ChemSpider 2D Image | Adapalene | C28H28O3

Adapalene

  • Molecular FormulaC28H28O3
  • Average mass412.520 Da
  • Monoisotopic mass412.203857 Da
  • ChemSpider ID54244

More details:

Featured data source
The Merck Index Online

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

106685-40-9 [RN]
2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)- [ACD/Index Name]
6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid
6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)naphthalen-2-carbonsäure [German]
6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)naphthalene-2-carboxylic acid
6-[3-(Adamantan-1-yl)-4-methoxyphenyl]-2-naphthoesäure [German] [ACD/IUPAC Name]
6-[3-(Adamantan-1-yl)-4-methoxyphenyl]-2-naphthoic acid [ACD/IUPAC Name]
6-[4-methoxy-3-(tricyclo[3.3.1.13,7]dec-1-yl)phenyl]naphthalene-2-carboxylic acid
acide 6-(4-méthoxy-3-tricyclo[3.3.1.13,7]déc-1-ylphényl)naphtalène-2-carboxylique [French]
Acide 6-[3-(adamantan-1-yl)-4-méthoxyphényl]-2-naphtoïque [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CD 271 [DBID]
D01112 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Ether; Ester; Drug; Dermatologic Agent; Anti-Inflammatory Agent, Non-Steroidal; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D4673

    • Target Organs:

      RXR/RAR agonist TargetMol T1093

    • Chemical Class:

      A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31174, CHEBI:31174

    • Bio Activity:

      Metabolism TargetMol T1093
      Nuclear Receptors Tocris Bioscience 2852
      RAR? and RAR? agonist Tocris Bioscience 2852
      Retinoic acid analog that is a RAR? and RAR? agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RAR?, RAR?, RAR? and RXR? receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cell in vitro. Displays comedolytic activity. Tocris Bioscience 2852
      Retinoic acid analog that is a RAR? and RAR? agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RAR?, RAR?, RAR? and RXR? receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cell in vitro. Displays comedolytic activity. Tocris Bioscience 2852
      Retinoic Acid Receptors Tocris Bioscience 2852
      RXR, RAR TargetMol T1093

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

Density: 1.2±0.1 g/cm3
Boiling Point: 606.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 94.8±3.0 kJ/mol
Flash Point: 205.9±25.0 °C
Index of Refraction: 1.655
Molar Refractivity: 122.6±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: 8.04
ACD/LogD (pH 5.5): 5.93
ACD/BCF (pH 5.5): 9348.75
ACD/KOC (pH 5.5): 10406.30
ACD/LogD (pH 7.4): 4.36
ACD/BCF (pH 7.4): 251.15
ACD/KOC (pH 7.4): 279.56
Polar Surface Area: 47 Å2
Polarizability: 48.6±0.5 10-24cm3
Surface Tension: 55.0±3.0 dyne/cm
Molar Volume: 334.3±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) =  8.51

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  575.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  247.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.24E-012  (Modified Grain method)
    Subcooled liquid VP: 3.25E-010 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):  0.0001384
       log Kow used: 8.51 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7.0436e-006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.82E-011  atm-m3/mole
   Group Method:   9.30E-012  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  4.863E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  8.51  (KowWin est)
  Log Kaw used:  -8.624  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.134
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6760
   Biowin2 (Non-Linear Model)     :   0.5245
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1052  (months      )
   Biowin4 (Primary Survey Model) :   3.1840  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3547
   Biowin6 (MITI Non-Linear Model):   0.0437
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5947
 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):  4.33E-008 Pa (3.25E-010 mm Hg)
  Log Koa (Koawin est  ): 17.134
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  69.2 
       Octanol/air (Koa) model:  3.34E+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 =  46.7358 E-12 cm3/molecule-sec
      Half-Life =     0.229 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.746 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    :  1.654E+006
      Log Koc:  6.219 

 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 = 1.000 (BCF = 10)
       log Kow used: 8.51 (estimated)

 Volatilization from Water:
    Henry LC:  9.3E-012 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 1.279E+008  hours   (5.328E+006 days)
    Half-Life from Model Lake : 1.395E+009  hours   (5.812E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              94.03  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.25  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       0.0281          5.49         1000       
   Water     1.29            1.44e+003    1000       
   Soil      35.4            2.88e+003    1000       
   Sediment  63.3            1.3e+004     0          
     Persistence Time: 5.29e+003 hr

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