2-deoxy-D-glucose (YMDB00294)

Identification
YMDB IDYMDB00294
Name2-deoxy-D-glucose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Deoxyglucose, also known as 2-deoxy-D-mannose or D-2DGLC, 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. 2-Deoxyglucose is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-(acetylamino)-2-deoxyhexose
  • 2-acetamido-2-deoxy-d-glucose
  • 2-Acetamido-2-deoxyglucose
  • 2-Acetamido-D-glucose
  • 2-Acetylamino-2-deoxy-beta-d-glucopyranose
  • 2-Acetylamino-2-deoxy-D-glucose
  • 2-Deoxy-D-arabino-hexose
  • 2-Deoxy-D-glucose
  • 2-Deoxy-D-mannose
  • Acetylglucosamine
  • D-2dGlc
  • D-arabino-2-Deoxyhexose
  • D-Glucose, 2-(acetylamino)-2-deoxy-
  • D-Glucose, 2-acetamido-2-deoxy-
  • Deoxyglucose
  • glcnac
  • Glucosamine Complex
  • N-Acetyl-alpha-D-glucosamine
  • N-acetyl-beta-D-glucosamine
  • N-Acetyl-D-glucosamine
  • N-Acetyl-D-glucosamine-Agarose
  • n-acetylchitosamine
  • N-acetylglucosamine
  • NAG
  • 2 Deoxy D glucose
  • 2 Deoxyglucose
  • 2 Desoxy D glucose
  • 2-Desoxy-D-glucose
CAS number7512-17-6
WeightAverage: 164.1565
Monoisotopic: 164.068473494
InChI KeyVRYALKFFQXWPIH-PBXRRBTRSA-N
InChIInChI=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
IUPAC Name(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
Traditional IUPAC Namedeoxyglucose
Chemical FormulaC6H12O5
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
StateSolid
Charge0
Melting point210 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility379 g/LALOGPS
logP-2ALOGPS
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 LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0q29-1951000000-06cc16a9680628545167JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0lkc-0951000000-39e56efe41d6473040e4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr5-0920000000-5f7dfef22a1b59cae284JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0920000000-6f9638179f688d51022eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ir0-9400000000-0d9dd630f3590782a74eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-054t-9258700000-0738ee18a80ba8e5b90aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-3900000000-45865b9816a45604d811JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ow-9200000000-7b5a5cbd361ec11efbbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0707-9000000000-c9e6d3430eb1073f0d79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-5900000000-90300437f9ab1170e562JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k96-9400000000-a11cb0518964ee7a83ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b4574a9d519fced6b332JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-6900000000-319e473c192f4b110b8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-d161d9b754ebaeb29a74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0a62c56f2a4845f4d597JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08ml-9700000000-9df4724be189ef01f655JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abc-9000000000-e85603d6bed71b3882e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4ed5058ebfd661cb8c61JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Zhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp.
External Links:
ResourceLink
CHEBI ID15866
HMDB IDHMDB00215
Pubchem Compound ID40
Kegg IDC00140
ChemSpider ID24824239
FOODB IDNot Available
Wikipedia2-Deoxy-D-glucose
BioCyc IDALPHA-D-GALACTOSYL-13-BETA-D-GALACTOS

Enzymes

Protein Details
1. 2-deoxyglucose-6-phosphate phosphatase 1
General function:
Involved in catalytic activity
Specific function:
Active on 2-DOG-6P, also very active on fructose-1P
Gene Name:
DOG1
Uniprot ID:
P38774
Molecular weight:
27099.59961
Reactions
2-deoxy-D-glucose 6-phosphate + H(2)O → 2-deoxy-D-glucose + phosphate.
Protein Details
2. 2-deoxyglucose-6-phosphate phosphatase 2
General function:
Involved in catalytic activity
Specific function:
Active on 2-DOG-6P, not very active on fructose-1p
Gene Name:
DOG2
Uniprot ID:
P38773
Molecular weight:
27164.80078
Reactions
2-deoxy-D-glucose 6-phosphate + H(2)O → 2-deoxy-D-glucose + phosphate.