ChemSpider 2D Image | sporidesmin | C18H20ClN3O6S2

sporidesmin

  • Molecular FormulaC18H20ClN3O6S2
  • Average mass473.951 Da
  • Monoisotopic mass473.048218 Da
  • ChemSpider ID89980

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(1R,2R,3S,11R,14R)-6-Chlor-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-trien-13,17-dion [German] [ACD/IUPAC Name]
(1R,2R,3S,11R,14R)-6-Chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione [ACD/IUPAC Name]
(1R,2R,3S,11R,14R)-6-Chloro-2,3-dihydroxy-7,8-diméthoxy-10,14,18-triméthyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadéca-4,6,8-triène-13,17-dione [French] [ACD/IUPAC Name]
(3R,5aR,10bS,11R,11aR)-9-chloro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-2,3,5a,6,10b,11-hexahydro-3,11a-epidithiopyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
1456-55-9 [RN]
3,11a-(Iminomethano)-11aH-[1,2,4]dithiazino[4',3':1,5]pyrrolo[2,3-b]indole-4,12(3H)-dione, 9-chloro-5a,6,10b,11-tetrahydro-10b,11-dihydroxy-7,8-dimethoxy-3,6,13-trimethyl-, (3R,5aR,10bS,11R,11aR)- [ACD/Index Name]
sporidesmin
Sporidesmin A
(3R,5aR,10bS,11R,11aR)-9-Chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
3,11a-Epidithio-11aH-pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-dione, 9-chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-, (3-α,5a-α,10b-α,11-β,11a-α)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C10618 [DBID]
CCRIS 5323 [DBID]
NSC 246152 [DBID]
  • Miscellaneous

    • Chemical Class:

      An organic heteropentacyclic compound that has formula C18H20ClN3O6S2, produced by the saprophyte fungus Pithomyces chartarum. It is a mycotoxin responsible for the hepatogenous photosensitisation dis ease facial eczema in ruminants. ChEBI CHEBI:9243

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

Density: 1.7±0.1 g/cm3
Boiling Point: 761.4±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 116.3±3.0 kJ/mol
Flash Point: 414.3±32.9 °C
Index of Refraction: 1.777
Molar Refractivity: 113.4±0.4 cm3
#H bond acceptors: 9
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.42
ACD/LogD (pH 5.5): 2.60
ACD/BCF (pH 5.5): 56.16
ACD/KOC (pH 5.5): 622.05
ACD/LogD (pH 7.4): 2.60
ACD/BCF (pH 7.4): 56.16
ACD/KOC (pH 7.4): 622.05
Polar Surface Area: 153 Å2
Polarizability: 45.0±0.5 10-24cm3
Surface Tension: 97.5±5.0 dyne/cm
Molar Volume: 271.1±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) =  2.89

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  649.31  (Adapted Stein & Brown method)
    Melting Pt (deg C):  282.34  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.2E-018  (Modified Grain method)
    Subcooled liquid VP: 8.46E-016 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):  3.609
       log Kow used: 2.89 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  17825 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.77E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.074E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.89  (KowWin est)
  Log Kaw used:  -12.710  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.600
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4253
   Biowin2 (Non-Linear Model)     :   0.1060
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   0.9894  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9448  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2663
   Biowin6 (MITI Non-Linear Model):   0.0035
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.7051
 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):  1.13E-013 Pa (8.46E-016 mm Hg)
  Log Koa (Koawin est  ): 15.600
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.66E+007 
       Octanol/air (Koa) model:  977 
   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 = 532.8244 E-12 cm3/molecule-sec
      Half-Life =     0.020 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    14.453 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   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 = 1.522 (BCF = 33.24)
       log Kow used: 2.89 (estimated)

 Volatilization from Water:
    Henry LC:  4.77E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.672E+011  hours   (1.113E+010 days)
    Half-Life from Model Lake : 2.915E+012  hours   (1.215E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               4.86  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.74  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       0.0066          0.482        1000       
   Water     10.8            4.32e+003    1000       
   Soil      88.9            8.64e+003    1000       
   Sediment  0.232           3.89e+004    0          
     Persistence Time: 3.41e+003 hr

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