CHEBI:59226 - N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose
ChEBI ID CHEBI:59226
ChEBI ASCII Name N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucose
Definition An amino trisaccharide that is the carbohydrate portion of ganglioside GM3. It comprises a linear sequence of α-N-acetylneuraminyl, β-D-galactosyl and β-D-glucose residues linked (2→3) and (1→4).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:85038
Supplier Information
Download Molfile XML SDF
Formula C23H39NO19
Net Charge 0
Average Mass 633.55110
Monoisotopic Mass 633.21163
InChI InChI=1S/C23H39NO19/c1-6(28)24-11-7(29)2-23(22(37)38,42-18(11)12(31)8(30)3-25)43-19-13(32)9(4-26)40-21(16(19)35)41-17-10(5-27)39-20(36)15(34)14(17)33/h7-21,25-27,29-36H,2-5H2,1H3,(H,24,28)(H,37,38)/t7-,8+,9+,10+,11+,12+,13-,14+,15+,16+,17+,18+,19-,20+,21-,23-/m0/s1
InChIKey CILYIEBUXJIHCO-UITFWXMXSA-N
SMILES CC(=O)N[C@@H]1[C@@H](O)C[C@@](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
mammalian metabolite
Any animal metabolite produced during a metabolic reaction in mammals.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->4)-D-glucose )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose (CHEBI:59226) has role epitope (CHEBI:53000)
N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose (CHEBI:59226) has role mammalian metabolite (CHEBI:75768)
N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose (CHEBI:59226) is a N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose (CHEBI:151472)
Incoming α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glc-yl group (CHEBI:142767) is substituent group from N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose (CHEBI:59226)
IUPAC Names
(6R)-5-(acetylamino)-3,5-dideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-β-L-threo-hex-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose
Synonyms Sources
(2→3')-a-Sialyllactose HMDB
(2→3')-alpha-Sialyllactose HMDB
(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid HMDB
3'-(N-Acetyl-a-neuraminosyl)lactose HMDB
3'-(N-Acetyl-alpha-neuraminosyl)lactose HMDB
3'-a-Sialyllactose HMDB
3'-alpha-Sialyllactose HMDB
3'-Monosialyllactose HMDB
3'-N-Acetylneuraminyl-D-lactose HMDB
3'-N-Acetylneuraminyl-delta-lactose HMDB
3'-Sialyl-D-lactose HMDB
3'-Sialyl-delta-lactose HMDB
3'-sialyllactose HMDB
32-N-Acetyl-a-neuraminyllactose HMDB
32-N-Acetyl-alpha-neuraminyllactose HMDB
a-Neu5Ac-(2→3)-b-D-Gal-(1→4)-D-Glc HMDB
A2,3-Sialyllactose HMDB
α-N-acetylneuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose ChEBI
α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glc ChEBI
alpha-Neu5Ac-(2→3)-beta-D-Gal-(→4)-D-Glc HMDB
alpha-Neu5Ac-(2→3)-beta-delta-Gal-(1→4)-delta-Glc HMDB
α-Neup5Ac-(2→3)-β-D-Galp-(1→4)-β-D-Glcp ChEBI
GM3 carbohydrate moiety ChEBI
N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose UniProt
N-Acetylneuraminoyllactose HMDB
Neu5Aca2-3Galb1-4Glcb ChEBI
Neu5Acα2-3Galβ1-4Glcβ ChEBI
O-5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranonosyl-(2→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose ChEBI
WURCS=2.0/3,3,2/[a2122h-1b_1-5][a2112h-1b_1-5][Aad21122h-2a_2-6_5*NCC/3=O]/1-2-3/a4-b1_b3-c2 GlyTouCan
Manual Xrefs Databases
G91237TK GlyGen
G91237TK GlyTouCan
HMDB0000825 HMDB
View more database links
Registry Numbers Types Sources
4632263 Reaxys Registry Number Reaxys
4632263 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
26 July 2023