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ChemSpider 2D Image | Tioguanine | C5H5N5S

Tioguanine

  • Molecular FormulaC5H5N5S
  • Average mass167.192 Da
  • Monoisotopic mass167.026566 Da
  • ChemSpider ID2005804

More details:



Featured data source



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

154-42-7 [RN]
1998
205-827-2 [EINECS]
2-Amino-1,7-dihydro-6H-purin-6-thion [Czech] [ACD/IUPAC Name]
2-Amino-1,7-dihydro-6H-purin-6-thion [German] [ACD/IUPAC Name]
2-Amino-1,7-dihydro-6H-purine-6-thione [ACD/IUPAC Name]
2-Amino-1,7-dihydro-6H-purine-6-thione [French] [ACD/IUPAC Name]
2-Amino-6-mercaptopurine
2-Amino-6-methoxy purine
2-Amino-6-purinethiol
More...

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

A4660_SIGMA [DBID]
A4882_SIGMA [DBID]
AI3-26078 [DBID]
AIDS021096 [DBID]
AIDS-021096 [DBID]
BW 5071 [DBID]
C07648 [DBID]
DivK1c_000428 [DBID]
HSDB 2504 [DBID]
KBio1_000428 [DBID]
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  • References
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Drug; Antimetabolite, Antineoplastic; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D4770
    • Safety:

      25 LKT Labs [T2835]
      25-68 Alfa Aesar B21280
      36/37-45 Alfa Aesar B21280
      6.1 Alfa Aesar B21280
      Danger Alfa Aesar B21280
      Danger Biosynth W-108030
      DANGER: POISON, irritates skin, eyes, lungs Alfa Aesar B21280
      GHS06 Biosynth W-108030
      H301 Biosynth W-108030
      H301 LKT Labs [T2835]
      H301-H341 Alfa Aesar B21280
      Irritant SynQuest 69559, 7H61-1-Y4
      L01BB03 Wikidata Q385347
      P281-P301+P310-P308+P313-P321-P405-P501a Alfa Aesar B21280
      P301+P310 Biosynth W-108030
      T LKT Labs [T2835]
      Toxic/Mutagenic SynQuest 7H61-1-Y4
      UN 2811 6.1/PG 3 LKT Labs [T2835]
    • Chemical Class:

      A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6<element>H</element>-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia. ChEBI CHEBI:9555
    • Compound Source:

      synthetic Microsource [01500573]
    • Bio Activity:

      6-Thioguanine(6-TG) belongs to the thiopurine family of drugs that also include mercaptopurine and azathioprine, which are examples of antimetabolites; a purine analogue of the nucleobase guanine. MedChem Express
      6-Thioguanine(6-TG) belongs to the thiopurine family of drugs that also include mercaptopurine and azathioprine, which are examples of antimetabolites; a purine analogue of the nucleobase guanine.; IC50 Value: 0.6 uM (ID50, 24 h exposure to HL-60 cell) [1]; Target: Nucleoside antimetabolite/analog; in vitro: 6-TG was toxic to HL-60 cells (ID50 = 0.6 microM; 24-h exposure) while IFN-alpha (up to 1000 IU/ml) had minimal cytotoxic activity [1]. MedChem Express HY-13765
      6-Thioguanine(6-TG) belongs to the thiopurine family of drugs that also include mercaptopurine and azathioprine, which are examples of antimetabolites; a purine analogue of the nucleobase guanine.;IC50 Value: 0.6 uM (ID50, 24 h exposure to HL-60 cell) [1];Target: Nucleoside antimetabolite/analog;In vitro: 6-TG was toxic to HL-60 cells (ID50 = 0.6 microM; 24-h exposure) while IFN-alpha (up to 1000 IU/ml) had minimal cytotoxic activity [1]. Paradoxically, inhibition of c-myc expression in the wild type HL-60 (HL-60/wt) cell, which is only weakly induced to differentiate by TG, was 5-fold more sensitive to the thiopurine (IC50 = 35 microM) [2].;In vivo: SOS did not occur in hypoxanthine-phosphoribosyl transferase-deficient C57Bl/6 mice, demonstrating that 6TG-SOS requires thioguanine nucleotides [3]. A higher fraction of the dose was recovered in urine as the parent thiopurine and the metabolites thiopurine riboside, thioxanthine, and thiouric acid after 6-TG treatment than after tr MedChem Express HY-13765
      Anticancer and immunosuppressive agent Tocris Bioscience 4061
      Anticancer and immunosuppressive agent often used to treat immune disorders and leukemia. Displays cytotoxic and antineoplastic properties; disrupts cytosine methylation by DNA methyltransferases afte r incorporation into DNA. Selectively kills BRCA2-defective tumors in a xenograft model. Also facilitates proteasome-mediated degradation of DNA (cytosine-5)-methyltransferase 1 (DNMT1). Tocris Bioscience 4061
      Anticancer and immunosuppressive agent often used to treat immune disorders and leukemia. Displays cytotoxic and antineoplastic properties; disrupts cytosine methylation by DNA methyltransferases after incorporation into DNA. Selectively kills BRCA2-defective tumors in a xenograft model. Also facilitates proteasome-mediated degradation of DNA (cytosine-5)-methyltransferase 1 (DNMT1). Tocris Bioscience 4061
      Cell Cycle/DNA Damage MedChem Express HY-13765
      Cell Cycle/DNA Damage; MedChem Express HY-13765
      Competitive hypoxanthine-guanine phosphoribosyltransferase substrate Hello Bio [HB1379]
      Competitive hypoxanthine-guanine phosphoribosyltransferase substrate. An antimetabolite guanine analogue that inhibits DNA methylation. Shows anti-cancer and anti-angiogenic actions. Hello Bio [HB1379]
      Enzymes/Transferase Hello Bio [HB1379]
      Immunosuppressants Tocris Bioscience 4061
      Nucleoside antimetabolite/analog MedChem Express HY-13765
      Other Pharmacology Tocris Bioscience 4061
      Proteins & peptides Hello Bio [HB1379]
  • Gas Chromatography

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

Density: 2.1±0.1 g/cm3
Boiling Point: 460.7±37.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 72.1±3.0 kJ/mol
Flash Point: 232.4±26.5 °C
Index of Refraction: 2.071
Molar Refractivity: 41.9±0.5 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: -0.99
ACD/LogD (pH 5.5): -2.84
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.59
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 116 Å2
Polarizability: 16.6±0.5 10-24cm3
Surface Tension: 98.6±7.0 dyne/cm
Molar Volume: 80.2±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) =  -1.18

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  514.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.26  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.01E-010  (Modified Grain method)
    Subcooled liquid VP: 1.19E-008 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):  3.134e+004
       log Kow used: -1.18 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.64E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.090E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.18  (KowWin est)
  Log Kaw used:  -12.722  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.542
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4342
   Biowin2 (Non-Linear Model)     :   0.2188
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6948  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4981  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0653
   Biowin6 (MITI Non-Linear Model):   0.0321
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4628
 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):  1.59E-006 Pa (1.19E-008 mm Hg)
  Log Koa (Koawin est  ): 11.542
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.89 
       Octanol/air (Koa) model:  0.0855 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.986 
       Mackay model           :  0.993 
       Octanol/air (Koa) model:  0.872 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  91.7559 E-12 cm3/molecule-sec
      Half-Life =     0.117 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.399 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.99 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: -1.18 (estimated)

 Volatilization from Water:
    Henry LC:  4.64E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.632E+011  hours   (6.798E+009 days)
    Half-Life from Model Lake :  1.78E+012  hours   (7.416E+010 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       7.01e-006       2.8          1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 973 hr




                    

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