ChemSpider 2D Image | Orantinib | C18H18N2O3

Orantinib

  • Molecular FormulaC18H18N2O3
  • Average mass310.347 Da
  • Monoisotopic mass310.131744 Da
  • ChemSpider ID4486261
  • Double-bond stereo - Double-bond stereo


More details:






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

(Z)-3-(2,4-dimethyl-5-((2-oxoindolin-3-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid
1H-Pyrrole-3-propanoic acid, 5-((1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-
1H-Pyrrole-3-propanoic acid, 5-[(Z)-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl- [ACD/Index Name]
210644-62-5 [RN]
252916-29-3 [RN]
3-(2,4-Dimethyl-5-((2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-1H-pyrrol-3-yl)propionic acid
3-(2,4-Dimethyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl)propionic acid
3-(2,4-dimethyl-5-{[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-1H-pyrrol-3-yl)propanoic acid
3-{2,4-Dimethyl-5-[(Z)-(2-oxo-1,2-dihydro-3H-indol-3-yliden)methyl]-1H-pyrrol-3-yl}propansäure [German] [ACD/IUPAC Name]
3-{2,4-Dimethyl-5-[(Z)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

9267 [DBID]
245036-27-5, 210644-62-5, 252916-29-3 [DBID]
NCI60_036760 [DBID]
NSC702827 [DBID]
PubChem Substance ID 329825761 [DBID]
SPP 100 | [DBID]
SU-6668 [DBID]
TSU 68 [DBID]
TSU-68 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is substituted by a 2-(2-carboxyethyl)-3,5-dimethylpyrrol-3-yl group. It is an ATP-competitive inhibitor of the tyrosine kinase activity of fibroblast growth factor receptor 1. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:91088, CHEBI:91088
    • Bio Activity:

      ATP-competitive PDGFR, VEGF and FGFR inhibitor (IC50 values are 0.06, 2.43, 3.04 and > 100 ?M at PDGFR?, VEGFR2, FGFR1 and EGFR respectively). Inhibits proliferation of HUVEC and NIH3T3 cells in vitro (IC50 values are 0.41, 9.3 and 16.5 ?M for VEGF, FGF and PDGF-stimulated growth respectively) and induces > 75% growth inhibition against a broad range of tumor types in vivo. Exhibits antiangiogenic, anti-inflammatory, antimetastatic and proapoptotic activity and is orally active. Tocris Bioscience 3335
      ATP-competitive PDGFR, VEGF and FGFR inhibitor (IC50 values are 0.06, 2.43, 3.04 and > 100 ?M at PDGFR?, VEGFR2, FGFR1 and EGFR respectively). Inhibits proliferation of HUVEC and NIH3T3 cells in vitro (IC50 values are 0.41, 9.3 and 16.5 ?M for VEGF, FGF and PDGF-stimulated growth respectively) and induces > 75% growth inhibition against a broad range of tumor types in vivo. Exhibits antiangiogenic , anti-inflammatory, antimetastatic and proapoptotic activity and is orally active. Tocris Bioscience 3335
      ATP-competitive PDGFR, VEGF and FGFR inhibitor (IC50 values are 0.06, 2.43, 3.04 and > 100 muM at PDGFRbeta, VEGFR2, FGFR1 and EGFR respectively). Inhibits proliferation of HUVEC and NIH3T3 cells in vitro (IC50 values are 0.41, 9.3 and 16.5 muM for VEGF, FGF and PDGF-stimulated growth respectively) and induces > 75% growth inhibition against a broad range of tumor types in vivo. Exhibits antiangiogenic, anti-inflammatory, antimetastatic and proapoptotic activity and is orally active. Tocris Bioscience 3335
      Enzyme-Linked Receptors Tocris Bioscience 3335
      PDGFR Tocris Bioscience 3335
      PDGFR MedChem Express HY-10517
      PDGFR, VEGFR and FGFR inhibitor Tocris Bioscience 3335
      Protein Tyrosine Kinase/RTK MedChem Express HY-10517
      Protein Tyrosine Kinase/RTK; MedChem Express HY-10517
      Receptor Tyrosine Kinases (RTKs) Tocris Bioscience 3335
      TSU-68 (SU6668; Orantinib) is a novel multiple receptor tyrosine kinase inhibitor with IC50 of 2.1 ?M, 8 nM and 1.2 ?M for VEGF-R1, PDGF-R? and FGF-R1, respectively; has greatest potency against PDGFR autophosphorylation.; IC50 value: 8 nM (Ki) [1]; Target: PDGF-R?; in vitro: TSU-68 is a competitive inhibitor, with regard to ATP, to Flk-1/KDR trans-phosphorylation, FGFR1 trans-phosphorylation, and PDGFR? kinases autophosphorylation. MedChem Express HY-10517

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

Density: 1.3±0.1 g/cm3
Boiling Point: 590.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 92.7±3.0 kJ/mol
Flash Point: 310.9±30.1 °C
Index of Refraction: 1.675
Molar Refractivity: 87.8±0.3 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 2.49
ACD/LogD (pH 5.5): 2.25
ACD/BCF (pH 5.5): 19.30
ACD/KOC (pH 5.5): 170.05
ACD/LogD (pH 7.4): 0.46
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.72
Polar Surface Area: 82 Å2
Polarizability: 34.8±0.5 10-24cm3
Surface Tension: 64.5±3.0 dyne/cm
Molar Volume: 233.7±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) =  3.36

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  557.27  (Adapted Stein & Brown method)
    Melting Pt (deg C):  239.35  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.57E-012  (Modified Grain method)
    Subcooled liquid VP: 9.47E-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):  14.52
       log Kow used: 3.36 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  28.292 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylamides-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.62E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.285E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.36  (KowWin est)
  Log Kaw used:  -16.568  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.928
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0466
   Biowin2 (Non-Linear Model)     :   0.9751
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5992  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7854  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2123
   Biowin6 (MITI Non-Linear Model):   0.0481
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8396
 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):  1.26E-007 Pa (9.47E-010 mm Hg)
  Log Koa (Koawin est  ): 19.928
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  23.8 
       Octanol/air (Koa) model:  2.08E+007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 233.2174 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.550 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    25.199999 E-17 cm3/molecule-sec
      Half-Life =     0.045 Days (at 7E11 mol/cm3)
      Half-Life =      1.091 Hrs
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1308
      Log Koc:  3.117 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 3.36 (estimated)

 Volatilization from Water:
    Henry LC:  6.62E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.558E+015  hours   (6.492E+013 days)
    Half-Life from Model Lake :   1.7E+016  hours   (7.082E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              10.22  percent
    Total biodegradation:        0.16  percent
    Total sludge adsorption:    10.06  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       7.39e-009       0.548        1000       
   Water     11.8            900          1000       
   Soil      87.5            1.8e+003     1000       
   Sediment  0.617           8.1e+003     0          
     Persistence Time: 1.83e+003 hr




                    

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