ChemSpider 2D Image | Nelarabine | C11H15N5O5

Nelarabine

  • Molecular FormulaC11H15N5O5
  • Average mass297.267 Da
  • Monoisotopic mass297.107330 Da
  • ChemSpider ID2280207
  • defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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

(2R,3S,4S,5R)-2-(2-Amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2R,3S,4S,5R)-2-(2-amino-6-méthoxy-9H-purin-9-yl)-5-(hydroxyméthyl)tétrahydrofurane-3,4-diol
121032-29-9 [RN]
2-Amino-9-b-D-arabinofuranosyl-6-methoxy-9H-purine
60158CV180
7704
9-(β-D-Arabinofuranosyl)-6-methoxy-9H-purin-2-amin [German] [ACD/IUPAC Name]
9-(β-D-Arabinofuranosyl)-6-methoxy-9H-purin-2-amine [ACD/IUPAC Name]
9-(β-D-Arabinofuranosyl)-6-méthoxy-9H-purin-2-amine [French] [ACD/IUPAC Name]
9-b-D-Arabinofuranosyl-6-methoxy-9H-purin-2-amine
More...

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

CHEBI:63612 [DBID]
AIDS215768 [DBID]
AIDS-215768 [DBID]
NSC-686673 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 090149
      L01BB07 Wikidata Q1216264
      P261; P262 Biosynth Q-101416
    • Chemical Class:

      A purine nucleoside in which <element>O</element>-methylguanine is attached to arabinofuranose via a <stereo>beta</stereo>-<element>N</element><smallsup>9</smallsup>-glycosidic bond. Inhibits DNA synt hesis and causes cell death; a prodrug of 9-<stereo>beta</stereo>-<stereo>D</stereo>-arabinofuranosylguanine (ara-G). ChEBI CHEBI:63612
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-13701
      Cell Cycle/DNA Damage; MedChem Express HY-13701
      Cell Metabolism Tocris Bioscience 6359
      DNA, RNA and Protein Synthesis Tocris Bioscience 6359
      Nelarabine (Arranon, 506U78) is a purine nucleoside analog and DNA synthesis inhibitor with IC50 from 0.067-2.15 ?M in tumor cells. MedChem Express HY-13701
      Nucleoside analog. Metabolized by adenosine deaminase to active metabolite, arabinofuranosylguanine (ara-G). Inhibits DNA synthesis and induces apoptosis. Inhibits growth of human T cell lymphoblastic leukemia cells in vitro and in vivo. Tocris Bioscience 6359
      Nucleoside antimetabolite/analog MedChem Express HY-13701
      Purine nuceloside analog; inhibits DNA synthesis Tocris Bioscience 6359

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

Density: 2.0±0.1 g/cm3
Boiling Point: 721.0±70.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 110.6±3.0 kJ/mol
Flash Point: 389.9±35.7 °C
Index of Refraction: 1.829
Molar Refractivity: 65.8±0.5 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 2
ACD/LogP: -0.58
ACD/LogD (pH 5.5): -0.98
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 6.95
ACD/LogD (pH 7.4): -0.98
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 6.98
Polar Surface Area: 149 Å2
Polarizability: 26.1±0.5 10-24cm3
Surface Tension: 91.1±7.0 dyne/cm
Molar Volume: 149.9±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) =  -1.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  560.98  (Adapted Stein & Brown method)
    Melting Pt (deg C):  241.09  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.32E-016  (Modified Grain method)
    Subcooled liquid VP: 1.81E-013 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):  4424
       log Kow used: -1.00 (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:
       Aromatic Amines
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.13E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.356E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.00  (KowWin est)
  Log Kaw used:  -17.060  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.060
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6330
   Biowin2 (Non-Linear Model)     :   0.2794
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8204  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7662  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4580
   Biowin6 (MITI Non-Linear Model):   0.0473
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8861
 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):  2.41E-011 Pa (1.81E-013 mm Hg)
  Log Koa (Koawin est  ): 16.060
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.24E+005 
       Octanol/air (Koa) model:  2.82E+003 
   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 = 239.1935 E-12 cm3/molecule-sec
      Half-Life =     0.045 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.537 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    :  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: -1.00 (estimated)

 Volatilization from Water:
    Henry LC:  2.13E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.739E+015  hours   (1.975E+014 days)
    Half-Life from Model Lake :  5.17E+016  hours   (2.154E+015 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       3.96e-005       1.07         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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