ChemSpider 2D Image | Darifenacin | C28H30N2O2

Darifenacin

  • Molecular FormulaC28H30N2O2
  • Average mass426.550 Da
  • Monoisotopic mass426.230713 Da
  • ChemSpider ID392054
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-a,a-diphenyl-3-pyrrolidineacetamide
(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-α,α-diphenyl-3-pyrrolidineacetamide
133099-04-4 [RN]
2-((3S)-1-(2-(2,3-Dihydro-1-benzofuran-5-yl)ethyl)-3-pyrrolidinyl)-2,2-diphenylacetamide
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofur-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamid [German]
2-{(3S)-1-[2-(2,3-dihydro-1-benzofur-5-yl)éthyl]pyrrolidin-3-yl}-2,2-diphénylacétamide [French]
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamid [German] [ACD/IUPAC Name]
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide [ACD/IUPAC Name]
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofuran-5-yl)éthyl]-3-pyrrolidinyl}-2,2-diphénylacétamide [French] [ACD/IUPAC Name]
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

UK-88525 [DBID]
D03654 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      G04BD10 Wikidata Q166476
    • Chemical Class:

      2-[(3<stereo>S</stereo>)-1-Ethylpyrrolidin-3-yl]-2,2-diphenylacetamide in which one of the hydrogens at the 2-position of the ethyl group is substituted by a 2,3-dihydro-1-benzofuran-5-yl group. It i s a selective antagonist for the M<smallsub>3</smallsub> muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions, and is used as the hydrobromide salt in the management of urinary incontinence. ChEBI CHEBI:391960
    • Bio Activity:

      Darifenacin(UK88525) is a selective M3 muscarinic receptor antagonist with pKi of 8.9. MedChem Express
      Darifenacin(UK88525) is a selective M3 muscarinic receptor antagonist with pKi of 8.9.; IC50 value: 8.9 (pKi) [1]; Target: M3 receptor; in vitro: Darifenacin exerts non-parallel rightward displacement of the agonist curve and also significant depression of the maximum response (+)-cis-Dioxolane produced concentration-dependent contraction of the isolated bladder of rat [1]. MedChem Express HY-A0033
      GPCR/G protein MedChem Express HY-A0033
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-A0033
      mAChR MedChem Express HY-A0033

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

Density: 1.2±0.1 g/cm3
Boiling Point: 614.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 91.2±3.0 kJ/mol
Flash Point: 325.3±31.5 °C
Index of Refraction: 1.624
Molar Refractivity: 126.3±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 4.50
ACD/LogD (pH 5.5): 1.15
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.26
ACD/LogD (pH 7.4): 2.33
ACD/BCF (pH 7.4): 12.54
ACD/KOC (pH 7.4): 63.94
Polar Surface Area: 56 Å2
Polarizability: 50.1±0.5 10-24cm3
Surface Tension: 53.0±3.0 dyne/cm
Molar Volume: 357.7±3.0 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) =  5.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  596.83  (Adapted Stein & Brown method)
    Melting Pt (deg C):  257.83  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.56E-013  (Modified Grain method)
    Subcooled liquid VP: 8.93E-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):  0.08736
       log Kow used: 5.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.07318 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.15E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.645E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.13  (KowWin est)
  Log Kaw used:  -14.328  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.458
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8629
   Biowin2 (Non-Linear Model)     :   0.9369
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5716  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9461  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1160
   Biowin6 (MITI Non-Linear Model):   0.0042
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.4253
 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):  1.19E-008 Pa (8.93E-011 mm Hg)
  Log Koa (Koawin est  ): 19.458
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  252 
       Octanol/air (Koa) model:  7.05E+006 
   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 = 148.8256 E-12 cm3/molecule-sec
      Half-Life =     0.072 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.862 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    :  1.352E+007
      Log Koc:  7.131 

 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 = 3.249 (BCF = 1772)
       log Kow used: 5.13 (estimated)

 Volatilization from Water:
    Henry LC:  1.15E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.051E+013  hours   (4.381E+011 days)
    Half-Life from Model Lake : 1.147E+014  hours   (4.78E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              81.42  percent
    Total biodegradation:        0.70  percent
    Total sludge adsorption:    80.72  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       2.8e-006        1.72         1000       
   Water     2.67            4.32e+003    1000       
   Soil      80.1            8.64e+003    1000       
   Sediment  17.3            3.89e+004    0          
     Persistence Time: 9.82e+003 hr




                    

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