ChemSpider 2D Image | Mycophenolic acid | C17H20O6

Mycophenolic acid

  • Molecular FormulaC17H20O6
  • Average mass320.337 Da
  • Monoisotopic mass320.125977 Da
  • ChemSpider ID393865
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofur-5-yl)-4-methylhex-4-ensäure [German]
(4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoic acid [ACD/IUPAC Name]
(4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexensäure [German] [ACD/IUPAC Name]
(4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4E)- [ACD/Index Name]
acide (4E)-6-(4-hydroxy-6-méthoxy-7-méthyl-3-oxo-1,3-dihydro-2-benzofur-5-yl)-4-méthylhex-4-énoïque [French]
Acide (4E)-6-(4-hydroxy-6-méthoxy-7-méthyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-méthyl-4-hexénoïque [French] [ACD/IUPAC Name]
Acide mycophenolique [French] [INN]
Acido micofenolico [Spanish] [INN]
Acidum mycophenolicum [Latin]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS007220 [DBID]
AIDS-007220 [DBID]
CCRIS 5565 [DBID]
DivK1c_000146 [DBID]
ERL-080 [DBID]
KBio1_000146 [DBID]
KBio2_002535 [DBID]
KBio2_005103 [DBID]
KBio2_007671 [DBID]
KBio3_001754 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Not Available Novochemy [NC-21821]
    • Safety:

      20/21/22 Novochemy [NC-21821]
      20/21/36/37/39 Novochemy [NC-21821]
      GHS07; GHS09 Novochemy [NC-21821]
      H332; H403 Novochemy [NC-21821]
      Harmful/Carcinogenic/Teratogenic SynQuest 2H25-1-1Q
      IRRITANT Matrix Scientific 090412
      P301+P310; P337+P313 Novochemy [NC-21821]
      R52/53 Novochemy [NC-21821]
      Warning Novochemy [NC-21821]
    • Target Organs:

      Dehydrogenase inhibitor TargetMol T1335
    • Chemical Class:

      benzofuran Microsource [01500674]
    • Compound Source:

      Penicillium brevicompactum and other Penicillium spp Microsource [01500674]
    • Bio Activity:

      Dehydrogenases Tocris Bioscience 1505
      Enzymes Tocris Bioscience 1505
      Immunosuppressive agent with antiviral and antitumor effects in vitro and in vivo. Potently inhibits inosine monophosphate dehydrogenase, thus inhibiting de novo GTP synthesis leading to decreased RNA and DNA synthesis. Reversibly inhibits proliferation of T and B lymphocytes and antibody formation. Tocris Bioscience 1505
      Immunosuppressive agent with antiviral and antitumor effects in vitro and in vivo. Potently inhibits inosine monophosphate dehydrogenase, thus inhibiting de novo GTP synthesis leading to decreased RNA and DNA synthesis. Reversibly inhibits proliferation of T and B lymphocytes and antibody formation. Tocris Bioscience 1505
      Inosine monophosphatase dehydrogenase inhibitor Tocris Bioscience 1505
      Metabolism TargetMol T1335
      Mycophenolic acid is an an immunosuppresant drug and has potent anti-proliferative activity. MedChem Express
      Mycophenolic acid is an an immunosuppresant drug and has potent anti-proliferative activity.; Target: Others; Mycophenolic acid(MPA) is an immunosuppressant drug used to prevent rejection in organ transplantation. MedChem Express HY-B0421
      Mycophenolic acid is an an immunosuppresant drug and has potent anti-proliferative activity.;Target: Mycophenolic acid(MPA) is an immunosuppressant drug used to prevent rejection in organ transplantation. It inhibits an enzyme needed for the growth of T cells and B cells. MPA did not block the initial phase of viral translation but did interfere with viral protein synthesis in the amplification phase. Quantitative RT-PCR demonstrated that MPA prevented the accumulation of viral positive- and negative-strand RNA as the infection proceeded. MPA inhibits flavivirus infection by preventing synthesis and accumulation of viral RNA [1]. The effects of mycophenolic acid (MPA) on DEN replication in monkey kidney (LLC-MK2) cells were examined. MPA (IC(50)=0.4+/-0.3 microM) inhibited DEN2 replication. Quantitative real-time RT-PCR of viral RNA and plaque assays of virions from DEN2-infected and MPA (10 microM) -treated cells showed a fivefold increase in defective viral RNA production b MedChem Express HY-B0421
      Other Dehydrogenases Tocris Bioscience 1505
      Others MedChem Express HY-B0421
      UGT;DH TargetMol T1335

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

Density: 1.3±0.1 g/cm3
Boiling Point: 611.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 95.5±3.0 kJ/mol
Flash Point: 225.8±25.0 °C
Index of Refraction: 1.585
Molar Refractivity: 83.1±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 2.92
ACD/LogD (pH 5.5): 2.57
ACD/BCF (pH 5.5): 32.56
ACD/KOC (pH 5.5): 238.88
ACD/LogD (pH 7.4): 0.76
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.77
Polar Surface Area: 93 Å2
Polarizability: 32.9±0.5 10-24cm3
Surface Tension: 54.7±3.0 dyne/cm
Molar Volume: 248.2±3.0 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) =  4.22

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  506.50  (Adapted Stein & Brown method)
    Melting Pt (deg C):  215.63  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.59E-010  (Modified Grain method)
    MP  (exp database):  141 deg C
    Subcooled liquid VP: 2.36E-009 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):  22.07
       log Kow used: 4.22 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  15.869 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters-acid
       Phenols-acid
       Salicylates-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.82E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.037E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.22  (KowWin est)
  Log Kaw used:  -9.806  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.026
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1990
   Biowin2 (Non-Linear Model)     :   0.9994
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8446  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9798  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5794
   Biowin6 (MITI Non-Linear Model):   0.4143
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7719
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  3.15E-007 Pa (2.36E-009 mm Hg)
  Log Koa (Koawin est  ): 14.026
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.53 
       Octanol/air (Koa) model:  26.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 292.5624 E-12 cm3/molecule-sec
      Half-Life =     0.037 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    26.323 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  496.4
      Log Koc:  2.696 

 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: 4.22 (estimated)

 Volatilization from Water:
    Henry LC:  3.82E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.743E+008  hours   (1.143E+007 days)
    Half-Life from Model Lake : 2.993E+009  hours   (1.247E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              40.99  percent
    Total biodegradation:        0.41  percent
    Total sludge adsorption:    40.58  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       0.00426         0.37         1000       
   Water     16.3            360          1000       
   Soil      80.4            720          1000       
   Sediment  3.35            3.24e+003    0          
     Persistence Time: 748 hr




                    

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