ChemSpider 2D Image | Fludarabine phosphate | C10H13FN5O7P

Fludarabine phosphate

  • Molecular FormulaC10H13FN5O7P
  • Average mass365.212 Da
  • Monoisotopic mass365.053650 Da
  • ChemSpider ID28532

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

[(2R,3S,4S,5R)-5-(6-Amino-2-fluor-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyldihydrogen-phosphat [German]
[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate
1X9VK9O1SC
2-Fluor-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amin [German] [ACD/IUPAC Name]
2-Fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amine [ACD/IUPAC Name]
2-Fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amine [French] [ACD/IUPAC Name]
2-Fluoroadenine arabinoside 5'-monophosphate
75607-67-9 [RN]
9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-
9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63599 [DBID]
D01907 [DBID]
NSC 312887 [DBID]
NSC 328002 [DBID]
NSC-312887 [DBID]
SHT-586 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Organofluoride; Ether; Drug; Antineoplastic Agent; Synthetic Compound Toxin, Toxin-Target Database T3D4736

    • Safety:

      L01BB05 Wikidata Q185916

    • Chemical Class:

      A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Once incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used for the treatment of adult patients with B-cell chroni c lymphocytic leukemia (CLL) who have not responded to, or whose disease has progressed during, treatment with at least one standard alkylating-agent containing regimenas. ChEBI CHEBI:63599

    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-B0028
      Cell Cycle/DNA Damage; MedChem Express HY-B0028
      Fludarabine Phosphate is an analogue of adenosine and deoxyadenosine, which is able to compete with dATP for incorporation into DNA and inhibit DNA synthesis. MedChem Express
      Fludarabine Phosphate is an analogue of adenosine and deoxyadenosine, which is able to compete with dATP for incorporation into DNA and inhibit DNA synthesis.; IC50 Value: N/A; Target: DNA/RNA Synthesis; in vitro: Fludarabine Phosphate is converted to F-ara-ATP in cells and then incorporated into DNA in a self-limiting manner. MedChem Express HY-B0028
      Nucleoside antimetabolite/analog MedChem Express HY-B0028

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 2.4±0.1 g/cm3
Boiling Point: 864.2±75.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 131.6±3.0 kJ/mol
Flash Point: 476.4±37.1 °C
Index of Refraction: 1.879
Molar Refractivity: 69.8±0.5 cm3
#H bond acceptors: 12
#H bond donors: 6
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: 0.41
ACD/LogD (pH 5.5): -5.68
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -6.62
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 196 Å2
Polarizability: 27.7±0.5 10-24cm3
Surface Tension: 130.7±7.0 dyne/cm
Molar Volume: 152.5±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) =  -1.48

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  480.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  90.27  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.06E-011  (Modified Grain method)
    Subcooled liquid VP: 8.76E-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):  4464
       log Kow used: -1.48 (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 :   1.17E-031  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.218E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.48  (KowWin est)
  Log Kaw used:  -29.320  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  27.840
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.5000
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1615  (months      )
   Biowin4 (Primary Survey Model) :   3.4751  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0835
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6549
 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):  1.17E-008 Pa (8.76E-011 mm Hg)
  Log Koa (Koawin est  ): 27.840
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  257 
       Octanol/air (Koa) model:  1.7E+015 
   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 = 258.0338 E-12 cm3/molecule-sec
      Half-Life =     0.041 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.845 Min
   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: -1.48 (estimated)

 Volatilization from Water:
    Henry LC:  1.17E-031 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.563E+027  hours   (3.985E+026 days)
    Half-Life from Model Lake : 1.043E+029  hours   (4.347E+027 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       1.35e-020       0.995        1000       
   Water     49.5            1.44e+003    1000       
   Soil      50.4            2.88e+003    1000       
   Sediment  0.0962          1.3e+004     0          
     Persistence Time: 1.17e+003 hr

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