ChemSpider 2D Image | MFCD00914626 | C21H20O7

MFCD00914626

  • Molecular FormulaC21H20O7
  • Average mass384.379 Da
  • Monoisotopic mass384.120911 Da
  • ChemSpider ID141208

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

Featured data source
Natural Product Updates

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

(5R,5aR,8aR)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
(5R,5aR,8aR)-5-(4-Hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-on [German] [ACD/IUPAC Name]
(5R,5aR,8aR)-5-(4-Hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one [ACD/IUPAC Name]
(5R,5aR,8aR)-5-(4-Hydroxy-3,5-diméthoxyphényl)-5,8,8a,9-tétrahydrofuro[3',4':6,7]naphto[2,3-d][1,3]dioxol-6(5aH)-one [French] [ACD/IUPAC Name]
3590-93-0 [RN]
4'-demethyldeoxypodophyllotoxin
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR)- [ACD/Index Name]
MFCD00914626
(-)-4'-demethyldeoxypodophyllotoxin
(-)-4'-demethyl-deoxypodophyllotoxin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

A 80198 [DBID]
C10552 [DBID]
NSC267714 [DBID]
ZINC03782246 [DBID]
  • Miscellaneous

    • Chemical Class:

      A member of the class of furonaphthodioxoles that is (5<stereo>R</stereo>,5a<stereo>R</stereo>,8a<stereo>R</stereo>)-5,8,8a,9-tetrahydro-2<element>H</element>-furo[3',4':6,7]naphtho[2,3-<ital>d</ital> ][1,3]dioxol-6(5a<element>H</element>)-one substituted at position 5 by a 4-hydroxy-3,5-dimethoxyphenyl group. ChEBI CHEBI:1729
      A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d; ][1,3]dioxol-6(5aH)-one substituted at position 5 by a 4-hydroxy-3,5-dimethoxyphe nyl group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:1729
      A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 4-hydroxy-3,5-dimethoxypheny l group. ChEBI CHEBI:1729

    • Compound Source:

      (-)-4'-desmethyl-epipodophyllotoxin biosynthesis PlantCyc CPD-18756
      Linum usitatissimum PlantCyc CPD-18756

    • Bio Activity:

      (-)-4'-demethyl-deoxypodophyllotoxin + NADPH + oxygen + H+ -> (-)-4'-demethyl-epipodophyllotoxin + NADP+ + H2O PlantCyc CPD-18756
      (-)-deoxypodophyllotoxin + 2 NADPH + oxygen + 2 H+ -> (-)-4'-demethyl-deoxypodophyllotoxin + methanol + 2 NADP+ + H2O PlantCyc CPD-18756

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

Density: 1.4±0.1 g/cm3
Boiling Point: 590.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 91.4±3.0 kJ/mol
Flash Point: 211.8±23.6 °C
Index of Refraction: 1.617
Molar Refractivity: 97.9±0.3 cm3
#H bond acceptors: 7
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.55
ACD/LogD (pH 5.5): 2.10
ACD/BCF (pH 5.5): 23.15
ACD/KOC (pH 5.5): 329.87
ACD/LogD (pH 7.4): 2.10
ACD/BCF (pH 7.4): 23.08
ACD/KOC (pH 7.4): 328.93
Polar Surface Area: 83 Å2
Polarizability: 38.8±0.5 10-24cm3
Surface Tension: 53.4±3.0 dyne/cm
Molar Volume: 279.8±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) =  -0.34

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  524.63  (Adapted Stein & Brown method)
    Melting Pt (deg C):  224.11  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.5E-012  (Modified Grain method)
    Subcooled liquid VP: 7.47E-010 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):  7356
       log Kow used: -0.34 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  259.96 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.44E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.792E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.34  (KowWin est)
  Log Kaw used:  -14.230  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.890
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0118
   Biowin2 (Non-Linear Model)     :   0.9991
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2114  (months      )
   Biowin4 (Primary Survey Model) :   3.6449  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5933
   Biowin6 (MITI Non-Linear Model):   0.2822
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4603
 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):  9.96E-008 Pa (7.47E-010 mm Hg)
  Log Koa (Koawin est  ): 13.890
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  30.1 
       Octanol/air (Koa) model:  19.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 211.5912 E-12 cm3/molecule-sec
      Half-Life =     0.051 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.607 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  8201
      Log Koc:  3.914 

 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: -0.34 (estimated)

 Volatilization from Water:
    Henry LC:  1.44E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.982E+012  hours   (3.326E+011 days)
    Half-Life from Model Lake : 8.708E+013  hours   (3.628E+012 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       2.94e-006       1.21         1000       
   Water     49.2            1.44e+003    1000       
   Soil      50.7            2.88e+003    1000       
   Sediment  0.096           1.3e+004     0          
     Persistence Time: 1.18e+003 hr

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