ChemSpider 2D Image | Tretinoin | C20H28O2

Tretinoin

  • Molecular FormulaC20H28O2
  • Average mass300.435 Da
  • Monoisotopic mass300.208923 Da
  • ChemSpider ID392618
  • Double-bond stereo - Double-bond stereo


More details:






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

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraensäure [German]
15-Apo-b-caroten-15-oic acid
206-129-0 [EINECS]
302-79-4 [RN]
5688UTC01R
Acid A Vit
acide (2E,4E,6E,8E)-3,7-diméthyl-9-(2,6,6-triméthylcyclohex-1-én-1-yl)nona-2,4,6,8-tétraénoïque [French]
all trans-Retinoic acid
All-Trans Retinoic Acid
More...

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

2875 [Beilstein] [DBID]
CHEBI:15367 [DBID]
DRG 0147 [DBID]
MFCD00001551 [DBID]
AGN 100335 [DBID]
AGN 192013 [DBID]
AIDS000179 [DBID]
AIDS-000179 [DBID]
ALRT 1057 [DBID]
Bio1_000106 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      yellow to orange crystalline powder OU Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable, but probably air and light sensitive. Combustible. Incompatiblewith strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details
    • Safety:

      22-63 Alfa Aesar 44540
      36/37 Alfa Aesar 44540
      CAUTION: May irritate eyes, skin, and respiratory tract Alfa Aesar 44540
      D10AD01 Wikidata Q29417
      H361-H302 Alfa Aesar 44540
      L01XX14 Wikidata Q29417
      Minimize exposure. OU Chemical Safety Data (No longer updated) More details
      P281-P264-P301+P312-P308+P313-P405-P501a Alfa Aesar 44540
      Warning Alfa Aesar 44540
      WARNING: Irritates skin and eyes, harmful if swallowed Alfa Aesar 44540
    • Target Organs:

      RXR/RAR agonist TargetMol T1051
    • Chemical Class:

      A retinoic acid in which all four exocyclic double bonds have <stereo>E</stereo>- (<stereo>trans</stereo>-) geometry. ChEBI CHEBI:15367
      A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15367, CHEBI:15367
    • Bio Activity:

      All-trans retinoic acid (ATRA; Vitamin A acid) has been widely investigated for treatments of many cancers including prostate cancer.; IC50 Value:; Target: RAR; in vitro: ATRA was able to induce the growth arrest and to increase HOXB13 expression in AR?prostate cancer cells. MedChem Express HY-14649
      Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RAR?, RAR? and RAR? receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of ROR? (Kd = 280 nM). Tocris Bioscience 695
      Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RAR?, RAR? and RAR? receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of ROR? (Kd = 280 nM). Tocris Bioscience 0695
      Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RARalpha, RARbeta and RARgamma receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of RORbeta (Kd = 280 nM). Activates autophagy. Tocris Bioscience 695
      Endogenous retinoic acid receptor agonist Tocris Bioscience 0695, 695
      Metabolism TargetMol T1051
      Nuclear Receptors Tocris Bioscience 695
      Others MedChem Express HY-14649
      Retinoic Acid Receptors Tocris Bioscience 695
      RXR, RAR TargetMol T1051
  • Gas Chromatography

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

Density: 1.0±0.1 g/cm3
Boiling Point: 462.8±14.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 79.3±6.0 kJ/mol
Flash Point: 350.6±11.0 °C
Index of Refraction: 1.556
Molar Refractivity: 95.5±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 6.83
ACD/LogD (pH 5.5): 5.06
ACD/BCF (pH 5.5): 2580.25
ACD/KOC (pH 5.5): 5560.61
ACD/LogD (pH 7.4): 3.26
ACD/BCF (pH 7.4): 41.02
ACD/KOC (pH 7.4): 88.40
Polar Surface Area: 37 Å2
Polarizability: 37.9±0.5 10-24cm3
Surface Tension: 39.1±3.0 dyne/cm
Molar Volume: 297.2±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) =  7.85
    Log Kow (Exper. database match) =  6.30
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  411.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  147.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.02E-007  (Modified Grain method)
    MP  (exp database):  181 deg C
    Subcooled liquid VP: 4.29E-006 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):  0.1263
       log Kow used: 6.30 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.23409 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 :   9.50E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.193E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.30  (exp database)
  Log Kaw used:  -3.411  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.711
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4933
   Biowin2 (Non-Linear Model)     :   0.0880
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6877  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6464  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1655
   Biowin6 (MITI Non-Linear Model):   0.0257
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5104
 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):  0.000572 Pa (4.29E-006 mm Hg)
  Log Koa (Koawin est  ): 9.711
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00524 
       Octanol/air (Koa) model:  0.00126 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.159 
       Mackay model           :  0.296 
       Octanol/air (Koa) model:  0.0917 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 292.5375 E-12 cm3/molecule-sec
      Half-Life =     0.037 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    26.325 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
   Fraction sorbed to airborne particulates (phi): 0.227 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9987
      Log Koc:  3.999 

 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: 6.30 (expkow database)

 Volatilization from Water:
    Henry LC:  9.5E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      108.6  hours   (4.525 days)
    Half-Life from Model Lake :       1330  hours   (55.42 days)

 Removal In Wastewater Treatment:
    Total removal:              93.09  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    92.31  percent
    Total to Air:                0.01  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0088          0.495        1000       
   Water     3.08            900          1000       
   Soil      32.3            1.8e+003     1000       
   Sediment  64.6            8.1e+003     0          
     Persistence Time: 2.7e+003 hr




                    

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