Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120121
Identification
Name: chitotriose
Description:A linear amino trisaccharide consisting of three N-acetyl-β-D-glucosamine residues linked (1→4).
Structure
Thumb
Synonyms:
  • (β)-N,N',N''-triacetyl chitotriose
  • β-D-GlcNAc-(1→4)-β-D-GlcNAc-(1→4)-β-D-GlcNAc
  • β-N,N',N''-triacetylchitotriose
  • GlcNAcb1-4GlcNAcb1-4GlcNAcb
  • GlcNAcβ1-4GlcNAcβ1-4GlcNAcβ
  • N,N',N''-triacetyl chitotriose β-anomer
  • N-acetyl-β-D-glucosaminyl-(1→4)-N-acetyl-β-D-glucosaminyl-(1→4)-N-acetyl-β-D-glucosamine
Chemical Formula: C24H41N3O16
Average Molecular Weight: 627.598
Monoisotopic Molecular Weight: 627.24866
InChI Key: WZZVUHWLNMNWLW-MEWKLCDLSA-N
InChI:InChI=1S/C24H41N3O16/c1-7(31)25-13-18(36)20(11(5-29)39-22(13)38)42-24-15(27-9(3)33)19(37)21(12(6-30)41-24)43-23-14(26-8(2)32)17(35)16(34)10(4-28)40-23/h10-24,28-30,34-38H,4-6H2,1-3H3,(H,25,31)(H,26,32)(H,27,33)/t10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22?,23+,24+/m1/s1
CAS number: Not Available
IUPAC Name:2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose
Traditional IUPAC Name: Not Available
SMILES:CC(=O)NC1(C(O)OC(CO)C(C(O)1)OC2(C(NC(C)=O)C(O)C(C(CO)O2)OC3(OC(C(O)C(O)C(NC(C)=O)3)CO)))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
Kingdom Organic compounds
Super ClassOrganic oxygen compounds
Class Organooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent Acylaminosugars
Alternative Parents
Substituents
  • Oligosaccharide
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
  • a chitodextrin (CPD-13227)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight627.597 g/molPubChem
XLogP3-AA-6.9 PubChem
Hydrogen Bond Donor Count11 PubChem
Hydrogen Bond Acceptor Count16 PubChem
Rotatable Bond Count10 PubChem
Exact Mass627.249 g/molPubChem
Monoisotopic Mass627.249 g/molPubChem
Topological Polar Surface Area295 A^2PubChem
Heavy Atom Count43 PubChem
Formal Charge0 PubChem
Complexity962 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count15 PubChem
Undefined Atom Stereocenter Count0 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra: Not Available
References
References:
  • von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS (2009)Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass. The Journal of allergy and clinical immunology 123, Pubmed: 19443021
  • Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S (2015)The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites. Science translational medicine 7, Pubmed: 25568069
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI71404
CHEMSPIDER392429
PUBCHEM444514