ChemSpider 2D Image | Cercosporamide | C16H13NO7

Cercosporamide

  • Molecular FormulaC16H13NO7
  • Average mass331.277 Da
  • Monoisotopic mass331.069214 Da
  • ChemSpider ID116130

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

(9aS)-8-Acetyl-1,3,7-trihydroxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamid [German] [ACD/IUPAC Name]
(9aS)-8-Acetyl-1,3,7-trihydroxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide [ACD/IUPAC Name]
(9aS)-8-Acétyl-1,3,7-trihydroxy-9a-méthyl-9-oxo-9,9a-dihydrodibenzo[b,d]furane-4-carboxamide [French] [ACD/IUPAC Name]
(9aS)-8-acetyl-9,9a-dihydro-1,3,7-trihydroxy-9a-methyl-9-oxo-4-dibenzofurancarboxamide
131436-22-1 [RN]
4-Dibenzofurancarboxamide, 8-acetyl-9,9a-dihydro-1,3,7-trihydroxy-9a-methyl-9-oxo-, (9aS)- [ACD/Index Name]
Cercosporamide
(-)-Cercosporamide
(9aS)-8-acetyl-1,3,7-trihydroxy-9a-methyl-9-oxodibenzofuran-4-carboxamide
(S)-8-Acetyl-1,3,7-trihydroxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CCRIS 4693 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A member of the class of dibenzofurans that is a potent broad spectrum antifungal agent isolated from the fungus <ital>Cercosporidium henningsii</ital>. ChEBI CHEBI:78696
      A member of the class of dibenzofurans that is a potent broad spectrum antifungal agent isolated from the fungus Cercosporidium henningsii. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:78696, CHEBI:78696

    • Bio Activity:

      Antifungal MedChem Express HY-16982
      Antifungal MNK MedChem Express HY-16982
      Anti-infection MedChem Express HY-16982
      Anti-infection; MAPK/ERK Pathway; MedChem Express HY-16982
      Cercosporamide is a potent and selective Mnk inhibitor, and a orally bioavailable antifungal agent, suppresses phosphorylation of eIF4E and exhibits antileukemic effects. MedChem Express
      Cercosporamide is a potent and selective Mnk inhibitor, and a orally bioavailable antifungal agent, suppresses phosphorylation of eIF4E and exhibits antileukemic effects.; IC50 value:; Target: Mnk1; in vitro: Cercosporamide inhibits phosphorylation of eIF4E on Ser209 in AML cells and exhibits direct suppressive effects on leukemic progenitor cell growth, enhancing the antileukemic properties of mTORC1 inhibition by Rapamycin and promoting the suppressive effects of Cytarabine. MedChem Express HY-16982
      Cercosporamide is a potent and selective Mnk inhibitor, and a orally bioavailable antifungal agent, suppresses phosphorylation of eIF4E and exhibits antileukemic effects.;IC50 value:;Target: Mnk1;In vitro: Cercosporamide inhibits phosphorylation of eIF4E on Ser209 in AML cells and exhibits direct suppressive effects on leukemic progenitor cell growth, enhancing the antileukemic properties of mTORC1 inhibition by Rapamycin and promoting the suppressive effects of Cytarabine. ;In vivo: Cercosporamide is a selective and orally bioavailable Mnk1 inhibitor, which is previously shown to have activity against experimental melanoma lung metastases and subcutaneous colon carcinoma xenograft tumors. Such suppression of Mnk kinase activity and eIF4E phosphorylation by Cercosporamide resulted in dose-dependent suppressive effects on primitive leukemic progenitors (CFU-L) from AML patients and enhanced the antileukemic properties of cytarabine (Ara-C) or mammalian target of rapamycin (mTOR) co MedChem Express HY-16982
      Enzymes Tocris Bioscience 4500
      Kinases Tocris Bioscience 4500
      Mnk Tocris Bioscience 4500
      Potent inhibitor of MAP-kinase interacting kinase-2 (Mnk2) and JAK3 (IC50 values are 11, 31 and 116 nM for Mnk2, JAK3 and Mnk1 respectively). Blocks eIF4E phosphorylation; exhibits antiproliferative a nd proapoptotic activity in cancer cells in vitro. Also inhibits Pkc1. Orally bioavailable. Tocris Bioscience 4500
      Potent inhibitor of MAP-kinase interacting kinase-2 (Mnk2) and JAK3 (IC50 values are 11, 31 and 116 nM for Mnk2, JAK3 and Mnk1 respectively). Blocks eIF4E phosphorylation; exhibits antiproliferative and proapoptotic activity in cancer cells in vitro. Also inhibits Pkc1. Orally bioavailable. Tocris Bioscience 4500
      Potent Mnk2 inhibitor Tocris Bioscience 4500

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

Density: 1.7±0.1 g/cm3
Boiling Point: 582.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 90.3±3.0 kJ/mol
Flash Point: 306.1±30.1 °C
Index of Refraction: 1.741
Molar Refractivity: 78.4±0.4 cm3
#H bond acceptors: 8
#H bond donors: 5
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 0.00
ACD/LogD (pH 5.5):
ACD/BCF (pH 5.5):
ACD/KOC (pH 5.5):
ACD/LogD (pH 7.4):
ACD/BCF (pH 7.4):
ACD/KOC (pH 7.4):
Polar Surface Area: 147 Å2
Polarizability: 31.1±0.5 10-24cm3
Surface Tension: 100.4±5.0 dyne/cm
Molar Volume: 194.3±5.0 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) =  -1.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  596.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  257.66  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.46E-016  (Modified Grain method)
    Subcooled liquid VP: 1.9E-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):  2.324e+005
       log Kow used: -1.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  18571 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols
       Vinyl/Allyl Ketones
       Vinyl/Allyl Ethers
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.98E-025  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.024E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.03  (KowWin est)
  Log Kaw used:  -23.092  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.062
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1520
   Biowin2 (Non-Linear Model)     :   0.9721
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3704  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6633  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6563
   Biowin6 (MITI Non-Linear Model):   0.3554
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7057
 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):  2.53E-011 Pa (1.9E-013 mm Hg)
  Log Koa (Koawin est  ): 22.062
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.18E+005 
       Octanol/air (Koa) model:  2.83E+009 
   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 = 433.9024 E-12 cm3/molecule-sec
      Half-Life =     0.025 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    17.748 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    10.935000 E-17 cm3/molecule-sec
      Half-Life =     0.105 Days (at 7E11 mol/cm3)
      Half-Life =      2.515 Hrs
   Reaction With Nitrate Radicals May Be Important!
   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: -1.03 (estimated)

 Volatilization from Water:
    Henry LC:  1.98E-025 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.382E+021  hours   (2.243E+020 days)
    Half-Life from Model Lake : 5.871E+022  hours   (2.446E+021 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       2.29e-011       0.479        1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 973 hr

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