N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucose (CHEBI:59226)

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

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ChEBI ID	CHEBI:59226
ChEBI Name	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose
Stars
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).
Secondary ChEBI ID	CHEBI:85038
Last Modified	13 January 2025
Submitter	namrata, Steve
Downloads	Molfile

Formula	C23H39NO19
Net Charge	0
Average Mass	633.553
Monoisotopic Mass	633.21163
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](O)O[C@@H]3CO)[C@@H]2O)(C(=O)O)C[C@H](O)[C@H]1NC(C)=O
WURCS	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
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

Roles Classification

Chemical Roles:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	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).

ChEBI Ontology

Outgoing Relation(s)
	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)
	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose (CHEBI:59226) is conjugate acid of N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose(1−) (CHEBI:232876)
Incoming Relation(s)
	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose(1−) (CHEBI:232876) is conjugate base of N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-β-D-glucose (CHEBI:59226)
	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
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose
(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

Synonyms	Source
(2→3')-alpha-Sialyllactose	HMDB
(2→3')-a-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
32-N-Acetyl-alpha-neuraminyllactose	HMDB
32-N-Acetyl-a-neuraminyllactose	HMDB
3'-alpha-Sialyllactose	HMDB

Manual Xrefs	Databases
G91237TK	GlyGen
G91237TK	GlyTouCan
HMDB0000825	HMDB

Registry Numbers	Sources
Reaxys:4632263	Reaxys
Beilstein:4632263	Beilstein

Citations