ChemSpider 2D Image | Pisatin | C17H14O6

Pisatin

  • Molecular FormulaC17H14O6
  • Average mass314.289 Da
  • Monoisotopic mass314.079041 Da
  • ChemSpider ID91879
  • defined stereocentres - 2 of 2 defined stereocentres


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(+)-pisatin
(6aR,12aR)-3-Methoxy-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-6a(12aH)-ol [ACD/IUPAC Name]
(6aR,12aR)-3-Methoxy-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-6a(12aH)-ol [German] [ACD/IUPAC Name]
(6aR,12aR)-3-Méthoxy-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromén-6a(12aH)-ol [French] [ACD/IUPAC Name]
20186-22-5 [RN]
469-01-2 [RN]
6H-(1,3)Dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-6a(12aH)-ol, 3-methoxy-, (6aR-cis)-
6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-6a(12aH)-ol, 3-methoxy-, (6aR,12aR)- [ACD/Index Name]
Pisatin
(6aR,12aR)-3-methoxy-6H-[1.3]-dioxolo[5,6][1]benzofuro[3,2-c]chromen-6a(12aH)-ol
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

V6L86DZ4N3 [DBID]
C10516 [DBID]
UNII:V6L86DZ4N3 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A member of the class of pterocarpans that is the 3-<element>O</element>-methyl ether of (+)-6a-hydroxymaackiain (the 6a<stereo>R</stereo>,12a<stereo>R</stereo> stereoisomer). A phytoalexin found in p ods of garden peas (<ital>Pisum sativum</ital>) and other plants of the pea family, including <ital>Tephrosia candida</ital>. ChEBI CHEBI:67347
      A member of the class of pterocarpans that is the 3-O-methyl ether of (+)-6a-hydroxymaackiain (the 6aR,12aR stereoisomer). A phytoalexin found in p; ods of garden peas (Pisum sativum) and other plants of the pea family, including Tephrosia candida. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:67347
    • Compound Source:

      (+)-pisatin biosynthesis PlantCyc CPD-3944
      Cicer arietinum PlantCyc CPD-3944
      Glycine max PlantCyc CPD-3944
      Linum usitatissimum PlantCyc CPD-3944
      Lotus japonicus PlantCyc CPD-3944
      Medicago truncatula PlantCyc CPD-3944
      Phaseolus vulgaris PlantCyc CPD-3944
      superpathway of pterocarpan biosynthesis (via formononetin) PlantCyc CPD-3944
      Trifolium pratense PlantCyc CPD-3944
    • Bio Activity:

      S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain -> (+)-pisatin + S-adenosyl-L-homocysteine + H+ PlantCyc CPD-3944

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

Density: 1.5±0.1 g/cm3
Boiling Point: 483.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 78.8±3.0 kJ/mol
Flash Point: 245.9±28.7 °C
Index of Refraction: 1.675
Molar Refractivity: 78.6±0.3 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 2.13
ACD/LogD (pH 5.5): 2.17
ACD/BCF (pH 5.5): 26.33
ACD/KOC (pH 5.5): 361.73
ACD/LogD (pH 7.4): 2.17
ACD/BCF (pH 7.4): 26.33
ACD/KOC (pH 7.4): 361.71
Polar Surface Area: 66 Å2
Polarizability: 31.2±0.5 10-24cm3
Surface Tension: 70.6±3.0 dyne/cm
Molar Volume: 209.3±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) =  -0.46

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  421.29  (Adapted Stein & Brown method)
    Melting Pt (deg C):  175.83  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.19E-009  (Modified Grain method)
    Subcooled liquid VP: 4.36E-008 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):  7.956e+004
       log Kow used: -0.46 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4079.7 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.46E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.205E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.46  (KowWin est)
  Log Kaw used:  -13.578  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.118
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5938
   Biowin2 (Non-Linear Model)     :   0.9147
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0491  (months      )
   Biowin4 (Primary Survey Model) :   3.5381  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6953
   Biowin6 (MITI Non-Linear Model):   0.5894
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1930
 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):  5.81E-006 Pa (4.36E-008 mm Hg)
  Log Koa (Koawin est  ): 13.118
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.516 
       Octanol/air (Koa) model:  3.22 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.949 
       Mackay model           :  0.976 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 253.5878 E-12 cm3/molecule-sec
      Half-Life =     0.042 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.506 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.963 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  263
      Log Koc:  2.420 

 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: -0.46 (estimated)

 Volatilization from Water:
    Henry LC:  6.46E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.609E+012  hours   (6.706E+010 days)
    Half-Life from Model Lake : 1.756E+013  hours   (7.315E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       1.9e-007        1.01         1000       
   Water     49.2            1.44e+003    1000       
   Soil      50.7            2.88e+003    1000       
   Sediment  0.096           1.3e+004     0          
     Persistence Time: 1.17e+003 hr




                    

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