ChemSpider 2D Image | Enalaprilat | C18H24N2O5

Enalaprilat

  • Molecular FormulaC18H24N2O5
  • Average mass348.394 Da
  • Monoisotopic mass348.168518 Da
  • ChemSpider ID4575429

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

((S)-1-carboxy-3-phenylpropyl)-L-alanyl-L-proline
(2S)-1-[(2S)-2-[[(1S)-1-carboxy-3-phenyl-propyl]amino]propanoyl]pyrrolidine-2-carboxylic acid
(2S)-1-[(2S)-2-{[(1S)-1-Carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidin-2-carbonsäure [German]
(2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid
acide (2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phénylpropyl]amino}propanoyl]pyrrolidine-2-carboxylique [French]
Enalaprilat [USP] [Wiki]
L-Proline, N-((1S)-1-carboxy-3-phenylpropyl)-L-alanyl-
L-Proline, N-[(1S)-1-carboxy-3-phenylpropyl]alanyl- [ACD/Index Name]
MFCD00865786
N-[(1S)-1-Carboxy-3-phenylpropyl]alanyl-L-prolin [German] [ACD/IUPAC Name]
More...

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

5424 [DBID]
3656856 [DBID]
C11720 [DBID]
MK-422 [DBID]
  • Miscellaneous

    • Chemical Class:

      Enalapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid. Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor and is used (often in the form of its prodrug, enalapril) in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial inf arction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is given by intravenous injection, usually as the dihydrate. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4786, CHEBI:4786

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

Density: 1.3±0.1 g/cm3
Boiling Point: 601.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 94.1±3.0 kJ/mol
Flash Point: 317.3±31.5 °C
Index of Refraction: 1.580
Molar Refractivity: 90.1±0.3 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.54
ACD/LogD (pH 5.5): -2.22
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.68
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 107 Å2
Polarizability: 35.7±0.5 10-24cm3
Surface Tension: 59.9±3.0 dyne/cm
Molar Volume: 270.7±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) =  -0.94
    Log Kow (Exper. database match) =  -0.74
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  567.41  (Adapted Stein & Brown method)
    Melting Pt (deg C):  316.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.92E-011  (Modified Grain method)
    MP  (exp database):  148-151 deg C
    Subcooled liquid VP: 5.18E-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):  11.32
       log Kow used: -0.74 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  930.09 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 :   7.85E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.182E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.74  (exp database)
  Log Kaw used:  -16.494  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.754
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2738
   Biowin2 (Non-Linear Model)     :   0.9960
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0758  (weeks       )
   Biowin4 (Primary Survey Model) :   4.3013  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2034
   Biowin6 (MITI Non-Linear Model):   0.0337
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2676
 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):  6.91E-008 Pa (5.18E-010 mm Hg)
  Log Koa (Koawin est  ): 15.754
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  43.4 
       Octanol/air (Koa) model:  1.39E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 126.6718 E-12 cm3/molecule-sec
      Half-Life =     0.084 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.013 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    :  7761
      Log Koc:  3.890 

 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: -0.74 (expkow database)

 Volatilization from Water:
    Henry LC:  7.85E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.392E+015  hours   (5.801E+013 days)
    Half-Life from Model Lake : 1.519E+016  hours   (6.328E+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       7.59e-010       2.03         1000       
   Water     38.9            360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 580 hr

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