CHEBI:144806 - N-glycolylneuraminyllactosylceramide

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name N-glycolylneuraminyllactosylceramide
ChEBI ID CHEBI:144806
ChEBI ASCII Name N-glycolylneuraminyllactosylceramide
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:144807
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C59H108N2O22
Net Charge 0
Average Mass 1197.505
Monoisotopic Mass 1196.73937
InChI InChI=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
InChIKey HWIQEEBMCAQYHW-LGDSWWPFSA-N
SMILES O([C@@H]1[C@H]([C@@H](O[C@@H]([C@@H]1O)CO)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2CO)OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(CCCCCCCCCCCCCCCCC)=O)O)O)O)[C@]3(O[C@]([C@@H]([C@H](C3)O)NC(CO)=O)([C@@H]([C@H](O)CO)O)[H])C(=O)O
Roles Classification
Biological Role(s): tumour antigen
An antigenic substance produced in tumour cells, which triggers an immune response in the host.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-(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
(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
Synonyms Sources
(5α,17α)-N-deacetyl-N-(hydroxyacetyl)-ganglioside GM3 ChemIDplus
1-O-(O-(N-(hydroxyacetyl)-α-neuraminosyl)-(2-3)-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranosyl)-ceramide ChemIDplus
GM3-Neugc ChemIDplus
HD3 ChemIDplus
HD3 ganglioside ChEBI
N-glycoloyl-GM3 ChemIDplus
N-glycoloyl-GM3 ChemIDplus
N-glycolyl-neuraminyl-lactosyl-ceramide ChemIDplus
Neugc(α2-3)gal(β1-4)glc(β1-1)cer ChemIDplus
Neugc-GM3 ChemIDplus
Registry Number Type Source
69345-49-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1392562 PubMed citation Europe PMC
19435393 PubMed citation Europe PMC
19748674 PubMed citation Europe PMC
25403557 PubMed citation Europe PMC
3170597 PubMed citation Europe PMC
3487502 PubMed citation Europe PMC
7849044 PubMed citation Europe PMC
Last Modified
12 September 2019