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NeuAc(a2-8)NeuAc(a2-6)[Gal(b1-3)]GalNAc(b1-4)Gal(b1-4)b-Glc

PubChem CID
91859133
Structure
NeuAc(a2-8)NeuAc(a2-6)[Gal(b1-3)]GalNAc(b1-4)Gal(b1-4)b-Glc_small.png
Molecular Formula
Synonyms
  • CHEBI:150455
  • NeuAc(a2-8)NeuAc(a2-6)[Gal(b1-3)]GalNAc(b1-4)Gal(b1-4)b-Glc
  • 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonic acid-(2->8)-5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonic acid-(2->6)-[beta-D-galacto-hexopyranosyl-(1->3)]-2-acetamido-2-deoxy-beta-D-galacto-hexopyranosyl-(1->4)-beta-D-galacto-hexopyranosyl-(1->4)-beta-D-gluco-hexopyranose
  • WURCS=2.0/4,6,5/[a2122h-1b_1-5][a2112h-1b_1-5][a2112h-1b_1-5_2*NCC/3=O][Aad21122h-2a_2-6_5*NCC/3=O]/1-2-3-2-4-4/a4-b1_b4-c1_c3-d1_c6-e2_e8-f2
Molecular Weight
1290.1 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2015-09-10
  • Modify:
    2025-01-18
Description
(2R,4S,5R,6R)-5-Acetamido-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3-hydroxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-4-hydroxyoxane-2-carboxylic acid is a member of neuraminic acids.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
NeuAc(a2-8)NeuAc(a2-6)[Gal(b1-3)]GalNAc(b1-4)Gal(b1-4)b-Glc.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
NeuAc(a2-8)NeuAc(a2-6)[Gal(b1-3)]GalNAc(b1-4)Gal(b1-4)b-Glc
LINUCS
[][b-D-Glcp]{[(4+1)][b-D-Galp]{[(4+1)][b-D-GalpNAc]{[(3+1)][b-D-Galp]{}[(6+2)][a-NeupAc]{[(8+2)][a-NeupAc]{}}}}}
IUPAC
5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonic acid-(2->8)-5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosylonic acid-(2->6)-[beta-D-galacto-hexopyranosyl-(1->3)]-2-acetamido-2-deoxy-beta-D-galacto-hexopyranosyl-(1->4)-beta-D-galacto-hexopyranosyl-(1->4)-beta-D-gluco-hexopyranose
2 of 2
Permethylated Mass
Monosaccharide Composition

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2R,4S,5R,6R)-5-acetamido-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3-hydroxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-4-hydroxyoxane-2-carboxylic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C48H79N3O37/c1-12(57)49-23-16(61)5-48(46(76)77,88-39(23)26(63)17(62)6-52)86-19(8-54)28(65)40-24(50-13(2)58)15(60)4-47(87-40,45(74)75)78-11-22-29(66)38(85-43-34(71)30(67)27(64)18(7-53)80-43)25(51-14(3)59)42(82-22)83-37-21(10-56)81-44(35(72)32(37)69)84-36-20(9-55)79-41(73)33(70)31(36)68/h15-44,52-56,60-73H,4-11H2,1-3H3,(H,49,57)(H,50,58)(H,51,59)(H,74,75)(H,76,77)/t15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25+,26+,27-,28+,29-,30-,31+,32+,33+,34+,35+,36+,37-,38+,39+,40+,41+,42-,43-,44-,47+,48+/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

MDFCBSYYDAGMHA-SHSTWFPUSA-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[C@@](O[C@H]1[C@@H]([C@@H](CO)O[C@@]2(C[C@@H]([C@H]([C@@H](O2)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)O)(C(=O)O)OC[C@@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)O[C@H]4[C@H](O[C@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@H]([C@@H]([C@H]5O)O)O)CO)CO)NC(=O)C)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C48H79N3O37
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
1290.1 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-14
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
24
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
37
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
25
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
1289.4392404 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
1289.4392404 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
648 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
88
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
2320
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
32
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 Classification

6.1 ChEBI Ontology

6.2 Glycan Naming and Subsumption Ontology (GNOme)

6.3 MolGenie Organic Chemistry Ontology

7 Information Sources

  1. ChEBI
    (2R,4S,5R,6R)-5-Acetamido-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3-hydroxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-4-hydroxyoxane-2-carboxylic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:150455
  2. GlyGen
  3. PubChem
  4. Glycan Naming and Subsumption Ontology (GNOme)
    GNOme
  5. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS