ChemSpider 2D Image | Nafadotride | C22H27N3O2

Nafadotride

  • Molecular FormulaC22H27N3O2
  • Average mass365.469 Da
  • Monoisotopic mass365.210327 Da
  • ChemSpider ID2652798

More details:






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

149649-22-9 [RN]
2-Naphthalenecarboxamide, N-[(1-butyl-2-pyrrolidinyl)methyl]-4-cyano-1-methoxy- [ACD/Index Name]
N-[(1-Butyl-2-pyrrolidinyl)methyl]-4-cyan-1-methoxy-2-naphthamid [German] [ACD/IUPAC Name]
N-[(1-Butyl-2-pyrrolidinyl)méthyl]-4-cyano-1-méthoxy-2-naphtamide [French] [ACD/IUPAC Name]
N-[(1-Butyl-2-pyrrolidinyl)methyl]-4-cyano-1-methoxy-2-naphthamide [ACD/IUPAC Name]
N-[(1-Butylpyrrolidin-2-yl)methyl]-4-cyano-1-methoxy-2-naphthamide
N-[(1-butylpyrrolidin-2-yl)methyl]-4-cyano-1-methoxynaphthalene-2-carboxamide
Nafadotride
(±)-nafadotride
[149649-22-9] [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:64191 [DBID]
Bay 11-7083 | [DBID]
JP25MZ26IQ [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Sold with the permission of INSERM and BIOPROJET Tocris Bioscience 1347
    • Chemical Class:

      A naphthalenecarboxamide resulting from the formal condensation of the carboxylic acid group of 4-cyano-1-methoxynaphthalene-2-carboxylic acid with the primary amino group of 1-(1-butylpyrrolidin-2-yl ]methanamine. It is a highly potent, competitive, preferential dopamine D<smallsub>3</smallsub> receptor antagonist, centrally active upon systemic administration. ChEBI CHEBI:64191
      A naphthalenecarboxamide resulting from the formal condensation of the carboxylic acid group of 4-cyano-1-methoxynaphthalene-2-carboxylic acid with the primary amino group of 1-(1-butylpyrrolidin-2-yl ]methanamine. It is a highly potent, competitive, preferential dopamine D3 receptor antagonist, centrally active upon systemic administration. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64191
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 1347
      D3 Receptors Tocris Bioscience 1347
      Dopamine Receptors Tocris Bioscience 1347
      Highly potent, competitive, preferential dopamine D3 receptor antagonist. Ki values are 0.52, 5, and 269 nM for human cloned D3, D2 and D4 receptors respectively. Centrally active upon systemic admini stration. Tocris Bioscience 1347
      Highly potent, competitive, preferential dopamine D3 receptor antagonist. Ki values are 0.52, 5, and 269 nM for human cloned D3, D2 and D4 receptors respectively. Centrally active upon systemic administration. Tocris Bioscience 1347
      Highly potent, preferential D3 antagonist Tocris Bioscience 1347

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

Density: 1.2±0.1 g/cm3
Boiling Point: 556.5±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 83.8±3.0 kJ/mol
Flash Point: 290.4±27.3 °C
Index of Refraction: 1.604
Molar Refractivity: 107.1±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 3.66
ACD/LogD (pH 5.5): 0.65
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.14
ACD/LogD (pH 7.4): 1.38
ACD/BCF (pH 7.4): 1.80
ACD/KOC (pH 7.4): 11.40
Polar Surface Area: 65 Å2
Polarizability: 42.5±0.5 10-24cm3
Surface Tension: 53.8±5.0 dyne/cm
Molar Volume: 311.5±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) =  3.97

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  557.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  239.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.4E-012  (Modified Grain method)
    Subcooled liquid VP: 9.19E-010 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):  1.093
       log Kow used: 3.97 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.9918 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.25E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.936E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.97  (KowWin est)
  Log Kaw used:  -13.877  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.847
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1258
   Biowin2 (Non-Linear Model)     :   0.9991
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2403  (months      )
   Biowin4 (Primary Survey Model) :   3.5189  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2447
   Biowin6 (MITI Non-Linear Model):   0.0297
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7993
 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):  1.23E-007 Pa (9.19E-010 mm Hg)
  Log Koa (Koawin est  ): 17.847
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  24.5 
       Octanol/air (Koa) model:  1.73E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 122.8558 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.045 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3.751E+004
      Log Koc:  4.574 

 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 = 2.361 (BCF = 229.4)
       log Kow used: 3.97 (estimated)

 Volatilization from Water:
    Henry LC:  3.25E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.444E+012  hours   (1.435E+011 days)
    Half-Life from Model Lake : 3.757E+013  hours   (1.565E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              28.71  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.40  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       2.35e-006       2.09         1000       
   Water     8.53            1.44e+003    1000       
   Soil      89.1            2.88e+003    1000       
   Sediment  2.38            1.3e+004     0          
     Persistence Time: 2.92e+003 hr




                    

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