ChemSpider 2D Image | (Z)-Afimoxifene | C26H29NO2

(Z)-Afimoxifene

  • Molecular FormulaC26H29NO2
  • Average mass387.514 Da
  • Monoisotopic mass387.219818 Da
  • ChemSpider ID395987
  • Double-bond stereo - Double-bond stereo


More details:






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

(Z)-Afimoxifene
Hydroxytamoxifen
(cis)-Afimoxifene
(Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol
(Z)-4-Hydroxytamoxifen
(Z)-4-OHT
4-[(1Z)-1-{4-[2-(Dimethylamino)ethoxy]phenyl}-2-phenyl-1-buten-1-yl]phenol [ACD/IUPAC Name]
4-[(1Z)-1-{4-[2-(Dimethylamino)ethoxy]phenyl}-2-phenyl-1-buten-1-yl]phenol [German] [ACD/IUPAC Name]
4-[(1Z)-1-{4-[2-(Diméthylamino)éthoxy]phényl}-2-phényl-1-butén-1-yl]phénol [French] [ACD/IUPAC Name]
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

95K54647BZ [DBID]
CHEBI:44616 [DBID]
BRN 4910749 [DBID]
C05011 [DBID]
H6278_SIGMA [DBID]
H7904_SIGMA [DBID]
ICI 79280 [DBID]
MLS000069742 [DBID]
nchembio775-comp3 [DBID]
SMR000058939 [DBID]
More...
  • References
    • Fema No:

      -4 Hello Bio [HB2508] , [HB6040] , [HB6095]
      4 Hello Bio [HB2508] , [HB6040] , [HB6095] , [HB2508] , [HB6040] , [HB6095]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Ether; Drug; Metabolite; Natural Compound Toxin, Toxin-Target Database T3D4937
    • Safety:

      IRRITANT Matrix Scientific 099612
    • Chemical Class:

      A tertiary amino compound that is tamoxifen in which the phenyl group which is in a <stereo>Z</stereo>- relationship to the ethyl substituent is hydroxylated at the <ital>para</ital>- position. It is the active metabolite of tamoxifen. ChEBI CHEBI:44616
      A tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is ; the active metabolite of tam oxifen. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44616
    • Bio Activity:

      <p>Cell permeable, synthetic estrogen receptor ligand. Widely used in genome engineering. (E) and (Z) isomer mix (50:50).<br /><span style=text-decoration: underline;></span></p> <p></p> <p><br /><span style=text-decoration: underline;>CreER system</span>:</p> <p>De facto standard compound in drug-inducible manipulation of CreER recombinase. Allows external temporal control of Cre activity <em> in vivo </em>.<br /><span style=text-decoration: underline;></span></p> <p></p> <p><br /><span style=text-decoration: underline;>CRISPR/Cas9 gene editing</span>:</p> <p>Activates an inactived Cas9 nuclease (rendered inactive by insertion of a 4-OHT dependent-intein) to reduce off-target CRISPR-mediated gene editing (once bound with 4-OHT, conditionally active Cas9s modify target genomic sites with ~25-fold higher specificity than wild-type Cas9). <br /><br />Also allows tight, repeated on-off control of the nuclease activity of the &lsquo;iCas&rsquo; Cas9 variant which shows high editing efficiency at multiple loci once bound with 4-OHT.</p> <p></p> <p><br />Pure <a href=/z-4-hydroxytamoxifen.html title=Pure Z-4-hydroxytamoxifen | Hello Bio target=_self>(Z)-4-hydroxytamoxifen</a> also available.</p> <p>&ge;70% Z isomer (remainder primarily E-isomer)&nbsp;<a href=/4-hydroxytamoxifen.html title=4-Hydroxytamoxifen (70:30 mix) | Hello Bio target=_self>4-Hydroxytamoxifen</a> also available.</p> Hello Bio [HB2508] , [HB6040] , [HB6095]
      <p>Cell permeable, synthetic estrogen receptor ligand. Widely used in genome engineering. <br /><span style=text-decoration: underline;></span></p> <p></p> <p><span style=text-decoration: underline;><br />CreER system</span>:</p> <p>De facto standard compound in drug-inducible manipulation of CreER recombinase. Allows external temporal control of Cre activity <em> in vivo</em>.<br /><span style=text-decoration: underline;></span></p> <p></p> <p><br /><span style=text-decoration: underline;>CRISPR/Cas9 gene editing</span>:</p> <p>Activates an inactived Cas9 nuclease (rendered inactive by insertion of a 4-OHT dependent-intein) to reduce off-target CRISPR-mediated gene editing (once bound with 4-OHT, conditionally active Cas9s modify target genomic sites with ~25-fold higher specificity than wild-type Cas9). <br /><br />Also allows tight, repeated on-off control of the nuclease activity of the &lsquo;iCas&rsquo; Cas9 variant which shows high editing efficiency at multiple loci once bound with 4-OHT.</p> <p></p> <p><br /><a title=70:30 4-hydroxytamoxifen | Hello Bio href=4-hydroxytamoxifen.html target=_self>4-Hydroxytamoxifen</a> (70:30 mixture of (Z):(E) isomers) also available.</p> Hello Bio [HB2508] , [HB6040] , [HB6095]
      <p>Cell permeable, synthetic estrogen receptor ligand. Widely used in genome engineering.&nbsp;&ge;70% Z isomer (remainder primarily E-isomer).<br /><span style=text-decoration: underline;></span></p> <p></p> <p><br /><span style=text-decoration: underline;>CreER system</span>:</p> <p>De facto standard compound in drug-inducible manipulation of CreER recombinase. Allows external temporal control of Cre activity <em> in vivo </em>.<br /><span style=text-decoration: underline;></span></p> <p></p> <p><br /><span style=text-decoration: underline;>CRISPR/Cas9 gene editing</span>:</p> <p>Activates an inactived Cas9 nuclease (rendered inactive by insertion of a 4-OHT dependent-intein) to reduce off-target CRISPR-mediated gene editing (once bound with 4-OHT, conditionally active Cas9s modify target genomic sites with ~25-fold higher specificity than wild-type Cas9). <br /><br />Also allows tight, repeated on-off control of the nuclease activity of the &lsquo;iCas&rsquo; Cas9 variant which shows high editing efficiency at multiple loci once bound with 4-OHT.</p> <p></p> <p><br />Pure <a href=/z-4-hydroxytamoxifen.html title=Pure Z-4-hydroxytamoxifen | Hello Bio target=_self>(Z)-4-hydroxytamoxifen</a> also available.</p> Hello Bio [HB2508] , [HB6040] , [HB6095]
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB2508] , [HB6040] , [HB6095]
      Cell process/DNA / RNA & protein synthesis/Genome editing / engineering Hello Bio [HB2508] , [HB6040] , [HB6095]
      Estrogen and Related Receptors Tocris Bioscience 3412
      Estrogen receptor antagonist. Tamoxifen (Cat. No. 0999) metabolite; exhibits greater potency than the parent compound. Chemotherapeutic agent. Tocris Bioscience 3412
      Estrogen receptor antagonist. Tamoxifen (Cat. No. 0999) metabolite; exhibits greater potency than the parent compound. Chemotherapeutic agent. Also activates intein-linked inactive Cas9, reducing off-target CRISPR-mediated gene editing. Tocris Bioscience 3412
      Estrogen receptor antagonist. Tamoxifen (Cat. No. 0999) metabolite; exhibits greater potency than the parent compound. Chemotherapeutic agent. Also activates intein-linked inactive Cas9, reducing off-target CRISPR-mediated gene editing; system has ~25-fold higher specificity than wtCas9. Tocris Bioscience 3412
      Metabolite of tamoxifen (Cat. No. 0999) Tocris Bioscience 3412
      Nuclear Receptors Tocris Bioscience 3412
      Receptors & Transporters/Nuclear hormone/Estrogen and related/Non-selective Hello Bio [HB2508] , [HB6040] , [HB6095]
      Synthetic estrogen receptor ligand. Widely used in genome engineering (e.g. CreER/ CRISPR-Cas9). Hello Bio [HB2508] , [HB6040] , [HB6095]

