ChemSpider 2D Image | Benazeprilat | C22H24N2O5

Benazeprilat

  • Molecular FormulaC22H24N2O5
  • Average mass396.436 Da
  • Monoisotopic mass396.168518 Da
  • ChemSpider ID4576478

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(2S)-2-{[(3S)-1-(Carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid [ACD/IUPAC Name]
(2S)-2-{[(3S)-1-(Carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutansäure [German] [ACD/IUPAC Name]
(S-(R*,R*))-3-((1-Carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid
1H-1-Benzazepine-1-acetic acid, 3-[[(1S)-1-carboxy-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, (3S)- [ACD/Index Name]
86541-78-8 [RN]
Acide (2S)-2-{[(3S)-1-(carboxyméthyl)-2-oxo-2,3,4,5-tétrahydro-1H-1-benzazépin-3-yl]amino}-4-phénylbutanoïque [French] [ACD/IUPAC Name]
Benazeprilat [USAN] [Wiki]
JRM708L703
(2S)-2-[[(3S)-1-(carboxymethyl)-2-keto-4,5-dihydro-3H-1-benzazepin-3-yl]amino]-4-phenyl-butyric acid
(2S)-2-[[(3S)-1-(Carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino]-4-phenylbutanoic Acid (Benazeprilat)
More...

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

6128 [DBID]
CGS 14831 [DBID]
Cgs-14831 [DBID]
D03077 [DBID]
  • Miscellaneous

    • Chemical Class:

      A benzazepine that is 1,3,4,5-tetrahydro-2<element>H</element>-1-benzazepin-2-one in which the hydrogen attached to the nitrogen is replaced by a carboxy methyl group and in which the 3-<ital>pro</ita l>-<stereo>S</stereo> hydrogen is replaced by the amino group of (2<stereo>S</stereo>)-2-amino-4-phenylbutanoic acid. An angiotensin-converting enzyme inhibitor, it is used as its monoester prodrug be nazepril in the treatment of hypertension and heart failure. ChEBI CHEBI:88200
      A benzazepine that is 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in which the hydrogen attached to the nitrogen is replaced by a carboxy methyl group and in which the 3-pro-S hydrogen is replaced by the amino group of (2S)-2-amino-4-phenylbutanoic acid. An angiotensin-converting enzyme inhibitor, it is used as its monoester prodrug benazepril in the treatment of hypertension and heart failure. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88200, CHEBI:88200

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

Density: 1.3±0.1 g/cm3
Boiling Point: 711.3±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 109.2±3.0 kJ/mol
Flash Point: 384.0±32.9 °C
Index of Refraction: 1.643
Molar Refractivity: 106.6±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 2.98
ACD/LogD (pH 5.5): -1.31
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.76
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 107 Å2
Polarizability: 42.3±0.5 10-24cm3
Surface Tension: 68.1±5.0 dyne/cm
Molar Volume: 294.8±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) =  0.11

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  652.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  329.17  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.13E-015  (Modified Grain method)
    Subcooled liquid VP: 3.12E-012 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):  1.086
       log Kow used: 0.11 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  17.494 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.15E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.428E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.11  (KowWin est)
  Log Kaw used:  -16.328  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.438
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3056
   Biowin2 (Non-Linear Model)     :   0.9956
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8948  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1634  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0979
   Biowin6 (MITI Non-Linear Model):   0.0127
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2597
 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):  4.16E-010 Pa (3.12E-012 mm Hg)
  Log Koa (Koawin est  ): 16.438
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.21E+003 
       Octanol/air (Koa) model:  6.73E+003 
   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 = 128.3629 E-12 cm3/molecule-sec
      Half-Life =     0.083 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.000 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    :  2.138E+004
      Log Koc:  4.330 

 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: 0.11 (estimated)

 Volatilization from Water:
    Henry LC:  1.15E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.014E+015  hours   (4.224E+013 days)
    Half-Life from Model Lake : 1.106E+016  hours   (4.608E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       2.1e-005        2            1000       
   Water     38.3            360          1000       
   Soil      61.6            720          1000       
   Sediment  0.0709          3.24e+003    0          
     Persistence Time: 583 hr

Click to predict properties on the Chemicalize site


Advertisement