ChemSpider 2D Image | Sacubitril | C24H29NO5

Sacubitril

  • Molecular FormulaC24H29NO5
  • Average mass411.491 Da
  • Monoisotopic mass411.204559 Da
  • ChemSpider ID7987587

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

[1,1'-Biphenyl]-4-pentanoic acid, γ-[(3-carboxy-1-oxopropyl)amino]-α-methyl-, α-ethyl ester, (αR,γS)- [ACD/Index Name]
149709-62-6 [RN]
17ERJ0MKGI
4-{[(2S,4R)-1-(4-Biphenylyl)-5-ethoxy-4-methyl-5-oxo-2-pentanyl]amino}-4-oxobutanoic acid [ACD/IUPAC Name]
4-{[(2S,4R)-1-(4-Biphenylyl)-5-ethoxy-4-methyl-5-oxo-2-pentanyl]amino}-4-oxobutansäure [German] [ACD/IUPAC Name]
Acide 4-{[(2S,4R)-1-(4-biphénylyl)-5-éthoxy-4-méthyl-5-oxo-2-pentanyl]amino}-4-oxobutanoïque [French] [ACD/IUPAC Name]
AHU377
Sacubitril [INN] [USAN] [Wiki]
Sacubitril [French] [INN]
Sacubitrilo [Spanish] [INN]
More...

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

9819 [DBID]
CCRIS 4693 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      AHU-377 is a potent neprilysin inhibitor with IC50 of 5.0 nM; a component of LCZ696. MedChem Express
      AHU-377 is a potent neprilysin inhibitor with IC50 of 5.0 nM; a component of LCZ696.; IC50 Value: 5.0 nM; Target: neprilysin; in vitro:; in vivo: LCZ696 is a novel single molecule comprising molecular moieties of valsartan and NEP inhibitor prodrug AHU377 (1:1 ratio). MedChem Express HY-15407
      AHU-377 is a potent neprilysin inhibitor with IC50 of 5.0 nM; a component of LCZ696.;IC50 Value: 5.0 nM;Target: neprilysin;In vitro:;In vivo: LCZ696 is a novel single molecule comprising molecular moieties of valsartan and NEP inhibitor prodrug AHU377 (1:1 ratio). Oral administration of LCZ696 caused dose-dependent increases in atrial natriuretic peptide immunoreactivity (due to NEP inhibition) in Sprague-Dawley rats and provided sustained, dose-dependent blood pressure reductions in hypertensive double-transgenic rats. In healthy participants, a randomized, double-blind, placebo-controlled study (n = 80) of single-dose (200-1200 mg) and multiple-dose (50-900 mg once daily for 14 days) oral administration of LCZ696 showed that peak plasma concentrations were reached rapidly for valsartan (1.6-4.9 hours), AHU377 (0.5-1.1 hours), and its active moiety, LBQ657 (1.8-3.5 hours). [1]. LCZ696 is superior to valsartan alone in reducing blood pressure. Preliminary results from a Phase II t MedChem Express HY-15407
      Neprilysin MedChem Express HY-15407
      Others MedChem Express HY-15407

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

Density: 1.2±0.1 g/cm3
Boiling Point: 656.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 101.6±3.0 kJ/mol
Flash Point: 351.1±31.5 °C
Index of Refraction: 1.549
Molar Refractivity: 113.6±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 0
ACD/LogP: 3.96
ACD/LogD (pH 5.5): 3.01
ACD/BCF (pH 5.5): 65.95
ACD/KOC (pH 5.5): 366.69
ACD/LogD (pH 7.4): 1.20
ACD/BCF (pH 7.4): 1.04
ACD/KOC (pH 7.4): 5.76
Polar Surface Area: 93 Å2
Polarizability: 45.0±0.5 10-24cm3
Surface Tension: 45.7±3.0 dyne/cm
Molar Volume: 357.4±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) =  4.37

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  603.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  260.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.6E-013  (Modified Grain method)
    Subcooled liquid VP: 6.07E-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):  0.4815
       log Kow used: 4.37 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.0612 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.48E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.799E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.37  (KowWin est)
  Log Kaw used:  -15.218  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.588
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1914
   Biowin2 (Non-Linear Model)     :   0.9990
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6876  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0104  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2549
   Biowin6 (MITI Non-Linear Model):   0.0852
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5225
 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):  8.09E-009 Pa (6.07E-011 mm Hg)
  Log Koa (Koawin est  ): 19.588
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  371 
       Octanol/air (Koa) model:  9.51E+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 =  34.2919 E-12 cm3/molecule-sec
      Half-Life =     0.312 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.743 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    :  1.889E+004
      Log Koc:  4.276 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.453E-002  L/mol-sec
  Kb Half-Life at pH 8:       1.512  years  
  Kb Half-Life at pH 7:      15.118  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 4.37 (estimated)

 Volatilization from Water:
    Henry LC:  1.48E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.025E+013  hours   (3.344E+012 days)
    Half-Life from Model Lake : 8.754E+014  hours   (3.648E+013 days)

 Removal In Wastewater Treatment:
    Total removal:              49.06  percent
    Total biodegradation:        0.47  percent
    Total sludge adsorption:    48.59  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       2.7e-006        7.49         1000       
   Water     10.3            900          1000       
   Soil      83.9            1.8e+003     1000       
   Sediment  5.75            8.1e+003     0          
     Persistence Time: 1.95e+003 hr

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