ChemSpider 2D Image | DAPT | C23H26F2N2O4

DAPT

  • Molecular FormulaC23H26F2N2O4
  • Average mass432.460 Da
  • Monoisotopic mass432.186066 Da
  • ChemSpider ID4470783

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(2S)-({N-[2-(3,5-Difluorophényl)acétyl]-L-alanyl}amino)(phényl)acétate de 2-méthyl-2-propanyle [French] [ACD/IUPAC Name]
208255-80-5 [RN]
2-Methyl-2-propanyl (2S)-({N-[(3,5-difluorophenyl)acetyl]-L-alanyl}amino)(phenyl)acetate [ACD/IUPAC Name]
2-Methyl-2-propanyl-(2S)-({N-[(3,5-difluorphenyl)acetyl]-L-alanyl}amino)(phenyl)acetat [German] [ACD/IUPAC Name]
Benzeneacetic acid, α-[[(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]-1-oxopropyl]amino]-, 1,1-dimethylethyl ester, (αS)- [ACD/Index Name]
DAPT
γ-Secretase inhibitor IX
tert-butyl (2S)-({N-[(3,5-difluorophenyl)acetyl]-L-alanyl}amino)(phenyl)ethanoate
tert-butyl (2S)-2-[(2S)-2-[2-(3,5-difluorophenyl)acetamido]propanamido]-2-phenylacetate
(S)-{(S)-2-[2-(3,5-Difluoro-phenyl)-acetylamino]-propionylamino}-phenyl-acetic acid tert-butyl ester
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A dipeptide consisting of alanylphenylglycine derivatised as a 3,5-difluorophenylacetamide at the amino terminal and a <ital>tert</ital>-butyl ester at the carboxy terminal. A <greek>gamma</greek>-sec retase inhibitor. ChEBI CHEBI:86193
      A dipeptide consisting of alanylphenylglycine derivatised as a 3,5-difluorophenylacetamide at the amino terminal and a tert-butyl ester at the carboxy terminal. A gamma-sec; retase inhibitor. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:86193
      A dipeptide consisting of alanylphenylglycine derivatised as a 3,5-difluorophenylacetamide at the amino terminal and a tert-butyl ester at the carboxy terminal. A gamma-secretase inhibitor. ChEBI CHEBI:86193

    • Bio Activity:

