ContaminantDB: Chitobiose

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:34 UTC

Update Date

2026-04-06 13:27:59 UTC

Accession Number

CHEM003428

Identification

Common Name

Chitobiose

Class

Small Molecule

Description

Chitobiose 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.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CBS	HMDB
Chitodextrin	HMDB
Diacetylchitobiose	HMDB

Chemical Formula

C₁₅H₂₆N₂O₁₂

Average Molecular Mass

426.373 g/mol

Monoisotopic Mass

426.149 g/mol

CAS Registry Number

577-76-4

IUPAC Name

Not Available

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

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 Key

HSRZMOSQMYFZBL-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Testes

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Tay-Sachs Disease	SMP00390	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	101 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-4.8	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	227.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.39 m³·mol⁻¹	ChemAxon
Polarizability	39.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pvj-8639200000-6c3347b5dbe3b3f9c2c3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-004i-4431129000-6a66b04ba8ecc3e96ae2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kyr-1029500000-cd23e338ffeece93c8d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0l6r-1596200000-dfb00a2cbc9b167897ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xu-8879000000-3e843b304076403ca7ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6x-2291000000-09b27f575d21cfe14882	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pi0-7595200000-da369f627875da3f63d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-114i-9720000000-64ac9bbabb821260cc03	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0019200000-24a05e9c2b0aef9d97c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0acc-4229100000-ea4966254c54c4e1c671	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-9342000000-d67950a3955201982141	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0140900000-421220daa6be82144fb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1984300000-1dd32aad758490afc646	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0wmu-9710000000-b4b4aee4a3748673917c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

There is ambiguity as to which structure the name refers, owing to the method by which it was first isolated.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0003556

FooDB ID

FDB023196

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CHITOBIOSE

METLIN ID

6953

PDB ID

Not Available

Wikipedia Link

Chitobiose

Chemspider ID

17216232

ChEBI ID

Not Available

PubChem Compound ID

22833609

Kegg Compound ID

C01674

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Cottaz, 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.

MSDS

Not Available

General References

1. Cottaz, 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.

2. 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.

3. 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.

4. 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.

Chitobiose (CHEM003428)

Structure for CHEM003428: Chitobiose