ChemSpider 2D Image | lefradafiban | C23H25N3O6

lefradafiban

  • Molecular FormulaC23H25N3O6
  • Average mass439.461 Da
  • Monoisotopic mass439.174347 Da
  • ChemSpider ID7851357

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(3S-trans)-5-(((4'-(Imino((methoxycarbonyl)amino)methyl)(1,1'-biphenyl)-4-yl)oxy)methyl)-2-oxo-3-pyrrolidineacetic Acid Methyl Ester
{(3S,5S)-5-[({4'-[N-(Méthoxycarbonyl)carbamimidoyl]-4-biphénylyl}oxy)méthyl]-2-oxo-3-pyrrolidinyl}acétate de méthyle [French] [ACD/IUPAC Name]
0R4888YXR5
149503-79-7 [RN]
3-Pyrrolidineacetic acid, 5-[[[4'-[imino[(methoxycarbonyl)amino]methyl][1,1'-biphenyl]-4-yl]oxy]methyl]-2-oxo-, methyl ester, (3S,5S)- [ACD/Index Name]
lefradafiban [INN]
lefradafiban [French] [INN]
lefradafibán [Spanish] [INN]
lefradafibanum [Latin] [INN]
Methyl {(3S,5S)-5-[({4'-[N-(methoxycarbonyl)carbamimidoyl]-4-biphenylyl}oxy)methyl]-2-oxo-3-pyrrolidinyl}acetate [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

7277 [DBID]
  • Miscellaneous

    • Chemical Class:

      A member of the class of pyrrolidin-2-ones that is pyrrolidin-2-one in which the 3-<ital>pro</ital>-<stereo>S</stereo>-hydrogen is substituted by a 2-methoxy-2-oxoethyl group, while the 5-<ital>pro</i tal>-<stereo>S</stereo>-hydrogen is substituted by a ({4'-[<element>N</element>-(methoxycarbonyl)carbamimidoyl]biphenyl-4-yl}oxy)methyl group. It is an orally active prodrug of fradafiban, a figrinoge n receptor antagonist. ChEBI CHEBI:60634
      A member of the class of pyrrolidin-2-ones that is pyrrolidin-2-one in which the 3-pro-S-hydrogen is substituted by a 2-methoxy-2-oxoethyl group, while the 5-pro-S-hydrogen is substituted by a ({4'-[N -(methoxycarbonyl)carbamimidoyl]biphenyl-4-yl}oxy)methyl group. It is an orally active prodrug of fradafiban, a figrinogen receptor antagonist. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:60634, CHEBI:60634

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

Density: 1.3±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.609
Molar Refractivity: 115.3±0.5 cm3
#H bond acceptors: 9
#H bond donors: 3
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 0
ACD/LogP: 0.40
ACD/LogD (pH 5.5): 1.80
ACD/BCF (pH 5.5): 12.81
ACD/KOC (pH 5.5): 198.25
ACD/LogD (pH 7.4): 1.92
ACD/BCF (pH 7.4): 16.85
ACD/KOC (pH 7.4): 260.70
Polar Surface Area: 127 Å2
Polarizability: 45.7±0.5 10-24cm3
Surface Tension: 49.8±7.0 dyne/cm
Molar Volume: 332.8±7.0 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) =  2.22

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  609.32  (Adapted Stein & Brown method)
    Melting Pt (deg C):  263.66  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.02E-013  (Modified Grain method)
    Subcooled liquid VP: 4.21E-011 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):  22.2
       log Kow used: 2.22 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  125.17 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.24E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.657E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.22  (KowWin est)
  Log Kaw used:  -16.295  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.515
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0546
   Biowin2 (Non-Linear Model)     :   0.9969
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2559  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7252  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2803
   Biowin6 (MITI Non-Linear Model):   0.0248
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2936
 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):  5.61E-009 Pa (4.21E-011 mm Hg)
  Log Koa (Koawin est  ): 18.515
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  534 
       Octanol/air (Koa) model:  8.04E+005 
   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 =  81.1247 E-12 cm3/molecule-sec
      Half-Life =     0.132 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.582 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    :  6.225E+005
      Log Koc:  5.794 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.784E-002  L/mol-sec
  Kb Half-Life at pH 8:       1.231  years  
  Kb Half-Life at pH 7:      12.311  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.007 (BCF = 10.16)
       log Kow used: 2.22 (estimated)

 Volatilization from Water:
    Henry LC:  1.24E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.898E+014  hours   (4.124E+013 days)
    Half-Life from Model Lake :  1.08E+016  hours   (4.499E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               2.51  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.41  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       4.26e-007       3.16         1000       
   Water     19.4            900          1000       
   Soil      80.5            1.8e+003     1000       
   Sediment  0.1             8.1e+003     0          
     Persistence Time: 1.53e+003 hr

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