ChemSpider 2D Image | fradafiban | C20H21N3O4

fradafiban

  • Molecular FormulaC20H21N3O4
  • Average mass367.398 Da
  • Monoisotopic mass367.153198 Da
  • ChemSpider ID59392
  • defined stereocentres - 2 of 2 defined stereocentres


More details:






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

(3S,5S)-5-[[[4'-(Aminoiminomethyl)[1,1'-biphenyl]-4-yl]oxy]methyl]-2-oxo-3-pyrrolidineacetic Acid
[(3S,5S)-5-{[(4'-Carbamimidoyl-4-biphenylyl)oxy]methyl}-2-oxo-3-pyrrolidinyl]acetic acid [ACD/IUPAC Name]
[(3S,5S)-5-{[(4'-Carbamimidoyl-4-biphenylyl)oxy]methyl}-2-oxo-3-pyrrolidinyl]essigsäure [German] [ACD/IUPAC Name]
[(3S,5S)-5-{[(4'-Carbamimidoylbiphenyl-4-yl)oxy]methyl}-2-oxopyrrolidin-3-yl]acetic acid
148396-36-5 [RN]
3-Pyrrolidineacetic acid, 5-[[[4'-(aminoiminomethyl)[1,1'-biphenyl]-4-yl]oxy]methyl]-2-oxo-, (3S,5S)- [ACD/Index Name]
7271
Acide [(3S,5S)-5-{[(4'-carbamimidoyl-4-biphénylyl)oxy]méthyl}-2-oxo-3-pyrrolidinyl]acétique [French] [ACD/IUPAC Name]
DQ0H2B8YKN
fradafiban [INN]
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  • Miscellaneous
    • Chemical Class:

      A pyrrolidinone that is pyrrolidin-2-one which is substituted at positions 3 and 5 by carboxymethyl and hydroxymethyl groups, respectively, and in which the hydrogen of the resulting alcoholic hydroxy group is replaced by a 4'-carbamimidoylbiphenyl-4-yl group (the <stereo>S</stereo>,<stereo>S</stereo>-diastereoisomer). A figrinogen receptor antagonist. ChEBI CHEBI:73266
      A pyrrolidinone that is pyrrolidin-2-one which is substituted at positions 3 and 5 by carboxymethyl and hydroxymethyl groups, respectively, and in which the hydrogen of the resulting alcoholic hydroxy group is replaced by a 4'-carbamimidoylbiphenyl-4-yl group (the S,S-diastereoisomer). A figrinogen receptor antagonist. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:73266

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

Density: 1.4±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.659
Molar Refractivity: 97.9±0.5 cm3
#H bond acceptors: 7
#H bond donors: 5
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 1
ACD/LogP: -0.27
ACD/LogD (pH 5.5): -1.63
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.69
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 126 Å2
Polarizability: 38.8±0.5 10-24cm3
Surface Tension: 57.9±7.0 dyne/cm
Molar Volume: 265.5±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) =  1.53

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  631.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  273.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.06E-014  (Modified Grain method)
    Subcooled liquid VP: 1.14E-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):  237.9
       log Kow used: 1.53 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  491.5 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.13E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.186E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.53  (KowWin est)
  Log Kaw used:  -20.060  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.590
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9874
   Biowin2 (Non-Linear Model)     :   0.9669
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6395  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.9858  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3313
   Biowin6 (MITI Non-Linear Model):   0.0502
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1196
 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):  1.52E-009 Pa (1.14E-011 mm Hg)
  Log Koa (Koawin est  ): 21.590
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.97E+003 
       Octanol/air (Koa) model:  9.55E+008 
   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 =  82.3770 E-12 cm3/molecule-sec
      Half-Life =     0.130 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.558 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    :  1.093E+004
      Log Koc:  4.039 

 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: 1.53 (estimated)

 Volatilization from Water:
    Henry LC:  2.13E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.269E+018  hours   (2.195E+017 days)
    Half-Life from Model Lake : 5.748E+019  hours   (2.395E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               1.98  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.89  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       3.66e-010       3.12         1000       
   Water     32.3            900          1000       
   Soil      67.6            1.8e+003     1000       
   Sediment  0.0831          8.1e+003     0          
     Persistence Time: 1.2e+003 hr




                    

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