ChemSpider 2D Image | Lomeguatrib | C10H8BrN5OS

Lomeguatrib

  • Molecular FormulaC10H8BrN5OS
  • Average mass326.172 Da
  • Monoisotopic mass324.963287 Da
  • ChemSpider ID2291573

More details:






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

192441-08-0 [RN]
2-Amino-6-[(4-bromo-2-thienyl)methoxy]-9H-purine
6-[(4-Brom-2-thienyl)methoxy]-7H-purin-2-amin [German] [ACD/IUPAC Name]
6-[(4-Bromo-2-thienyl)methoxy]-7H-purin-2-amine [ACD/IUPAC Name]
6-[(4-Bromo-2-thiényl)méthoxy]-7H-purin-2-amine [French] [ACD/IUPAC Name]
6-[(4-bromothiophen-2-yl)methoxy]-7H-purin-2-amine
7H-Purin-2-amine, 6-[(4-bromo-2-thienyl)methoxy]- [ACD/Index Name]
8401
lomeguatrib [Spanish] [INN]
lomeguatrib [French] [INN]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 2223
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2223
      no pictogram Axon Medchem 2223
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2223
      Warning Axon Medchem 2223
    • Target Organs:

      DNA Methyltransferase inhibitor TargetMol T2495
    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB1376]
      Cell Cycle/DNA Damage MedChem Express HY-13668
      Cell Cycle/DNA Damage; MedChem Express HY-13668
      Chromatin/Epigenetic TargetMol T2495
      DNA Methyltransferases Tocris Bioscience 4359
      DNMT MedChem Express HY-13668
      Enzymes Tocris Bioscience 4359
      Enzymes/Transferase Hello Bio [HB1376]
      Inhibitor of O6-methylguanine-DNA methyltransferase (MGMT); (IC50 = 0.009 ?M in cell-free extracts from HeLa S3 cells); attenuates MGMT activity in vitro and in vivo. Enhances the antitumor activity o f temozolomide (Cat. No. 2706) in both human melanoma and MCF-7 xenografts. Tocris Bioscience 4359
      Inhibitor of O6-methylguanine-DNA methyltransferase (MGMT); (IC50 = 0.009 ?M in cell-free extracts from HeLa S3 cells); attenuates MGMT activity in vitro and in vivo. Enhances the antitumor activity of temozolomide (Cat. No. 2706) in both human melanoma and MCF-7 xenografts. Tocris Bioscience 4359
      Inhibitor of O6-methylguanine-DNA methyltransferase (MGMT); (IC50 = 0.009 muM in cell-free extracts from HeLa S3 cells); attenuates MGMT activity in vitro and in vivo. Enhances the antitumor activity of temozolomide (Cat. No. 2706) in both human melanoma and MCF-7 xenografts. Tocris Bioscience 4359
      Lomeguatrib (PaTrin-2) is a modified guanine base, which can repress the activity of DNA repair protein O(6)-alkylguanine-DNA alkyltransferase (MGMT) with an IC50 value of 6 nM. MedChem Express
      Lomeguatrib (PaTrin-2) is a modified guanine base, which can repress the activity of DNA repair protein O(6)-alkylguanine-DNA alkyltransferase (MGMT) with an IC50 value of 6 nM.; IC50 Value: 6 nM [1]; Target: MGMT; in vitro: PaTrin-2 effectively inactivated MGMT in MCF-7 cells (IC50 approximately 6 nM) and in xenografts there was complete inactivation of MGMT within 2 h of dosing (20 mg kg(-1) i.p.) and only slight recovery by 24 h. MedChem Express HY-13668
      Lomeguatrib (PaTrin-2) is a modified guanine base, which can repress the activity of DNA repair protein O(6)-alkylguanine-DNA alkyltransferase (MGMT) with an IC50 value of 6 nM.;IC50 Value: 6 nM [1];Target: MGMT;In vitro: PaTrin-2 effectively inactivated MGMT in MCF-7 cells (IC50 approximately 6 nM) and in xenografts there was complete inactivation of MGMT within 2 h of dosing (20 mg kg(-1) i.p.) and only slight recovery by 24 h. MGMT inactivation in a range of murine host tissues varied between complete and approximately 60%, with extensive recovery by 24 h. PaTrin-2 (10 microM) substantially increased the growth inhibitory effects of temozolomide in MCF-7 cells (D(60)=10 microM with PaTrin-2 vs 400 microM without)[1]. growth of A2780 cell treated only with temozolomide (5 microg/mL) was 91% of control growth, whereas additional exposure to PaTrin-2 alone (10 micromol/L) or oblimersen alone (33 nmol/L) reduced this to 81% and 66%, respectively, and the combination of PaTrin-2 (10 MedChem Express HY-13668
      MGMT inhibitor Tocris Bioscience 4359
      O6-alkylguanine-DNA-alkyltransferase TargetMol T2495
      Potent MGMT inhibitor Hello Bio [HB1376]
      Potent O<sup>6</sup>-methylguanine-DNA methyltransferase (MGMT) inhibitor (IC<sub>50</sub> = 9 nM). Acts as a pseudosubstrate. Enhances temozolomide anti-tumor activity. Shows anti-cancer actions. Hello Bio [HB1376]
      Transferases Tocris Bioscience 4359

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

Density: 1.9±0.1 g/cm3
Boiling Point: 683.8±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 100.3±3.0 kJ/mol
Flash Point: 367.3±34.3 °C
Index of Refraction: 1.797
Molar Refractivity: 74.3±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 2.36
ACD/LogD (pH 5.5): 2.08
ACD/BCF (pH 5.5): 22.45
ACD/KOC (pH 5.5): 322.06
ACD/LogD (pH 7.4): 2.08
ACD/BCF (pH 7.4): 22.39
ACD/KOC (pH 7.4): 321.20
Polar Surface Area: 118 Å2
Polarizability: 29.4±0.5 10-24cm3
Surface Tension: 93.4±3.0 dyne/cm
Molar Volume: 174.2±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) =  2.08

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  531.33  (Adapted Stein & Brown method)
    Melting Pt (deg C):  227.23  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.96E-011  (Modified Grain method)
    Subcooled liquid VP: 4.38E-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):  145.4
       log Kow used: 2.08 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1334.1 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.35E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.737E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.08  (KowWin est)
  Log Kaw used:  -10.017  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.097
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3801
   Biowin2 (Non-Linear Model)     :   0.0493
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1493  (months      )
   Biowin4 (Primary Survey Model) :   3.1924  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0849
   Biowin6 (MITI Non-Linear Model):   0.0063
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4427
 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):  5.84E-007 Pa (4.38E-009 mm Hg)
  Log Koa (Koawin est  ): 12.097
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.14 
       Octanol/air (Koa) model:  0.307 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.995 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  0.961 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 220.6045 E-12 cm3/molecule-sec
      Half-Life =     0.048 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.582 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.996 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  486.5
      Log Koc:  2.687 

 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 = 0.898 (BCF = 7.905)
       log Kow used: 2.08 (estimated)

 Volatilization from Water:
    Henry LC:  2.35E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:   4.5E+008  hours   (1.875E+007 days)
    Half-Life from Model Lake : 4.909E+009  hours   (2.045E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               2.33  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.23  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       0.00446         1.16         1000       
   Water     22.1            1.44e+003    1000       
   Soil      77.8            2.88e+003    1000       
   Sediment  0.0964          1.3e+004     0          
     Persistence Time: 1.85e+003 hr




                    

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