ChemSpider 2D Image | Ubenimex | C16H24N2O4

Ubenimex

  • Molecular FormulaC16H24N2O4
  • Average mass308.373 Da
  • Monoisotopic mass308.173615 Da
  • ChemSpider ID65145

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

Featured data source
Natural Product Updates

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

([2S,3R]-3-Amino-2-hydroxy-4-phenylbutanoyl)-L-leucine
(2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid
[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine
[S-(R*,S*)]-N-(3-Amino-2-hydroxy-1-oxo-4-phenylbutyl)-L-leucine
Bestatin [Trade name]
I0J33N5627
L-Leucine, N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]- [ACD/Index Name]
MFCD00083262 [MDL number]
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucin [German] [ACD/IUPAC Name]
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine [ACD/IUPAC Name]
More...

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

5940 [DBID]
NK-421 [DBID]
482609_ALDRICH [DBID]
AIDS002934 [DBID]
AIDS-002934 [DBID]
Bio2_000273 [DBID]
Bio2_000753 [DBID]
BRN 4704312 [DBID]
KBio2_000273 [DBID]
KBio2_002841 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Aminopeptidase MedChem Express HY-B0134
      Aminopeptidase inhibitor Tocris Bioscience 1956
      Aminopeptidase inhibitor (Ki = 0.001 - 90 mM); inhibits enkephalin metabolism and leukotriene A4 hydrolase. Inhibits tumor cell proliferation. Tocris Bioscience 1956
      Aminopeptidases Tocris Bioscience 1956
      Bestatin (Ubenimex) is a competitive aminopeptidase inhibitor, which is studied for use in the treatment of acute myelocytic leukemia. MedChem Express
      Bestatin (Ubenimex) is a competitive aminopeptidase inhibitor, which is studied for use in the treatment of acute myelocytic leukemia.; Target: aminopeptidase; Bestatin, also known as Ubenimex (INN), is a competitive protease inhibitor. MedChem Express HY-B0134
      Bestatin (Ubenimex) is a competitive aminopeptidase inhibitor, which is studied for use in the treatment of acute myelocytic leukemia.;Target: aminopeptidaseBestatin, also known as Ubenimex (INN), is a competitive protease inhibitor. It is an inhibitor of aminopeptidase B, leukotriene A4 hydrolase, aminopeptidase N. It is being studied for use in the treatment of acute myelocytic leukemia.Bestatin can be administered, with low toxicity, to cultured cells, intact animals and humans. It has become a useful tool in elucidating the physiological role of some mammalian exopeptidases in the regulation of the immune system, in the growth of tumors and their invasion of surrounding tissues, and in the degradation of cellular proteins. MedChem Express HY-B0134
      Enzymes Tocris Bioscience 1956
      Metabolism/Protease MedChem Express HY-B0134
      Metabolism/Protease; MedChem Express HY-B0134
      Proteases Tocris Bioscience 1956

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

Density: 1.2±0.1 g/cm3
Boiling Point: 604.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 94.5±3.0 kJ/mol
Flash Point: 319.5±31.5 °C
Index of Refraction: 1.557
Molar Refractivity: 83.0±0.3 cm3
#H bond acceptors: 6
#H bond donors: 5
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 1
ACD/LogP: 2.64
ACD/LogD (pH 5.5): -0.86
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.07
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 113 Å2
Polarizability: 32.9±0.5 10-24cm3
Surface Tension: 52.2±3.0 dyne/cm
Molar Volume: 257.6±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) =  0.18

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  545.63  (Adapted Stein & Brown method)
    Melting Pt (deg C):  313.61  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.06E-014  (Modified Grain method)
    MP  (exp database):  234.5 deg C
    Subcooled liquid VP: 7.36E-012 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):  377.5
       log Kow used: 0.18 (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-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.58E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.364E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.18  (KowWin est)
  Log Kaw used:  -14.977  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.157
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3789
   Biowin2 (Non-Linear Model)     :   0.9986
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9597  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1029  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1299
   Biowin6 (MITI Non-Linear Model):   0.0435
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4123
 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):  9.81E-010 Pa (7.36E-012 mm Hg)
  Log Koa (Koawin est  ): 15.157
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.06E+003 
       Octanol/air (Koa) model:  352 
   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 = 137.4365 E-12 cm3/molecule-sec
      Half-Life =     0.078 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.934 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    :  59.42
      Log Koc:  1.774 

 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: 0.18 (estimated)

 Volatilization from Water:
    Henry LC:  2.58E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.985E+013  hours   (1.66E+012 days)
    Half-Life from Model Lake : 4.347E+014  hours   (1.811E+013 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       1.87e-005       1.87         1000       
   Water     38.2            360          1000       
   Soil      61.7            720          1000       
   Sediment  0.0709          3.24e+003    0          
     Persistence Time: 584 hr

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