ChemSpider 2D Image | Floxuridine | C9H11FN2O5

Floxuridine

  • Molecular FormulaC9H11FN2O5
  • Average mass246.192 Da
  • Monoisotopic mass246.065201 Da
  • ChemSpider ID5586
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



Featured data source



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

(+)-5-Fluoro-2'-deoxyuridine
(+)-5-fluoro-2′-deoxyuridine
1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracil
1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-fluoro-4-hydroxy-2(1H)-pyrimidinone [ACD/IUPAC Name]
1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-fluorpyrimidin-2,4(1H,3H)-dion
1-(2-Desoxy-β-D-erythro-pentofuranosyl)-5-fluor-4-hydroxy-2(1H)-pyrimidinon [German] [ACD/IUPAC Name]
1-(2-Désoxy-β-D-érythro-pentofuranosyl)-5-fluoro-4-hydroxy-2(1H)-pyrimidinone [French] [ACD/IUPAC Name]
2(1H)-Pyrimidinone, 1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-fluoro-4-hydroxy- [ACD/Index Name]
2′-Deoxy-5-fluorouridine
200-072-5 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

039LU44I5M [DBID]
MFCD00006530 [DBID]
AI3-50691 [DBID]
AIDS008673 [DBID]
AIDS-008673 [DBID]
BRN 0090221 [DBID]
C11736 [DBID]
CCRIS 4693 [DBID]
F0503_SIGMA [DBID]
HSDB 3227 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      solid Oxford University Chemical Safety Data (No longer updated) More details
      White Powder Novochemy [NC-05444]
    • Stability:

      Stable. Incompatible with strong oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 215 mg kg-1, ORL-MUS LD50 147 mg kg-1, IPR-RAT LD50 1600 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      20/21/36/37/39 Novochemy [NC-05444]
      36/37/38 Novochemy [NC-05444]
      53-20-36/37-45 Alfa Aesar L16497
      6.1 Alfa Aesar L16497
      61-22-68 Alfa Aesar L16497
      Danger Biosynth Q-201118
      GHS06 Biosynth Q-201118
      GHS07; GHS09 Novochemy [NC-05444]
      H301 Biosynth Q-201118
      H332; H403 Novochemy [NC-05444]
      P301+P310 Biosynth Q-201118
      P332+P313; P305+P351+P338 Novochemy [NC-05444]
      R52/53 Novochemy [NC-05444]
      Safety glasses, adequate ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      Warning Novochemy [NC-05444]
    • Target Organs:

      DNA/RNA Synthesis inhibitor TargetMol T0964
    • Chemical Class:

      A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract. ChEBI CHEBI:60761
    • Bio Activity:

      Antineoplastic antimetabolite. Exhibits antiproliferative activity; inhibits thymidylate synthetase and disrupts DNA replication in human cells. Induces double-strand DNA breaks; activates ATR and ATM signaling pathways. Induces phosphorylation of Chk1 and Chk2 in OVCAR-8 and SKOV3ip ovarian cancer cell lines. Tocris Bioscience 4659
      Antineoplastic antimetabolite. Exhibits antiproliferative activity; inhibits thymidylate synthetase and disrupts DNA replication in human cells. Induces double-strand DNA breaks; activates ATR and ATM signaling pathways. Induces phosphorylation of Chk1 and Chk2 in OVCAR-8 and SKOV3ip ovarian cancer cell lines. Tocris Bioscience 4659
      Cell Cycle/DNA Damage MedChem Express HY-B0097
      Cell Cycle/DNA Damage; MedChem Express HY-B0097
      DNA Damage/DNA Repair TargetMol T0964
      Enzymes Tocris Bioscience 4659
      Floxuridine (5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites with an GI50 of 5.1 ?M for the inhibition of PEPT1. MedChem Express HY-B0097
      Inhibitor of thymidylate synthetase; anticancer agent Tocris Bioscience 4659
      Nucleoside antimetabolite/analog MedChem Express HY-B0097
      Other Synthases/Synthetases Tocris Bioscience 4659
      Synthases/Synthetases Tocris Bioscience 4659
      Thymidylate synthase TargetMol T0964
      Thymidylate Synthetase Tocris Bioscience 4659
      Thymidylate synthetase inhibitor Tocris Bioscience 4659

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: 1.609
Molar Refractivity: 51.9±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -1.43
ACD/LogD (pH 5.5): -1.32
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.53
ACD/LogD (pH 7.4): -1.53
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.79
Polar Surface Area: 99 Å2
Polarizability: 20.6±0.5 10-24cm3
Surface Tension: 72.4±5.0 dyne/cm
Molar Volume: 150.0±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) =  -1.14
    Log Kow (Exper. database match) =  -1.16
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  519.54  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.73  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.57E-013  (Modified Grain method)
    MP  (exp database):  150.5 deg C
    Subcooled liquid VP: 1.43E-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):  1.19e+004
       log Kow used: -1.16 (expkow database)
       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]:  2.061E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.16  (exp database)
  Log Kaw used:  -15.218  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.058
      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)    :   0.4335
   Biowin6 (MITI Non-Linear Model):   0.0017
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7952
 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):  1.91E-009 Pa (1.43E-011 mm Hg)
  Log Koa (Koawin est  ): 14.058
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.57E+003 
       Octanol/air (Koa) model:  28.1 
   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 =  67.2648 E-12 cm3/molecule-sec
      Half-Life =     0.159 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.908 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: -1.16 (expkow database)

 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       4.7e-006        3.78         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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