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2-Deoxyglucose (M2MDB000480)

Record Information
Version2.0
Creation Date2012-05-31 13:57:58 -0600
Update Date2015-06-03 15:54:20 -0600
Secondary Accession Numbers
  • ECMDB03174
Identification
Name:2-Deoxyglucose
Description2-Deoxyglucose is a glucose molecule that has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. It can be used as a glycolysis inhibitor. 2-deoxyglucose is taken up by E. coli and is phosphorylated to 2-deoxyglucose-6P. Glucosamine, mannose and 2-deoxyglucose enter Escherichia coli by the component of the phosphotransferase system coded for by the gene ptsM. 2-Deoxyglucose is an unnatural glucose analog and is not considered a natural E. coli substrate or metabolite. 2-Deoxyglucose is a relatively rare yet natural monosaccharide that can be made from D-glucose, D-aminoglucose and a variety of amino-polysaccharides.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Deoxy-D-arabino-hexopyranose
  • 2-Deoxy-D-arabino-hexose
  • 2-Deoxy-D-arabinohexose
  • 2-Deoxy-D-glucose
  • 2-Deoxy-D-mannose
  • 2-deoxyglucose
  • 2-Deoxyhexose
  • 2-Desoxy-D-glucose
  • D-2-Deoxyglucose
  • D-2dGlc
  • D-Arabino-2-Deoxyhexose
  • D-Arabino-Hexose, 2-deoxy- ( )
  • Deoxyglucose
Chemical Formula:C6H12O5
Weight:Average: 164.1565
Monoisotopic: 164.068473494
InChI Key:VRYALKFFQXWPIH-PBXRRBTRSA-N
InChI:InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1
CAS number:154-17-6
IUPAC Name:(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
Traditional IUPAC Name:deoxyglucose
SMILES:[H]C([H])(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Medium-chain aldehyde
  • Beta-hydroxy aldehyde
  • Alpha-hydrogen aldehyde
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:146.5 °C
Experimental Properties:
PropertyValueSource
LogP:-2.361PhysProp
Predicted Properties
PropertyValueSource
Water Solubility379 g/LALOGPS
logP-1.9ALOGPS
logP-2.9ChemAxon
logS0.36ALOGPS
pKa (Strongest Acidic)12.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.01 m³·mol⁻¹ChemAxon
Polarizability15.47 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + 2-Deoxy-D-glucose 6-phosphate > Phosphate + 2-Deoxyglucose
2-Deoxy-D-glucose 6-phosphate + Water > 2-Deoxyglucose + Inorganic phosphate
2-Deoxyglucose + HPr - phosphorylated > 2-Deoxy-D-glucose 6-phosphate + HPr
SMPDB Pathways:
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0q29-1951000000-06cc16a9680628545167View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0lkc-0951000000-39e56efe41d6473040e4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr5-0920000000-5f7dfef22a1b59cae284View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0920000000-6f9638179f688d51022eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ir0-9400000000-0d9dd630f3590782a74eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-054t-9258700000-0738ee18a80ba8e5b90aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-3900000000-45865b9816a45604d811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ow-9200000000-7b5a5cbd361ec11efbbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0707-9000000000-c9e6d3430eb1073f0d79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-5900000000-90300437f9ab1170e562View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k96-9400000000-a11cb0518964ee7a83ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b4574a9d519fced6b332View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-6900000000-319e473c192f4b110b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-d161d9b754ebaeb29a74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0a62c56f2a4845f4d597View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08ml-9700000000-9df4724be189ef01f655View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abc-9000000000-e85603d6bed71b3882e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4ed5058ebfd661cb8c61View in MoNA
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
1D NMR13C 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15866
HMDB IDHMDB0062477
Pubchem Compound ID108223
Kegg IDC00586
ChemSpider ID97292
Wikipedia IDDeoxyglucose
BioCyc ID2-DEOXY-D-GLUCOSE
EcoCyc ID2-DEOXY-D-GLUCOSE

Enzymes

Protein Details
1. PTS system mannose-specific EIIAB component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
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 mannose transport
Gene Name:
manX
Uniprot ID:
P69797
Molecular weight:
35047
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. Mannose permease IIC component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
Protein Details
3. Mannose permease IID component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
Protein Details
4. 2-deoxyglucose-6-P phosphatase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yniC
Uniprot ID:
P77247
Molecular weight:
Not Available

Transporters

Protein Details
1. Mannose permease IIC component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
Protein Details
2. Mannose permease IID component
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303