ChemFOnt: Showing chemical card for 6-Sialyl-N-acetyllactosamine (CFc000002827)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:48 UTC

Chemfont ID

CFc000002827

Molecule Identification

Common Name

6-Sialyl-N-acetyllactosamine

Definition

6-Sialyl-N-acetyllactosamine is an oligosaccharide 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,3- or alpha,6-linked to galactose (Gal), alpha,6-linked to N-acetylgalactosamine (GalNAc) or alpha,8-linked to another sialic acid. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. The b-galactoside a2,6 sialyltransferase (EC 2.4.99.1, ST6Gal.I) is the only sialyltransferase so far identified able to catalyze the a2,6-sialylation of lactosamine. Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. The level of expression of the sialyl-alpha2,6-lactosaminyl structures and of ST6Gal.I show a strong dependence on neoplastic transformation and differentiation in several tissues. (PMID: 11425186 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6'-Sialyl-N-acetyllactosamine	HMDB
62-a-N-Acetylneuraminyl-N-acetyllactosam	HMDB
62-alpha-N-Acetylneuraminyl-N-acetyllactosam	HMDB
62-alpha-N-Acetylneuraminyl-N-acetyllactosamine	HMDB
NeuAc alpha,6gal beta1,4gicnac	HMDB
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-glucose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-glucose	HMDB
(2S,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-4,6-dihydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB

Chemical Formula

C₂₅H₄₂N₂O₁₉

Average Molecular Weight

674.603

Monoisotopic Molecular Weight

674.238177172

IUPAC Name

(2S,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-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

CAS Registry Number

78969-47-8

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(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-RAMSCCQBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

N-acylneuraminic acid
Acylaminosugar
Neuraminic acid
N-acyl-alpha-hexosamine
C-glucuronide
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Ketal
Pyran
Oxane
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Hemiacetal
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0006584)

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)

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	62.83 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

HMDB0006584

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023986

KNApSAcK ID

Not Available

Chemspider ID

17216384

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16212424

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

aulsen, Hans; Tietz, Holger. Building blocks of oligosaccharides. Part 43. Synthesis of trisaccharide units from N-acetylneuraminic acid and N-acetyllactosamine. Angewandte Chemie (1982), 94(12), 934-5.

Showing chemical card for 6-Sialyl-N-acetyllactosamine (CFc000002827)

MOL for CFc000002827 (6-Sialyl-N-acetyllactosamine)

3D MOL for CFc000002827 (6-Sialyl-N-acetyllactosamine)

3D SDF for CFc000002827 (6-Sialyl-N-acetyllactosamine)

3D-SDF for CFc000002827 (6-Sialyl-N-acetyllactosamine)

PDB for CFc000002827 (6-Sialyl-N-acetyllactosamine)

3D PDB for CFc000002827 (6-Sialyl-N-acetyllactosamine)

SMILES for CFc000002827 (6-Sialyl-N-acetyllactosamine)

INCHI for CFc000002827 (6-Sialyl-N-acetyllactosamine)

Structure for CFc000002827 (6-Sialyl-N-acetyllactosamine)

3D Structure for CFc000002827 (6-Sialyl-N-acetyllactosamine)