ChemSpider 2D Image | Mycophenolate mofetil | C23H31NO7

Mycophenolate mofetil

  • Molecular FormulaC23H31NO7
  • Average mass433.495 Da
  • Monoisotopic mass433.210052 Da
  • ChemSpider ID4444535

  • Double-bond stereo - Double-bond stereo

More details:

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

(4E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid 2-(4-morpholinyl)ethyl ester
(4E)-6-(4-hydroxy-6-méthoxy-7-méthyl-3-oxo-1,3-dihydro-2-benzofur-5-yl)-4-méthylhex-4-énoate de 2-morpholin-4-yléthyle
(4E)-6-(4-Hydroxy-6-méthoxy-7-méthyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-méthyl-4-hexénoate de 2-(4-morpholinyl)éthyle [French] [ACD/IUPAC Name]
(E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid 2-(4-Morpholinyl)ethyl Ester
128794-94-5 [RN]
2-(4-Morpholinyl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoate [ACD/IUPAC Name]
2-(4-Morpholinyl)ethyl-(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoat [German] [ACD/IUPAC Name]
2-(Morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
2-(Morpholin-4-yl)ethyl-(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofur-5-yl)-4-methylhex-4-enoat
2-morpholin-4-ylethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

9242ECW6R0 [DBID]
RS 61443 [DBID]
AIDS059828 [DBID]
AIDS-059828 [DBID]
C07908 [DBID]
D00752 [DBID]
NSC724229 [DBID]
R-99 [DBID]
RS-61443 [DBID]
UNII:9242ECW6R0 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      Dehydrogenase inhibitor TargetMol T0245

    • Chemical Class:

      A carboxylic ester resulting from the formal condensation between the carboxylic acid group of mycophenolic acid and the hydroxy group of 2-(morpholin-4-yl)ethanol. In the liver, it is metabolised to mycophenolic acid, an immunosuppressant for which it is a prodrug. It is widely used to prevent tissue rejection following organ transplants as well as for the treatment of certain autoimmune diseases . ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8764, CHEBI:8764

    • Bio Activity:

      Dehydrogenases Tocris Bioscience 4102
      Enzymes Tocris Bioscience 4102
      Immunosuppressant prodrug of mycophenolic acid (MPA) (Cat. No. 1505). Hydrolyzed by esterases to release MPA (a reversible inhibitor of inosine monophosphate dehydrogenase). Used to prevent organ reje ction after transplantation. Displays inhibitory activity of lymphocyte functions. Inhibits type 1 collagen expression, enhances MMP-1 expression, and reduces ?-smooth muscle actin gene expression. Tocris Bioscience 4102
      Immunosuppressant prodrug of mycophenolic acid (MPA) (Cat. No. 1505). Hydrolyzed by esterases to release MPA (a reversible inhibitor of inosine monophosphate dehydrogenase). Used to prevent organ rejection after transplantation. Displays inhibitory activity of lymphocyte functions. Inhibits type 1 collagen expression, enhances MMP-1 expression, and reduces ?-smooth muscle actin gene expression. Tocris Bioscience 4102
      Immunosuppressant prodrug of mycophenolic acid (MPA) (Cat. No. 1505). Hydrolyzed by esterases to release MPA (a reversible inhibitor of inosine monophosphate dehydrogenase). Used to prevent organ rejection after transplantation. Displays inhibitory activity of lymphocyte functions. Inhibits type 1 collagen expression, enhances MMP-1 expression, and reduces alpha-smooth muscle actin gene expression. Tocris Bioscience 4102
      IMPDH TargetMol T0245
      Inosine monophosphate dehydrogenase inhibitor Tocris Bioscience 4102
      Metabolism TargetMol T0245
      Mycophenolate Mofetil(RS 61443) is a non-competitive, selective and reversible inhibitor of inosine monophosphate dehydrogenase I/II with IC50 of 39 nM and 27 nM, respectively. MedChem Express
      Mycophenolate Mofetil(RS 61443) is a non-competitive, selective and reversible inhibitor of inosine monophosphate dehydrogenase I/II with IC50 of 39 nM and 27 nM, respectively.; IC50 value: 39 nM/27 nM (IMPDH1/2); Target: Inosine monophosphate dehydrogenase (IMPDH); Mycophenolate mofetil is an ester prodrug of the active immunosuppressant mycophenolic acid (MPA). MedChem Express HY-B0199
      Other Dehydrogenases Tocris Bioscience 4102
      Others MedChem Express HY-B0199

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

Density: 1.2±0.1 g/cm3
Boiling Point: 637.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 97.6±3.0 kJ/mol
Flash Point: 339.4±31.5 °C
Index of Refraction: 1.557
Molar Refractivity: 114.2±0.3 cm3
#H bond acceptors: 8
#H bond donors: 1
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 0
ACD/LogP: 3.15
ACD/LogD (pH 5.5): 2.99
ACD/BCF (pH 5.5): 78.22
ACD/KOC (pH 5.5): 527.05
ACD/LogD (pH 7.4): 3.59
ACD/BCF (pH 7.4): 309.60
ACD/KOC (pH 7.4): 2086.01
Polar Surface Area: 95 Å2
Polarizability: 45.3±0.5 10-24cm3
Surface Tension: 48.5±3.0 dyne/cm
Molar Volume: 354.6±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) =  3.81

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  568.29  (Adapted Stein & Brown method)
    Melting Pt (deg C):  244.50  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.89E-013  (Modified Grain method)
    Subcooled liquid VP: 4.54E-011 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):  40.63
       log Kow used: 3.81 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  37.019 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Esters
       Phenols
       Salicylates

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.52E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.653E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.81  (KowWin est)
  Log Kaw used:  -12.647  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.457
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6940
   Biowin2 (Non-Linear Model)     :   0.9752
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1067  (months      )
   Biowin4 (Primary Survey Model) :   3.3622  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4997
   Biowin6 (MITI Non-Linear Model):   0.1911
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0032
 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):  6.05E-009 Pa (4.54E-011 mm Hg)
  Log Koa (Koawin est  ): 16.457
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  496 
       Octanol/air (Koa) model:  7.03E+003 
   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 = 444.8781 E-12 cm3/molecule-sec
      Half-Life =     0.024 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    17.311 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): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4546
      Log Koc:  3.658 

 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 = 2.236 (BCF = 172.2)
       log Kow used: 3.81 (estimated)

 Volatilization from Water:
    Henry LC:  5.52E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.208E+011  hours   (9.202E+009 days)
    Half-Life from Model Lake : 2.409E+012  hours   (1.004E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              22.20  percent
    Total biodegradation:        0.26  percent
    Total sludge adsorption:    21.94  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       0.000764        0.303        1000       
   Water     9.17            1.44e+003    1000       
   Soil      89.1            2.88e+003    1000       
   Sediment  1.72            1.3e+004     0          
     Persistence Time: 2.71e+003 hr

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