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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
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 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
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

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.
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.