ChemSpider 2D Image | Rigosertib | C21H25NO8S

Rigosertib

  • Molecular FormulaC21H25NO8S
  • Average mass451.490 Da
  • Monoisotopic mass451.130096 Da
  • ChemSpider ID5293927

  • Double-bond stereo - Double-bond stereo

More details:

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

1910 Na
592542-59-1 [RN]
Glycine, N-[2-methoxy-5-[[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl]methyl]phenyl]- [ACD/Index Name]
N-[2-Methoxy-5-({[(E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfonyl}methyl)phenyl]glycin [German] [ACD/IUPAC Name]
N-[2-Methoxy-5-({[(E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfonyl}methyl)phenyl]glycine [ACD/IUPAC Name]
N-[2-Méthoxy-5-({[(E)-2-(2,4,6-triméthoxyphényl)vinyl]sulfonyl}méthyl)phényl]glycine [French] [ACD/IUPAC Name]
Rigosertib [INN] [USAN]
Rigosertib [Spanish] [INN]
Rigosertib [French] [INN]
Rigosertibum [Latin] [INN]
More...

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

67DOW7F9GL [DBID]
9516 [DBID]
ON 01910 [DBID]
UNII:67DOW7F9GL [DBID]
UNII-67DOW7F9GL [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An N-[2-methoxy-5-({[2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl}methyl)phenyl]glycine in which the double bond has E-configuration. It is a non-ATP-competitive inhibitor of PLK1 with an IC50 of 9 nM a nd exhibits anti-cancer properties. ChEBI CHEBI:145417

    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-12037A
      Cell Cycle/DNA Damage; MedChem Express HY-12037A
      Polo-like Kinase (PLK) MedChem Express HY-12037A
      Rigosertib (ON-01910) is a non-ATP-competitive inhibitor of PLK1 with IC50 of 9 nM; shows 30-fold greater selectivity against PLK2 and no activity to PLK3. MedChem Express
      Rigosertib (ON-01910) is a non-ATP-competitive inhibitor of PLK1 with IC50 of 9 nM; shows 30-fold greater selectivity against PLK2 and no activity to PLK3.; IC50 Value: 9 nM [1] ; Target: PLK1; in vitro: ON 01910.Na induced apoptosis in CLL B cells without significant toxicity against T cells or normal B cells. MedChem Express HY-12037A
      Rigosertib (ON-01910) is a non-ATP-competitive inhibitor of PLK1 with IC50 of 9 nM; shows 30-fold greater selectivity against PLK2 and no activity to PLK3.;IC50 Value: 9 nM [1] ;Target: PLK1;In vitro: ON 01910.Na induced apoptosis in CLL B cells without significant toxicity against T cells or normal B cells. ON 01910.Na was equally active against leukemic cells associated with a more aggressive disease course [immunoglobulin heavy-chain variable region unmutated, adverse cytogenetics] than against cells without these features. Gene expression profiling revealed two main mechanisms of action: PI3K/AKT inhibition and induction of ROS that resulted in an oxidative stress response through activating protein 1 (AP-1), c-jun-NH(2)-terminal kinase, and ATF3 culminating in the upregulation of NOXA. ROS scavengers and shRNA mediated knockdown of ATF3- and NOXA-protected cells from drug-induced apoptosis [2]. ON 01910.Na caused hyperphosphorylation of RanGAP1?SUMO1 within 4 hours that was su MedChem Express HY-12037A

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 756.1±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 115.6±3.0 kJ/mol
Flash Point: 411.1±32.9 °C
Index of Refraction: 1.589
Molar Refractivity: 114.1±0.4 cm3
#H bond acceptors: 9
#H bond donors: 2
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 0
ACD/LogP: 1.98
ACD/LogD (pH 5.5): 0.80
ACD/BCF (pH 5.5): 1.23
ACD/KOC (pH 5.5): 18.30
ACD/LogD (pH 7.4): -0.98
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 129 Å2
Polarizability: 45.2±0.5 10-24cm3
Surface Tension: 52.7±3.0 dyne/cm
Molar Volume: 338.7±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) =  1.79

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  601.58  (Adapted Stein & Brown method)
    Melting Pt (deg C):  260.05  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.8E-013  (Modified Grain method)
    Subcooled liquid VP: 6.71E-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):  106.3
       log Kow used: 1.79 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  116.17 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Sulfones-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.92E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.006E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.79  (KowWin est)
  Log Kaw used:  -17.438  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.228
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8992
   Biowin2 (Non-Linear Model)     :   0.9870
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1986  (months      )
   Biowin4 (Primary Survey Model) :   3.7820  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2222
   Biowin6 (MITI Non-Linear Model):   0.0138
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5333
 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):  8.95E-009 Pa (6.71E-011 mm Hg)
  Log Koa (Koawin est  ): 19.228
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  335 
       Octanol/air (Koa) model:  4.15E+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 = 274.0382 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 281.6382 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   28.102 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   27.344 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.050000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.091 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =   785.828 Min (at 7E11 mol/cm3) [Trans-isomer]
   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    :  3298
      Log Koc:  3.518 

 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: 1.79 (estimated)

 Volatilization from Water:
    Henry LC:  8.92E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.395E+016  hours   (5.811E+014 days)
    Half-Life from Model Lake : 1.521E+017  hours   (6.34E+015 days)

 Removal In Wastewater Treatment:
    Total removal:               2.09  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.00  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       1.69e-008       0.904        1000       
   Water     27.9            1.44e+003    1000       
   Soil      72              2.88e+003    1000       
   Sediment  0.0885          1.3e+004     0          
     Persistence Time: 1.7e+003 hr

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