ChemSpider 2D Image | URB597 | C20H22N2O3

URB597

  • Molecular FormulaC20H22N2O3
  • Average mass338.400 Da
  • Monoisotopic mass338.163055 Da
  • ChemSpider ID1156960

More details:






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

3'-(aminocarbonyl)-1,1'-biphenyl-3-yl cyclohexylcarbamate
3'-Carbamoyl-3-biphenylyl cyclohexylcarbamate [ACD/IUPAC Name]
3'-Carbamoyl-3-biphenylyl-cyclohexylcarbamat [German] [ACD/IUPAC Name]
3'-Carbamoylbiphenyl-3-yl cyclohexylcarbamate
Carbamic acid, N-cyclohexyl-, 3'-(aminocarbonyl)[1,1'-biphenyl]-3-yl ester [ACD/Index Name]
cyclohexyl carbamic acid 3'-carbamoylbiphenyl-3-yl ester
Cyclohexylcarbamate de 3'-carbamoyl-3-biphénylyle [French] [ACD/IUPAC Name]
Cyclohexyl-carbamic acid 3'-carbamoyl-biphenyl-3-yl ester
URB597 [Wiki]
(3'-(aminocarbonyl)[1,1'-biphenyl]-3-yl)-cyclohexylcarbamate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BAS 11143615 [DBID]
URB 597 [DBID]
URB-597 [DBID]
ZINC01238258 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 074768
    • Bio Activity:

      Enzymes Tocris Bioscience 4612
      FAAH MedChem Express HY-10864
      Fatty Acid Amide Hydrolase (FAAH) Tocris Bioscience 4612
      Hydrolases Tocris Bioscience 4612
      Neuronal Signaling MedChem Express HY-10864
      Neuronal Signaling; MedChem Express HY-10864
      Potent and selective FAAH inhibitor Tocris Bioscience 4612
      Potent and selective fatty acid amide hydrolase (FAAH) inhibitor (IC50 values are 3 and 5 nM in human liver and rat brain, respectively). Exhibits no significant inhibitory activity against a variety of receptors, ion channels and enzymes, including human cannabinoid receptors and rat monoacylglycerol lipase. Displays antiallodynic and antihyperalgesic activity in an inflammatory pain model. Tocris Bioscience 4612
      Potent and selective fatty acid amide hydrolase (FAAH) inhibitor (IC50 values are 3 and 5 nM in human liver and rat brain, respectively). Exhibits no significant inhibitory activity against a variety of receptors, ion channels and enzymes, including human cannabinoid receptors and rat monoacylglycerol lipase. Displays antiallodynic and antihyperalgesic activity in an inflammatory pain model. Tocris Bioscience 4612
      URB597 is a potent, orally bioavailable FAAH inhibitor with IC50 of 4.6 nM, with no activity on other cannabinoid-related targets.; IC50 value: 4.6 nM [1]; Target: FAAH ; in vitro: URB597 binds in the hydrophobic pocket and catalytic core of FAAH that connects the active site residues to the membrane surface of FAAH [1]. MedChem Express HY-10864
      URB597 is a potent, orally bioavailable FAAH inhibitor with IC50 of 4.6 nM, with no activity on other cannabinoid-related targets.;IC50 value: 4.6 nM [1];Target: FAAH ;In vitro: URB597 binds in the hydrophobic pocket and catalytic core of FAAH that connects the active site residues to the membrane surface of FAAH [1]. URB597 reduces the expression of the LPS-induced enzymes cyclo-oxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS; NOS2) in primary rat microglial cell, with a concomitant reduction in the release of the inflammatory mediators prostaglandin E2 (PGE2) and (NO) nitric oxide [2]. ;In vivo: URB597 inhibits [3H]anandamide hydrolysis in rat brain membranes with a parallel increase in brain anandamide, OEA, and PEA content by inhibition of FAAH. URB597 enhances the hypothermia effect induced by ethanolamide by inhibiting FAAH [3]. When delivered intraperitonealy (0.3 mg/kg) URB597 reduces allodynia and hyperalgesia through cannabinoid CB1 and CB2 receptor-mediate MedChem Express HY-10864

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

Density: 1.2±0.1 g/cm3
Boiling Point: 533.2±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 80.9±3.0 kJ/mol
Flash Point: 276.3±30.1 °C
Index of Refraction: 1.618
Molar Refractivity: 95.7±0.4 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 3.51
ACD/LogD (pH 5.5): 3.18
ACD/BCF (pH 5.5): 153.63
ACD/KOC (pH 5.5): 1278.45
ACD/LogD (pH 7.4): 3.18
ACD/BCF (pH 7.4): 153.62
ACD/KOC (pH 7.4): 1278.39
Polar Surface Area: 81 Å2
Polarizability: 37.9±0.5 10-24cm3
Surface Tension: 57.3±5.0 dyne/cm
Molar Volume: 273.2±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) =  3.95

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  530.44  (Adapted Stein & Brown method)
    Melting Pt (deg C):  226.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.16E-011  (Modified Grain method)
    Subcooled liquid VP: 4.62E-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):  3.073
       log Kow used: 3.95 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.4414 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.92E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.579E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.95  (KowWin est)
  Log Kaw used:  -9.923  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.873
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8761
   Biowin2 (Non-Linear Model)     :   0.8703
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3504  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7586  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0347
   Biowin6 (MITI Non-Linear Model):   0.0194
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0558
 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):  6.16E-007 Pa (4.62E-009 mm Hg)
  Log Koa (Koawin est  ): 13.873
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.87 
       Octanol/air (Koa) model:  18.3 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.994 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  38.6992 E-12 cm3/molecule-sec
      Half-Life =     0.276 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.317 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.996 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1098
      Log Koc:  3.041 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.493E+000  L/mol-sec
  Kb Half-Life at pH 8:       3.218  days   
  Kb Half-Life at pH 7:      32.180  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.342 (BCF = 220)
       log Kow used: 3.95 (estimated)

 Volatilization from Water:
    Henry LC:  2.92E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.689E+008  hours   (1.537E+007 days)
    Half-Life from Model Lake : 4.024E+009  hours   (1.677E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              27.83  percent
    Total biodegradation:        0.30  percent
    Total sludge adsorption:    27.53  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       0.00591         6.63         1000       
   Water     11.1            900          1000       
   Soil      86.5            1.8e+003     1000       
   Sediment  2.34            8.1e+003     0          
     Persistence Time: 1.85e+003 hr




                    

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