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

Density: 1.1±0.1 g/cm3
Boiling Point: 514.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 81.6±3.0 kJ/mol
Flash Point: 264.9±30.1 °C
Index of Refraction: 1.597
Molar Refractivity: 120.8±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 1
ACD/LogP: 7.34
ACD/LogD (pH 5.5): 3.60
ACD/BCF (pH 5.5): 67.24
ACD/KOC (pH 5.5): 110.48
ACD/LogD (pH 7.4): 5.14
ACD/BCF (pH 7.4): 2335.78
ACD/KOC (pH 7.4): 3838.15
Polar Surface Area: 33 Å2
Polarizability: 47.9±0.5 10-24cm3
Surface Tension: 43.9±3.0 dyne/cm
Molar Volume: 354.7±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) =  5.82

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  503.04  (Adapted Stein & Brown method)
    Melting Pt (deg C):  211.01  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.11E-011  (Modified Grain method)
    Subcooled liquid VP: 2.94E-009 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):  1.51
       log Kow used: 5.82 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.72919 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.67E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.050E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.82  (KowWin est)
  Log Kaw used:  -11.719  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.539
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7336
   Biowin2 (Non-Linear Model)     :   0.5594
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1083  (months      )
   Biowin4 (Primary Survey Model) :   3.1223  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0098
   Biowin6 (MITI Non-Linear Model):   0.0083
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1632
 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):  3.92E-007 Pa (2.94E-009 mm Hg)
  Log Koa (Koawin est  ): 17.539
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.65 
       Octanol/air (Koa) model:  8.49E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.996 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 270.5636 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.463 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  1965.599854 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      0.840 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.242E+007
      Log Koc:  7.094 

 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 = 3.783 (BCF = 6070)
       log Kow used: 5.82 (estimated)

 Volatilization from Water:
    Henry LC:  4.67E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.468E+010  hours   (1.028E+009 days)
    Half-Life from Model Lake : 2.692E+011  hours   (1.122E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              91.21  percent
    Total biodegradation:        0.76  percent
    Total sludge adsorption:    90.45  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       4.24e-005       0.0138       1000       
   Water     3.07            1.44e+003    1000       
   Soil      50.6            2.88e+003    1000       
   Sediment  46.3            1.3e+004     0          
     Persistence Time: 4.49e+003 hr




                    

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