An official website of the United States government

beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->3)-alpha-D-GalpNAc

PubChem CID
56627468
Structure
beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->3)-alpha-D-GalpNAc_small.png
beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->3)-alpha-D-GalpNAc_3D_Structure.png
Molecular Formula
Synonyms
  • GlcNAcbeta1-3Galbeta1-3GalNAcalpha
  • beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->3)-alpha-D-GalpNAc
  • beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->3)-alpha-D-GalNAc
  • N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosamine
  • 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-alpha-D-galactopyranose
Molecular Weight
586.5 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2012-02-25
  • Modify:
    2025-01-18
Description
Beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->3)-alpha-D-GalpNAc is a linear amino trisaccharide comprised of a (1->3)-linked sequence of N-acetyl-beta-D-glucosamine, beta-D-galactose and N-acetyl-beta-D-galactosamine residues. It has a role as an epitope. It is an amino trisaccharide, a glucosamine oligosaccharide and a galactosamine oligosaccharide.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->3)-alpha-D-GalpNAc.png

1.2 3D Conformer

2 Biologic Description

1 of 2
SVG Image
SVG Image
IUPAC Condensed
GlcNAc(b1-3)Gal(b1-3)a-GalNAc
LINUCS
[][a-D-GalpNAc]{[(3+1)][b-D-Galp]{[(3+1)][b-D-GlcpNAc]{}}}
IUPAC
2-acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->3)-beta-D-galacto-hexopyranosyl-(1->3)-2-acetamido-2-deoxy-alpha-D-galacto-hexopyranose
2 of 2
GlyGen Classification
Permethylated Mass
Monosaccharide Composition

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

N-[(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C22H38N2O16/c1-6(28)23-11-16(33)13(30)8(3-25)37-21(11)40-19-15(32)10(5-27)38-22(17(19)34)39-18-12(24-7(2)29)20(35)36-9(4-26)14(18)31/h8-22,25-27,30-35H,3-5H2,1-2H3,(H,23,28)(H,24,29)/t8-,9-,10-,11-,12-,13-,14+,15+,16-,17-,18-,19+,20+,21+,22+/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

UHXCBMGDLOQUHX-GJGNTVEQSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@H]2[C@H]([C@H](O[C@H]([C@@H]2O)O[C@@H]3[C@H]([C@H](O[C@@H]([C@@H]3O)CO)O)NC(=O)C)CO)O)CO)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C22H38N2O16
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 ChEBI ID

3.3.2 Metabolomics Workbench ID

3.3.3 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
586.5 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-5.8
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
11
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
16
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
586.22213313 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
586.22213313 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
286 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
40
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
854
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
15
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

6 Literature

6.1 Consolidated References

6.2 Chemical Co-Occurrences in Literature

6.3 Chemical-Gene Co-Occurrences in Literature

7 Patents

7.1 Depositor-Supplied Patent Identifiers

8 Interactions and Pathways

8.1 Chemical-Target Interactions

GlycoGene Database (GGDB): https://acgg.asia/db/ggdb

9 Classification

9.1 ChEBI Ontology

9.2 Glycan Naming and Subsumption Ontology (GNOme)

9.3 MolGenie Organic Chemistry Ontology

10 Information Sources

CONTENTS