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

AR-100 [DBID]
D02742 [DBID]
NSC 105823 [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
      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
      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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