ChemSpider 2D Image | (+)-Staurosporine | C28H26N4O3

(+)-Staurosporine

  • Molecular FormulaC28H26N4O3
  • Average mass466.531 Da
  • Monoisotopic mass466.200500 Da
  • ChemSpider ID40272
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(+)-Staurosporine
(2S,3R,4R,6R)-3-Methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-on [German] [ACD/IUPAC Name]
(2S,3R,4R,6R)-3-Methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one [ACD/IUPAC Name]
(2S,3R,4R,6R)-3-Méthoxy-2-méthyl-4-(méthylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaén-16-one [French] [ACD/IUPAC Name]
6,10-Epoxy-6H,16H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-16-one, 7,8,9,10,17,18-hexahydro-7-methoxy-6-methyl-8-(methylamino)-, (6S,7R,8R,10R)- [ACD/Index Name]
62996-74-1 [RN]
AM-2282
Antibiotic 230
antibiotic am 2282
Staurosporin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS001539 [DBID]
AIDS-001539 [DBID]
Bio1_000264 [DBID]
Bio1_000753 [DBID]
Bio1_001242 [DBID]
CBiol_001978 [DBID]
CCRIS 3272 [DBID]
CGP 39360 [DBID]
CHEBI:15738 [DBID]
MolMap_000047 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Broad spectrum protein kinase inhibitor. Enzymes inhibited include protein kinase C (IC50 = 3 nM), protein kinase A (IC50 = 7 nM), p60v-src tyrosine protein kinase (IC50 = 6 nM) and CaM kinase II (IC5 0 = 20 nM). Tocris Bioscience 1285
      Non-selective protein kinase inhibitor Tocris Bioscience 1285
      PKC MedChem Express HY-15141
      Staurosporine is a prototypical potent ATP-competitive kinase inhibitor with IC50 of 0.7, 7, 8.5, 6, 20 nM for PKC, PKA,PKG, p60v-src tyrosine protein kinase, CaM kinase II, respectively. MedChem Express
      Staurosporine is a prototypical potent ATP-competitive kinase inhibitor with IC50 of 0.7, 7, 8.5, 6, 20 nM for PKC, PKA,PKG, p60v-src tyrosine protein kinase, CaM kinase II, respectively.; IC50 value:; Target: PKC; The main biological activity of staurosporine is the inhibition of protein kinases through the prevention of ATP binding to the kinase. MedChem Express HY-15141
      Staurosporine is a prototypical potent ATP-competitive kinase inhibitor with IC50 of 0.7, 7, 8.5, 6, 20 nM for PKC, PKA,PKG, p60v-src tyrosine protein kinase, CaM kinase II, respectively.;IC50 value:;Target: PKC;The main biological activity of staurosporine is the inhibition of protein kinases through the prevention of ATP binding to the kinase. This is achieved through the stronger affinity of staurosporine to the ATP-binding site on the kinase. Staurosporine is a prototypical ATP-competitive kinase inhibitor in that it binds to many kinases with high affinity, though with little selectivity. This lack of specificity has precluded its clinical use, but has made it a valuable research tool. In research, staurosporine is used to induce apoptosis. The mechanism of how it mediates this is not well understood. It has been found that one way in which staurosporine induces apoptosis is by activating caspase-3. MedChem Express HY-15141
      TGF-beta/Smad MedChem Express HY-15141
      TGF-beta/Smad; MedChem Express HY-15141

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

Density: 1.6±0.1 g/cm3
Boiling Point: 677.5±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 99.5±3.0 kJ/mol
Flash Point: 363.6±31.5 °C
Index of Refraction: 1.810
Molar Refractivity: 128.8±0.5 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 4.40
ACD/LogD (pH 5.5): 0.83
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.08
ACD/LogD (pH 7.4): 2.22
ACD/BCF (pH 7.4): 12.11
ACD/KOC (pH 7.4): 74.92
Polar Surface Area: 69 Å2
Polarizability: 51.1±0.5 10-24cm3
Surface Tension: 62.9±7.0 dyne/cm
Molar Volume: 298.7±7.0 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) =  5.24

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  681.64  (Adapted Stein & Brown method)
    Melting Pt (deg C):  297.44  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.75E-016  (Modified Grain method)
    Subcooled liquid VP: 5.17E-013 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):  0.00305
       log Kow used: 5.24 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.8308 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.44E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.560E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.24  (KowWin est)
  Log Kaw used:  -19.001  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  24.241
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3998
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.3993  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.6744  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5467
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -3.5641
 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):  6.89E-011 Pa (5.17E-013 mm Hg)
  Log Koa (Koawin est  ): 24.241
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.35E+004 
       Octanol/air (Koa) model:  4.28E+011 
   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 = 488.5445 E-12 cm3/molecule-sec
      Half-Life =     0.022 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    15.763 Min
   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    :  3.788E+004
      Log Koc:  4.578 

 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 = 3.334 (BCF = 2158)
       log Kow used: 5.24 (estimated)

 Volatilization from Water:
    Henry LC:  2.44E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.183E+017  hours   (2.16E+016 days)
    Half-Life from Model Lake : 5.654E+018  hours   (2.356E+017 days)

 Removal In Wastewater Treatment:
    Total removal:              83.98  percent
    Total biodegradation:        0.72  percent
    Total sludge adsorption:    83.26  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       1.25e-008       0.525        1000       
   Water     2.47            4.32e+003    1000       
   Soil      77.4            8.64e+003    1000       
   Sediment  20.1            3.89e+004    0          
     Persistence Time: 1.02e+004 hr




                    

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