3-hydroxy-2-(stearoylamino)octadec-4-en-1-yl N-acetylneuraminyl-(2→3)-β-D-galactosaminyl-(1→4)-β-D-glucoside.
Last Modified9 January 2012
SubmitterSteve
DownloadsMolfile
FormulaC59H107N3O19
Net Charge0
Average Mass1162.507
Monoisotopic Mass1161.74988
SMILES[H][C@@]1([C@H](O)[C@H](O)CO)O[C@@]2(C[C@H](O)[C@H]1NC(C)=O)O[C@H]1[C@@H](O)[C@@H](CO)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)[C@@H]1NC2=O
InChIInChI=1S/C59H107N3O19/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(70)61-40(41(67)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-76-57-52(74)51(73)53(45(37-65)78-57)79-56-48-55(50(72)44(36-64)77-56)81-59(58(75)62-48)34-42(68)47(60-39(3)66)54(80-59)49(71)43(69)35-63/h30,32,40-45,47-57,63-65,67-69,71-74H,4-29,31,33-38H2,1-3H3,(H,60,66)(H,61,70)(H,62,75)/b32-30+/t40-,41+,42-,43+,44+,45+,47+,48+,49+,50-,51+,52+,53+,54+,55+,56-,57+,59-/m0/s1
InChIKeyRETZCXQFOHADIK-ISAHSDPDSA-N
ChEBI Ontology
Outgoing Relation(s)
GM3 lactam (CHEBI:63532) is a azaspiro compound (CHEBI:35624)
GM3 lactam (CHEBI:63532) is a ganglioside derivative (CHEBI:63535)
GM3 lactam (CHEBI:63532) is a lactam (CHEBI:24995)
GM3 lactam (CHEBI:63532) is a oxaspiro compound (CHEBI:37948)
IUPAC Name 
N-{(2S,3R,4E)-1-[(4-O-{(2S,4S,4a'R,5R,5'S,6R,7'R,8'R,8a'R)-5-acetamido-4,8'-dihydroxy-7'-(hydroxymethyl)-3'-oxo-6-[(1R,2R)-1,2,3-trihydroxypropyl]decahydro-5'H-spiro[pyran-2,2'-pyrano[4,3-b][1,4]oxazin]-5'-yl}-β-D-glucopyranosyl)oxy]-3-hydroxyoctadec-4-en-2-yl}octadecanamide
Synonyms  Source
GM3-lactam ceramideChEBI
(2S,3R,4E)-3-hydroxy-2-(octadecanamide)octadec-4-enyl 4-O-[2-amino-2-deoxy-3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''[*]2'-lactam)-β-D-galactopyranosyl]-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:7245914Reaxys
Citations