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-Hydroxy tamoxifen
(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]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

95K54647BZ [DBID]
CHEBI:44616 [DBID]
68047-06-3; 68392-35-8 [DBID]
BRN 4910749 [DBID]
C05011 [DBID]
H6278_SIGMA [DBID]
H7904_SIGMA [DBID]
ICI 79280 [DBID]
MLS000069742 [DBID]
nchembio775-comp3 [DBID]
More...
  • References
  • Experimental Physico-chemical Properties

    • Experimental Solubility:

      Soluble in DMSO (100 mM) and in ethanol (50 mM) Hello Bio HB6040, HB2508
      Soluble to 100 mM in DMSO and to 50 mM in ethanol Tocris Bioscience 3412
      Soluble to 50 mM in ethanol Tocris Bioscience 3412
  • Miscellaneous

    • Toxicity:

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

    • 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
      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 tamox ifen. ChEBI CHEBI:44616

    • Bio Activity:

      <p>Cell permeable, synthetic estrogen receptor ligand. Active metabolite of tamoxifen. Widely used for inducible genome manipulation. ?70% Z isomer (remainder primarily E-isomer).</p> <p> </p> <p><span style="text-decoration: underline;">Cre-LoxP / CreER system</span>:</p> <p>De facto standard for use in the inducible Cre-LoxP system for manipulation of CreER/CreERT2 recombinase for genome/ genetic manipulation (e.g. gene deletion). 4-OHT allows external temporal control of Cre activity <em>in vivo</em>.</p> <p> </p> <p><span style="text-decoration: underline;">TRAP / TRAP2</span></p> <p>Used as part of the TRAP/TRAP2 systems (targeted recombination in active populations) (e.g. FosTRAP, ArcTRAP) to provide genetic access to neurons.</p><p> </p><p><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 ‘iCas’ Cas9 variant which shows high editing efficiency at multiple loci once bound with 4-OHT.</p> <p> </p> <p><span style="text-decoration: underline;">Cancer:</span></p> <p>Chemotherapeutic agent. Induces apoptosis through an ER-dependent mechanism and inhibits proliferation of multiple myeloma cells <em>in vitro</em>.</p> <p> </p> <p>Pure <a title="Pure Z-4-hydroxytamoxifen | Hello Bio" href="/z-4-hydroxytamoxifen.html" target="_self">(Z)-4-hydroxytamoxifen</a> (100% isomer) also available.</p> Hello Bio HB6040, HB2508
      <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 [HB6095] , HB6040, HB2508
      <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>May also be used for TRAPing / in the TRAP / TRAP2 system (Targeted recombination in active populations).</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 HB6040, HB2508
      <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 [HB6095] , HB6040, HB2508
      <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 [HB6095] , HB6040, HB2508
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB6095] , HB6040, HB2508
      Cell process/DNA / RNA & protein synthesis/Genome editing / engineering Hello Bio [HB6095] , HB6040, HB2508
      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 [HB6095] , HB6040, HB2508
      Synthetic estrogen receptor ligand. Widely used in genome engineering (e.g. CreER/ CRISPR-Cas9). Hello Bio [HB6095] , HB6040, HB2508

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

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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