ChemSpider 2D Image | Acitretin | C21H26O3

Acitretin

  • Molecular FormulaC21H26O3
  • Average mass326.429 Da
  • Monoisotopic mass326.188202 Da
  • ChemSpider ID4447573
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(methyloxy)phenyl]nona-2,4,6,8-tetraenoic acid
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid [ACD/IUPAC Name]
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraensäure [German] [ACD/IUPAC Name]
(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraensäure [German]
2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (2E,4E,6E,8E)- [ACD/Index Name]
2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (all-E)-
259-474-4 [EINECS]
5530
Acetretinate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

DRG 0218 [DBID]
44707_FLUKA [DBID]
CCRIS 4693 [DBID]
CCRIS 5534 [DBID]
D02754 [DBID]
DRG-0218 [DBID]
HSDB 7187 [DBID]
PubChem Substance ID 329768124 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      GREENISH-YELLOW CRYSTALLINE POWDER NIH Clinical Collection [SMR000499573]
    • Safety:

      D05BB02 Wikidata Q341500
    • Target Organs:

      RXR/RAR inhibitor TargetMol T1330
    • Bio Activity:

      Acitretin(Ro 10-1670) is a second-generation, systemic retinoid that has been used in the treatment of psoriasis. MedChem Express
      Acitretin(Ro 10-1670) is a second-generation, systemic retinoid that has been used in the treatment of psoriasis.; Target: RAR/RXR; Acitretin is a second-generation, systemic retinoid that has been approved for the treatment of psoriasis since 1997. MedChem Express HY-B0107
      Acitretin(Ro 10-1670) is a second-generation, systemic retinoid that has been used in the treatment of psoriasis.;Target: RAR/RXRAcitretin is a second-generation, systemic retinoid that has been approved for the treatment of psoriasis since 1997. It can be considered one of the treatments of choice for pustular and erythrodermic psoriasis. However, the efficacy of acitretin as a monotherapy for plaque psoriasis is less, although it is often used in combination therapy with other systemic psoriasis therapies, especially ultraviolet B or psoralen plus ultraviolet A phototherapy, to increase efficacy. Such combination treatments may potentially minimise toxicity by using lower doses of each of the two agent [1].;Thirty-nine male adult Wistar albino rats were divided into 3 groups as two experimental groups and one control group. The first group consisting 14 rats were applied orally standard dose (0.75 mg/kg/day) acitretin and the second group consisting 16 rats were applied high dos MedChem Express HY-B0107
      Metabolism TargetMol T1330
      Others MedChem Express HY-B0107
      RAR, RXR TargetMol T1330
      RAR/RXR MedChem Express HY-B0107
      Used for treatment of psoriasis, antineoplastic agent ; Zerenex Molecular [ZBioX-0002]
  • Gas Chromatography

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

Density: 1.1±0.1 g/cm3
Boiling Point: 521.3±38.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 83.6±3.0 kJ/mol
Flash Point: 180.3±20.3 °C
Index of Refraction: 1.570
Molar Refractivity: 101.8±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 5.73
ACD/LogD (pH 5.5): 4.51
ACD/BCF (pH 5.5): 982.46
ACD/KOC (pH 5.5): 2769.54
ACD/LogD (pH 7.4): 2.71
ACD/BCF (pH 7.4): 15.59
ACD/KOC (pH 7.4): 43.96
Polar Surface Area: 47 Å2
Polarizability: 40.3±0.5 10-24cm3
Surface Tension: 38.7±3.0 dyne/cm
Molar Volume: 310.4±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) =  7.19
    Log Kow (Exper. database match) =  6.40
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  451.39  (Adapted Stein & Brown method)
    Melting Pt (deg C):  172.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3E-009  (Modified Grain method)
    MP  (exp database):  228-230 deg C
    Subcooled liquid VP: 4.54E-007 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):  0.0729
       log Kow used: 6.40 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.03512 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 :   5.08E-009  atm-m3/mole
   Group Method:   1.28E-010  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.768E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.40  (exp database)
  Log Kaw used:  -6.683  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.083
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9607
   Biowin2 (Non-Linear Model)     :   0.9524
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5597  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6339  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2883
   Biowin6 (MITI Non-Linear Model):   0.0403
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6897
 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):  6.05E-005 Pa (4.54E-007 mm Hg)
  Log Koa (Koawin est  ): 13.083
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0496 
       Octanol/air (Koa) model:  2.97 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.642 
       Mackay model           :  0.799 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 388.9586 E-12 cm3/molecule-sec
      Half-Life =     0.027 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    19.799 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    68.445000 E-17 cm3/molecule-sec
      Half-Life =     0.017 Days (at 7E11 mol/cm3)
      Half-Life =     24.110 Min
   Fraction sorbed to airborne particulates (phi): 0.72 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.638E+004
      Log Koc:  4.214 

 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 = 1.750 (BCF = 56.23)
       log Kow used: 6.40 (expkow database)

 Volatilization from Water:
    Henry LC:  1.28E-010 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 8.264E+006  hours   (3.443E+005 days)
    Half-Life from Model Lake : 9.016E+007  hours   (3.757E+006 days)

 Removal In Wastewater Treatment:
    Total removal:              93.28  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    92.51  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       0.00236         0.25         1000       
   Water     2.62            900          1000       
   Soil      37              1.8e+003     1000       
   Sediment  60.4            8.1e+003     0          
     Persistence Time: 3.14e+003 hr




                    

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