ChemSpider 2D Image | napabucasin | C14H8O4

napabucasin

  • Molecular FormulaC14H8O4
  • Average mass240.211 Da
  • Monoisotopic mass240.042252 Da
  • ChemSpider ID8507304

More details:

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

2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione
2-acetylbenzo[f][1]benzofuran-4,9-dione
2-Acetylnaphtho[2,3-b]furan-4,9-dion [German] [ACD/IUPAC Name]
2-Acetylnaphtho[2,3-b]furan-4,9-dione [ACD/IUPAC Name]
2-Acetyl-naphtho[2,3-b]furan-4,9-dione
2-Acétylnaphto[2,3-b]furane-4,9-dione [French] [ACD/IUPAC Name]
83280-65-3 [RN]
napabucasin [INN] [USAN]
napabucasina [Spanish] [INN]
napabucasine [French] [INN]
More...

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

9848 [DBID]
BBI608 [DBID]
BBI-608 [DBID]
CCRIS 4693 [DBID]
PubChem Substance ID 329825761 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Cell Biology Tocris Bioscience 5522
      Cytokine and NF-kB Signaling Tocris Bioscience 5522
      Napabucasin is an orally-administered small molecule which can block cancer stem cell (CSC) self-renewal and induces cell death in CSCs as well as non-stem cancer cells. MedChem Express
      Napabucasin is an orally-administered small molecule which can block cancer stem cell (CSC) self-renewal and induces cell death in CSCs as well as non-stem cancer cells.; IC50 Value: ; Target: cancer cell stemness; Napabucasin is an orally available cancer cell stemness inhibitor with potential antineoplastic activity. MedChem Express HY-13919
      Napabucasin is an orally-administered small molecule which can block cancer stem cell (CSC) self-renewal and induces cell death in CSCs as well as non-stem cancer cells.;IC50 Value: ;Target: cancer cell stemnessNapabucasin is an orally available cancer cell stemness inhibitor with potential antineoplastic activity. Even though the exact target has yet to be fully elucidated, Napabucasin appears to target and inhibit multiple pathways involved in cancer cell stemness. This may ultimately inhibit cancer stemness cell (CSC) growth as well as heterogeneous cancer cell growth. CSCs, self-replicating cells that are able to differentiate into heterogeneous cancer cells, appear to be responsible for the malignant growth, recurrence and resistance to conventional chemotherapies.Adverse events for Napabucasin were generally mild; the most common being grade 1-2 diarrhea, nausea, anorexia and fatigue with a total of 4 grade 3 events (diarrhea and fatigue), and there were no grade 4 events. MedChem Express HY-13919
      Others MedChem Express HY-13919
      Signal Transduction Tocris Bioscience 5522
      STAT Tocris Bioscience 5522
      STAT3 inhibitor. Blocks spherogenesis of cancer stem cells (CSC), but not hematopoietic stem cells. Inhibits PaCa-2 xenograft tumor growth in mice, even after cessation of treatment, and decreases pop ulation of CSCs in PaCa-2 tumors from treated mice. Also blocks spleen and liver metastases of colon cancer cells in a mouse model. Tocris Bioscience 5522
      STAT3 inhibitor. Blocks spherogenesis of cancer stem cells (CSC), but not hematopoietic stem cells. Inhibits PaCa-2 xenograft tumor growth in mice, even after cessation of treatment, and decreases population of CSCs in PaCa-2 tumors from treated mice. Also blocks spleen and liver metastases of colon cancer cells in a mouse model. Tocris Bioscience 5522
      STAT3 inhibitor; also blocks cancer stem cell self-renewal Tocris Bioscience 5522
      STAT3 inhibitor; blocks cancer stem cell self-renewal Tocris Bioscience 5522

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

Density: 1.4±0.1 g/cm3
Boiling Point: 444.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 70.2±3.0 kJ/mol
Flash Point: 216.4±21.4 °C
Index of Refraction: 1.621
Molar Refractivity: 61.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.68
ACD/LogD (pH 5.5): 2.07
ACD/BCF (pH 5.5): 21.98
ACD/KOC (pH 5.5): 317.82
ACD/LogD (pH 7.4): 2.07
ACD/BCF (pH 7.4): 21.98
ACD/KOC (pH 7.4): 317.82
Polar Surface Area: 64 Å2
Polarizability: 24.2±0.5 10-24cm3
Surface Tension: 55.7±3.0 dyne/cm
Molar Volume: 173.4±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) =  2.15

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  389.30  (Adapted Stein & Brown method)
    Melting Pt (deg C):  152.16  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.64E-007  (Modified Grain method)
    Subcooled liquid VP: 1.51E-005 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):  30.5
       log Kow used: 2.15 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  50.807 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.78E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.918E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.15  (KowWin est)
  Log Kaw used:  -9.627  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.777
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6537
   Biowin2 (Non-Linear Model)     :   0.1466
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6009  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4345  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3922
   Biowin6 (MITI Non-Linear Model):   0.2161
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8963
 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):  0.00201 Pa (1.51E-005 mm Hg)
  Log Koa (Koawin est  ): 11.777
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00149 
       Octanol/air (Koa) model:  0.147 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0511 
       Mackay model           :  0.107 
       Octanol/air (Koa) model:  0.922 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   7.4105 E-12 cm3/molecule-sec
      Half-Life =     1.443 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    17.320 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0788 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  497.4
      Log Koc:  2.697 

 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 = 0.113 (BCF = 1.298)
       log Kow used: 2.15 (estimated)

 Volatilization from Water:
    Henry LC:  5.78E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.57E+008  hours   (6.542E+006 days)
    Half-Life from Model Lake : 1.713E+009  hours   (7.136E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               2.41  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.31  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       5.61e-005       34.6         1000       
   Water     20.5            900          1000       
   Soil      79.4            1.8e+003     1000       
   Sediment  0.0957          8.1e+003     0          
     Persistence Time: 1.5e+003 hr

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