ChemSpider 2D Image | Cilastatin | C16H26N2O5S

Cilastatin

  • Molecular FormulaC16H26N2O5S
  • Average mass358.453 Da
  • Monoisotopic mass358.156250 Da
  • ChemSpider ID4940183
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


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

(2Z)-7-{[(2R)-2-Amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)-2-heptenoic acid [ACD/IUPAC Name]
(2Z)-7-{[(2R)-2-Amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)-2-heptensäure [German] [ACD/IUPAC Name]
(2Z)-7-{[(2R)-2-Amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid
(2Z)-7-{[(2R)-2-Amino-2-carboxyethyl]sulfanyl}-2-[(Z)-{[(1S)-2,2-dimethylcyclopropyl](hydroxy)methylen}amino]-2-heptensäure [German] [ACD/IUPAC Name]
(2Z)-7-{[(2R)-2-Amino-2-carboxyethyl]sulfanyl}-2-[(Z)-{[(1S)-2,2-dimethylcyclopropyl](hydroxy)methylene}amino]-2-heptenoic acid [ACD/IUPAC Name]
[R-[R*,S*(Z)]]-7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)carbonyl]amino]-2-heptenoic Acid
141A6AMN38
2-Heptenoic acid, 7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[(1Z)-[(1S)-2,2-dimethylcyclopropyl]hydroxymethylene]amino]-, (2Z)- [ACD/Index Name]
2-Heptenoic acid, 7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-, (2Z)- [ACD/Index Name]
5457
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MK 791 [DBID]
MK 0791 [DBID]
MK-791 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      The thioether resulting from the formal oxidative coupling of the thiol group of <stereo>L</stereo>-cysteine with the 7-position of (2<stereo>Z</stereo>)-2-({[(1<stereo>S</stereo>)-2,2-dimethylcyclopr opyl]carbonyl}amino)hept-2-enoic acid. It is an inhibitor of dehydropeptidase I (membrane dipeptidase, 3.4.13.19), an enzyme found in the brush border of renal tubes and responsible for degrading the antibiotic imipenem. Cilastatin is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and poten tially nephrotoxic products. Cilastatin also acts as a leukotriene D<smallsub>4</smallsub> dipeptidase inhibitor, preventing the metabolism of leukotriene D<smallsub>4</smallsub> to leukotriene E<smal lsub>4</smallsub>. ChEBI CHEBI:3697

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

Density: 1.3±0.1 g/cm3
Boiling Point: 655.5±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.3 mmHg at 25°C
Enthalpy of Vaporization: 105.3±6.0 kJ/mol
Flash Point: 350.2±31.5 °C
Index of Refraction: 1.570
Molar Refractivity: 92.2±0.3 cm3
#H bond acceptors: 7
#H bond donors: 5
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 1
ACD/LogP: 2.41
ACD/LogD (pH 5.5): -1.76
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.90
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 155 Å2
Polarizability: 36.5±0.5 10-24cm3
Surface Tension: 58.6±3.0 dyne/cm
Molar Volume: 281.0±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) =  -1.38

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  609.37  (Adapted Stein & Brown method)
    Melting Pt (deg C):  322.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.82E-014  (Modified Grain method)
    Subcooled liquid VP: 4.2E-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):  34.71
       log Kow used: -1.38 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2180.9 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 :   4.36E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.473E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.38  (KowWin est)
  Log Kaw used:  -18.749  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.369
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9023
   Biowin2 (Non-Linear Model)     :   0.7829
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8943  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1970  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4712
   Biowin6 (MITI Non-Linear Model):   0.0886
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1357
 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):  5.6E-009 Pa (4.2E-011 mm Hg)
  Log Koa (Koawin est  ): 17.369
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  536 
       Octanol/air (Koa) model:  5.74E+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 =  86.4975 E-12 cm3/molecule-sec
      Half-Life =     0.124 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.484 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   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    :  5495
      Log Koc:  3.740 

 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: -1.38 (estimated)

 Volatilization from Water:
    Henry LC:  4.36E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.542E+017  hours   (1.059E+016 days)
    Half-Life from Model Lake : 2.774E+018  hours   (1.156E+017 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       5.75e-009       2.64         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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