ChemSpider 2D Image | fumagillin | C26H34O7

fumagillin

  • Molecular FormulaC26H34O7
  • Average mass458.544 Da
  • Monoisotopic mass458.230438 Da
  • ChemSpider ID5292885
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 6 of 6 defined stereocentres


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(2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxo-2,4,6,8-decatetraenoic acid [ACD/IUPAC Name]
(2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxo-2,4,6,8-decatetraensäure [German] [ACD/IUPAC Name]
(2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
2,4,6,8-Decatetraenedioic acid, mono[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester, (2E,4E,6E,8E)- [ACD/Index Name]
225
23110-15-8 [RN]
7OW73204U1
Acide (2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-méthoxy-4-[(2R,3R)-2-méthyl-3-(3-méthyl-2-butén-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxo-2,4,6,8-décatétraénoïque [French] [ACD/IUPAC Name]
fumagilina [Spanish] [INN]
fumagillin [INN] [Wiki]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

NSC9168 [DBID]
SR-90144 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A meroterpenoid resulting from the formal condensation of the hydroxy group of fumagillol with the carboxylic acid group of (all-<stereo>E</stereo>)-deca-2,4,6,8-tetraenedioic acid. Originally isolate d from the fungus <ital>Aspergillus fumigatus</ital>, it is used for the control of <ital>Nosema</ital> infection in honey bees. ChEBI CHEBI:48635
      A meroterpenoid resulting from the formal condensation of the hydroxy group of fumagillol with the carboxylic acid group of (all-E)-deca-2,4,6,8-tetraenedioic acid. Originally isolate; d from the fung us Aspergillus fumigatus, it is used for the control of Nosema infection in honey bees. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48635
    • Bio Activity:

      Aminopeptidases Tocris Bioscience 1768
      Antibiotic and antiangiogenic agent; covalently binds and inhibits methionine aminopeptidase-2. Inhibits endothelial cell proliferation in vitro and tumor-induced angiogenesis in vivo. Also inhibits t umor growth in mice. Analog available, TNP 470 (Cat.No. 3750). Tocris Bioscience 1768
      Antibiotic and antiangiogenic agent; covalently binds and inhibits methionine aminopeptidase-2. Inhibits endothelial cell proliferation in vitro and tumor-induced angiogenesis in vivo. Also inhibits tumor growth in mice. Tocris Bioscience 1768
      Anti-infection MedChem Express HY-B0751
      Anti-infection; MedChem Express HY-B0751
      Antiparasitic MedChem Express HY-B0751
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB3901]
      Enzymes Tocris Bioscience 1768
      Enzymes/Protease / Peptidase/Methionine aminopeptidase-2 Hello Bio [HB3901]
      Fumagillin(NSC9168) is a complex biomolecule and used as an antimicrobial agent. MedChem Express
      Fumagillin(NSC9168) is a complex biomolecule and used as an antimicrobial agent.; Target: Antiparasitic; Fumagillin is an active amebicide and anti-infective isolated from the fungus Aspergillus fumigatus. MedChem Express HY-B0751
      Fumagillin(NSC9168) is a complex biomolecule and used as an antimicrobial agent.;Target: AntiparasiticFumagillin is an active amebicide and anti-infective isolated from the fungus Aspergillus fumigatus. Fumagillin does exhibit some side effects that have deterred its acceptance as a viable treatment, but the current body of research on the synthesis of novel analogs of this molecule shows an exciting and promising revival of this drug as both an anti-infective and antiangiogenic agent [1]. MedChem Express HY-B0751
      Methionine aminopeptidase-2 inhibitor Hello Bio [HB3901]
      Methionine aminopeptidase-2 inhibitor; antiangiogenic Tocris Bioscience 1768
      Potent, selective and covalent Methionine aminopeptidase-2 (MetAP2) inhibitor. Impairs endothelial cell growth and alters gene expression. Inhibits endothelial cell proliferation in vitro and tumor-induced angiogenesis in vivo. Shows anti-angiogenisis, antiviral, anticancer, antimicrobial, antimalarial and amoebicidal activity. Hello Bio [HB3901]
      Proteases Tocris Bioscience 1768

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

Density: 1.2±0.1 g/cm3
Boiling Point: 606.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.7 mmHg at 25°C
Enthalpy of Vaporization: 98.5±6.0 kJ/mol
Flash Point: 198.9±25.0 °C
Index of Refraction: 1.562
Molar Refractivity: 124.3±0.4 cm3
#H bond acceptors: 7
#H bond donors: 1
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 0
ACD/LogP: 3.26
ACD/LogD (pH 5.5): 2.00
ACD/BCF (pH 5.5): 9.66
ACD/KOC (pH 5.5): 77.61
ACD/LogD (pH 7.4): 0.21
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.28
Polar Surface Area: 98 Å2
Polarizability: 49.3±0.5 10-24cm3
Surface Tension: 48.4±5.0 dyne/cm
Molar Volume: 383.2±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) =  4.79

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  542.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  232.68  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.65E-011  (Modified Grain method)
    MP  (exp database):  194.5 deg C
    Subcooled liquid VP: 2.2E-009 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):  0.2653
       log Kow used: 4.79 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  11.101 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates-acid
       Diepoxides-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.18E-015  atm-m3/mole
   Group Method:   1.34E-021  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  8.301E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.79  (KowWin est)
  Log Kaw used:  -13.317  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.107
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.6338
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2404  (months      )
   Biowin4 (Primary Survey Model) :   3.4646  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2282
   Biowin6 (MITI Non-Linear Model):   0.0033
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4018
 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):  2.93E-007 Pa (2.2E-009 mm Hg)
  Log Koa (Koawin est  ): 18.107
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  10.2 
       Octanol/air (Koa) model:  3.14E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 233.3187 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.550 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.619999 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     36.984 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  133.7
      Log Koc:  2.126 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.203E-003  L/mol-sec
  Kb Half-Life at pH 8:       9.968  years  
  Kb Half-Life at pH 7:      99.676  years  

  Total Ka (acid-catalyzed) at 25 deg C :  1.940E-001  L/mol-sec
  Ka Half-Life at pH 7:       1.132  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 4.79 (estimated)

 Volatilization from Water:
    Henry LC:  1.18E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.063E+012  hours   (4.427E+010 days)
    Half-Life from Model Lake : 1.159E+013  hours   (4.83E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              69.95  percent
    Total biodegradation:        0.62  percent
    Total sludge adsorption:    69.33  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       1.07e-006       0.395        1000       
   Water     6.9             1.44e+003    1000       
   Soil      79.9            2.88e+003    1000       
   Sediment  13.2            1.3e+004     0          
     Persistence Time: 3.29e+003 hr




                    

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