ChemSpider 2D Image | Vorinostat | C14H20N2O3

Vorinostat

  • Molecular FormulaC14H20N2O3
  • Average mass264.320 Da
  • Monoisotopic mass264.147400 Da
  • ChemSpider ID5120

More details:

Featured data source
The Merck Index Online

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

149647-78-9 [RN]
58IFB293JI
M344
MFCD00945317 [MDL number]
N1-hydroxy-N8-phenyl-octanediamide
N-Hydroxy-N'-phenyloctandiamid [German] [ACD/IUPAC Name]
N-hydroxy-N'-phenyl-octanediamide
N-Hydroxy-N'-phenyloctanediamide [ACD/IUPAC Name]
N-Hydroxy-N'-phényloctanediamide [French] [ACD/IUPAC Name]
Octanediamide, N1-hydroxy-N8-phenyl- [ACD/Index Name]
More...

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

8661 [DBID]
CCRIS 8456 [DBID]
MK-0683 [DBID]
nchembio815-comp18 [DBID]
SW-064652 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      L01XX38 Wikidata Q905901

    • Target Organs:

      HDAC inhibitor TargetMol T1583

    • Chemical Class:

      A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cut aneous T cell lymphoma (CTCL). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45716, CHEBI:45716

    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB1396]
      Cell Cycle/DNA Damage MedChem Express HY-10221
      Cell Cycle/DNA Damage; MedChem Express HY-10221
      Chromatin/Epigenetic TargetMol T1583
      Class I and II HDAC inhibitor Tocris Bioscience 4652
      Class I and II histone deacetylase (HDAC) inhibitor (IC<sub>50</sub> values are 10 and 20 nM for HDAC1 and HDAC3 respectively). Reduces pro-inflammatory cytokine production. Shows anti-inflammatory, anti-retroviral, growth inhibitory and anti-cancer actions. Hello Bio [HB1396]
      Deacetylases Tocris Bioscience 4652
      Enzymes Tocris Bioscience 4652
      Enzymes/Deacetylase/Histone deacetylase (HDAC) Hello Bio [HB1396]
      HDAC MedChem Express HY-10221
      HDAC inhibitor Hello Bio [HB1396]
      HDAC1, HDAC2, HDAC3, HDAC6, HDAC8 TargetMol T1583
      Histone Deacetylases Tocris Bioscience 4652
      Inhibits Class I and II histone deacetylases (HDACs); induces accumulation of acetylated histones H2A, H2B, H3 and H4 in transformed cultured cells. Suppresses cell growth in a range of cancer cell li nes; induces apoptosis in cutaneous T cell lymphoma cells in vitro. Tocris Bioscience 4652
      Inhibits Class I and II histone deacetylases (HDACs); induces accumulation of acetylated histones H2A, H2B, H3 and H4 in transformed cultured cells. Suppresses cell growth in a range of cancer cell lines; induces apoptosis in cutaneous T cell lymphoma cells in vitro. Tocris Bioscience 4652
      Inhibits Class I and II histone deacetylases (HDACs); induces accumulation of acetylated histones H2A, H2B, H3 and H4 in transformed cultured cells. Suppresses cell growth in a range of cancer cell lines; induces apoptosis in cutaneous T cell lymphoma cells in vitro. Activates autophagy. Tocris Bioscience 4652
      Vorinostat (SAHA) is an HDAC1/3 inhibitor with IC50 of ~10 nM. MedChem Express
      Vorinostat (SAHA) is an HDAC1/3 inhibitor with IC50 of ~10 nM.; IC50 Value: ~10 nM; Target: HDACs; in vitro: Vorinostat inhibits the activities of HDAC1 and HDAC3 with IC50 of 10 nM and 20 nM, respectively. MedChem Express HY-10221

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

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.567
Molar Refractivity: 73.5±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 0.86
ACD/LogD (pH 5.5): 1.20
ACD/BCF (pH 5.5): 4.80
ACD/KOC (pH 5.5): 106.99
ACD/LogD (pH 7.4): 1.20
ACD/BCF (pH 7.4): 4.76
ACD/KOC (pH 7.4): 106.12
Polar Surface Area: 78 Å2
Polarizability: 29.1±0.5 10-24cm3
Surface Tension: 50.4±3.0 dyne/cm
Molar Volume: 225.0±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) =  1.44

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  523.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  223.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.6E-013  (Modified Grain method)
    Subcooled liquid VP: 3.48E-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):  1167
       log Kow used: 1.44 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3166 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.23E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.749E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.44  (KowWin est)
  Log Kaw used:  -12.299  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.739
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9599
   Biowin2 (Non-Linear Model)     :   0.9769
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5828  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6767  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3900
   Biowin6 (MITI Non-Linear Model):   0.2608
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1652
 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):  4.64E-009 Pa (3.48E-011 mm Hg)
  Log Koa (Koawin est  ): 13.739
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  647 
       Octanol/air (Koa) model:  13.5 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  31.4266 E-12 cm3/molecule-sec
      Half-Life =     0.340 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.084 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    :  1337
      Log Koc:  3.126 

 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 = 0.406 (BCF = 2.547)
       log Kow used: 1.44 (estimated)

 Volatilization from Water:
    Henry LC:  1.23E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.739E+010  hours   (3.225E+009 days)
    Half-Life from Model Lake : 8.442E+011  hours   (3.518E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.96  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.86  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       0.0053          8.17         1000       
   Water     34.1            900          1000       
   Soil      65.8            1.8e+003     1000       
   Sediment  0.0835          8.1e+003     0          
     Persistence Time: 1.16e+003 hr

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