ChemSpider 2D Image | entecavir | C12H15N5O3

entecavir

  • Molecular FormulaC12H15N5O3
  • Average mass277.279 Da
  • Monoisotopic mass277.117493 Da
  • ChemSpider ID135679
  • defined stereocentres - 3 of 3 defined stereocentres


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142217-69-4 [RN]
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylencyclopentyl]-1,9-dihydro-6H-purin-6-on [German] [ACD/IUPAC Name]
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one [ACD/IUPAC Name]
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxyméthyl)-2-méthylènecyclopentyl]-1,9-dihydro-6H-purin-6-one [French] [ACD/IUPAC Name]
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidencyclopentyl]-1,9-dihydro-6H-purin-6-on [German]
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxyméthyl)-2-méthylidènecyclopentyl]-1,9-dihydro-6H-purin-6-one [French]
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-9H-purin-6-ol
6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-
6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS098045 [DBID]
AIDS-098045 [DBID]
BMS 200475 [DBID]
BMS-200475 [DBID]
SQ-34676 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 090228
      J05AF10 Wikidata Q418586
      P261; P262 Biosynth Q-201059
    • Target Organs:

      Reverse Transcriptase inhibitor TargetMol T0085L
    • Chemical Class:

      Guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor wit h selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural subs trate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B. ChEBI CHEBI:473990
    • Bio Activity:

      Anti-infection MedChem Express HY-13623
      Anti-infection; MedChem Express HY-13623
      DNA Damage/DNA Repair;Microbiology & Virology TargetMol T0085L
      Entecavir(BMS200475; SQ34676) is a guanosine analogue that inhibits reverse transcription, DNA replication and transcription in the viral replication process; oral antiHBV drug. MedChem Express
      Entecavir(BMS200475; SQ34676) is a guanosine analogue that inhibits reverse transcription, DNA replication and transcription in the viral replication process; oral antiHBV drug.; IC50 value:; Target: AntiHBV drug; Both entecavir and adefovir dipivoxil maintain activity against hepatitis B virus in patients with chronic hepatitis B who are refractory to lamivudine, and both agents are reasonable first-line treatment options. MedChem Express HY-13623
      Entecavir(BMS200475; SQ34676) is a guanosine analogue that inhibits reverse transcription, DNA replication and transcription in the viral replication process; oral antiHBV drug.;IC50 value:;Target: AntiHBV drugBoth entecavir and adefovir dipivoxil maintain activity against hepatitis B virus in patients with chronic hepatitis B who are refractory to lamivudine, and both agents are reasonable first-line treatment options. Longer trials involving nucleoside-naive, lamivudine-refractory patients are needed to determine entecavir's optimal treatment duration, long-term safety, and durability of response, including rate of resistance [1]. Entecavir is used to treat chronic hepatitis B. It also helps prevent the hepatitis B virus from multiplying and infecting new liver cells. Entecavir is also indicated for the treatment of chronic hepatitis B in adults with HIV/AIDS infection. However, entecavir is not active against HIV. MedChem Express HY-13623
      Enzymes Tocris Bioscience 6234
      HBV MedChem Express HY-13623
      Polymerases Tocris Bioscience 6234
      Potent and selective hepatitis B virus inhibitor Tocris Bioscience 6234
      Potent and selective hepatitis B virus reverse transcriptase inhibitor (EC50 = 3 nM); guanine analog. Inhibits hepatitis B virus replication in HepG2.2.15 cells. Displays selectively over HCMV, HSV-1, VZV, HIV and influenza (EC50 values are 15, 32, 30-60, >10 and >80 muM respectively). Orally bioavailable. Tocris Bioscience 6234
      Reverse Transcriptase TargetMol T0085L
      RNA/DNA Polymerase Tocris Bioscience 6234

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

Density: 1.8±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.837
Molar Refractivity: 67.6±0.5 cm3
#H bond acceptors: 8
#H bond donors: 5
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: -0.96
ACD/LogD (pH 5.5): -0.80
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 8.69
ACD/LogD (pH 7.4): -0.81
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 8.65
Polar Surface Area: 126 Å2
Polarizability: 26.8±0.5 10-24cm3
Surface Tension: 84.2±7.0 dyne/cm
Molar Volume: 153.0±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) =  -3.07

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  568.24  (Adapted Stein & Brown method)
    Melting Pt (deg C):  244.48  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.62E-015  (Modified Grain method)
    Subcooled liquid VP: 3.88E-013 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):  1e+006
       log Kow used: -3.07 (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:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.17E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.910E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.07  (KowWin est)
  Log Kaw used:  -17.675  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.605
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9330
   Biowin2 (Non-Linear Model)     :   0.7870
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9063  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7066  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3408
   Biowin6 (MITI Non-Linear Model):   0.0368
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0183
 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):  5.17E-011 Pa (3.88E-013 mm Hg)
  Log Koa (Koawin est  ): 14.605
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.8E+004 
       Octanol/air (Koa) model:  98.9 
   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 = 191.6285 E-12 cm3/molecule-sec
      Half-Life =     0.056 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.670 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.375000 E-17 cm3/molecule-sec
      Half-Life =     0.833 Days (at 7E11 mol/cm3)
      Half-Life =     20.003 Hrs
   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    :  48.61
      Log Koc:  1.687 

 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: -3.07 (estimated)

 Volatilization from Water:
    Henry LC:  5.17E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.886E+016  hours   (7.857E+014 days)
    Half-Life from Model Lake : 2.057E+017  hours   (8.572E+015 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       4.57e-006       1.26         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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