ChemSpider 2D Image | (-)-Podophyllotoxin | C22H22O8

(-)-Podophyllotoxin

  • Molecular FormulaC22H22O8
  • Average mass414.405 Da
  • Monoisotopic mass414.131470 Da
  • ChemSpider ID10162
  • defined stereocentres - 4 of 4 defined stereocentres


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(-)-Podophyllotoxin
(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
(5R,5aR,8aR,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-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,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-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,9R)-9-Hydroxy-5-(3,4,5-triméthoxyphényl)-5,8,8a,9-tétrahydrofuro[3',4':6,7]naphto[2,3-d][1,3]dioxol-6(5aH)-one [French] [ACD/IUPAC Name]
[5R-(5a,5ab,8aa,9a)]-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
1-Hydroxy-2-hydroxymethyl-6,7-methylenedioxy-4-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylic Acid Lactone
208-250-4 [EINECS]
518-28-5 [RN]
Condyline [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

81125_FLUKA [DBID]
858447_ALDRICH [DBID]
AI3-50456 [DBID]
AIDS002471 [DBID]
AIDS-002471 [DBID]
C10874 [DBID]
CCRIS 565 [DBID]
DivK1c_000292 [DBID]
HSDB 7238 [DBID]
KBio1_000292 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      D06BB04 Wikidata Q421193
      IRRITANT Matrix Scientific 079670
    • Target Organs:

      Microtubule Associated inhibitor TargetMol T1121
    • Chemical Class:

      An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of <ital>Podophyllum</ital> species and is used for the topical treatment of genital warts. ChEBI CHEBI:50305
    • Drug Status:

      approved BIONET-Key Organics KS-1281
    • Compound Source:

      Isol. from Podophyllum emodi, Diphylleia grayi and others Zerenex Molecular [ZBioX-0285]
      Podophylum peltatum; podophylotoxin Microsource [02300332]
    • Bio Activity:

      Cell Cycle/Checkpoint TargetMol T1121
      Cell Cycle/DNA Damage MedChem Express HY-15552
      Cell Cycle/DNA Damage; MedChem Express HY-15552
      Cytostatic Zerenex Molecular [ZBioX-0285]
      Microtubule/Tubulin MedChem Express HY-15552
      Microtubule/Tubulin Topoisomerase MedChem Express HY-15552
      Microtubule/Tubulin;Topoisomerase II TargetMol T1121
      Podophyllotoxin is a potent inhibitor of microtubule assembly and DNA topoisomerase II. MedChem Express
      Podophyllotoxin is a potent inhibitor of microtubule assembly and DNA topoisomerase II.; IC50 Value:; Target: Topoisomerase II; Microtubule/Tubulin; Podophyllotoxin, a kind of non-alkaloid toxin lignan extracted from the roots and rhizomes of Podophyllum plant, has been shown to inhibit the growth of various carcinoma cells. MedChem Express HY-15552
      Podophyllotoxin is a potent inhibitor of microtubule assembly and DNA topoisomerase II.;IC50 Value:;Target: Topoisomerase II; Microtubule/TubulinPodophyllotoxin, a kind of non-alkaloid toxin lignan extracted from the roots and rhizomes of Podophyllum plant, has been shown to inhibit the growth of various carcinoma cells. Podophyllotoxin is a natural product that inhibits the polymerization of tubulin and has served as a prototype for the development of diverse antitumor agents in clinical use. MedChem Express HY-15552

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

Density: 1.4±0.1 g/cm3
Boiling Point: 597.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 93.6±3.0 kJ/mol
Flash Point: 210.2±23.6 °C
Index of Refraction: 1.606
Molar Refractivity: 104.3±0.3 cm3
#H bond acceptors: 8
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 1.60
ACD/LogD (pH 5.5): 1.95
ACD/BCF (pH 5.5): 17.77
ACD/KOC (pH 5.5): 273.01
ACD/LogD (pH 7.4): 1.95
ACD/BCF (pH 7.4): 17.77
ACD/KOC (pH 7.4): 273.01
Polar Surface Area: 93 Å2
Polarizability: 41.3±0.5 10-24cm3
Surface Tension: 52.8±3.0 dyne/cm
Molar Volume: 302.4±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) =  -1.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  549.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  235.86  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.91E-014  (Modified Grain method)
    Subcooled liquid VP: 5.47E-012 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):  1.632e+005
       log Kow used: -1.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  282.68 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.99E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.746E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.54  (KowWin est)
  Log Kaw used:  -15.913  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.373
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1176
   Biowin2 (Non-Linear Model)     :   0.9998
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2653  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.8370  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8425
   Biowin6 (MITI Non-Linear Model):   0.6094
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7657
 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):  7.29E-010 Pa (5.47E-012 mm Hg)
  Log Koa (Koawin est  ): 14.373
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.11E+003 
       Octanol/air (Koa) model:  57.9 
   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 = 219.6237 E-12 cm3/molecule-sec
      Half-Life =     0.049 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.584 Hrs
   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    :  809
      Log Koc:  2.908 

 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: -1.54 (estimated)

 Volatilization from Water:
    Henry LC:  2.99E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.991E+014  hours   (1.663E+013 days)
    Half-Life from Model Lake : 4.354E+015  hours   (1.814E+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       1.07e-005       1.17         1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 973 hr




                    

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