ChemSpider 2D Image | Gemcitabine | C9H11F2N3O4

Gemcitabine

  • Molecular FormulaC9H11F2N3O4
  • Average mass263.198 Da
  • Monoisotopic mass263.071747 Da
  • ChemSpider ID54753

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

1-(2-Deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)-4-imino-1,4-dihydro-2-pyrimidinol [ACD/IUPAC Name]
1-(2-Désoxy-2,2-difluoro-β-D-érythro-pentofuranosyl)-4-imino-1,4-dihydro-2-pyrimidinol [French] [ACD/IUPAC Name]
1-(2-Desoxy-2,2-difluor-β-D-erythro-pentofuranosyl)-4-imino-1,4-dihydro-2-pyrimidinol [German] [ACD/IUPAC Name]
1-(2-Oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose
2'-Deoxy-2',2'-difluorocytidine [ACD/IUPAC Name]
2'-Deoxy-2',2'-difluoro-cytidine
2'-Desoxy-2',2'-difluorcytidin [German] [ACD/IUPAC Name]
2'-Désoxy-2',2'-difluorocytidine [French] [ACD/IUPAC Name]
2-Pyrimidinol, 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)-1,4-dihydro-4-imino- [ACD/Index Name]
4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6515 [DBID]
5382060 [DBID]
AIDS001419 [DBID]
AIDS-001419 [DBID]
C07650 [DBID]
CCRIS 4693 [DBID]
CCRIS 8984 [DBID]
D02368 [DBID]
LY 188011 [DBID]
LY-188011 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      L01BC05 Wikidata Q414143

    • Target Organs:

      UMP-CMP kinase inhibitor;Autophagy activator;DNA Synthesis inhibitor; Thymidylate synthase inhibitor TargetMol T0251

    • Chemical Class:

      A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small c ell lung cancer, pancreatic cancer, bladder cancer and breast cancer. ChEBI CHEBI:175901

    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-17026
      Cell Cycle/DNA Damage; MedChem Express HY-17026
      DNA Damage/DNA Repair; Ubiquitination TargetMol T0251
      Gemcitabine(LY-188011; NSC 613327) is a DNA synthesis inhibitor with IC50 of 50 nM, 40 nM, 18 nM and 12 nM in PANC1, MIAPaCa2, BxPC3 and Capan2 cells, respectively. MedChem Express
      Gemcitabine(LY-188011; NSC 613327) is a DNA synthesis inhibitor with IC50 of 50 nM, 40 nM, 18 nM and 12 nM in PANC1, MIAPaCa2, BxPC3 and Capan2 cells, respectively.; IC50 Value: 50 nM( PANC1); 40 nM(MIAPaCa2); 18 nM(BxPC3 ); 12 nM(Capan2); Target: Nucleoside antimetabolite/analog; Gemcitabine is converted intracellularly to the active metabolites difluorodeoxycytidine di- and triphosphate (dFdCDP, dFdCTP). MedChem Express HY-17026
      Nucleoside antimetabolite/analog MedChem Express HY-17026
      UMP-CMP kinase;Autophagy ;DNA;Thymidylate synthase TargetMol T0251

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

Density: 1.8±0.1 g/cm3
Boiling Point: 482.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 86.2±6.0 kJ/mol
Flash Point: 245.7±31.5 °C
Index of Refraction: 1.652
Molar Refractivity: 52.1±0.5 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -0.47
ACD/LogD (pH 5.5): -1.38
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.15
ACD/LogD (pH 7.4): -1.36
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 4.33
Polar Surface Area: 108 Å2
Polarizability: 20.6±0.5 10-24cm3
Surface Tension: 65.4±7.0 dyne/cm
Molar Volume: 142.3±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) =  -2.01

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  405.89  (Adapted Stein & Brown method)
    Melting Pt (deg C):  168.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.7E-009  (Modified Grain method)
    Subcooled liquid VP: 5.15E-008 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):  5.139e+004
       log Kow used: -2.01 (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:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.70E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.146E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.01  (KowWin est)
  Log Kaw used:  -15.158  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.148
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4084
   Biowin2 (Non-Linear Model)     :   0.0254
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7167  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5637  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4544
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5074
 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):  6.87E-006 Pa (5.15E-008 mm Hg)
  Log Koa (Koawin est  ): 13.148
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.437 
       Octanol/air (Koa) model:  3.45 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.94 
       Mackay model           :  0.972 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  40.2048 E-12 cm3/molecule-sec
      Half-Life =     0.266 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.192 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): 0.956 (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: -2.01 (estimated)

 Volatilization from Water:
    Henry LC:  1.7E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.587E+013  hours   (2.328E+012 days)
    Half-Life from Model Lake : 6.095E+014  hours   (2.54E+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       5.03e-009       6.13         1000       
   Water     46.5            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 973 hr

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