ChemSpider 2D Image | 2-DG | C6H12O5

2-DG

  • Molecular FormulaC6H12O5
  • Average mass164.156 Da
  • Monoisotopic mass164.068466 Da
  • ChemSpider ID388402
  • defined stereocentres - 3 of 4 defined stereocentres


More details:



Featured data source



Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(4R,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol
(4R,5S,6R)-6-(Hydroxyméthyl)tétrahydro-2H-pyran-2,4,5-triol
2-Deoxy-D-arabino-hexopyranose [ACD/IUPAC Name]
2-Deoxy-D-glucose
2-deoxyglucose
2-Desoxy-D-arabino-hexopyranose [German] [ACD/IUPAC Name]
2-Désoxy-D-arabino-hexopyranose [French] [ACD/IUPAC Name]
2-DG
D-arabino-2-Desoxyhexose
D-arabino-Hexopyranose, 2-deoxy- [ACD/Index Name]
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Ba 2758 [DBID]
AIDS000097 [DBID]
AIDS-000097 [DBID]
Bio1_000485 [DBID]
Bio1_000974 [DBID]
Bio1_001463 [DBID]
C00586 [DBID]
D3179_SIGMA [DBID]
D6134_SIGMA [DBID]
D8375_SIGMA [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Irritant SynQuest 2H12-1-X4, 68060
      R36/37/38 SynQuest 2H12-1-X4, 68060
    • Bio Activity:

      2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its actions on hexokinase, the rate limiting step of glycolysis. MedChem Express HY-13966, http://www.medchemexpress.com/AMG-837.html
      2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its actions on hexokinase, the rate limiting step of glycolysis. It is phosphorylated by hexokinase to 2-DG-P which cannot be further metabolized by phosphoglucose isomerase.;IC50 Value: ;Target: Hexokinase; Glycolysis inhibitor;In vitro: Across all 16 tumor cell lines, there was a significant correlation between DG uptake and 3-O-MG transport (p = 0.0012, F test), but not between DG uptake and hexokinase activity. Hexokinase activity of the tumor cells was comparable to that of the human fibroblast cells in the exponential growth phase. Most tumor cells showed higher DG uptake and 3-O-MG transport than the human fibroblast cells [1]. 2-DG treatment increased the levels of pentose phosphate pathway (PPP) metabolites and augmented the generation of NADPH by glucose-6-phosphate dehydrogenase. An increase in NADPH and upregulation of glutathione synthetase expression resulted in the increase in the red MedChem Express HY-13966
      Enzymes Tocris Bioscience 4515
      Hexokinase MedChem Express HY-13966
      Hexokinases Tocris Bioscience 4515
      Kinases Tocris Bioscience 4515
      Non-metabolizable glucose analog. Inhibits phosphorylation of glucose by hexokinase; causes depletion of cellular ATP. Also inhibits phosphoglucose isomerase (PGI) competitively. Causes cell cycle inh ibition and cell death in in vitro models of hypoxia; blocks tumor cell growth in animal models. Also shown to induce the unfolded protein response (UPR). Tocris Bioscience 4515
      Non-metabolizable glucose analog. Inhibits phosphorylation of glucose by hexokinase; causes depletion of cellular ATP. Also inhibits phosphoglucose isomerase (PGI) competitively. Causes cell cycle inhibition and cell death in in vitro models of hypoxia; blocks tumor cell growth in animal models. Also shown to induce the unfolded protein response (UPR). Tocris Bioscience 4515
      Non-metabolizable glucose analog; hexokinase substrate Tocris Bioscience 4515
      Others MedChem Express HY-13966

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.5±0.1 g/cm3
Boiling Point: 411.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 76.6±6.0 kJ/mol
Flash Point: 202.3±28.7 °C
Index of Refraction: 1.581
Molar Refractivity: 35.7±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -1.46
ACD/LogD (pH 5.5): -1.08
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 6.18
ACD/LogD (pH 7.4): -1.08
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 6.18
Polar Surface Area: 90 Å2
Polarizability: 14.1±0.5 10-24cm3
Surface Tension: 66.9±3.0 dyne/cm
Molar Volume: 107.0±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -2.76

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  344.27  (Adapted Stein & Brown method)
    Melting Pt (deg C):  107.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.78E-007  (Modified Grain method)
    Subcooled liquid VP: 1.8E-006 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1e+006
       log Kow used: -2.76 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.66E-013  atm-m3/mole
   Group Method:   8.48E-022  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  6.005E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.76  (KowWin est)
  Log Kaw used:  -10.964  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.204
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9570
   Biowin2 (Non-Linear Model)     :   0.8481
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.4676  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.1190  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9887
   Biowin6 (MITI Non-Linear Model):   0.8634
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.1737
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.00024 Pa (1.8E-006 mm Hg)
  Log Koa (Koawin est  ): 8.204
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0125 
       Octanol/air (Koa) model:  3.93E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.311 
       Mackay model           :  0.5 
       Octanol/air (Koa) model:  0.00313 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  95.3881 E-12 cm3/molecule-sec
      Half-Life =     0.112 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.346 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.406 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -2.76 (estimated)

 Volatilization from Water:
    Henry LC:  2.66E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  2.82E+009  hours   (1.175E+008 days)
    Half-Life from Model Lake : 3.076E+010  hours   (1.282E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       1.4e-005        2.69         1000       
   Water     34.5            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr




                    

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