ChemSpider 2D Image | Tritace | C23H32N2O5

Tritace

  • Molecular FormulaC23H32N2O5
  • Average mass416.511 Da
  • Monoisotopic mass416.231110 Da
  • ChemSpider ID4514937

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrol-2-carbonsäure [German]
(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-Ethoxy-1-oxo-4-phenyl-2-butanyl]amino}propanoyl]octahydrocyclopenta[b]pyrrol-2-carbonsäure [German] [ACD/IUPAC Name]
(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-Ethoxy-1-oxo-4-phenyl-2-butanyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid [ACD/IUPAC Name]
(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
(2S,3aS,6aS)-1-[(S)-N-[(S)-1-Carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid 1-Ethyl Ester
(2S,3aS,6aS)-1-{2-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
[2S,3aS,6aS]-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
[2S-[1[R*(R*)],2a,3ab,6ab]]-1-[2-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5561 [DBID]
CHEBI:8774 [DBID]
D00421 [DBID]
HOE 498 [DBID]
HOE-498 [DBID]
KBio2_002504 [DBID]
KBio2_005072 [DBID]
KBio2_007640 [DBID]
KBio3_002849 [DBID]
KBioGR_001858 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      C09AA05 Wikidata Q412666

    • Target Organs:

      RAAS inhibitor; ACE inhibitor TargetMol T1645

    • Chemical Class:

      A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressu re and congestive heart failure. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8774, CHEBI:8774

    • Bio Activity:

      ACE;ChE TargetMol T1645
      Angiogenesis;Endocrinology/ Hormones TargetMol T1645
      Angiotensin-converting Enzyme Tocris Bioscience 5250
      Angiotensin-converting Enzyme (ACE) MedChem Express HY-B0279
      Enzymes Tocris Bioscience 5250
      Metabolism/Protease MedChem Express HY-B0279
      Metabolism/Protease; MedChem Express HY-B0279
      Non-peptide, competitive angiotensin converting enzyme (ACE) inhibitor (IC50 = 5 nM). Prodrug which is hydrolyzed in vivo to the active metabolite ramiprilat. Displays protective effects on endotheliu m against high-glucose induced dysfunction. Exhibits antihypertensive effects. Tocris Bioscience 5250
      Non-peptide, competitive angiotensin converting enzyme (ACE) inhibitor (IC50 = 5 nM). Prodrug which is hydrolyzed in vivo to the active metabolite ramiprilat. Displays protective effects on endothelium against high-glucose induced dysfunction. Exhibits antihypertensive effects. Tocris Bioscience 5250
      Non-peptide, competitive angiotensin-converting enzyme (ACE) inhibitor Tocris Bioscience 5250
      Proteases Tocris Bioscience 5250
      Ramipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM. MedChem Express
      Ramipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM.; Target: ACE; Ramipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM [1]. MedChem Express HY-B0279
      Ramipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM.;Target: ACERamipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM [1]. Ramipril enhances the activity of ACE-associated CK2 and the phosphorylation of ACE Ser1270 in cultured endothelial cells, but is unable to activate JNK or stimulate the nuclear accumulation of c-Jun in endothelial cells expressing a S1270A ACE mutant or in ACE-deficient cells. Prolonged Ramipril treatment increases ACE expression in primary cultures of human endothelial cells and in vivo (mouse lung), which can be prevented by pretreatment with the JNK inhibitor SP600125 [2].Chronic in vivo administration of Ramipril to rats at a dosage that has similar hypotensive effects in vitro HUVECs significantly reduces the rate of LPS-induced apoptosis compared to the other ACE inhibitors, which contrasts with the apoptosis effect in vitro [3]. Ramipril inhibits systolic blood pressure (SBP) with IC50 of 1.97 mg/kg MedChem Express HY-B0279

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

Density: 1.2±0.1 g/cm3
Boiling Point: 616.2±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 96.1±3.0 kJ/mol
Flash Point: 326.4±31.5 °C
Index of Refraction: 1.556
Molar Refractivity: 111.4±0.3 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 0
ACD/LogP: 3.41
ACD/LogD (pH 5.5): 1.17
ACD/BCF (pH 5.5): 1.31
ACD/KOC (pH 5.5): 9.57
ACD/LogD (pH 7.4): -0.13
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 96 Å2
Polarizability: 44.2±0.5 10-24cm3
Surface Tension: 50.2±3.0 dyne/cm
Molar Volume: 346.8±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) =  3.32

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  579.38  (Adapted Stein & Brown method)
    Melting Pt (deg C):  318.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.8E-011  (Modified Grain method)
    MP  (exp database):  109 deg C
    Subcooled liquid VP: 2.54E-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):  3.551
       log Kow used: 3.32 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1106.5 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.44E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.865E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.32  (KowWin est)
  Log Kaw used:  -13.852  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.172
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3429
   Biowin2 (Non-Linear Model)     :   0.9997
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7009  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0464  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2577
   Biowin6 (MITI Non-Linear Model):   0.0270
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3772
 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):  3.39E-008 Pa (2.54E-010 mm Hg)
  Log Koa (Koawin est  ): 17.172
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  88.6 
       Octanol/air (Koa) model:  3.65E+004 
   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 = 123.2510 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.041 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    :  1674
      Log Koc:  3.224 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.747E-003  L/mol-sec
  Kb Half-Life at pH 8:      12.575  years  
  Kb Half-Life at pH 7:     125.745  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 3.32 (estimated)

 Volatilization from Water:
    Henry LC:  3.44E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.474E+012  hours   (1.447E+011 days)
    Half-Life from Model Lake : 3.789E+013  hours   (1.579E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               9.54  percent
    Total biodegradation:        0.16  percent
    Total sludge adsorption:     9.39  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       7.88e-008       2.08         1000       
   Water     11.9            900          1000       
   Soil      87.5            1.8e+003     1000       
   Sediment  0.566           8.1e+003     0          
     Persistence Time: 1.82e+003 hr

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