EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:144806 - N-glycolylneuraminyllactosylceramide

ChEBI IDCHEBI:144806
ChEBI NameN-glycolylneuraminyllactosylceramide
Stars
ASCII NameN-glycolylneuraminyllactosylceramide
DefinitionA sialotriaosylceramide in which the triaosyl group is 3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl attached to the primary hydroxy function of ceramide. A tumour antigen found in solid tumors such as breast carcinoma, nonsmall cell lung cancer, and melanoma, but not usually detected in normal human cells.
Secondary ChEBI IDCHEBI:144807
Last Modified12 September 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC59H108N2O22
Net Charge0
Average Mass1197.505
Monoisotopic Mass1196.73937
SMILES[H][C@@]1([C@H](O)[C@H](O)CO)O[C@@](O[C@H]2[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]2O)(C(=O)O)C[C@H](O)[C@H]1NC(=O)CO
InChIInChI=1S/C59H108N2O22/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-45(69)60-39(40(66)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)38-78-56-51(74)50(73)53(44(36-64)80-56)81-57-52(75)55(49(72)43(35-63)79-57)83-59(58(76)77)33-41(67)47(61-46(70)37-65)54(82-59)48(71)42(68)34-62/h29,31,39-44,47-57,62-68,71-75H,3-28,30,32-38H2,1-2H3,(H,60,69)(H,61,70)(H,76,77)/b31-29+/t39-,40+,41-,42+,43+,44+,47+,48+,49-,50+,51+,52+,53+,54+,55-,56+,57-,59-/m0/s1
InChIKeyHWIQEEBMCAQYHW-LGDSWWPFSA-N
Roles Classification
Biological Role:
tumour antigen  An antigenic substance produced in tumour cells, which triggers an immune response in the host.
ChEBI Ontology
Outgoing Relation(s)
N-glycolylneuraminyllactosylceramide (CHEBI:144806) has role tumour antigen (CHEBI:144829)
N-glycolylneuraminyllactosylceramide (CHEBI:144806) is a sialotriaosylceramide (CHEBI:36541)
IUPAC Names 
(2S,3R,4E)-3-hydroxy-2-(stearoylamino)octadec-4-en-1-yl 3,5-dideoxy-5-(glycoloylamino)-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
(2S,3R,4E)-3-hydroxy-2-(octadecanoylamino)octadec-4-en-1-yl 3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
Synonyms  Source
Neugc(α2-3)gal(β1-4)glc(β1-1)cerChemIDplus
N-glycolyl-neuraminyl-lactosyl-ceramideChemIDplus
GM3-NeugcChemIDplus
N-glycoloyl-GM3ChemIDplus
HD3 gangliosideChEBI
Neugc-GM3ChemIDplus
Registry NumbersSources
CAS:69345-49-9ChemIDplus
Citations