ChemSpider 2D Image | Sapacitabine | C26H42N4O5

Sapacitabine

  • Molecular FormulaC26H42N4O5
  • Average mass490.635 Da
  • Monoisotopic mass490.315521 Da
  • ChemSpider ID135703

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

1-(2-Cyan-2-desoxy-β-D-arabinofuranosyl)-4-(palmitoylamino)-2(1H)-pyrimidinon [German] [ACD/IUPAC Name]
1-(2-Cyano-2-deoxy-β-D-arabinofuranosyl)-4-(palmitoylamino)-2(1H)-pyrimidinone [ACD/IUPAC Name]
1-(2-Cyano-2-désoxy-β-D-arabinofuranosyl)-4-(palmitoylamino)-2(1H)-pyrimidinone [French] [ACD/IUPAC Name]
151823-14-2 [RN]
2(1H)-Pyrimidinone, 1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-4-[(1-oxohexadecyl)amino]- [ACD/Index Name]
N-{1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}hexadecanamide
Sapacitabine [INN] [USAN] [Wiki]
(S)-pyrrolidin-3-ol
1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-4-(hexadecanoylamino)pyrimidin-2(1H)-one
CS682
More...

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

CS-682 [DBID]
CYC682 [DBID]
CS 682 [DBID]
CYC-682 [DBID]
  • Miscellaneous

    • Chemical Class:

      A nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical developmen t for the treatment of acute myeloid leukemia (AML). ChEBI CHEBI:145429

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

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.575
Molar Refractivity: 133.9±0.5 cm3
#H bond acceptors: 9
#H bond donors: 3
#Freely Rotating Bonds: 18
#Rule of 5 Violations: 1
ACD/LogP: 5.67
ACD/LogD (pH 5.5): 4.81
ACD/BCF (pH 5.5): 2673.39
ACD/KOC (pH 5.5): 9853.34
ACD/LogD (pH 7.4): 4.81
ACD/BCF (pH 7.4): 2676.62
ACD/KOC (pH 7.4): 9865.24
Polar Surface Area: 135 Å2
Polarizability: 53.1±0.5 10-24cm3
Surface Tension: 47.4±7.0 dyne/cm
Molar Volume: 405.4±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) =  3.98

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  719.03  (Adapted Stein & Brown method)
    Melting Pt (deg C):  314.91  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.16E-021  (Modified Grain method)
    Subcooled liquid VP: 3.92E-018 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):  0.1795
       log Kow used: 3.98 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  368.73 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.04E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.769E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.98  (KowWin est)
  Log Kaw used:  -19.906  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  23.886
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1096
   Biowin2 (Non-Linear Model)     :   0.9825
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5879  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7983  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5783
   Biowin6 (MITI Non-Linear Model):   0.0681
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2798
 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):  5.23E-016 Pa (3.92E-018 mm Hg)
  Log Koa (Koawin est  ): 23.886
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.74E+009 
       Octanol/air (Koa) model:  1.89E+011 
   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 = 122.4267 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.048 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 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    :  2879
      Log Koc:  3.459 

 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 = 2.362 (BCF = 230)
       log Kow used: 3.98 (estimated)

 Volatilization from Water:
    Henry LC:  3.04E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.266E+018  hours   (1.778E+017 days)
    Half-Life from Model Lake : 4.654E+019  hours   (1.939E+018 days)

 Removal In Wastewater Treatment:
    Total removal:              29.16  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.84  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       0.00122         2.07         1000       
   Water     11.1            900          1000       
   Soil      86.5            1.8e+003     1000       
   Sediment  2.49            8.1e+003     0          
     Persistence Time: 1.87e+003 hr

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