      &gamma;-secretase inhibitor. Classical notch inhibitor. Induces neuronal differentiation Hello Bio HB3345
      ?-secretase MedChem Express HY-13027
      ?-secretase inhibitor Tocris Bioscience 2634
      <p><span style="text-decoration: underline;">Overview</span></p> <p><span style="text-decoration: underline;"></span>DAPT is a &gamma;-secretase inhibitor which blocks notch signaling. It is a classical notch inhibitor.</p> <p>It has been reported to inhibit amyloid beta (A&beta;) in a dose-dependent manner although at low doses, an increase in A&beta; production in cell culture and animal models has also been reported.<span style="text-decoration: underline;"></span></p> <p>&nbsp;</p> <p><span style="text-decoration: underline;">Uses &amp; applications</span></p> <p style="margin-bottom: 2em;">DAPT is used in a variety of stem cell applications.</p> <p style="margin-bottom: 2em;">It has been shown that in combination with other small molecules that inhibit SMAD (SB 431542, LDN193189), activate WNT (CHIR99021) and inhibit FGF-signaling (SU5402), DAPT yields 75% post-mitotic neurons in 11 days of differentiation. These are defined as peripheral sensory neurons.</p> <p style="margin-bottom: 2em;">Recently, DAPT in combination with LDN193189, SB431542, XAV939, PD0325901 and SU5402 has been shown to accelerate induction of early-born cortical neurons that have mature electrophysiological properties by day 16 of differentiation.</p> <p>DAPT also enhances neuronal differentiation in ESC-derived embryoid bodies independent of Hh-signaling.</p> <p>Additionally, the compound promotes cardiac differentiation of murine pluripotent stem cells and enhances the reprogramming of mouse fibroblasts to iCLMs (induced cardiac-like myocytes).</p> <p>It is also used as a 3D Growth matrix component and used in cerebral organoid differentiation media.</p> <p>&nbsp;</p> Hello Bio HB3345
      <p><span style=text-decoration: underline;>Overview</span></p> <p><span style=text-decoration: underline;></span>DAPT is a &gamma;-secretase inhibitor which blocks notch signaling. It is a classical notch inhibitor.</p> <p>It has been reported to inhibit amyloid beta (A&beta;) in a dose-dependent manner although at low doses, an increase in A&beta; production in cell culture and animal models has also been reported.<span style=text-decoration: underline;></span></p> <p>&nbsp;</p> <p><span style=text-decoration: underline;>Uses &amp; applications</span></p> <p style=margin-bottom: 2em;>DAPT is used in a variety of stem cell applications.</p> <p style=margin-bottom: 2em;>It has been shown that in combination with other small molecules that inhibit SMAD (SB 431542, LDN193189), activate WNT (CHIR99021) and inhibit FGF-signaling (SU5402), DAPT yields 75% post-mitotic neurons in 11 days of differentiation. These are defined as peripheral sensory neurons.</p> <p style=margin-bottom: 2em;>Recently, DAPT in combination with LDN193189, SB431542, XAV939, PD0325901 and SU5402 has been shown to accelerate induction of early-born cortical neurons that have mature electrophysiological properties by day 16 of differentiation.</p> <p>DAPT also enhances neuronal differentiation in ESC-derived embryoid bodies independent of Hh-signaling.</p> <p>Additionally, the compound promotes cardiac differentiation of murine pluripotent stem cells and enhances the reprogramming of mouse fibroblasts to iCLMs (induced cardiac-like myocytes).</p> <p>&nbsp;</p> Hello Bio HB3345
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB3345
      Cell process/Stem cells/Differentiation Hello Bio HB3345
      DAPT(GSI-IX) is an inhibitor of ?-secretase; DAPT causes a reduction in A?40 and A?42 levels in human primary neuronal cultures (IC50 values are 115 and 200 nM for total A? and A?42 respectively) and in brain extract, cerebrospinal fluid and plasma in vivo. MedChem Express HY-13027
      Enzymes Tocris Bioscience 2634
      Enzymes/Protease / Peptidase/Secretase/&gamma; Hello Bio HB3345
      Gamma-Secretase Tocris Bioscience 2634
      gamma-secretase inhibitor Tocris Bioscience 2634
      Inhibitor of ?-secretase; causes a reduction in A?40 and A?42 levels in human primary neuronal cultures (IC50 values are 115 and 200 nM for total A? and A?42 respectively) and in brain extract, cerebr ospinal fluid and plasma in vivo. Does not affect APP? and APP? levels. Blocks Notch signaling in hybrid human-mouse fetal thymus organ culture (FTOC). Activity causes ESCs to commit to neuronal diffe rentiation. Tocris Bioscience 2634
      Inhibitor of ?-secretase; causes a reduction in A?40 and A?42 levels in human primary neuronal cultures (IC50 values are 115 and 200 nM for total A? and A?42 respectively) and in brain extract, cerebrospinal fluid and plasma in vivo. Does not affect APP? and APP? levels. Blocks Notch signaling in hybrid human-mouse fetal thymus organ culture (FTOC). Activity causes ESCs to commit to neuronal differentiation. Tocris Bioscience 2634
      Inhibitor of gamma-secretase; causes a reduction in Abeta40 and Abeta42 levels in human primary neuronal cultures (IC50 values are 115 and 200 nM for total Abeta and Abeta42 respectively) and in brain extract, cerebrospinal fluid and plasma in vivo. Does not affect APPalpha and APPbeta levels. Blocks Notch signaling in hybrid human-mouse fetal thymus organ culture (FTOC). Activity causes ESCs to commit to neuronal differentiation. Tocris Bioscience 2634
      Neuronal Signaling MedChem Express HY-13027
      Neuronal Signaling; MedChem Express HY-13027
      Proteases Tocris Bioscience 2634

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

Density: 1.2±0.1 g/cm3
Boiling Point: 612.2±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 90.9±3.0 kJ/mol
Flash Point: 324.1±31.5 °C
Index of Refraction: 1.535
Molar Refractivity: 110.9±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 0
ACD/LogP: 3.98
ACD/LogD (pH 5.5): 3.44
ACD/BCF (pH 5.5): 243.64
ACD/KOC (pH 5.5): 1778.46
ACD/LogD (pH 7.4): 3.44
ACD/BCF (pH 7.4): 243.64
ACD/KOC (pH 7.4): 1778.45
Polar Surface Area: 85 Å2
Polarizability: 44.0±0.5 10-24cm3
Surface Tension: 42.5±3.0 dyne/cm
Molar Volume: 356.5±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) =  3.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  586.01  (Adapted Stein & Brown method)
    Melting Pt (deg C):  252.77  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.65E-013  (Modified Grain method)
    Subcooled liquid VP: 1.71E-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):  1.827
       log Kow used: 3.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  169.66 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.39E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.760E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.54  (KowWin est)
  Log Kaw used:  -10.858  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.398
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.4850
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.1964  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.6734  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0762
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5801
 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):  2.28E-008 Pa (1.71E-010 mm Hg)
  Log Koa (Koawin est  ): 14.398
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  132 
       Octanol/air (Koa) model:  61.4 
   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 =  33.3921 E-12 cm3/molecule-sec
      Half-Life =     0.320 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.844 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    :  1.326E+005
      Log Koc:  5.122 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.433E-003  L/mol-sec
  Kb Half-Life at pH 8:       6.397  years  
  Kb Half-Life at pH 7:      63.972  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.025 (BCF = 105.8)
       log Kow used: 3.54 (estimated)

 Volatilization from Water:
    Henry LC:  3.39E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.592E+009  hours   (1.497E+008 days)
    Half-Life from Model Lake : 3.918E+010  hours   (1.633E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              13.97  percent
    Total biodegradation:        0.19  percent
    Total sludge adsorption:    13.78  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       0.00488         7.69         1000       
   Water     4.89            4.32e+003    1000       
   Soil      94.5            8.64e+003    1000       
   Sediment  0.595           3.89e+004    0          
     Persistence Time: 7.27e+003 hr

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