ChemSpider 2D Image | imiquimod | C14H16N4

imiquimod

  • Molecular FormulaC14H16N4
  • Average mass240.304 Da
  • Monoisotopic mass240.137497 Da
  • ChemSpider ID51809

More details:



Featured data source



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

1-Isobutyl-1H-imidazo[4,5-c]chinolin-4-amin [German] [ACD/IUPAC Name]
1-Isobutyl-1H-imidazo[4,5-c]quinoléin-4-amine [French] [ACD/IUPAC Name]
imiquimod [French] [INN]
imiquimod [Spanish] [INN]
imiquimodum [Latin] [INN]
إيميكيمود [Arabic] [INN]
咪喹莫德 [Chinese] [INN]
[99011-02-6]
1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS070973 [DBID]
AIDS-070973 [DBID]
CHEBI:36704 [DBID]
D02500 [DBID]
DZ-2636 [DBID]
I5159_SIGMA [DBID]
MLS000083577 [DBID]
MTD-39 [DBID]
R 837 [DBID]
R-837 [DBID]
More...
  • Experimental Physico-chemical Properties
    • Experimental Melting Point:

      294 °C TCI I0747
      292-294 °C Oxford University Chemical Safety Data (No longer updated) More details
      292 °C LKT Labs [I5034]
      293 °C Jean-Claude Bradley Open Melting Point Dataset 15049, 16444
      292-294 °C LabNetwork LN00860846
    • Experimental LogP:

      3.457 Vitas-M STK583860
    • Experimental Solubility:

      DMSO 3 mg/mL (12 mM); Water <1 mg/mL (<1 mM) MedChem Express HY-B0180
      Insoluble in water, DMSO (3 mg/mL) or DMF. slightly soluble in water (warm to 37?C, vortex); insoluble in 100% ethanol. LKT Labs [I5034]
      No data available MedChem Express HY-B0180
      Soluble to 10 mM in DMSO Tocris Bioscience 3700
      Soluble to 5 mM in DMSO Tocris Bioscience 3700
      Soluble to 5 mM in DMSO with gentle warming Tocris Bioscience 3700
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      solid Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Incompatible with strong oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      25 36/37/38 LKT Labs [I5034]
      H300 H315 H319 H335 LKT Labs [I5034]
      Safety glasses, gloves, good ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      T LKT Labs [I5034]
      UN 2811 6.1/PG 3 LKT Labs [I5034]
    • Target Organs:

      TLR agonist TargetMol T0134
    • Drug Status:

      approved BIONET-Key Organics KS-5218
    • Bio Activity:

      Enzyme-Linked Receptors Tocris Bioscience 3700
      Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist and is commonly used topically to treat warts on the skin of the genital and anal areas. MedChem Express
      Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist and is commonly used topically to treat warts on the skin of the genital and anal areas.; Target: TLR7; Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist and is commonly used topically to treat warts on the skin of the genital and anal areas. MedChem Express HY-B0180
      Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist and is commonly used topically to treat warts on the skin of the genital and anal areas.;Target: TLR7;Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist and is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod is a patient-applied cream used to treat certain diseases of the skin, including skin cancers (basal cell carcinoma, Bowen's disease, superficial squamous cell carcinoma, some superficial malignant melanomas, and actinic keratosis) as well as genital warts. However, Imiquimod is generally secondary to surgery, because surgery has a better chance to effectively treat at least some forms of skin cancer.;It is known that imiquimod signals to the innate arm of the immune system through the toll-like receptor 7 (TLR7), commonly involved in pathogen recognition. Cells activated by imiquimod via TLR-7 secrete cytokines (prim MedChem Express HY-B0180
      Immunology/Inflammation MedChem Express HY-B0180
      Immunology/Inflammation TargetMol T0134
      Immunology/Inflammation; MedChem Express HY-B0180
      Immunomodulator that displays antiviral and antitumor activity. Acts as a Toll-like receptor 7 (TLR7) agonist; stimulates proinflammatory cytokine production and activates NF-?B. Tocris Bioscience 3700
      Immunomodulator that displays antiviral and antitumor activity. Acts as a Toll-like receptor 7 (TLR7) agonist; stimulates proinflammatory cytokine production and activates NF-kappaB. Tocris Bioscience 3700
      Immunostimulant; Zerenex Molecular [ZBioX-0650]
      TLR-7, 8 TargetMol T0134
      Toll-like Receptor (TLR) MedChem Express HY-B0180
      Toll-like receptor 7 (TLR7) agonist Tocris Bioscience 3700
      Toll-like Receptors Tocris Bioscience 3700

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

Density: 1.3±0.1 g/cm3
Boiling Point: 456.7±48.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 71.7±3.0 kJ/mol
Flash Point: 230.0±29.6 °C
Index of Refraction: 1.681
Molar Refractivity: 71.0±0.5 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.46
ACD/LogD (pH 5.5): 1.27
ACD/BCF (pH 5.5): 2.54
ACD/KOC (pH 5.5): 27.80
ACD/LogD (pH 7.4): 2.52
ACD/BCF (pH 7.4): 45.33
ACD/KOC (pH 7.4): 495.30
Polar Surface Area: 57 Å2
Polarizability: 28.2±0.5 10-24cm3
Surface Tension: 48.8±7.0 dyne/cm
Molar Volume: 187.7±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) =  3.06

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  452.58  (Adapted Stein & Brown method)
    Melting Pt (deg C):  190.45  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.82E-009  (Modified Grain method)
    Subcooled liquid VP: 4.24E-007 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):  5.095
       log Kow used: 3.06 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  6255.1 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.26E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.853E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.06  (KowWin est)
  Log Kaw used:  -10.471  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.531
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3994
   Biowin2 (Non-Linear Model)     :   0.0902
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5332  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3926  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1198
   Biowin6 (MITI Non-Linear Model):   0.0093
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2179
 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):  5.65E-005 Pa (4.24E-007 mm Hg)
  Log Koa (Koawin est  ): 13.531
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0531 
       Octanol/air (Koa) model:  8.34 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.657 
       Mackay model           :  0.809 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 114.2851 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.123 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.733 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.843E+004
      Log Koc:  4.266 

 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 = 1.653 (BCF = 45.02)
       log Kow used: 3.06 (estimated)

 Volatilization from Water:
    Henry LC:  8.26E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.099E+009  hours   (4.578E+007 days)
    Half-Life from Model Lake : 1.199E+010  hours   (4.995E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               6.23  percent
    Total biodegradation:        0.13  percent
    Total sludge adsorption:     6.11  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       2.3e-005        2.25         1000       
   Water     12.6            900          1000       
   Soil      87              1.8e+003     1000       
   Sediment  0.329           8.1e+003     0          
     Persistence Time: 1.79e+003 hr




                    

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