ChemSpider 2D Image | Lenalidomide | C13H13N3O3

Lenalidomide

  • Molecular FormulaC13H13N3O3
  • Average mass259.261 Da
  • Monoisotopic mass259.095703 Da
  • ChemSpider ID187515

More details:

Featured data source
The Merck Index Online

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

191732-72-6 [RN]
1-Oxo-4-amino-2-(2,6-dioxopiperidin-3-yl)isoindole
2,6-Piperidinedione, 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)- [ACD/Index Name]
3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione
3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-piperidinedione [ACD/IUPAC Name]
3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-pipéridinedione [French] [ACD/IUPAC Name]
3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidin-2,6-dion
3-(4-amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione
3-(4-amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)pipéridine-2,6-dione [French]
3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8505 [DBID]
CC-5013 [DBID]
CDC-501 [DBID]
CHEBI:63791 [DBID]
F0P408N6V4 [DBID]
UNII:F0P408N6V4 [DBID]
CC 5013 [DBID]
CCRIS 4693 [DBID]
CDC 501 [DBID]
CDC-5013 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      L04AX04 Wikidata Q425681

    • Target Organs:

      TNF-alpha inhibitor; Cadherin inhibitor TargetMol T1642

    • Chemical Class:

      A dicarboximide that consists of 1-oxoisoindoline bearing an amino substituent at position 4 and a 2,6-dioxopiperidin-3-yl group at position 2. Inhibits the secretion of TNF-<greek>alpha</greek>. ChEBI CHEBI:63791
      A dicarboximide that consists of 1-oxoisoindoline bearing an amino substituent at position 4 and a 2,6-dioxopiperidin-3-yl group at position 2. Inhibits the secretion of TNF-alpha. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63791, CHEBI:63791

    • Bio Activity:

      Apoptosis MedChem Express HY-A0003
      Apoptosis ; MedChem Express HY-A0003
      Cereblon binder; induces ubiquitination and degradation of CK1alpha by E3 ubiquitin ligase Tocris Bioscience 6305
      Enzymes Tocris Bioscience 6305
      Immunology/Inflammation TargetMol T1642
      Lenalidomide (Revlimid, CC-5013) is a TNF-? secretion inhibitor with IC50 of 13 nM.; IC50 Value: 13 nM [1]; Target: TNF-alpha; in vitro: Lenalidomide strongly induces IL-2 and sIL-2R production. MedChem Express HY-A0003
      Ligases Tocris Bioscience 6305
      Thalidomide analog. Immune modulatory drug and cereblon binding compound. Induces ubiquitination and degradation of casein kinase (CK) 1alpha by the E3 ubiquitin ligase CRL4CRBN. Also TNF-alpha inhibitor and angiogenesis inhibitor. Tocris Bioscience 6305
      TNF-??;Cadherin-5;Prostaglandin G/H synthase ;CRBN TargetMol T1642
      TNF-alpha MedChem Express HY-A0003
      Ubiquitin E3 Ligases Tocris Bioscience 6305

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

Density: 1.5±0.1 g/cm3
Boiling Point: 614.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 91.1±3.0 kJ/mol
Flash Point: 325.1±31.5 °C
Index of Refraction: 1.672
Molar Refractivity: 66.5±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -1.39
ACD/LogD (pH 5.5): -0.48
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 12.98
ACD/LogD (pH 7.4): -0.48
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 13.00
Polar Surface Area: 93 Å2
Polarizability: 26.3±0.5 10-24cm3
Surface Tension: 73.3±3.0 dyne/cm
Molar Volume: 177.5±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) =  -1.99

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  601.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  260.14  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.78E-013  (Modified Grain method)
    Subcooled liquid VP: 6.63E-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):  5.169e+004
       log Kow used: -1.99 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4.0694e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.26E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.175E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.99  (KowWin est)
  Log Kaw used:  -15.288  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.298
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6005
   Biowin2 (Non-Linear Model)     :   0.5278
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4371  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5707  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0694
   Biowin6 (MITI Non-Linear Model):   0.0088
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5038
 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):  8.84E-009 Pa (6.63E-011 mm Hg)
  Log Koa (Koawin est  ): 13.298
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  339 
       Octanol/air (Koa) model:  4.88 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.997 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 100.6351 E-12 cm3/molecule-sec
      Half-Life =     0.106 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.275 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  39.92
      Log Koc:  1.601 

 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: -1.99 (estimated)

 Volatilization from Water:
    Henry LC:  1.26E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.482E+013  hours   (3.118E+012 days)
    Half-Life from Model Lake : 8.162E+014  hours   (3.401E+013 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       4.22e-006       2.55         1000       
   Water     46.5            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 973 hr

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