ChemSpider 2D Image | Tenofovir | C9H14N5O4P

Tenofovir

  • Molecular FormulaC9H14N5O4P
  • Average mass287.212 Da
  • Monoisotopic mass287.078339 Da
  • ChemSpider ID408154
  • defined stereocentres - 1 of 1 defined stereocentres


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Featured data source



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

(((1R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)phosphonic acid
({[(2R)-1-(6-Amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)phosphonic acid [ACD/IUPAC Name]
({[(2R)-1-(6-Amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)phosphonsäure [German] [ACD/IUPAC Name]
({[(2R)-1-(6-Amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
(R)-9-(2-Phosphonomethoxypropyl)adenine
(R)-9-(2-Phosphonylmethoxypropyl)adenine
{[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl}phosphonic acid
147127-20-6 [RN]
7913
Acide ({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}méthyl)phosphonique [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63625 [DBID]
GS 1275 [DBID]
AIDS021800 [DBID]
AIDS-021800 [DBID]
AIDS224015 [DBID]
AIDS-224015 [DBID]
AIDS224022 [DBID]
AIDS-224022 [DBID]
GS-1278 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS07 Biosynth Q-201788
      H315; H319; H335 Biosynth Q-201788
      IRRITANT Matrix Scientific 074030
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-201788
      Warning Biosynth Q-201788
    • Target Organs:

      Antiviral;Reverse Transcriptase inhibitor TargetMol T1649
    • Chemical Class:

      A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV- 1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection. ChEBI CHEBI:63625
    • Drug Status:

      approved BIONET-Key Organics KS-5021
    • Bio Activity:

      Anti-infection MedChem Express HY-13910
      Anti-infection; MedChem Express HY-13910
      Enzymes Tocris Bioscience 3666
      HIV MedChem Express HY-13910
      HIV NRTIs MedChem Express HY-13910
      Microbiology & Virology TargetMol T1649
      Polymerases Tocris Bioscience 3666
      Reverse Transcriptase TargetMol T1649
      Reverse transcriptase inhibitor Tocris Bioscience 3666
      RNA/DNA Polymerase Tocris Bioscience 3666
      Selectively inhibits HIV reverse transcriptase (RNA-dependent DNA polymerase). Prevents cytotoxicity in SIV-infected C-8166 cells in vitro (IC50 = 1.5 ?M). Antiviral agent. Tocris Bioscience 3666
      Selectively inhibits HIV reverse transcriptase (RNA-dependent DNA polymerase). Prevents cytotoxicity in SIV-infected C-8166 cells in vitro (IC50 = 1.5 muM). Antiviral agent. Tocris Bioscience 3666
      Tenofovir(GS 1278, PMPA) is an antiretroviral drug known as nucleotide analogue reverse transcriptase inhibitors (NRTIs), which block reverse transcriptase, a crucial virus enzyme in HIV-1 and HBV.; IC50 Value:0.5-2.2 uM (HIV-1); 1.6-4.9 uM (HIV-2) [1]; Target: NRTIs; in vitro: Tenofovir hydrate reduces the viral cytopathic effect of HIV-1(IIIB), HIV-2(ROD) and HIV(EHO) with EC50 of 1.15 ?g/mL, 1.12 ?g/mL and 1.05 ?g/mL in MT-4 cells. MedChem Express HY-13910

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

Density: 1.8±0.1 g/cm3
Boiling Point: 616.1±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 96.1±3.0 kJ/mol
Flash Point: 326.4±34.3 °C
Index of Refraction: 1.740
Molar Refractivity: 64.6±0.5 cm3
#H bond acceptors: 9
#H bond donors: 4
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: -1.71
ACD/LogD (pH 5.5): -4.32
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -5.05
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 146 Å2
Polarizability: 25.6±0.5 10-24cm3
Surface Tension: 90.3±7.0 dyne/cm
Molar Volume: 160.2±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) =  -1.57

 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):  6.06E-011  (Modified Grain method)
    Subcooled liquid VP: 2.58E-010 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):  1.55e+004
       log Kow used: -1.57 (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-acid
       Imidazoles-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.11E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.478E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.57  (KowWin est)
  Log Kaw used:  -21.680  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.110
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0297
   Biowin2 (Non-Linear Model)     :   0.0016
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4208  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3152  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2335
   Biowin6 (MITI Non-Linear Model):   0.0023
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0833
 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):  3.44E-008 Pa (2.58E-010 mm Hg)
  Log Koa (Koawin est  ): 20.110
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  87.2 
       Octanol/air (Koa) model:  3.16E+007 
   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 = 221.8493 E-12 cm3/molecule-sec
      Half-Life =     0.048 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.579 Hrs
   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: -1.57 (estimated)

 Volatilization from Water:
    Henry LC:  5.11E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.942E+020  hours   (8.091E+018 days)
    Half-Life from Model Lake : 2.118E+021  hours   (8.826E+019 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       2.41e-013       1.16         1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 973 hr




                    

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