ChemSpider 2D Image | GW-311616 | C19H31N3O4S

GW-311616

  • Molecular FormulaC19H31N3O4S
  • Average mass397.532 Da
  • Monoisotopic mass397.203522 Da
  • ChemSpider ID7976723

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(3S,3aS,6aR)-3-Isopropyl-1-(methylsulfonyl)-4-[(2E)-4-(1-piperidinyl)-2-butenoyl]hexahydropyrrolo[3,2-b]pyrrol-2(1H)-on [German] [ACD/IUPAC Name]
(3S,3aS,6aR)-3-Isopropyl-1-(methylsulfonyl)-4-[(2E)-4-(1-piperidinyl)-2-butenoyl]hexahydropyrrolo[3,2-b]pyrrol-2(1H)-one [ACD/IUPAC Name]
(3S,3aS,6aR)-3-Isopropyl-1-(méthylsulfonyl)-4-[(2E)-4-(1-pipéridinyl)-2-butenoyl]hexahydropyrrolo[3,2-b]pyrrol-2(1H)-one [French] [ACD/IUPAC Name]
198062-54-3 [RN]
GW-311616
L8012V52PN
Pyrrolo[3,2-b]pyrrol-2(1H)-one, hexahydro-3-(1-methylethyl)-1-(methylsulfonyl)-4-[(2E)-1-oxo-4-(1-piperidinyl)-2-buten-1-yl]-, (3S,3aS,6aR)- [ACD/Index Name]
(3aR,6S,6aS)-4-methylsulfonyl-1-[(E)-4-piperidin-1-ylbut-2-enoyl]-6-propan-2-yl-3,3a,6,6a-tetrahydro-2H-pyrrolo[2,3-d]pyrrol-5-one
(3aR,6S,6aS)-4-methylsulfonyl-1-[(E)-4-piperidin-1-ylbut-2-enoyl]-6-propan-2-yl-3,3a,6,6a-tetrahydro-2H-pyrrolo[3,2-b]pyrrol-5-one
(3aR,6S,6aS)-6-isopropyl-4-mesyl-1-[(E)-4-piperidinobut-2-enoyl]-3,3a,6,6a-tetrahydro-2H-pyrrolo[2,3-d]pyrrol-5-one
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Elastase MedChem Express HY-15891
      GW311616 is a potent, intracellular, orally bioavailable, long duration inhibitor of human neutrophil elastase(HNE) with IC50 of 22 nM; free base form of GW311616A. MedChem Express
      GW311616 is a potent, intracellular, orally bioavailable, long duration inhibitor of human neutrophil elastase(HNE) with IC50 of 22 nM; free base form of GW311616A.; IC50 value: 22 nM [1]; Target: neutrophil elastase; The HNE inhibitor GW311616A is selective over other human serine proteases (IC50 values >100 uM for trypsin, cathepsin G, and plasmin, >3 mM for chymotrypsin and tissue plasminogen activator). MedChem Express HY-15891
      GW311616 is a potent, intracellular, orally bioavailable, long duration inhibitor of human neutrophil elastase(HNE) with IC50 of 22 nM; free base form of GW311616A.;IC50 value: 22 nM [1];Target: neutrophil elastase;The HNE inhibitor GW311616A is selective over other human serine proteases (IC50 values >100 uM for trypsin, cathepsin G, and plasmin, >3 mM for chymotrypsin and tissue plasminogen activator). Acetylcholinesterase is not inhibited by GW311616A at 100 uM.GW311616A is more potent than thetrifluoromethylketone inhibitor ZD8321 (Ki=13 nM). GW311616A is orallybioavailable in rat, dog (Table 4) and hamster despite moderate to high plasmaclearance, which indicates that clearance is predominantly extrahepatic. MedChem Express HY-15891
      Metabolism/Protease MedChem Express HY-15891
      Metabolism/Protease; MedChem Express HY-15891

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

Density: 1.3±0.1 g/cm3
Boiling Point: 583.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.2±3.0 kJ/mol
Flash Point: 306.8±32.9 °C
Index of Refraction: 1.582
Molar Refractivity: 104.4±0.4 cm3
#H bond acceptors: 7
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: -0.09
ACD/LogD (pH 5.5): -2.00
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.35
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 5.20
Polar Surface Area: 86 Å2
Polarizability: 41.4±0.5 10-24cm3
Surface Tension: 54.7±5.0 dyne/cm
Molar Volume: 312.9±5.0 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) =  0.69

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  552.60  (Adapted Stein & Brown method)
    Melting Pt (deg C):  237.17  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.4E-012  (Modified Grain method)
    Subcooled liquid VP: 1.25E-009 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):  814.8
       log Kow used: 0.69 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  43194 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.91E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.109E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.69  (KowWin est)
  Log Kaw used:  -12.617  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.307
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5632
   Biowin2 (Non-Linear Model)     :   0.1027
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0117  (months      )
   Biowin4 (Primary Survey Model) :   3.1916  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2410
   Biowin6 (MITI Non-Linear Model):   0.0008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.0540
 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):  1.67E-007 Pa (1.25E-009 mm Hg)
  Log Koa (Koawin est  ): 13.307
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  18 
       Octanol/air (Koa) model:  4.98 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  0.997 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 184.8798 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 187.5398 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.694 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.684 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.568750 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.015 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.007 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.307E+004
      Log Koc:  4.116 

 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: 0.69 (estimated)

 Volatilization from Water:
    Henry LC:  5.91E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.975E+011  hours   (8.23E+009 days)
    Half-Life from Model Lake : 2.155E+012  hours   (8.978E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.87  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       7.35e-005       1.35         1000       
   Water     46.2            1.44e+003    1000       
   Soil      53.7            2.88e+003    1000       
   Sediment  0.0942          1.3e+004     0          
     Persistence Time: 1.23e+003 hr

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