ChemSpider 2D Image | Captopril | C9H15NO3S

Captopril

  • Molecular FormulaC9H15NO3S
  • Average mass217.285 Da
  • Monoisotopic mass217.077271 Da
  • ChemSpider ID40130
  • defined stereocentres - 2 of 2 defined stereocentres


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(-)-Captopril
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidin-2-carbonsäure [German]
(S)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline
1-((2S)-3-Mercapto-2-methylpropionyl)-L-proline
1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline
1-(D-3-Mercapto-2-methyl-1-oxopropyl)-L-proline (S,S)
1-[(2S)-2-Methyl-3-sulfanylpropanoyl]-L-prolin [German] [ACD/IUPAC Name]
1-[(2S)-2-Methyl-3-sulfanylpropanoyl]-L-proline [ACD/IUPAC Name]
1-[(2S)-2-Méthyl-3-sulfanylpropanoyl]-L-proline [French] [ACD/IUPAC Name]
1-[(2S)-3-Mercapto-2-methyl-1-oxopropyl]-L-proline
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C4042_SIAL [DBID]
C8856_SIAL [DBID]
CHEBI:3380 [DBID]
D00251 [DBID]
DivK1c_000208 [DBID]
EU-0100302 [DBID]
HSDB 6527 [DBID]
KBio1_000208 [DBID]
KBio2_001168 [DBID]
KBio2_003736 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white crystalline powder Oxford University Chemical Safety Data (No longer updated) More details
      WHITE POWDER NIH Clinical Collection [SMR000059061]
    • Stability:

      Stable. Incompatible with strong oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 4245 mg kg-1, ORL-MUS LD50 2500 mg kg-1, IVN-MUS LD50 663 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      C09AA01 Wikidata Q421119
      P261; P262 Biosynth Q-200792
      Safety glasses, gloves, adequate ventilation. Oxford University Chemical Safety Data (No longer updated) More details
    • Target Organs:

      Collagenase inhibitor;hydrolase;MMP inhibitor;RAAS inhibitor TargetMol T1462
    • Chemical Class:

      A <stereo>L</stereo>-proline derivative in which <stereo>L</stereo>-proline is substituted on nitrogen with a (2<stereo>S</stereo>)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensi ve ACE inhibitor drug. ChEBI CHEBI:3380
    • Drug Status:

      approved BIONET-Key Organics KS-5025
    • Compound Source:

      synthetic Microsource [01500682]
    • Bio Activity:

      72 kDa type IV collagenase;LTA4H;MMP-9;RAAS TargetMol T1462
      ACE inhibitor; also inhibits LTA4 hydrolase Tocris Bioscience 4455
      Angiotensin-Converting Enzyme Tocris Bioscience 4455
      Angiotensin-converting Enzyme (ACE) MedChem Express HY-B0368
      Angiotensin-converting enzyme (ACE) inhibitor (IC50 = 0.022 ?M). Also displays reversible, competitive inhibition of leukotriene A4 (LTA4) hydrolase. Tocris Bioscience 4455
      Angiotensin-converting enzyme (ACE) inhibitor (IC50 = 0.022 muM). Also displays reversible, competitive inhibition of leukotriene A4 (LTA4) hydrolase. Tocris Bioscience 4455
      Antihypertensive agent; Zerenex Molecular [ZBioX-0494]
      Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE). MedChem Express
      Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE).; Target: ACE; Captopril has been shown to have similar morbidity and mortality benefits to those of diuretics and beta-blockers in hypertensive patients. MedChem Express HY-B0368
      Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE).;Target: ACECaptopril has been shown to have similar morbidity and mortality benefits to those of diuretics and beta-blockers in hypertensive patients. Captopril has been shown to delay the progression of diabetic nephropathy, and enalapril and lisinopril prevent the development of nephropathy in normoalbuminuric patients with diabetes [1]. an equimolar ratio of the cis and trans states of captopril exists in solution and that the enzyme selects only the trans state of the inhibitor that presents architectural and stereoelectronic complementarity with its substrate binding groove [2]. MedChem Express HY-B0368
      Endocrinology/ Hormones;Proteases/Proteasome TargetMol T1462
      Enzymes Tocris Bioscience 4455
      Metabolism/Protease MedChem Express HY-B0368
      Metabolism/Protease; MedChem Express HY-B0368
      Proteases Tocris Bioscience 4455
  • Gas Chromatography
    • Retention Index (Normal Alkane):

      1926 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 12 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 40 C; End T: 290 C; Start time: 1 min; CAS no: 62571862; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Neill, G.P.; Davies, N.W.; McLean, S., Automated screening procedure using gas chromatography-mass spectrometry for identification of drugs after their extraction from biological samples, J. Chromatogr., 565, 1991, 207-224.) NIST Spectra nist ri

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

Density: 1.3±0.1 g/cm3
Boiling Point: 427.0±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 74.8±6.0 kJ/mol
Flash Point: 212.1±27.3 °C
Index of Refraction: 1.551
Molar Refractivity: 54.4±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.27
ACD/LogD (pH 5.5): -1.23
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.83
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 96 Å2
Polarizability: 21.6±0.5 10-24cm3
Surface Tension: 54.3±3.0 dyne/cm
Molar Volume: 170.7±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) =  0.84
    Log Kow (Exper. database match) =  0.34
       Exper. Ref:  Ranadive,SA et al. (1992)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  369.60  (Adapted Stein & Brown method)
    Melting Pt (deg C):  133.83  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.25E-006  (Modified Grain method)
    MP  (exp database):  106 deg C
    Subcooled liquid VP: 4.5E-005 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):  1.823e+004
       log Kow used: 0.34 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.5621e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.89E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.137E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.34  (exp database)
  Log Kaw used:  -10.799  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.139
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9269
   Biowin2 (Non-Linear Model)     :   0.9629
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0294  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1252  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4443
   Biowin6 (MITI Non-Linear Model):   0.3106
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0850
 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):  0.006 Pa (4.5E-005 mm Hg)
  Log Koa (Koawin est  ): 11.139
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0005 
       Octanol/air (Koa) model:  0.0338 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0177 
       Mackay model           :  0.0385 
       Octanol/air (Koa) model:  0.73 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  88.2716 E-12 cm3/molecule-sec
      Half-Life =     0.121 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.454 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0281 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  20.35
      Log Koc:  1.309 

 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: 0.34 (expkow database)

 Volatilization from Water:
    Henry LC:  3.89E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.219E+009  hours   (9.244E+007 days)
    Half-Life from Model Lake :  2.42E+010  hours   (1.008E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  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       9.14e-006       2.91         1000       
   Water     37.9            360          1000       
   Soil      62.1            720          1000       
   Sediment  0.0707          3.24e+003    0          
     Persistence Time: 586 hr




                    

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