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beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap

PubChem CID
45266825
Structure
beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap_small.png
Molecular Formula
Synonyms
  • CHEBI:59322
  • beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap
  • 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->2)-6-deoxy-alpha-L-mannopyranosyl-(1->2)-[alpha-D-glucopyranosyl-(1->3)]-6-deoxy-alpha-L-mannopyranosyl-(1->3)-6-deoxy-alpha-L-mannopyranose
  • 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->2)-alpha-L-rhamnopyranosyl-(1->2)-[alpha-D-glucopyranosyl-(1->3)]-alpha-L-rhamnopyranosyl-(1->3)-alpha-L-rhamnopyranose
  • Epitope ID:130671
Molecular Weight
821.8 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2010-05-07
  • Modify:
    2025-01-25
Description
Beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap is a branched amino pentasaccharide comprising an acetylated glucosamine residue, a glucose residue and three rhamnose residues, one of which is at the reducing end.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap.png

1.2 3D Status

Conformer generation is disallowed since too many atoms

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
GlcNAc(b1-2)Rha(a1-2)[Glc(a1-3)]Rha(a1-3)a-Rha
LINUCS
[][a-L-Rhap]{[(3+1)][a-L-Rhap]{[(2+1)][a-L-Rhap]{[(2+1)][b-D-GlcpNAc]{}}[(3+1)][a-D-Glcp]{}}}
IUPAC
2-acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->2)-6-deoxy-alpha-L-manno-hexopyranosyl-(1->2)-[alpha-D-gluco-hexopyranosyl-(1->3)]-6-deoxy-alpha-L-manno-hexopyranosyl-(1->3)-6-deoxy-alpha-L-manno-hexopyranose

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[(2S,3R,4R,5S,6S)-5-hydroxy-6-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2R,3R,4R,5S,6S)-2,3,5-trihydroxy-6-methyloxan-4-yl]oxyoxan-3-yl]oxy-6-methyloxan-3-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/C32H55NO23/c1-7-14(37)21(44)26(55-29-13(33-10(4)36)19(42)17(40)11(5-34)51-29)31(49-7)56-27-25(54-30-22(45)20(43)18(41)12(6-35)52-30)16(39)9(3)50-32(27)53-24-15(38)8(2)48-28(47)23(24)46/h7-9,11-32,34-35,37-47H,5-6H2,1-4H3,(H,33,36)/t7-,8-,9-,11+,12+,13+,14-,15-,16-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28+,29-,30+,31-,32-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

TVQIRVOJYMVJNS-NHLPNOMKSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)NC(=O)C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C32H55NO23
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
821.8 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-7.5
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
14
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
23
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
11
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
821.31648700 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
821.31648700 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
375 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
56
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1270
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

7 Classification

7.1 ChEBI Ontology

7.2 Glycan Naming and Subsumption Ontology (GNOme)

7.3 MolGenie Organic Chemistry Ontology

8 Information Sources

  1. ChEBI
    Beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59322
  2. Metabolomics Workbench
    beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=60552
  3. Wikidata
    beta-D-GlcpNAc-(1->2)-alpha-L-Rhap-(1->2)-[alpha-D-Glcp-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap
    https://www.wikidata.org/wiki/Q27126628
  4. PubChem
  5. Glycan Naming and Subsumption Ontology (GNOme)
    GNOme
  6. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS