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
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:
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 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
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

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.
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
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
General function:
Not Available
Specific function:
Not Available
Gene Name:
yniC
Uniprot ID:
P77247
Molecular weight:
Not Available

Transporters

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
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