ChemSpider 2D Image | Reversine | C21H27N7O


  • Molecular FormulaC21H27N7O
  • Average mass393.485 Da
  • Monoisotopic mass393.227722 Da
  • ChemSpider ID182286

More details:

Featured data source

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

1H-purine-2,6-diamine, N6-cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-
656820-32-5 [RN]
9H-Purine-2,6-diamine, N6-cyclohexyl-N2-[4-(4-morpholinyl)phenyl]- [ACD/Index Name]
N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-3H-purin-2,6-diamin [German] [ACD/IUPAC Name]
N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-3H-purine-2,6-diamine [ACD/IUPAC Name]
N6-Cyclohexyl-N2-[4-(4-morpholinyl)phényl]-3H-purine-2,6-diamine [French] [ACD/IUPAC Name]
Reversine [Wiki]

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

  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1629
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1629
      no pictogram Axon Medchem 1629
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1629
      Warning Axon Medchem 1629
    • Target Organs:

      Adenosine receptor antagonist;Aurora kinase inhibitor TargetMol T1825
    • Chemical Class:

      A member of the class of purines that is 9<element>H</element>-purine in which the hydrogens at positions 2 and 6 are replaced by a [4-(morpholin-4-yl)phenyl]nitrilo group and a cyclohexylamino group, respectively. ChEBI CHEBI:70723
    • Bio Activity:

      Aurora Kinase MedChem Express HY-14711
      Cell Cycle/DNA Damage MedChem Express HY-14711
      Cell Cycle/DNA Damage; MedChem Express HY-14711
      GPCR/G Protein TargetMol T1825
      human A3 adenosine receptor; Aurora A/B/C TargetMol T1825
      Reversine, a small synthetic purine analogue (2,6-disubstituted purine), is a potent inhibitior of Aurora A/B/C with IC50s of 150-500 nM. MedChem Express, HY-14711
      Reversine, a small synthetic purine analogue (2,6-disubstituted purine), is a potent inhibitior of Aurora A/B/C with IC50s of 150-500 nM. ;IC50 Value: 150 nM (Aurora Kinase A); 500 nM (Aurora Kinase B); 400 nM (Aurora Kinase C) [1];Target: pan-Aurora Kinase;In vitro: Reversine induced apoptosis in PDTC cells with caspase-3 and caspase-8 activation, but not caspase-9. Use of a pan-caspase inhibitor before treatment with reversine attenuated cell death [2]. Reversine significantly suppressed the proliferation of two OSCC cell lines (OC2 and OCSL) and markedly rendered cell cycle arrest at G2/M stage. Reversine also induced cell death via both caspase-dependent and -independent apoptosis. In addition,reversine could inhibit Akt/mTORC1 signaling pathway, accounting for its ability to induce autophagy [3]. Reversine pre-treatment, at very low concentration (50 nM), caused a marked increase in the differentiation yields of both BMSCs and ASCs [4].;In vivo: In the therapeutic mouse model MedChem Express HY-14711

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

Density: 1.3±0.1 g/cm3
Boiling Point: 736.4±70.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 107.4±3.0 kJ/mol
Flash Point: 399.2±35.7 °C
Index of Refraction: 1.712
Molar Refractivity: 114.6±0.3 cm3
#H bond acceptors: 8
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.23
ACD/LogD (pH 5.5): 2.12
ACD/BCF (pH 5.5): 18.43
ACD/KOC (pH 5.5): 204.36
ACD/LogD (pH 7.4): 2.59
ACD/BCF (pH 7.4): 54.47
ACD/KOC (pH 7.4): 604.06
Polar Surface Area: 91 Å2
Polarizability: 45.4±0.5 10-24cm3
Surface Tension: 77.8±3.0 dyne/cm
Molar Volume: 292.9±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) =  4.04

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  630.09  (Adapted Stein & Brown method)
    Melting Pt (deg C):  273.37  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.21E-014  (Modified Grain method)
    Subcooled liquid VP: 1.2E-011 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):  1.199
       log Kow used: 4.04 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  457.95 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.11E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.543E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.04  (KowWin est)
  Log Kaw used:  -15.064  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.104
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.4599
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7962  (months      )
   Biowin4 (Primary Survey Model) :   2.7655  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.6262
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.5695
 Ready Biodegradability Prediction:   NO

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.6E-009 Pa (1.2E-011 mm Hg)
  Log Koa (Koawin est  ): 19.104
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.87E+003 
       Octanol/air (Koa) model:  3.12E+006 
   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 = 509.1800 E-12 cm3/molecule-sec
      Half-Life =     0.021 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    15.125 Min
   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    :  1625
      Log Koc:  3.211 

 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 = 2.408 (BCF = 256)
       log Kow used: 4.04 (estimated)

 Volatilization from Water:
    Henry LC:  2.11E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.504E+013  hours   (2.293E+012 days)
    Half-Life from Model Lake : 6.005E+014  hours   (2.502E+013 days)

 Removal In Wastewater Treatment:
    Total removal:              31.92  percent
    Total biodegradation:        0.34  percent
    Total sludge adsorption:    31.59  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       1.39e-005       0.504        1000       
   Water     8.44            1.44e+003    1000       
   Soil      88.8            2.88e+003    1000       
   Sediment  2.79            1.3e+004     0          
     Persistence Time: 2.93e+003 hr


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