ChemSpider 2D Image | Thaxtomin A | C22H22N4O6

Thaxtomin A

  • Molecular FormulaC22H22N4O6
  • Average mass438.433 Da
  • Monoisotopic mass438.153931 Da
  • ChemSpider ID156732
  • defined stereocentres - 2 of 2 defined stereocentres


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(3R,6S)-3-Hydroxy-3-(3-hydroxybenzyl)-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazindion [German] [ACD/IUPAC Name]
(3R,6S)-3-Hydroxy-3-(3-hydroxybenzyl)-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione [ACD/IUPAC Name]
(3R,6S)-3-Hydroxy-3-(3-hydroxybenzyl)-1,4-diméthyl-6-[(4-nitro-1H-indol-3-yl)méthyl]-2,5-pipérazinedione [French] [ACD/IUPAC Name]
2,5-Piperazinedione, 3-hydroxy-3-((3-hydroxyphenyl)methyl)-1,4-dimethyl-6-((4-nitro-1H-indol-3-yl)methyl)-, (3R,6S)-
2,5-Piperazinedione, 3-hydroxy-3-((3-hydroxyphenyl)methyl)-1,4-dimethyl-6-((4-nitro-1H-indol-3-yl)methyl)-, (3R-trans)-
2,5-Piperazinedione, 3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-, (3R,6S)- [ACD/Index Name]
Thaxtomin A
(3R,6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione
(3R,6S)-3-hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione
122380-18-1 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

NSC630669 [DBID]
  • Miscellaneous
    • Bio Activity:

      Biochemicals & small molecules Hello Bio [HB4107]
      Cell process/Apoptosis & cell cycle Hello Bio [HB4107]
      Phytotoxin. Plant cell necrosis inducer. Hello Bio [HB4107]
      Phytotoxin. Plant cell necrosis inducer. Induces common scab disease of potato. Hello Bio [HB4107]

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

Density: 1.5±0.1 g/cm3
Boiling Point: 794.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 121.2±3.0 kJ/mol
Flash Point: 434.3±32.9 °C
Index of Refraction: 1.710
Molar Refractivity: 115.8±0.3 cm3
#H bond acceptors: 10
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 1.10
ACD/LogD (pH 5.5): 1.38
ACD/BCF (pH 5.5): 6.65
ACD/KOC (pH 5.5): 135.05
ACD/LogD (pH 7.4): 1.38
ACD/BCF (pH 7.4): 6.62
ACD/KOC (pH 7.4): 134.49
Polar Surface Area: 143 Å2
Polarizability: 45.9±0.5 10-24cm3
Surface Tension: 78.3±3.0 dyne/cm
Molar Volume: 296.3±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) =  0.45

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  709.83  (Adapted Stein & Brown method)
    Melting Pt (deg C):  310.61  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.82E-020  (Modified Grain method)
    Subcooled liquid VP: 4.51E-017 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):  1135
       log Kow used: 0.45 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  12205 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.00E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.433E-023 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.45  (KowWin est)
  Log Kaw used:  -18.087  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.537
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6953
   Biowin2 (Non-Linear Model)     :   0.4991
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6468  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.2668  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4271
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8940
 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):  6.01E-015 Pa (4.51E-017 mm Hg)
  Log Koa (Koawin est  ): 18.537
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.99E+008 
       Octanol/air (Koa) model:  8.45E+005 
   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 = 156.8321 E-12 cm3/molecule-sec
      Half-Life =     0.068 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.818 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  2.5E+004
      Log Koc:  4.398 

 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: 0.45 (estimated)

 Volatilization from Water:
    Henry LC:  2E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  6.13E+016  hours   (2.554E+015 days)
    Half-Life from Model Lake : 6.687E+017  hours   (2.786E+016 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       0.00749         1.64         1000       
   Water     52.4            4.32e+003    1000       
   Soil      47.5            8.64e+003    1000       
   Sediment  0.106           3.89e+004    0          
     Persistence Time: 1.47e+003 hr




                    

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