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ChemSpider 2D Image | Thalidomide | C13H10N2O4

Thalidomide

  • Molecular FormulaC13H10N2O4
  • Average mass258.229 Da
  • Monoisotopic mass258.064056 Da
  • ChemSpider ID5233

More details:

Featured data source
The Merck Index Online

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

Thalidomide
(±)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
(±)-Thalidomide
(±)-Thalidomide
1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)- [ACD/Index Name]
2-(2,6-Dioxo-3-piperidinyl)-1H-isoindol-1,3(2H)-dion [German] [ACD/IUPAC Name]
2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione [ACD/IUPAC Name]
2-(2,6-Dioxo-3-pipéridinyl)-1H-isoindole-1,3(2H)-dione [French] [ACD/IUPAC Name]
2-(2,6-Dioxopiperidin-3-yl)-1H-isoindol-1,3(2H)-dion
2-(2,6-Dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione
More...

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

762 [DBID]
AI3-50606 [DBID]
AIDS000513 [DBID]
AIDS-000513 [DBID]
Bio1_000387 [DBID]
Bio1_000876 [DBID]
Bio1_001365 [DBID]
Bio2_000418 [DBID]
Bio2_000898 [DBID]
BRN 0030233 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      white powder or crystals OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable. Combustible. Incompatible with strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      Organic Compound; Amine; Amide; Ester; Drug; Leprostatic Agent; Immunosuppressive Agent; Metabolite; Angiogenesis Inhibitor; Teratogen; Synthetic Compound Toxin, Toxin-Target Database T3D3539
      ORL-RAT LD50 113 mg kg-1, SKN-RAT LD50 1550 mg kg-1, ORL-MUS LD50 2000 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      L04AX02 Wikidata Q203174
      Safety glasses, adequate ventilation, gloves. Do not handle if pregnant. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      NF-??B inhibitor;TNF inhibitor;COX;FGFR inhibitor TargetMol T0213

    • Chemical Class:

      A dicarboximide that is isoindole-1,3(2<element>H</element>)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group. ChEBI CHEBI:74947
      A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:74947, CHEBI:74947

    • Bio Activity:

      Binds cereblon, inhibiting ubiquitin ligase activity; alsoTNF-a synthesis inhibitor Tocris Bioscience 652
      Cell Biology Tocris Bioscience 652
      Cytokine and NF-kB Signaling Tocris Bioscience 652
      Enzymes Tocris Bioscience 652
      Ligases Tocris Bioscience 652
      Neuroscience;Immunology/Inflammation TargetMol T0213
      NF-??B;TNF;Protein cereblon;??1-acid glycoprotein;Prostaglandin G/H synthase 2;FGFR2 TargetMol T0213
      Selective inhibitor of tumor necrosis factor alpha (TNF-alpha) synthesis. Also binds cereblon, inhibiting ubiquitin ligase activity. Teratogen, sedative-hypnotic with inherent anti-inflammatory properties. Tocris Bioscience 652
      Signal Transduction Tocris Bioscience 652
      Teratogen, sedative-hypnotic with inherent anti-inflammatory properties. A selective inhibitor of tumor necrosis factor ? (TNF-?) synthesis. Tocris Bioscience 0652, 652
      Thalidomide can directly inhibit angiogenesis induced by bFGF or VEGF in vivo. MedChem Express
      Thalidomide can directly inhibit angiogenesis induced by bFGF or VEGF in vivo.;IC50 value:;Target:;Thalidomide was commonly used therapeutically in the late 1950's; however, it was withdrawn from the market when it was discovered to cause birth defects. More recent research has found Thalidomide to affect key biochemical pathways yielding antiangiogenic and immunomodulatory activities. This compound has been shown to: selectively inhibit tumor necrosis factor-alpha (TNF alpha) biosynthesis and basic fibroblast growth factor (bFGF)-induced angiogenesis, induce apoptosis in human monocytes via a cytochrome c-dependent pathway, and to inhibit HIV-1 replication in a monocytoid (U1) line. These new found uses make Thalidomide an extremely valuable research tool. MedChem Express HY-14658
      TNF-? synthesis inhibitor Tocris Bioscience 0652, 652
      Ubiquitin E3 Ligases Tocris Bioscience 652
  • Gas Chromatography

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

Density: 1.6±0.1 g/cm3
Boiling Point: 487.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 79.4±3.0 kJ/mol
Flash Point: 248.8±31.5 °C
Index of Refraction: 1.744
Molar Refractivity: 65.2±0.5 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.03
ACD/LogD (pH 5.5): -0.39
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 8.84
ACD/LogD (pH 7.4): -2.09
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 87 Å2
Polarizability: 25.9±0.5 10-24cm3
Surface Tension: 71.6±7.0 dyne/cm
Molar Volume: 161.0±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) =  -0.24
    Log Kow (Exper. database match) =  0.33
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  632.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  274.67  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.05E-014  (Modified Grain method)
    MP  (exp database):  270 deg C
    Subcooled liquid VP: 1.01E-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):  544.8
       log Kow used: 0.33 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  545 mg/L (25 deg C)
        Exper. Ref:  BUDAVARI,S ET AL. (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  11836 mg/L
    Wat Sol (Exper. database match) =  545.00
       Exper. Ref:  BUDAVARI,S ET AL. (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.29E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.279E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.33  (exp database)
  Log Kaw used:  -14.278  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.608
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6246
   Biowin2 (Non-Linear Model)     :   0.3411
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6285  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4752  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0287
   Biowin6 (MITI Non-Linear Model):   0.0162
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2538
 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):  1.35E-009 Pa (1.01E-011 mm Hg)
  Log Koa (Koawin est  ): 14.608
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.23E+003 
       Octanol/air (Koa) model:  99.5 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  43.6545 E-12 cm3/molecule-sec
      Half-Life =     0.245 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.940 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    :  20.48
      Log Koc:  1.311 

 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: 0.33 (expkow database)

 Volatilization from Water:
    Henry LC:  1.29E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.293E+012  hours   (3.039E+011 days)
    Half-Life from Model Lake : 7.957E+013  hours   (3.315E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.000264        5.88         1000       
   Water     45              900          1000       
   Soil      54.9            1.8e+003     1000       
   Sediment  0.0883          8.1e+003     0          
     Persistence Time: 991 hr

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