ChemSpider 2D Image | Dexverapamil | C27H38N2O4

Dexverapamil

  • Molecular FormulaC27H38N2O4
  • Average mass454.602 Da
  • Monoisotopic mass454.283173 Da
  • ChemSpider ID59223
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

(+)-(R)-3-(3,4-Dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrile
(+)-(R)-5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
(+)-(R)-Verapamil
(2R)-2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile [ACD/IUPAC Name]
(2R)-2-(3,4-Diméthoxyphényl)-5-{[2-(3,4-diméthoxyphényl)éthyl](méthyl)amino}-2-isopropylpentanenitrile [French] [ACD/IUPAC Name]
(2R)-2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentannitril [German] [ACD/IUPAC Name]
(aR)-a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)benzeneacetonitrile
(R)-a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)benzeneacetonitrile
(R)-Verapamil
38321-02-7 [RN]
More...

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

D-365 [DBID]
Lopac-V-4629 [DBID]
NCGC00016083-01 [DBID]
NCGC00016412-01 [DBID]
NCGC00024710-01 [DBID]
NCI60_010786 [DBID]
NCIMech_000868 [DBID]
Tocris-0654 [DBID]
  • Miscellaneous
    • Chemical Class:

      A 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has <stereo>R</stereo> configuration. It competitively inhibits the multidrug resistance ef flux pump P-glycoprotein (MDR-1, EC 3.6.3.44), thereby potentially increasing the effectiveness of a wide range of antineoplastic drugs which are inactivated by MDR-1 mechanisms. Dexverapamil exhibits lower calcium antagonistic activity and toxicity than racemic verapamil. ChEBI CHEBI:77734
      A 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has R configuration. It competitively inhibits the multidrug resistance ef; flux pump P-gly coprotein (MDR-1, EC 3.6.3.44), thereby potentially increasing the effectiveness of a wide range of antineoplastic drugs which are inactivated by MDR-1 mechanisms. Dexverapamil exhibits lower calcium antagonistic activity and toxicity than racemic verapamil. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:77734

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

Density: 1.1±0.1 g/cm3
Boiling Point: 586.2±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.5±3.0 kJ/mol
Flash Point: 308.3±30.1 °C
Index of Refraction: 1.526
Molar Refractivity: 131.9±0.3 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 14
#Rule of 5 Violations: 0
ACD/LogP: 3.90
ACD/LogD (pH 5.5): 1.01
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.81
ACD/LogD (pH 7.4): 2.38
ACD/BCF (pH 7.4): 16.01
ACD/KOC (pH 7.4): 90.75
Polar Surface Area: 64 Å2
Polarizability: 52.3±0.5 10-24cm3
Surface Tension: 37.7±3.0 dyne/cm
Molar Volume: 429.4±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) =  4.80
    Log Kow (Exper. database match) =  3.79
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  532.15  (Adapted Stein & Brown method)
    Melting Pt (deg C):  227.62  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.18E-009  (Modified Grain method)
    MP  (exp database):  < 25 deg C
    BP  (exp database):  243-246 @ 0.01 mm Hg deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  4.471
       log Kow used: 3.79 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.01495 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.79E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.592E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.79  (exp database)
  Log Kaw used:  -12.444  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.234
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0312
   Biowin2 (Non-Linear Model)     :   0.9989
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.3379  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9251  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3385
   Biowin6 (MITI Non-Linear Model):   0.0405
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1742
 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):  5.57E-007 Pa (4.18E-009 mm Hg)
  Log Koa (Koawin est  ): 16.234
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.38 
       Octanol/air (Koa) model:  4.21E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.995 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 185.8488 E-12 cm3/molecule-sec
      Half-Life =     0.058 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.691 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.996 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.634E+006
      Log Koc:  6.666 

 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 = 2.218 (BCF = 165.3)
       log Kow used: 3.79 (expkow database)

 Volatilization from Water:
    Henry LC:  8.79E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.42E+011  hours   (5.917E+009 days)
    Half-Life from Model Lake : 1.549E+012  hours   (6.455E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              21.47  percent
    Total biodegradation:        0.25  percent
    Total sludge adsorption:    21.22  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       4.74e-008       1.38         1000       
   Water     4.29            4.32e+003    1000       
   Soil      94.7            8.64e+003    1000       
   Sediment  1.05            3.89e+004    0          
     Persistence Time: 7.93e+003 hr




                    

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