ChemSpider 2D Image | Marimastat | C15H29N3O5

Marimastat

  • Molecular FormulaC15H29N3O5
  • Average mass331.408 Da
  • Monoisotopic mass331.210724 Da
  • ChemSpider ID106358

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(2S,3R)-N'-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-N,2-dihydroxy-3-(2-methylpropyl)butanediamide
(2S,3R)-N4-[(2S)-3,3-Dimethyl-1-(methylamino)-1-oxo-2-butanyl]-N1,2-dihydroxy-3-isobutylsuccinamid [German] [ACD/IUPAC Name]
(2S,3R)-N4-[(2S)-3,3-Dimethyl-1-(methylamino)-1-oxo-2-butanyl]-N1,2-dihydroxy-3-isobutylsuccinamide [ACD/IUPAC Name]
(2S,3R)-N4-[(2S)-3,3-Diméthyl-1-(méthylamino)-1-oxo-2-butanyl]-N1,2-dihydroxy-3-isobutylsuccinamide [French] [ACD/IUPAC Name]
(2S,3R)-N4-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide
(2S,3R)-N4-[(2S)-3,3-Dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N1,2-dihydroxy-3-isobutylsuccinamide
(2S,3R)-N4-((1S)-2,2-Dimethyl-1-((methylamino)carbonyl)propyl)-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide
154039-60-8 [RN]
BB2516, (2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl] propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide
Butanediamide, N4-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)-, (2S,3R)- [ACD/Index Name]
More...

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

7480 [DBID]
097 [DBID]
BB 2516 [DBID]
BB-2516 [DBID]
D03795 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A secondary carboxamide resulting from the foraml condensation of the carboxy group of (2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the alpha-amino group of N,3-dime thyl-L-valinamide. ChEBI CHEBI:50662
      A secondary carboxamide resulting from the foraml condensation of the carboxy group of (2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with; the alpha-amino group of N,3-di methyl-L-valinamide. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50662

    • Bio Activity:

      Broad spectrum inhibitor of MMPs (IC50 values are 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 respectively). Inhibits peritoneal dissemination of human gastric cancer cells in vivo through inhibition of tumor angiogenesis. Tocris Bioscience 2631
      Broad spectrum inhibitor of MMPs (IC50 values are 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 respectively). Inhibits peritoneal dissemination of human gastric cancer cells in vivo through inhibition of tumor angiogenesis. Tocris Bioscience 2631
      Broad spectrum MMP inhibitor Tocris Bioscience 2631
      Enzymes Tocris Bioscience 2631
      Marimastat(BB 2516; TA2516) is a broad spectrum inhibitor of MMPs (IC50 values are 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 respectively). MedChem Express http://www.medchemexpress.com/Marimastat.html, HY-12169
      Marimastat(BB 2516; TA2516) is a broad spectrum inhibitor of MMPs (IC50 values are 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 respectively). ;IC50 value: 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 [1];Target: MMPs inhibitor;In vitro: Marimastat early downregulated the expression of Notch target genes, such as Hes1 and Hes5. MMP-2 and MMP-9 profiling on proliferating and differentiating NPs [2].;In vivo: The marimastat was administered at a dose of 8.7 mg/kg/day over a 14-day period via a subcutaneous osmotic pump. The control group received vehicle only via a subcutaneous osmotic pump.Chemoradiation + marimastat therapy had delayed tumor growth, compared to the chemoradiation alone [3]. MedChem Express HY-12169
      Matrix Metalloprotease Tocris Bioscience 2631
      Metabolism/Protease MedChem Express HY-12169
      Metabolism/Protease; MedChem Express HY-12169
      MMP MedChem Express HY-12169
      Proteases Tocris Bioscience 2631

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

Density: 1.1±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.499
Molar Refractivity: 85.3±0.3 cm3
#H bond acceptors: 8
#H bond donors: 5
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 1
ACD/LogP: -0.16
ACD/LogD (pH 5.5): -0.21
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 18.22
ACD/LogD (pH 7.4): -0.22
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 18.09
Polar Surface Area: 128 Å2
Polarizability: 33.8±0.5 10-24cm3
Surface Tension: 43.5±3.0 dyne/cm
Molar Volume: 290.5±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) =  -1.09

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  617.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  267.36  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.12E-017  (Modified Grain method)
    Subcooled liquid VP: 9.72E-015 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):  3370
       log Kow used: -1.09 (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:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.57E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.743E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.09  (KowWin est)
  Log Kaw used:  -17.193  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.103
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9849
   Biowin2 (Non-Linear Model)     :   0.9561
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3062  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7565  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0574
   Biowin6 (MITI Non-Linear Model):   0.0237
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6160
 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):  1.3E-012 Pa (9.72E-015 mm Hg)
  Log Koa (Koawin est  ): 16.103
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.31E+006 
       Octanol/air (Koa) model:  3.11E+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 =  59.0785 E-12 cm3/molecule-sec
      Half-Life =     0.181 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.173 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    :  616.1
      Log Koc:  2.790 

 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: -1.09 (estimated)

 Volatilization from Water:
    Henry LC:  1.57E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.789E+015  hours   (2.829E+014 days)
    Half-Life from Model Lake : 7.406E+016  hours   (3.086E+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       0.000374        4.34         1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 973 hr

Click to predict properties on the Chemicalize site


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