ChemSpider 2D Image | (+)-tephrorin B | C30H28O6

(+)-tephrorin B

  • Molecular FormulaC30H28O6
  • Average mass484.540 Da
  • Monoisotopic mass484.188599 Da
  • ChemSpider ID8800084

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(+)-tephrorin B
(2E)-3-Phénylacrylate de (3S,4S)-4-[(2S)-7-hydroxy-4-oxo-2-phényl-3,4-dihydro-2H-chromén-8-yl]-2,2-diméthyltétrahydro-3-furanyle [French] [ACD/IUPAC Name]
(3S,4S)-4-[(2S)-7-Hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-chromen-8-yl]-2,2-dimethyltetrahydro-3-furanyl (2E)-3-phenylacrylate [ACD/IUPAC Name]
(3S,4S)-4-[(2S)-7-Hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-chromen-8-yl]-2,2-dimethyltetrahydro-3-furanyl-(2E)-3-phenylacrylat [German] [ACD/IUPAC Name]
(3S,4S)-4-[(2S)-3,4-dihydro-7-hydroxy-4-oxo-2-phenyl-2H-1-benzopyran-8-yl]tetrahydro-2,2-dimethyl-3-furanyl(2E)-3-phenyl-2-propenoate
  • Miscellaneous

    • Chemical Class:

      A monohydroxyflavanone that is (2<stereo>S</stereo>)-7-hydroxyflavanone substituted at position 8 by a tetrahydrofuran ring which in turn is substituted by geminal methyl groups at position 2 and a cinnamoyloxy group at position 3. Isolated from <ital>Tephrosia purpurea</ital>, it exhibits antineoplastic activity. ChEBI CHEBI:66200
      A monohydroxyflavanone that is (2S)-7-hydroxyflavanone substituted at position 8 by a tetrahydrofuran ring which in turn is substituted by geminal methyl groups at position 2 and a ; cinnamoyloxy gr oup at position 3. Isolated from Tephrosia purpurea, it exhibits antineoplastic activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66200
      A monohydroxyflavanone that is (2S)-7-hydroxyflavanone substituted at position 8 by a tetrahydrofuran ring which in turn is substituted by geminal methyl groups at position 2 and a cinnamoyloxy grou p at position 3. Isolated from Tephrosia purpurea, it exhibits antineoplastic activity. ChEBI CHEBI:66200

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

Density: 1.3±0.1 g/cm3
Boiling Point: 632.4±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 96.9±3.0 kJ/mol
Flash Point: 207.4±25.0 °C
Index of Refraction: 1.646
Molar Refractivity: 134.5±0.4 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 6.01
ACD/LogD (pH 5.5): 5.76
ACD/BCF (pH 5.5): 13924.38
ACD/KOC (pH 5.5): 32083.40
ACD/LogD (pH 7.4): 5.48
ACD/BCF (pH 7.4): 7336.45
ACD/KOC (pH 7.4): 16904.04
Polar Surface Area: 82 Å2
Polarizability: 53.3±0.5 10-24cm3
Surface Tension: 60.8±5.0 dyne/cm
Molar Volume: 370.3±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) =  4.29

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  626.86  (Adapted Stein & Brown method)
    Melting Pt (deg C):  271.86  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.99E-017  (Modified Grain method)
    Subcooled liquid VP: 2.08E-014 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):  0.1939
       log Kow used: 4.29 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.022251 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.56E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.312E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.29  (KowWin est)
  Log Kaw used:  -15.837  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.127
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2341
   Biowin2 (Non-Linear Model)     :   0.0161
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2206  (months      )
   Biowin4 (Primary Survey Model) :   3.3217  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1261
   Biowin6 (MITI Non-Linear Model):   0.0057
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1991
 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):  2.77E-012 Pa (2.08E-014 mm Hg)
  Log Koa (Koawin est  ): 20.127
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.08E+006 
       Octanol/air (Koa) model:  3.29E+007 
   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 = 429.3003 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 431.9603 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   17.939 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   17.828 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   317.125000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =   318.175018 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     5.204 Min (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     5.187 Min (at 7E11 mol/cm3) [Trans-isomer]
   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    :  513
      Log Koc:  2.710 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.134E-004  L/mol-sec
  Kb Half-Life at pH 8:     193.639  years  
  Kb Half-Life at pH 7:    1936.386  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.606 (BCF = 403.4)
       log Kow used: 4.29 (estimated)

 Volatilization from Water:
    Henry LC:  3.56E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.62E+014  hours   (1.508E+013 days)
    Half-Life from Model Lake : 3.949E+015  hours   (1.646E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              44.73  percent
    Total biodegradation:        0.44  percent
    Total sludge adsorption:    44.29  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       0.000809        0.0757       1000       
   Water     9.86            1.44e+003    1000       
   Soil      84.2            2.88e+003    1000       
   Sediment  5.94            1.3e+004     0          
     Persistence Time: 2.34e+003 hr

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