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GlcNAcbeta1-2Manalpha1-3Manbeta1-4GlcNAcbeta1-4GlcNAcbeta

PubChem CID
91847546
Structure
GlcNAcbeta1-2Manalpha1-3Manbeta1-4GlcNAcbeta1-4GlcNAcbeta_small.png
Molecular Formula
Synonyms
  • CHEBI:180492
  • GlcNAcbeta1-2Manalpha1-3Manbeta1-4GlcNAcbeta1-4GlcNAcbeta
  • 2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->2)-alpha-D-mannopyranosyl-(1->3)-beta-D-mannopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranose
  • 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->2)-alpha-D-mannopyranosyl-(1->3)-beta-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranose
  • beta-D-GlcNAc-(1->2)-alpha-D-Man-(1->3)-beta-D-Man-(1->4)-beta-GlcNAc-(1->4)-beta-D-GlcNAc
Molecular Weight
951.9 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2015-09-10
  • Modify:
    2025-02-01
Description
Beta-D-GlcpNAc-(1->2)-alpha-D-Manp-(1->3)-beta-D-Manp-(1->4)-beta-GlcpNAc-(1->4)-beta-D-GlcpNAc is an amino pentasaccharide derivative that is beta-D-Man-(1->4)-beta-D-GlcNAc-(1->4)-beta-D-GlcNAc in which the mannosyl group is substituted at position 3 by a beta-D-GlcNAc-(1->2)-alpha-D-Man group. It is an amino pentasaccharide and a glucosamine oligosaccharide.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
GlcNAcbeta1-2Manalpha1-3Manbeta1-4GlcNAcbeta1-4GlcNAcbeta.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Biologic Description

1 of 2
SVG Image
SVG Image
IUPAC Condensed
GlcNAc(b1-2)Man(a1-3)Man(b1-4)GlcNAc(b1-4)b-GlcNAc
LINUCS
[][b-D-GlcpNAc]{[(4+1)][b-D-GlcpNAc]{[(4+1)][b-D-Manp]{[(3+1)][a-D-Manp]{[(2+1)][b-D-GlcpNAc]{}}}}}
IUPAC
2-acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->2)-alpha-D-manno-hexopyranosyl-(1->3)-beta-D-manno-hexopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-gluco-hexopyranose
2 of 2
Permethylated Mass
Monosaccharide Composition

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

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

3.1.2 InChI

InChI=1S/C36H61N3O26/c1-9(45)37-17-24(52)28(15(7-43)57-32(17)56)62-34-19(39-11(3)47)25(53)29(16(8-44)61-34)63-35-27(55)30(22(50)14(6-42)59-35)64-36-31(26(54)21(49)13(5-41)60-36)65-33-18(38-10(2)46)23(51)20(48)12(4-40)58-33/h12-36,40-44,48-56H,4-8H2,1-3H3,(H,37,45)(H,38,46)(H,39,47)/t12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26+,27+,28-,29-,30+,31+,32-,33+,34+,35+,36-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

JZLBUVTUAPMXMU-AQMCSCSJSA-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)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)NC(=O)C)O)O)NC(=O)C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C36H61N3O26
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 ChEBI ID

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
951.9 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-10.1
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
17
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
26
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
16
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
951.35432906 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
951.35432906 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
454 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
65
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1560
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
25
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

6.4 Chemical-Disease Co-Occurrences in Literature

7 Interactions and Pathways

7.1 Protein Bound 3D Structures

7.2 Chemical-Target Interactions

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

8 Classification

8.1 ChEBI Ontology

8.2 Glycan Naming and Subsumption Ontology (GNOme)

8.3 MolGenie Organic Chemistry Ontology

9 Information Sources

  1. ChEBI
    Beta-D-GlcpNAc-(1->2)-alpha-D-Manp-(1->3)-beta-D-Manp-(1->4)-beta-GlcpNAc-(1->4)-beta-D-GlcpNAc
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:180492
  2. GlyCosmos Glycoscience Portal
    LICENSE
    All copyrightable parts of the datasets in GlyCosmos are under the Creative Commons Attribution (CC BY 4.0) License.
    https://glycosmos.org/license
  3. GlyGen
  4. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  5. PubChem
  6. Glycan Naming and Subsumption Ontology (GNOme)
    GNOme
  7. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS