ChemSpider 2D Image | Cytochalasin B | C29H37NO5

Cytochalasin B

  • Molecular FormulaC29H37NO5
  • Average mass479.608 Da
  • Monoisotopic mass479.267181 Da
  • ChemSpider ID4470791
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 8 of 8 defined stereocentres


More details:






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

Cytochalasin B [Wiki]
(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-Benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylen-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-2H-oxacyclotetradecino[2,3-d]isoindol-2,18(5H)-dion [German] [ACD/IUPAC Name]
(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-Benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylene-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione [ACD/IUPAC Name]
(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-Benzyl-5,13-dihydroxy-9,15-diméthyl-14-méthylène-6,7,8,9,10,12a,13,14,15,15a,16,17-dodécahydro-2H-oxacyclotétradécino[2,3-d]isoindole-2,18(5H)-dione [French] [ACD/IUPAC Name]
(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
14930-96-2 [RN]
2H-Oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione, 6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (3E,5R,9R,11E,12aS,13S,15S,15aS,16S,1 8aS)- [ACD/Index Name]
2H-Oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione, 6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
Phomin
(1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
More...

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

30380_FLUKA [DBID]
C6762_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments. ChEBI CHEBI:23527
    • Therapeutical Effect:

      antineoplastic, cytotoxin, teratogen, mutagen Microsource [01504253]
    • Compound Source:

      Helminthosporium & Phoma sp. Microsource [01504253]
    • Bio Activity:

      Actin Tocris Bioscience 5474
      Cytoskeleton and Motor Proteins Tocris Bioscience 5474
      Inhibitor of actin polymerization Tocris Bioscience 5474
      Inhibitor of actin polymerization. Inhibits cell division, migration and glucose transport. Causes G2/M cell cycle arrest and apoptosis in HCT-116 colorectal carcinoma cells. Cell permeable. Tocris Bioscience 5474

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

Density: 1.2±0.1 g/cm3
Boiling Point: 740.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.6 mmHg at 25°C
Enthalpy of Vaporization: 113.4±3.0 kJ/mol
Flash Point: 401.7±32.9 °C
Index of Refraction: 1.596
Molar Refractivity: 135.0±0.4 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.71
ACD/LogD (pH 5.5): 3.49
ACD/BCF (pH 5.5): 265.52
ACD/KOC (pH 5.5): 1891.38
ACD/LogD (pH 7.4): 3.49
ACD/BCF (pH 7.4): 265.52
ACD/KOC (pH 7.4): 1891.38
Polar Surface Area: 96 Å2
Polarizability: 53.5±0.5 10-24cm3
Surface Tension: 53.3±5.0 dyne/cm
Molar Volume: 396.8±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) =  3.25
    Log Kow (Exper. database match) =  3.37
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  701.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  306.86  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.04E-020  (Modified Grain method)
    Subcooled liquid VP: 1.49E-017 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):  1.28
       log Kow used: 3.37 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.9969 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylates
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.28E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.128E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.37  (exp database)
  Log Kaw used:  -14.031  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.401
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2198
   Biowin2 (Non-Linear Model)     :   0.9971
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2802  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6320  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3349
   Biowin6 (MITI Non-Linear Model):   0.0077
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8136
 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):  1.99E-015 Pa (1.49E-017 mm Hg)
  Log Koa (Koawin est  ): 17.401
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.51E+009 
       Octanol/air (Koa) model:  6.18E+004 
   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 = 178.0895 E-12 cm3/molecule-sec
      Half-Life =     0.060 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.721 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    22.337502 E-17 cm3/molecule-sec
      Half-Life =     0.051 Days (at 7E11 mol/cm3)
      Half-Life =      1.231 Hrs
   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    :  1.732E+004
      Log Koc:  4.239 

 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 = 1.895 (BCF = 78.51)
       log Kow used: 3.37 (expkow database)

 Volatilization from Water:
    Henry LC:  2.28E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.624E+012  hours   (2.343E+011 days)
    Half-Life from Model Lake : 6.135E+013  hours   (2.556E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              10.40  percent
    Total biodegradation:        0.16  percent
    Total sludge adsorption:    10.23  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       0.0288          0.664        1000       
   Water     18.1            900          1000       
   Soil      80.9            1.8e+003     1000       
   Sediment  0.967           8.1e+003     0          
     Persistence Time: 1.07e+003 hr




                    

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