ChemSpider 2D Image | (+)-Doxifluridine | C9H11FN2O5

(+)-Doxifluridine

  • Molecular FormulaC9H11FN2O5
  • Average mass246.192 Da
  • Monoisotopic mass246.065201 Da
  • ChemSpider ID17322
  • defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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

(+)-Doxifluridine
(+)-5-Fluoro-5'-deoxyuridine
1-(b-D-5'-Deoxyribofuranosyl)-5-fluorouracil
221-440-1 [EINECS]
3094-09-5 [RN]
4913
5'-Deoxy-5-fluorouridine [ACD/IUPAC Name]
5'-Désoxy-5-fluorouridine [French] [ACD/IUPAC Name]
5'-Desoxy-5-fluoruridin [German] [ACD/IUPAC Name]
5'-dFUrd
More...

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

537314_ALDRICH [DBID]
AIDS184530 [DBID]
AIDS-184530 [DBID]
D01309 [DBID]
EU-0100537 [DBID]
F8791_SIGMA [DBID]
MFCD00866530 [DBID]
Ro 219738 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Nucleoside antimetabolite/analog TargetMol [T1600]
    • Chemical Class:

      A pyrimidine 5'-deoxyribonucleoside that is 5-fluorouridine in which the hydroxy group at the 5' position is replaced by a hydrogen. It is an oral prodrug of the antineoplastic agent 5-fluorouracil. Designed to circumvent the rapid degradation of 5-fluorouracil by dihydropyrimidine dehydrogenase in the gut wall, it is converted into 5-fluorouracil in the presence of pyrimidine nucleoside phosphor ylase. ChEBI CHEBI:31521
      DNA Metabolism EU-OpenScreen [F 8791]
    • Drug Status:

      approved BIONET-Key Organics KS-5065
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-B0021
      Cell Cycle/DNA Damage; MedChem Express HY-B0021
      DNA Damage/DNA Repair TargetMol [T1600]
      Doxifluridine(Ro 21-9738; 5'-DFUR) is a thymidine phosphorylase activator for PC9-DPE2 cells with IC50 of 0.62 ?M. MedChem Express HY-B0021
      Nucleoside antimetabolite/analog MedChem Express HY-B0021
      thymidine phosphorylase activator TargetMol [T1600]

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

Density: 1.6±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.605
Molar Refractivity: 51.9±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.96
ACD/LogD (pH 5.5): -1.10
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 6.01
ACD/LogD (pH 7.4): -1.33
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.50
Polar Surface Area: 99 Å2
Polarizability: 20.6±0.5 10-24cm3
Surface Tension: 69.9±5.0 dyne/cm
Molar Volume: 150.7±5.0 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) =  -1.40

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  512.43  (Adapted Stein & Brown method)
    Melting Pt (deg C):  218.40  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.51E-013  (Modified Grain method)
    MP  (exp database):  190 deg C
    Subcooled liquid VP: 2.42E-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):  1.917e+004
       log Kow used: -1.40 (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:
       Imides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.48E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.621E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.40  (KowWin est)
  Log Kaw used:  -15.218  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.818
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6004
   Biowin2 (Non-Linear Model)     :   0.1570
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9664  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7417  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3772
   Biowin6 (MITI Non-Linear Model):   0.0008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8491
 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):  3.23E-009 Pa (2.42E-011 mm Hg)
  Log Koa (Koawin est  ): 13.818
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  930 
       Octanol/air (Koa) model:  16.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  66.9387 E-12 cm3/molecule-sec
      Half-Life =     0.160 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.917 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.070000 E-17 cm3/molecule-sec
      Half-Life =    16.371 Days (at 7E11 mol/cm3)
   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: -1.40 (estimated)

 Volatilization from Water:
    Henry LC:  1.48E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.207E+013  hours   (2.586E+012 days)
    Half-Life from Model Lake : 6.771E+014  hours   (2.821E+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       8.51e-006       3.8          1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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