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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:41:28 UTC
Update Date2020-07-09 17:45:25 UTC
HMDB IDHMDB0003556
Secondary Accession Numbers
  • HMDB03556
Metabolite Identification
Common NameChitobiose
DescriptionChitobiose, also known as CBS or chitodextrin, 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. Chitobiose is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, chitobiose participates in a number of enzymatic reactions. In particular, chitobiose can be biosynthesized from chitin through the action of the enzyme chitotriosidase-1. In addition, chitobiose can be converted into N-acetyl-D-glucosamine; which is catalyzed by the enzyme Beta-hexosaminidase subunit alpha. In humans, chitobiose is involved in the metabolic disorder called the tay-sachs disease pathway. Chitobiose is a potentially toxic compound.
Structure
Data?1594316725
Synonyms
ValueSource
CBSHMDB
ChitodextrinHMDB
DiacetylchitobioseHMDB
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
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carbamic acid
  • Carbamic acid derivative
  • Carboxamide group
  • Hemiacetal
  • Carbonic acid derivative
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organonitrogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Area227.5 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.39 m³·mol⁻¹ChemAxon
Polarizability39.64 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pvj-8639200000-6c3347b5dbe3b3f9c2c3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-4431129000-6a66b04ba8ecc3e96ae2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kyr-1029500000-cd23e338ffeece93c8d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l6r-1596200000-dfb00a2cbc9b167897ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-8879000000-3e843b304076403ca7adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-2291000000-09b27f575d21cfe14882Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-7595200000-da369f627875da3f63d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-114i-9720000000-64ac9bbabb821260cc03Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Testis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023196
KNApSAcK IDNot Available
Chemspider ID17216232
KEGG Compound IDC01674
BioCyc IDCHITOBIOSE
BiGG IDNot Available
Wikipedia LinkChitobiose
METLIN ID6953
PubChem Compound22833609
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDHC00822
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