ChemSpider 2D Image | yadanziolide B | C20H26O11

yadanziolide B

  • Molecular FormulaC20H26O11
  • Average mass442.414 Da
  • Monoisotopic mass442.147522 Da
  • ChemSpider ID9918759

  • defined stereocentres - 12 of 12 defined stereocentres

More details:

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

(1β,6α,11β,12α,15β)-1,6,11,12,14,15,21-Heptahydroxy-13,20-epoxypicras-3-en-2,16-dion [German] [ACD/IUPAC Name]
(1β,6α,11β,12α,15β)-1,6,11,12,14,15,21-Heptahydroxy-13,20-epoxypicras-3-ene-2,16-dione [ACD/IUPAC Name]
(1β,6α,11β,12α,15β)-1,6,11,12,14,15,21-Heptahydroxy-13,20-époxypicras-3-ène-2,16-dione [French] [ACD/IUPAC Name]
Picras-3-ene-2,16-dione, 13,20-epoxy-1,6,11,12,14,15,21-heptahydroxy-, (1β,6α,11β,12α,15β)- [ACD/Index Name]
yadanziolide B
(1R,2R,3R,6S,7R,8S,12S,13S,14R,15R,16S,17R)-2,3,7,12,15,16-hexahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione
95258-13-2 [RN]
  • Miscellaneous

    • Chemical Class:

      A quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 6, 11, 12, 14, 15 and 21 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of <ital>Brucea mollis</ital>, it exhibits cytotoxic activity. ChEBI CHEBI:68932
      A quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 6, 11, 12, 14, 15 and 21 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68932, CHEBI:68932

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

Density: 1.8±0.1 g/cm3
Boiling Point: 765.8±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±5.9 mmHg at 25°C
Enthalpy of Vaporization: 127.2±6.0 kJ/mol
Flash Point: 271.9±26.4 °C
Index of Refraction: 1.715
Molar Refractivity: 98.4±0.4 cm3
#H bond acceptors: 11
#H bond donors: 7
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 2
ACD/LogP: -1.01
ACD/LogD (pH 5.5): -1.44
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.92
ACD/LogD (pH 7.4): -1.44
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.92
Polar Surface Area: 194 Å2
Polarizability: 39.0±0.5 10-24cm3
Surface Tension: 107.5±5.0 dyne/cm
Molar Volume: 250.5±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) =  -2.16

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  693.67  (Adapted Stein & Brown method)
    Melting Pt (deg C):  303.06  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.06E-021  (Modified Grain method)
    Subcooled liquid VP: 5.2E-018 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):  1.153e+005
       log Kow used: -2.16 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Vinyl/Allyl Ketones

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.35E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.050E-026 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.16  (KowWin est)
  Log Kaw used:  -14.258  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.098
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5872
   Biowin2 (Non-Linear Model)     :   0.0369
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4419  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5694  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   1.2719
   Biowin6 (MITI Non-Linear Model):   0.5608
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1926
 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):  6.93E-016 Pa (5.2E-018 mm Hg)
  Log Koa (Koawin est  ): 12.098
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.33E+009 
       Octanol/air (Koa) model:  0.308 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.961 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 170.6994 E-12 cm3/molecule-sec
      Half-Life =     0.063 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.752 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 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    :  25.5
      Log Koc:  1.407 

 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: -2.16 (estimated)

 Volatilization from Water:
    Henry LC:  1.35E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.122E+012  hours   (3.801E+011 days)
    Half-Life from Model Lake : 9.951E+013  hours   (4.146E+012 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       0.0797          1.07         1000       
   Water     53.1            900          1000       
   Soil      46.7            1.8e+003     1000       
   Sediment  0.102           8.1e+003     0          
     Persistence Time: 608 hr

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