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Record Information
Version3.6
Creation Date2006-08-12 23:41:28 UTC
Update Date2013-02-09 00:12:38 UTC
HMDB IDHMDB03556
Secondary Accession NumbersNone
Metabolite Identification
Common NameChitobiose
DescriptionChitobiose is a dimer of beta-1,4-linked glucosamine units. There is ambiguity as to which structure the name refers, owing to the method by which it was first isolated.
Structure
Thumb
Synonyms
  1. CBS
  2. Chitodextrin
  3. Diacetylchitobiose
Chemical FormulaC15H26N2O12
Average Molecular Weight426.3731
Monoisotopic Molecular Weight426.148574306
IUPAC Name[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamic acid
Traditional Name(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-ylcarbamic acid
CAS Registry Number577-76-4
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(O)=O)[C@@H]1O
InChI Identifier
InChI=1S/C15H26N2O12/c1-4(20)16-7-11(23)12(6(3-19)27-13(7)24)29-14-8(17-15(25)26)10(22)9(21)5(2-18)28-14/h5-14,17-19,21-24H,2-3H2,1H3,(H,16,20)(H,25,26)/t5-,6-,7-,8-,9-,10-,11-,12-,13-,14+/m1/s1
InChI KeyHSRZMOSQMYFZBL-CGKOVJDHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassDisaccharides
Sub ClassDihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Carbamic Acid
  • Carboxamide Group
  • Glucosamine
  • Glyco Amino Acid
  • Glycosyl Compound
  • Hemiacetal
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentDihexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility101 g/LALOGPS
logP-2.9ALOGPS
logP-4.8ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area227.5ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.39ChemAxon
Polarizability39.64ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023196
KNApSAcK IDNot Available
Chemspider ID17216232
KEGG Compound IDC01674
BioCyc IDCHITOBIOSE
BiGG IDNot Available
Wikipedia LinkChitobiose
NuGOwiki LinkHMDB03556
Metagene LinkHMDB03556
METLIN ID6953
PubChem Compound22833609
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceCottaz, Sylvain; Samain, Eric. Genetic engineering of Escherichia coli for the production of NI,NII-diacetylchitobiose (chitinbiose) and its utilization as a primer for the synthesis of complex carbohydrates. Metabolic Engineering (2005), 7(4), 311-317.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van Pelt J, Hard K, Kamerling JP, Vliegenthart JF, Reuser AJ, Galjaard H: Isolation and structural characterization of twenty-one sialyloligosaccharides from galactosialidosis urine. An intact N,N'-diacetylchitobiose unit at the reducing end of a diantennary structure. Biol Chem Hoppe Seyler. 1989 Mar;370(3):191-203. Pubmed: 2713102
  2. Collin M, Olsen A: EndoS, a novel secreted protein from Streptococcus pyogenes with endoglycosidase activity on human IgG. EMBO J. 2001 Jun 15;20(12):3046-55. Pubmed: 11406581
  3. Nimtz M, Grabenhorst E, Gambert U, Costa J, Wray V, Morr M, Thiem J, Conradt HS: In vitro alpha1-3 or alpha1-4 fucosylation of type I and II oligosaccharides with secreted forms of recombinant human fucosyltransferases III and VI. Glycoconj J. 1998 Sep;15(9):873-83. Pubmed: 10052591

Enzymes

General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
Gene Name:
HEXB
Uniprot ID:
P07686
Molecular weight:
Not Available
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues. The form B is active against certain oligosaccharides. The form S has no measurable activity.
Gene Name:
HEXA
Uniprot ID:
P06865
Molecular weight:
Not Available
General function:
Involved in chitin binding
Specific function:
Degrades chitin, chitotriose and chitobiose. May participate in the defense against nematodes and other pathogens. Isoform 3 has no enzymatic activity.
Gene Name:
CHIT1
Uniprot ID:
Q13231
Molecular weight:
Not Available