N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->4)-D-glucose (CHEBI:151472)

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CHEBI:151472 - N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose

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ChEBI ID	CHEBI:151472
ChEBI Name	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose
Stars
ASCII Name	N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->4)-D-glucose
Definition	An amino trisaccharide that comprises of a linear sequence of α-N-acetylneuraminyl, β-D-galactosyl and D-glucose residues linked (2→3) and (1→4). It is found in human milk.
Last Modified	1 August 2023
Submitter	Gareth Owen
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(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-1x_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-METZQCMUSA-N

Species of Metabolite	Component	Source	Comments
Homo sapiens (ncbitaxon:9606)	milk (BTO:0000868)	PubMed (26613816)

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:	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)-D-glucose (CHEBI:151472) has role human metabolite (CHEBI:77746)
	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose (CHEBI:151472) is a acetamides (CHEBI:22160)
	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose (CHEBI:151472) is a amino trisaccharide (CHEBI:59266)
	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose (CHEBI:151472) is a monocarboxylic acid (CHEBI:25384)
	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose (CHEBI:151472) is conjugate acid of α-N-acetylneuraminosyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose(1−) (CHEBI:156068)
Incoming Relation(s)
	N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-α-D-glucose (CHEBI:45660) 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 a N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose (CHEBI:151472)
	α-N-acetylneuraminosyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose(1−) (CHEBI:156068) is conjugate base of N-acetyl-α-neuraminyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose (CHEBI:151472)

IUPAC Name
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranonosyl-(2→3)-β-D-galactopyranosyl-(1→4)-D-glucopyranose

Synonyms	Source
3'-sialyllactose	KEGG GLYCAN
3'-SL	KEGG GLYCAN
5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid-(2→3)-β-D-galacto-hexopyranosyl-(1→4)-D-gluco-hexopyranose	SUBMITTER
NeuAc(a2-3)Gal(b1-4)Glc	SUBMITTER
alpha-N-acetylneuraminosyl-(2→3)-β-D-galactosyl-(1→4)-D-glucose	ChEBI
α-Neu5Ac-(2→3)-β-Gal-(1→4)-Glc	ChEBI

Manual Xrefs	Databases
FDB021795	FooDB
G00436	KEGG GLYCAN
G56516VH	GlyGen
G56516VH	GlyTouCan
HMDB0000825	HMDB

Registry Numbers	Sources
Reaxys:75357	Reaxys
CAS:35890-38-1	ChEBI

Citations