ChemSpider 2D Image | Acadesine | C9H14N4O5

Acadesine

  • Molecular FormulaC9H14N4O5
  • Average mass258.231 Da
  • Monoisotopic mass258.096405 Da
  • ChemSpider ID16560
  • defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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

1H-Imidazole-4-carboxamide, 5-amino-1-β-D-ribofuranosyl- [ACD/Index Name]
1H-Imidazole-4-carboxamide, 5-amino-1-β-D-ribofuranosyl-
220-097-5 [EINECS]
2627-69-2 [RN]
53IEF47846
5-Amino-1-(β-D-ribofuranosyl)-1H-imidazol-4-carboxamid [German] [ACD/IUPAC Name]
5-Amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxamide [ACD/IUPAC Name]
5-Amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxamide [French] [ACD/IUPAC Name]
5-Amino-1-b-D-ribofuranosyl-1H-imidazole-4-carboxamide
5-Amino-1-β-ribofuranosyl-imidazole-4-carboxamide
More...

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

AR-100 [DBID]
D02742 [DBID]
NSC 105823 [DBID]
R 33812 | [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS07 Biosynth W-202116
      H315; H319; H335 Biosynth W-202116
      IRRITANT Matrix Scientific 094525
      Irritant/Hygroscopic/Store under Argon/Store at -20?C SynQuest 4H56-1-K6, 64674
      Irritant/Hygroscopic/Store under Argon/Store at -20°C SynQuest 4H56-1-K6
      P261; P305+P351+P338 Biosynth W-202116
      Warning Biosynth W-202116
    • Target Organs:

      AMPK activator TargetMol T1477
    • Chemical Class:

      A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analog ue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects. ChEBI CHEBI:28498
    • Bio Activity:

      AICAR (Acadesine), is an AMP-activated protein kinase activator, which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes.; Target: AMPK; AICAR, also known as 5-aminoimidazole-4-carboxamide-1-?-D-ribofuranoside, AICA-riboside, and Acadesine, is an AMP-activated protein kinase activator, which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes. MedChem Express HY-13417
      AMPK Tocris Bioscience 2840
      AMPK MedChem Express HY-13417
      AMPK TargetMol T1477
      AMPK activator Tocris Bioscience 2840
      AMPK activator. Promotes osteogenic differentiation of bone marrow-derived MSCs. Hello Bio [HB2152]
      Biochemicals & small molecules/Agonists & activators Hello Bio [HB2152]
      Cell permeable AMP-activated protein kinase (AMPK) activator. Down-regulates insulin receptor expression. Promotes differentiation and mineralization of MC3T3-E1 osteoblastic cells. Also promotes osteogenic differentiation of mensenchymal stem cells and induces astroglial differentiation in neural stem cells. Additionaly induces expression of several key regulators of pulripotency in somatic cells. Hello Bio [HB2152]
      Cell process/Stem cells/Differentiation Hello Bio [HB2152]
      Cell-permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI cells and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes. Promotes osteogenic differentiation of hAMSCs and BM-MSCs in vitro. Tocris Bioscience 2840
      Cell-permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI cells and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes. Promotes osteogenic differentiation of hAMSCs and BM-MSCs in vitro. Tocris Bioscience 2840
      Enzymes Tocris Bioscience 2840
      Enzymes/Kinase/AMPK Hello Bio [HB2152]
      Kinases Tocris Bioscience 2840
      PI3K/Akt/mTOR MedChem Express HY-13417
      PI3K/Akt/mTOR Signaling TargetMol T1477
      PI3K/Akt/mTOR; MedChem Express HY-13417

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

Density: 2.1±0.1 g/cm3
Boiling Point: 726.3±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 111.3±3.0 kJ/mol
Flash Point: 393.1±32.9 °C
Index of Refraction: 1.821
Molar Refractivity: 54.6±0.5 cm3
#H bond acceptors: 9
#H bond donors: 7
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: -2.93
ACD/LogD (pH 5.5): -2.49
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.04
ACD/LogD (pH 7.4): -2.49
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.05
Polar Surface Area: 157 Å2
Polarizability: 21.6±0.5 10-24cm3
Surface Tension: 106.5±7.0 dyne/cm
Molar Volume: 125.2±7.0 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) =  -2.12

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  567.01  (Adapted Stein & Brown method)
    Melting Pt (deg C):  243.90  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.14E-015  (Modified Grain method)
    MP  (exp database):  213 dec deg C
    Subcooled liquid VP: 1.14E-013 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):  6.793e+004
       log Kow used: -2.12 (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:
       Aromatic Amines
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.65E-025  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.702E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.12  (KowWin est)
  Log Kaw used:  -22.451  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.331
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7298
   Biowin2 (Non-Linear Model)     :   0.5125
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9106  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9508  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5051
   Biowin6 (MITI Non-Linear Model):   0.0885
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2198
 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):  1.52E-011 Pa (1.14E-013 mm Hg)
  Log Koa (Koawin est  ): 20.331
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.97E+005 
       Octanol/air (Koa) model:  5.26E+007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  94.1292 E-12 cm3/molecule-sec
      Half-Life =     0.114 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.364 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 1 (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: -2.12 (estimated)

 Volatilization from Water:
    Henry LC:  8.65E-025 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.088E+021  hours   (4.532E+019 days)
    Half-Life from Model Lake : 1.187E+022  hours   (4.944E+020 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       1.1e-010        2.73         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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