ChemSpider 2D Image | Lisinopril | C21H31N3O5

Lisinopril

  • Molecular FormulaC21H31N3O5
  • Average mass405.488 Da
  • Monoisotopic mass405.226379 Da
  • ChemSpider ID4514933
  • defined stereocentres - 3 of 3 defined stereocentres


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

(2S)-1-[(2S)-6-Amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]-2-pyrrolidinecarboxylic acid
(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
1-{N2-[(1S)-1-Carboxy-3-phenylpropyl]-L-lysyl}-L-prolin
278-488-1 [EINECS]
5425
76547-98-3 [RN]
7Q3P4BS2FD
L-Proline, N2-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl- [ACD/Index Name]
N2-[(1S)-1-Carboxy-3-phenylpropyl]-L-lysyl-L-prolin [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 4276619 [DBID]
CCRIS 3568 [DBID]
CHEBI:6503 [DBID]
DivK1c_001037 [DBID]
KBio1_001037 [DBID]
KBio2_000977 [DBID]
KBio2_003545 [DBID]
KBio2_006113 [DBID]
KBio3_002002 [DBID]
KBioGR_001599 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C09AA03 Wikidata Q412208
    • Compound Source:

      synthetic Microsource [01501217]
    • Bio Activity:

      Angiotensin-converting Enzyme (ACE) MedChem Express HY-18206
      Antihypertensive agent Zerenex Molecular [ZBioX-0550]
      Lisinopril is angiotensin-converting enzyme inhibitor, used in treatment of hypertension, congestive heart failure, and heart attacks. MedChem Express
      Lisinopril is angiotensin-converting enzyme inhibitor, used in treatment of hypertension, congestive heart failure, and heart attacks.; Target: ACE; Lisinopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). MedChem Express HY-18206
      Lisinopril is angiotensin-converting enzyme inhibitor, used in treatment of hypertension, congestive heart failure, and heart attacks.;Target: ACELisinopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Lisinopril may be used to treat hypertension and symptomatic congestive heart failure, to improve survival in certain individuals following myocardial infarction, and to prevent progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy [1, 2]. MedChem Express HY-18206
      Metabolism/Protease MedChem Express HY-18206
      Metabolism/Protease; MedChem Express HY-18206

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

Density: 1.3±0.1 g/cm3
Boiling Point: 666.4±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 102.9±3.0 kJ/mol
Flash Point: 356.9±31.5 °C
Index of Refraction: 1.578
Molar Refractivity: 107.5±0.3 cm3
#H bond acceptors: 8
#H bond donors: 5
#Freely Rotating Bonds: 12
#Rule of 5 Violations: 1
ACD/LogP: 1.19
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): -1.80
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 133 Å2
Polarizability: 42.6±0.5 10-24cm3
Surface Tension: 60.4±3.0 dyne/cm
Molar Volume: 323.9±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) =  -1.22
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  632.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  326.37  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.95E-015  (Modified Grain method)
    Subcooled liquid VP: 1.01E-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):  13
       log Kow used: -1.22 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  9.7e+004 mg/L ( deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1490.2 mg/L
    Wat Sol (Exper. database match) =  97000.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.89E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.621E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.22  (exp database)
  Log Kaw used:  -20.112  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.892
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.4004
   Biowin2 (Non-Linear Model)     :   0.9971
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9741  (weeks       )
   Biowin4 (Primary Survey Model) :   4.2622  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2641
   Biowin6 (MITI Non-Linear Model):   0.0268
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0932
 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):  1.35E-009 Pa (1.01E-011 mm Hg)
  Log Koa (Koawin est  ): 18.892
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.23E+003 
       Octanol/air (Koa) model:  1.91E+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 = 168.2442 E-12 cm3/molecule-sec
      Half-Life =     0.064 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.763 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    :  7.068E+004
      Log Koc:  4.849 

 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: -1.22 (expkow database)

 Volatilization from Water:
    Henry LC:  1.89E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.238E+018  hours   (2.599E+017 days)
    Half-Life from Model Lake : 6.805E+019  hours   (2.835E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       1.06e-009       1.53         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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