ChemSpider 2D Image | ilomastat | C20H28N4O4

ilomastat

  • Molecular FormulaC20H28N4O4
  • Average mass388.461 Da
  • Monoisotopic mass388.211060 Da
  • ChemSpider ID117009
  • defined stereocentres - 2 of 2 defined stereocentres


More details:






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

(2R)-N4-Hydroxy-N1-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxo-2-propanyl]-2-isobutylsuccinamid [German] [ACD/IUPAC Name]
(2R)-N4-Hydroxy-N1-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxo-2-propanyl]-2-isobutylsuccinamide [ACD/IUPAC Name]
(2R)-N4-Hydroxy-N1-[(2S)-3-(1H-indol-3-yl)-1-(méthylamino)-1-oxo-2-propanyl]-2-isobutylsuccinamide [French] [ACD/IUPAC Name]
(2R)-N4-Hydroxy-N1-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-isobutylsuccinamide
(2R)-N4-(hydroxy)-N1-((1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)butanediamide
(S-(R*,S*))-N4-Hydroxy-N{1}-(1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)butanediamide
142880-36-2 [RN]
7383
Butanediamide, N4-hydroxy-N1-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)-, (2R)- [ACD/Index Name]
I0403ML141
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CS 610 [DBID]
Bio1_000169 [DBID]
Bio1_000658 [DBID]
Bio1_001147 [DBID]
Bio2_000370 [DBID]
Bio2_000850 [DBID]
CBiol_001883 [DBID]
CCRIS 4693 [DBID]
CS-610 [DBID]
D03793 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      MMP inhibitor TargetMol T2743
    • Chemical Class:

      An <element>N</element>-acyl-amino acid obtained by formal condensation of the carboxy group of (2<stereo>R</stereo>)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the amino group of <el ement>N</element>-methyl-<stereo>L</stereo>-tryptophanamide. A cell permeable broad-spectrum matrix metalloproteinase (MMP) inhibitor ChEBI CHEBI:137236
    • Bio Activity:

      Broad spectrum MMP inhibitor Tocris Bioscience 2983
      Broad spectrum MMP inhibitor. Reduces infarct volume following middle cerebral artery occlusion in an ischemic mouse model. Also inhibits human skin fibroblast collagenase (Ki = 0.4 nM). Tocris Bioscience 2983
      Enzymes Tocris Bioscience 2983
      GM6001 (galardin, ilomastat) is a broad spectrum MMPs inhibitor for MMP-1, MMP-2, MMP-3, MMP-7, MMP-8, MMP-9, MMP-12, MMP-14, and MMP-26 with Ki of 0.4-27 nM. MedChem Express
      GM6001 (galardin, ilomastat) is a broad spectrum MMPs inhibitor for MMP-1, MMP-2, MMP-3, MMP-7, MMP-8, MMP-9, MMP-12, MMP-14, and MMP-26 with Ki of 0.4-27 nM.; IC50 Value: 0.4-27 nM (Ki) [1]; Target: MMPs; in vitro: GM6001 (galardin, ilomastat) is a broad spectrum matrix metalloprotease (MMP) inhibitor for MMP-1, MMP-2, MMP-3, MMP-7, MMP-8, MMP-9, MMP-12, MMP-14, and MMP-26 with Ki of 0.4 nM, 0.5 nM, 27 nM, 3.7 nM, 0.1 nM, 0.2 nM, 3.6 nM, 13.4 nM, 0.36 nM, respectively. MedChem Express HY-15768
      GM6001 (galardin, ilomastat) is a broad spectrum MMPs inhibitor for MMP-1, MMP-2, MMP-3, MMP-7, MMP-8, MMP-9, MMP-12, MMP-14, and MMP-26 with Ki of 0.4-27 nM.;IC50 Value: 0.4-27 nM (Ki) [1];Target: MMPs;In vitro: GM6001 (galardin, ilomastat) is a broad spectrum matrix metalloprotease (MMP) inhibitor for MMP-1, MMP-2, MMP-3, MMP-7, MMP-8, MMP-9, MMP-12, MMP-14, and MMP-26 with Ki of 0.4 nM, 0.5 nM, 27 nM, 3.7 nM, 0.1 nM, 0.2 nM, 3.6 nM, 13.4 nM, 0.36 nM, respectively. GM 6001 is one of the most potent inhibitors of human skin fibroblast collagenase yet reported. GM 6001 has a Ki of 20 nM against thermolysin and Pseudomonas aeruginosa elastase. Isomer 6B has a Ki of 7 nM against thermolysin and 2 nM against the elastase [1]. Addition of galardin to cells stimulated with bombesin or LPA specifically inhibited total EGFR phosphorylation, as well as site-specific phosphorylation of tyrosine 845, a putative Src phosphorylation site, and tyrosine 1068, a typical autophosphorylation site. MedChem Express HY-15768
      Matrix Metalloprotease Tocris Bioscience 2983
      Metabolism/Protease MedChem Express HY-15768
      Metabolism/Protease; MedChem Express HY-15768
      MMP MedChem Express HY-15768
      MMP-8/9/26/1 TargetMol T2743
      Proteases Tocris Bioscience 2983
      Proteases/Proteasome TargetMol T2743

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

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.590
Molar Refractivity: 106.7±0.3 cm3
#H bond acceptors: 8
#H bond donors: 5
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 1
ACD/LogP: 0.83
ACD/LogD (pH 5.5): 0.92
ACD/BCF (pH 5.5): 2.93
ACD/KOC (pH 5.5): 75.12
ACD/LogD (pH 7.4): 0.91
ACD/BCF (pH 7.4): 2.88
ACD/KOC (pH 7.4): 73.81
Polar Surface Area: 123 Å2
Polarizability: 42.3±0.5 10-24cm3
Surface Tension: 53.0±3.0 dyne/cm
Molar Volume: 316.2±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) =  0.85

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  728.24  (Adapted Stein & Brown method)
    Melting Pt (deg C):  319.22  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.52E-021  (Modified Grain method)
    Subcooled liquid VP: 1.14E-017 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):  675.5
       log Kow used: 0.85 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  85093 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.72E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.177E-024 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.85  (KowWin est)
  Log Kaw used:  -21.631  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.481
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0376
   Biowin2 (Non-Linear Model)     :   0.9693
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1574  (months      )
   Biowin4 (Primary Survey Model) :   3.6296  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2569
   Biowin6 (MITI Non-Linear Model):   0.0029
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5829
 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):  1.52E-015 Pa (1.14E-017 mm Hg)
  Log Koa (Koawin est  ): 22.481
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.97E+009 
       Octanol/air (Koa) model:  7.43E+009 
   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 = 244.9505 E-12 cm3/molecule-sec
      Half-Life =     0.044 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.524 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    :  7.094E+005
      Log Koc:  5.851 

 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: 0.85 (estimated)

 Volatilization from Water:
    Henry LC:  5.72E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.017E+020  hours   (8.406E+018 days)
    Half-Life from Model Lake : 2.201E+021  hours   (9.17E+019 days)

 Removal In Wastewater Treatment:
    Total removal:               1.87  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.78  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       1.25e-005       1.05         1000       
   Water     44.9            1.44e+003    1000       
   Soil      55              2.88e+003    1000       
   Sediment  0.0934          1.3e+004     0          
     Persistence Time: 1.25e+003 hr




                    

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