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Diacetylchitobiose-6-phosphate (M2MDB001353)

Record Information
Version2.0
Creation Date2012-05-31 14:50:02 -0600
Update Date2015-06-03 17:20:12 -0600
Secondary Accession Numbers
  • ECMDB20547
Identification
Name:Diacetylchitobiose-6-phosphate
DescriptionDiacetylchitobiose-6-phosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates. Diacetylchitobiose-6-phosphate is invovled in Chitobiose transport. r 15;80(8):2939-48.)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Chitobiose-6-phosphate
  • Chitobiose-6-phosphoric acid
  • Diacetylchitobiose-6-phosphoric acid
Chemical Formula:C16H29N2O14P
Weight:Average: 504.3802
Monoisotopic: 504.135640158
InChI Key:KYKNQNQCPWDNAK-MVGRPQHISA-N
InChI:InChI=1S/C16H29N2O14P/c1-5(20)17-9-13(24)14(7(3-19)30-15(9)25)32-16-10(18-6(2)21)12(23)11(22)8(31-16)4-29-33(26,27)28/h7-16,19,22-25H,3-4H2,1-2H3,(H,17,20)(H,18,21)(H2,26,27,28)/t7-,8-,9-,10-,11-,12-,13-,14-,15-,16-/m1/s1
CAS number:Not Available
IUPAC Name:N-[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
Traditional IUPAC Name:N-[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
SMILES:[H][C@@]1(O)O[C@]([H])(CO)[C@@]([H])(O[C@@]2([H])O[C@]([H])(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@]([H])(O)[C@@]1([H])N=C(C)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Disaccharide phosphate
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility35.6 g/LALOGPS
logP-2.2ALOGPS
logP-3.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area260.78 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity102.46 m³·mol⁻¹ChemAxon
Polarizability44.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Diacetylchitobiose-6-phosphate + Water > N-Acetyl-D-glucosamine + N-Acetyl-D-Glucosamine 6-Phosphate
Phosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + Chitobiose > Pyruvic acid + Diacetylchitobiose-6-phosphate
Diacetylchitobiose-6-phosphate + Water > N'-monoacetylchitobiose-6'-phosphate + Acetic acid
Diacetylchitobiose + HPr - phosphorylated > Diacetylchitobiose-6-phosphate + HPr
SMPDB Pathways:
Chitobiose DegradationPW002042 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_29) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bti-0020920000-d5283ea4ab5ca7458573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-1291500000-9665edc551e13bac5385View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-5494100000-70f30680c95a1814cafcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4429200000-928921e8dab8443a8d39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110100000-1804dcbc8687caab26bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-4b88275f462c34993c21View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25200795
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDDIACETYLCHITOBIOSE-6-PHOSPHATE
EcoCyc IDDIACETYLCHITOBIOSE-6-PHOSPHATE

Enzymes

Protein Details
1. PTS system mannitol-specific EIICBA component
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport
Gene Name:
mtlA
Uniprot ID:
P00550
Molecular weight:
67972
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
2. Phosphoenolpyruvate-protein phosphotransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
Protein Details
3. 6-phospho-beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
Gene Name:
chbF
Uniprot ID:
P17411
Molecular weight:
50512
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
Protein Details
4. Chitooligosaccharide deacetylase ChbG
General function:
polysaccharide catabolic process
Specific function:
ChbG is essential for growth on the acetylated chitooligosaccharides chitobiose and chitotriose but is dispensable for growth on cellobiose and chitosan dimer, the deacetylated form of chitobiose. Deacetylation of chitobiose-6-P and chitotriose-6-P is necessary for both the activation of the chb promoter by the regulatory protein ChbR and the hydrolysis of phosphorylated beta-glucosides by the phospho-beta-glucosidase ChbF. Catalyzes the removal of only one acetyl group from chitobiose-6-P to yield monoacetylchitobiose-6-P, the inducer of ChbR and the substrate of ChbF. It can also use chitobiose and chitotriose as substrates.
Gene Name:
chbG
Uniprot ID:
P37794
Molecular weight:
27773
Reactions
2-(acetylamino)-4-O-(2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose + H(2)O = 2-(acetylamino)-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose + acetate

Transporters

Protein Details
1. PTS system mannitol-specific EIICBA component
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport
Gene Name:
mtlA
Uniprot ID:
P00550
Molecular weight:
67972
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.