ChemSpider 2D Image | (+)-6a-hydroxymaackiain | C16H12O6

(+)-6a-hydroxymaackiain

  • Molecular FormulaC16H12O6
  • Average mass300.263 Da
  • Monoisotopic mass300.063385 Da
  • ChemSpider ID7822419

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(+)-6a-hydroxymaackiain
(6aR,12aR)-6H-[1,3]Dioxolo[5,6][1]benzofuro[3,2-c]chromen-3,6a(12aH)-diol [German] [ACD/IUPAC Name]
(6aR,12aR)-6H-[1,3]Dioxolo[5,6][1]benzofuro[3,2-c]chromene-3,6a(12aH)-diol [ACD/IUPAC Name]
(6aR,12aR)-6H-[1,3]Dioxolo[5,6][1]benzofuro[3,2-c]chromène-3,6a(12aH)-diol [French] [ACD/IUPAC Name]
(6aR,12aR)-6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3,6a(12aH)-diol
14602-93-8 [RN]
6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3,6a(12aH)-diol, (6aR,12aR)- [ACD/Index Name]
(+)-O-demethylpisatin
3,6a-Dihydroxy-8,9-methylenedioxypterocarpan
3,6a-dihydroxy-8,9-methylenedioxypterocarpan|DMDP
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  • Miscellaneous

    • Chemical Class:

      A member of the class of pterocarpans that is (6a<stereo>S</stereo>,11a<stereo>S</stereo>)-6a,11a-dihydro-6H-[1]benzofuro[3,2-<ital>c</ital>]chromene which is substituted by a hydroxy group at positio n 3, a second hydroxy group at position 6a (resulting in the CIP stereochemical designation changing to <stereo>R</stereo>,<stereo>R</stereo>), and a methylenedioxy group at positions 8-9. It is a met abolite of the pea phytoalexin (+)-pisatin, produced by the pea-pathogenic <ital>Fusarium oxysporum forma specialis pisi</ital>, and a number of other fungi, including <ital>Fusarium anruioides</ital> , <ital>Fusarium avenaceum</ital>, <ital>Mycosphaerella pinodes</ital>, and <ital>Stemphylium botryosum</ital>. ChEBI CHEBI:43129
      A member of the class of pterocarpans that is (6aS,11aS)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene which is substituted by a hydroxy group at positio; n 3, a second hydroxy group at position 6a (r esulting in the CIP stereochemical designation changing to R,R), and a methylenedioxy group at positions 8-9. It is a met; abolite of the pea phytoalexin (+)-pisatin, produced by the pea-pathogenic Fu sarium oxysporum forma specialis pisi, and a number of other fungi, including Fusarium anruioides; , Fusarium avenaceum, Mycosphaerella pinodes, and Stemphylium botryosum. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:43129
      A member of the class of pterocarpans that is (6aS,11aS)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene which is substituted by a hydroxy group at position 3, a second hydroxy group at position 6a (res ulting in the CIP stereochemical designation changing to R,R), and a methylenedioxy group at positions 8-9. It is a metabolite of the pea phytoalexin (+)-pisatin, produced by the pea-pathogenic Fusari um oxysporum forma specialis pisi, and a number of other fungi, including Fusarium anruioides, Fusarium avenaceum, Mycosphaerella pinodes, and Stemphylium botryosum. ChEBI CHEBI:43129

    • Compound Source:

      (+)-pisatin biosynthesis PlantCyc CPD-3942
      Cicer arietinum PlantCyc CPD-3942
      Glycine max PlantCyc CPD-3942
      Linum usitatissimum PlantCyc CPD-3942
      Lotus japonicus PlantCyc CPD-3942
      Medicago truncatula PlantCyc CPD-3942
      Phaseolus vulgaris PlantCyc CPD-3942
      superpathway of pterocarpan biosynthesis (via formononetin) PlantCyc CPD-3942
      Trifolium pratense PlantCyc CPD-3942

    • Bio Activity:

      (+)-maackiain + NADPH + H+ + oxygen -> (+)-6a-hydroxymaackiain + NADP+ + H2O PlantCyc CPD-3942
      (3R,4R)-7,2,4,2'-tetrahydroxy-4',5'-methylenedioxyisoflav-3-ene -> (+)-6a-hydroxymaackiain + H2O PlantCyc CPD-3942
      S-adenosyl-L-methionine + (+)-6a-hydroxymaackiain -> (+)-pisatin + S-adenosyl-L-homocysteine + H+ PlantCyc CPD-3942

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

Density: 1.6±0.1 g/cm3
Boiling Point: 518.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 83.3±3.0 kJ/mol
Flash Point: 267.5±30.1 °C
Index of Refraction: 1.736
Molar Refractivity: 73.8±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 1.72
ACD/LogD (pH 5.5): 1.77
ACD/BCF (pH 5.5): 13.15
ACD/KOC (pH 5.5): 220.11
ACD/LogD (pH 7.4): 1.77
ACD/BCF (pH 7.4): 13.00
ACD/KOC (pH 7.4): 217.58
Polar Surface Area: 77 Å2
Polarizability: 29.3±0.5 10-24cm3
Surface Tension: 89.4±3.0 dyne/cm
Molar Volume: 183.7±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) =  -1.02

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  432.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  181.06  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.81E-010  (Modified Grain method)
    Subcooled liquid VP: 2.03E-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):  1e+006
       log Kow used: -1.02 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.3548e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.14E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.907E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.02  (KowWin est)
  Log Kaw used:  -16.332  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.312
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5844
   Biowin2 (Non-Linear Model)     :   0.7741
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1946  (months      )
   Biowin4 (Primary Survey Model) :   3.5209  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6056
   Biowin6 (MITI Non-Linear Model):   0.4782
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1753
 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):  2.71E-006 Pa (2.03E-008 mm Hg)
  Log Koa (Koawin est  ): 15.312
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.11 
       Octanol/air (Koa) model:  504 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.976 
       Mackay model           :  0.989 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 252.8982 E-12 cm3/molecule-sec
      Half-Life =     0.042 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.508 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.982 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  136.1
      Log Koc:  2.134 

 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: -1.02 (estimated)

 Volatilization from Water:
    Henry LC:  1.14E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.914E+014  hours   (3.714E+013 days)
    Half-Life from Model Lake : 9.725E+015  hours   (4.052E+014 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       7.24e-010       1.01         1000       
   Water     49.4            1.44e+003    1000       
   Soil      50.5            2.88e+003    1000       
   Sediment  0.0961          1.3e+004     0          
     Persistence Time: 1.17e+003 hr

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