ChemSpider 2D Image | Fenretinide | C26H33NO2

Fenretinide

  • Molecular FormulaC26H33NO2
  • Average mass391.546 Da
  • Monoisotopic mass391.251129 Da
  • ChemSpider ID4450416
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

15-[(4-Hydroxyphenyl)amino]retinal [ACD/IUPAC Name]
15-[(4-Hydroxyphenyl)amino]retinal [German] [ACD/IUPAC Name]
15-[(4-Hydroxyphényl)amino]rétinal [French] [ACD/IUPAC Name]
4-Hydroxyphenyl retinamide
fenretinida
Fenretinide [Wiki]
fenretinidum
Retinal, 15-[(4-hydroxyphenyl)amino]- [ACD/Index Name]
(2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenamide
(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:42588 [DBID]
AIDS210898 [DBID]
AIDS-210898 [DBID]
Bio1_000134 [DBID]
Bio1_000623 [DBID]
Bio1_001112 [DBID]
Bio2_000139 [DBID]
Bio2_000619 [DBID]
BRN 5769490 [DBID]
CBiol_001848 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      332 312 302 319 335 315 360FD LKT Labs [H9613]
      60;61;20/21/22;36/37/38 LKT Labs [H9613]
      Xn Xi Repr LKT Labs [H9613]
    • Target Organs:

      RXR/RAR agonist TargetMol T1872
    • Therapeutical Effect:

      antineoplastic Microsource [01505602]
    • Drug Status:

      USAN, INN Microsource [01505602]
    • Compound Source:

      synthetic; MCN-R-1967 Microsource [01505602]
    • Bio Activity:

      Fenretinide (4-HPR) is a synthetic retinoid deriverative. MedChem Express http://www.medchemexpress.com/Ketone-Ester.html, HY-15373
      Fenretinide (4-HPR) is a synthetic retinoid deriverative. 4-HBR is shown to exhibit binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death.;IC50 value: ;Target: RARRetinoids are substances related to vitamin A. It has been investigated for potential use in the treatment of cancer, as well as in the treatment of cystic fibrosis, rheumatoid arthritis, acne, psoriasis, and has been found to also slow the production and accumulation of a toxin that leads to vision loss in Stargardt's patients. MedChem Express HY-15373
      Metabolism TargetMol T1872
      Nuclear Receptors Tocris Bioscience 1396
      Others MedChem Express HY-15373
      RAR/RAX TargetMol T1872
      RAR/RXR MedChem Express HY-15373
      Retinoic Acid Receptors Tocris Bioscience 1396
      Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids. Tocris Bioscience 1396
      Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids. Tocris Bioscience 1396
      Synthetic retinoid; antiproliferative and antioxidant Tocris Bioscience 1396
  • Gas Chromatography

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

Density: 1.1±0.1 g/cm3
Boiling Point: 597.6±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 92.3±3.0 kJ/mol
Flash Point: 315.2±27.9 °C
Index of Refraction: 1.607
Molar Refractivity: 125.1±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 7.41
ACD/LogD (pH 5.5): 6.49
ACD/BCF (pH 5.5): 50109.84
ACD/KOC (pH 5.5): 80496.50
ACD/LogD (pH 7.4): 6.49
ACD/BCF (pH 7.4): 49967.88
ACD/KOC (pH 7.4): 80268.45
Polar Surface Area: 49 Å2
Polarizability: 49.6±0.5 10-24cm3
Surface Tension: 46.2±3.0 dyne/cm
Molar Volume: 361.9±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) =  8.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  556.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  238.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.85E-013  (Modified Grain method)
    Subcooled liquid VP: 9.91E-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):  0.000475
       log Kow used: 8.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.19341 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols
       Acrylamides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.11E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.261E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  8.03  (KowWin est)
  Log Kaw used:  -9.343  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.373
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7032
   Biowin2 (Non-Linear Model)     :   0.3374
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1239  (months      )
   Biowin4 (Primary Survey Model) :   3.3745  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0630
   Biowin6 (MITI Non-Linear Model):   0.0039
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5661
 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):  1.32E-008 Pa (9.91E-011 mm Hg)
  Log Koa (Koawin est  ): 17.373
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  227 
       Octanol/air (Koa) model:  5.79E+004 
   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 = 346.7584 E-12 cm3/molecule-sec
      Half-Life =     0.031 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.209 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    24.180000 E-17 cm3/molecule-sec
      Half-Life =     0.047 Days (at 7E11 mol/cm3)
      Half-Life =      1.137 Hrs
   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    :  9.92E+005
      Log Koc:  5.997 

 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 = 3.393 (BCF = 2469)
       log Kow used: 8.03 (estimated)

 Volatilization from Water:
    Henry LC:  1.11E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.044E+008  hours   (4.349E+006 days)
    Half-Life from Model Lake : 1.139E+009  hours   (4.744E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              94.02  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.24  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       0.00442         0.448        1000       
   Water     1.4             1.44e+003    1000       
   Soil      30.2            2.88e+003    1000       
   Sediment  68.4            1.3e+004     0          
     Persistence Time: 4.71e+003 hr




                    

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