ChemSpider 2D Image | L-655,708 | C18H19N3O4

L-655,708

  • Molecular FormulaC18H19N3O4
  • Average mass341.361 Da
  • Monoisotopic mass341.137543 Da
  • ChemSpider ID4470723

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

(13aS)-7-Méthoxy-9-oxo-11,12,13,13a-tétrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazépine-1-carboxylate d'éthyle [French] [ACD/IUPAC Name]
130477-52-0 [RN]
9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid, 11,12,13,13a-tetrahydro-7-methoxy-9-oxo-, ethyl ester, (13aS)- [ACD/Index Name]
Ethyl (13aS)-7-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate [ACD/IUPAC Name]
Ethyl (S)-11,12,13,13a-Tetrahydro-7-methoxy-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate
Ethyl-(13aS)-7-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-carboxylat [German] [ACD/IUPAC Name]
L-655,708 [Wiki]
MFCD02684528
(13aS)-11,12,13,13a-Tetrahydro-7-methoxy-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid ethyl ester
(13aS)-11,12,13,13a-tetrahydro-7-methoxy-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid, ethyl ester
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

L-655708 [DBID]
EU-0100700 [DBID]
FG-8094 [DBID]
L9787_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Benzodiazepine inverse agonist; selective for ?5-containing GABAA receptors Tocris Bioscience 1327
      Benzodiazepine inverse agonist; selective for alpha5-containing GABAA receptors Tocris Bioscience 1327
      GABA Receptor MedChem Express HY-14426
      GABAA and A-rho Receptors Tocris Bioscience 1327
      Ion Channels Tocris Bioscience 1327
      L-655708 is a potent ?5 subunit-selective GABAA receptor inverse agonist (Ki = 0.45 nM).; IC50: 0.45 nM (Ki); Target: GABA; in vitro: L-655708 is a potent, selective inverse agonist for the benzodiazepine site of GABAA receptors containing the ?5 subunit (Ki = 0.45 nM). MedChem Express HY-14426
      Ligand-gated Ion Channels Tocris Bioscience 1327
      Membrane Tranporter/Ion Channel MedChem Express HY-14426
      Membrane Tranporter/Ion Channel; Neuronal Signaling; MedChem Express HY-14426
      Potent, selective inverse agonist for the benzodiazepine site of GABAA receptors containing the ?5 subunit (Ki = 0.45 nM). Displays 50-100-fold selectivity over GABAA receptors containing ?1, ?2, ?3 o r ?6 subunits in combination with ?3 and ?2. Enhances LTP in a mouse hippocampal slice model and increases spatial learning, without displaying proconvulsant activity. Tocris Bioscience 1327
      Potent, selective inverse agonist for the benzodiazepine site of GABAA receptors containing the ?5 subunit (Ki = 0.45 nM). Displays 50-100-fold selectivity over GABAA receptors containing ?1, ?2, ?3 or ?6 subunits in combination with ?3 and ?2. Enhances LTP in a mouse hippocampal slice model and increases spatial learning, without displaying proconvulsant activity. Tocris Bioscience 1327
      Potent, selective inverse agonist for the benzodiazepine site of GABAA receptors containing the alpha5 subunit (Ki = 0.45 nM). Displays 50-100-fold selectivity over GABAA receptors containing alpha1, alpha2, alpha3 or alpha6 subunits in combination with beta3 and gamma2. Enhances LTP in a mouse hippocampal slice model and increases spatial learning, without displaying proconvulsant activity. Tocris Bioscience 1327
      Potent, selective inverse agonist for the benzodiazepine site of GABAA receptors containing the alpha5 subunit (Ki = 0.45 nM). Displays 50-100-fold selectivity over GABAA receptors containing alpha1, alpha2, alpha3 or alpha6 subunits in combination with beta3 and gamma2. Enhances LTP in a mouse hippocampal slice model and increases spatial learning, without displaying proconvulsant activity. Tocris Bioscience 1327
      Selective for ?5-containing GABAA receptors Tocris Bioscience 1327

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

Density: 1.4±0.1 g/cm3
Boiling Point: 584.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.3±3.0 kJ/mol
Flash Point: 307.2±30.1 °C
Index of Refraction: 1.676
Molar Refractivity: 90.4±0.5 cm3
#H bond acceptors: 7
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 1.61
ACD/LogD (pH 5.5): 1.32
ACD/BCF (pH 5.5): 5.94
ACD/KOC (pH 5.5): 124.62
ACD/LogD (pH 7.4): 1.32
ACD/BCF (pH 7.4): 5.94
ACD/KOC (pH 7.4): 124.62
Polar Surface Area: 74 Å2
Polarizability: 35.8±0.5 10-24cm3
Surface Tension: 54.4±7.0 dyne/cm
Molar Volume: 240.4±7.0 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) =  1.71

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  536.05  (Adapted Stein & Brown method)
    Melting Pt (deg C):  229.44  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.11E-011  (Modified Grain method)
    Subcooled liquid VP: 3.32E-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):  18.96
       log Kow used: 1.71 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  144.5 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.90E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.999E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.71  (KowWin est)
  Log Kaw used:  -15.797  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.507
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1013
   Biowin2 (Non-Linear Model)     :   0.9992
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4727  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.8667  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4947
   Biowin6 (MITI Non-Linear Model):   0.3200
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2238
 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):  4.43E-007 Pa (3.32E-009 mm Hg)
  Log Koa (Koawin est  ): 17.507
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.78 
       Octanol/air (Koa) model:  7.89E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.996 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  40.0555 E-12 cm3/molecule-sec
      Half-Life =     0.267 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.204 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  523.7
      Log Koc:  2.719 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.776E-002  L/mol-sec
  Kb Half-Life at pH 8:     212.462  days   
  Kb Half-Life at pH 7:       5.817  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.613 (BCF = 4.103)
       log Kow used: 1.71 (estimated)

 Volatilization from Water:
    Henry LC:  3.9E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.774E+014  hours   (1.156E+013 days)
    Half-Life from Model Lake : 3.026E+015  hours   (1.261E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               2.05  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.96  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       1.69e-008       6.41         1000       
   Water     28.7            900          1000       
   Soil      71.2            1.8e+003     1000       
   Sediment  0.0835          8.1e+003     0          
     Persistence Time: 1.28e+003 hr

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