ChemFOnt: Showing chemical card for (N-acetylneuraminosyl(a2-6)lactosamine) (CFc000000850)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:21 UTC

Chemfont ID

CFc000000850

Molecule Identification

Common Name

(N-acetylneuraminosyl(a2-6)lactosamine)

Definition

(N-acetylneuraminosyl(alpha2-6)lactosamine) is widely distributed among tissues and is involved in biological processes such as the regulation of the immune response and the progression of colon cancer. Sialylation represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. Sialic acid is commonly found alpha,6-linked to N-acetylgalactosamine (GalNAc). The biosynthesis of the linkage is mediated by a member of the sialyltransferase family, the beta-galactoside alpha,6-sialyltransferase (EC 2.4.99.1, ST6Gal.I). Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. (PMID 11425186 )

6'-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid	ChEBI
(N-Acetylneuraminosyl(alpha2-6)lactosamine)	ChEBI
6'-Sialyllactosamine	ChEBI
6-Sialyllactosamine	ChEBI
alpha-N-Acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine	ChEBI
alpha-N-Acetylneuraminyl-2,6-beta-delta-galactosyl-1,4-N-acetyl-beta-delta-glucosamine	ChEBI
alpha-NeuNAc-(2->6)-beta-D-gal-(1->4)-beta-D-glcnac	ChEBI
alpha-NeupNAc-(2->6)-beta-D-galp-(1->4)-beta-D-glcpnac	ChEBI
N-Acetylneuraminosyl(alpha2-6)lactosamine	ChEBI
Neu5aca2-6galb1-4glcnacb	ChEBI
Neuac-lact	ChEBI
NeuAcalpha2,6galbeta1,4glcnac	ChEBI
Neuacalpha2,6galnacbeta1,4glcnac	ChEBI
Neuacalpha2-6galbeta1-4glcnacbeta	ChEBI
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-b-D-glucopyranose	ChEBI
O-(N-Acetyl-alpha-neuraminosyl)-(26)-O-beta-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranose	ChEBI
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranose	ChEBI
WURCS=2.0/3,3,2/[a2122h-1b_1-5_2ncc/3=o][a2112h-1b_1-5][aad21122h-2a_2-6_5ncc/3=o]/1-2-3/a4-b1_b6-C2	ChEBI
(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator
(N-Acetylneuraminosyl(α2-6)lactosamine)	Generator
a-N-Acetylneuraminyl-2,6-b-D-galactosyl-1,4-N-acetyl-b-D-glucosamine	Generator
Α-N-acetylneuraminyl-2,6-β-D-galactosyl-1,4-N-acetyl-β-D-glucosamine	Generator
a-N-Acetylneuraminyl-2,6-b-delta-galactosyl-1,4-N-acetyl-b-delta-glucosamine	Generator
Α-N-acetylneuraminyl-2,6-β-δ-galactosyl-1,4-N-acetyl-β-δ-glucosamine	Generator
a-NeuNAc-(2->6)-b-D-gal-(1->4)-b-D-glcnac	Generator
Α-neunac-(2->6)-β-D-gal-(1->4)-β-D-glcnac	Generator
a-NeupNAc-(2->6)-b-D-galp-(1->4)-b-D-glcpnac	Generator
Α-neupnac-(2->6)-β-D-galp-(1->4)-β-D-glcpnac	Generator
N-Acetylneuraminosyl(a2-6)lactosamine	Generator
N-Acetylneuraminosyl(α2-6)lactosamine	Generator
O-(N-Acetyl-a-neuraminosyl)-(26)-O-b-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-b-D-glucopyranose	Generator
O-(N-Acetyl-α-neuraminosyl)-(26)-O-β-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-β-D-glucopyranose	Generator
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-delta-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-b-delta-glucopyranose	Generator
O-(N-Acetyl-α-neuraminosyl)-(2->6)-O-β-δ-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-β-δ-glucopyranose	Generator
Neu5acbeta2-6galbeta1-4glcnacbeta	ChEBI, HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranose	HMDB
a-N-Acetylneuraminyl-(2->6)-b-D-galactosyl-(1->4)-N-acetyl-b-D-glucosamine	Generator, HMDB
Α-N-acetylneuraminyl-(2->6)-β-D-galactosyl-(1->4)-N-acetyl-β-D-glucosamine	Generator, HMDB

Chemical Formula

C₂₅H₄₂N₂O₁₉

Average Molecular Weight

674.603

Monoisotopic Molecular Weight

674.238177172

IUPAC Name

(2R,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

6-sialyllactosamine

CAS Registry Number

64364-50-7

SMILES

[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22+,23-,25+/m0/s1

InChI Key

RPSBVJXBTXEJJG-LURNZOHQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Neuraminic acids

Alternative Parents

Substituents

Neuraminic acid
N-acyl-alpha-hexosamine
C-glucuronide
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Ketal
Pyran
Oxane
Hemiacetal
Secondary alcohol
Acetal
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Polyol
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucosamine oligosaccharide (CHEBI:17725 )
amino trisaccharide (CHEBI:17725 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Breast milk (PMID: 10940350)
Breast milk (HMDB: HMDB0001081)

Cellular substructure

Cytoplasm (HMDB: HMDB0001081)

Source

Endogenous

Endogenous (HMDB: HMDB0001081)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	72.5 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-7.4	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	343.95 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	139.71 m³·mol⁻¹	ChemAxon
Polarizability	63.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001081

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022413

KNApSAcK ID

Not Available

Chemspider ID

111381

KEGG Compound ID

C04886

BioCyc ID

ALPHA-N-ACETYLNEURAMINYL-26-BETA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17725

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Dall'Olio F The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconjugate journal (2000), 17(10), 669-76.

Showing chemical card for (N-acetylneuraminosyl(a2-6)lactosamine) (CFc000000850)

MOL for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

3D MOL for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

3D SDF for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

3D-SDF for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

PDB for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

3D PDB for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

SMILES for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

INCHI for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

Structure for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))

3D Structure for CFc000000850 ((N-acetylneuraminosyl(a2-6)lactosamine))