ChemSpider 2D Image | Artemether | C16H26O5

Artemether

  • Molecular FormulaC16H26O5
  • Average mass298.375 Da
  • Monoisotopic mass298.178009 Da
  • ChemSpider ID62138
  • defined stereocentres - 8 of 8 defined stereocentres


More details:



Featured data source



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

(1R,4S,5R,8S,9R,10S,12R,13R)-10-Methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan [German] [ACD/IUPAC Name]
(1R,4S,5R,8S,9R,10S,12R,13R)-10-Methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane [ACD/IUPAC Name]
(1R,4S,5R,8S,9R,10S,12R,13R)-10-Méthoxy-1,5,9-triméthyl-11,14,15,16-tétraoxatétracyclo[10.3.1.04,13.08,13]hexadécane [French] [ACD/IUPAC Name]
(3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-methoxy-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene
(4S,5R,8S,9R,10S,12R,13R)-10-Methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane [ACD/IUPAC Name]
3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)- [ACD/Index Name]
3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (5aS,6R,8aS,9R,10S,12R,12aR)- [ACD/Index Name]
71963-77-4 [RN]
Artemetero [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:195280 [DBID]
D02483 [DBID]
NSC 665970 [DBID]
SM 224 [DBID]
SM 229 [DBID]
SM-224 [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P01BE02 Wikidata Q416199
    • Target Organs:

      Antibiotic TargetMol T1323
    • Chemical Class:

      An artemisinin derivative that is artemisinin in which the lactone has been converted to the corresponding lactol methyl ether. It is used in combination with lumefantrine as an antimalarial for the t reatment of multi-drug resistant strains of <ital>falciparum</ital> malaria. ChEBI CHEBI:195280
    • Drug Status:

      approved BIONET-Key Organics KS-5314
    • Bio Activity:

      Anti-infection; MedChem Express HY-N0402
      Antiparasitic MedChem Express HY-N0402
      Artemether is an antimalarial for the treatment of resistant strains of falciparum malaria. MedChem Express
      Artemether is an antimalarial for the treatment of resistant strains of falciparum malaria.;Target: AntiparasiticArtemether is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with lumefantrine for improved efficacy. Artemether exhibits the highest activity against juvenile stages of the parasites, while adult worms are significantly less susceptible. There was no indication of neurotoxicity following repeated high doses of artemether given fortnightly for up to 5 months. Artemether-integrated with other control strategies-has considerable potential for reducing the current burden of schistosomiasis in different epidemiological settings [1]. There were remarkably inhibitory effects of artmeter on brain glioma growth and angiogenesis in SD rats and the mechanism that artemether inhibited brain glioma growth might be penetrating the blood-brain barrier and inhibiting angiogenesis [2]. MedChem Express HY-N0402
      Microbiology & Virology TargetMol T1323
      Others TargetMol T1323

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

Density: 1.2±0.1 g/cm3
Boiling Point: 357.5±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 57.9±3.0 kJ/mol
Flash Point: 140.5±27.8 °C
Index of Refraction: 1.518
Molar Refractivity: 76.5±0.4 cm3
#H bond acceptors: 5
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 3.07
ACD/LogD (pH 5.5): 3.08
ACD/BCF (pH 5.5): 129.93
ACD/KOC (pH 5.5): 1133.97
ACD/LogD (pH 7.4): 3.08
ACD/BCF (pH 7.4): 129.93
ACD/KOC (pH 7.4): 1133.97
Polar Surface Area: 46 Å2
Polarizability: 30.3±0.5 10-24cm3
Surface Tension: 40.0±5.0 dyne/cm
Molar Volume: 252.5±5.0 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) =  3.06
    Log Kow (Exper. database match) =  3.53
       Exper. Ref:  Avery,MA et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  345.46  (Adapted Stein & Brown method)
    Melting Pt (deg C):  119.52  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.02E-005  (Modified Grain method)
    Subcooled liquid VP: 0.000348 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):  12.13
       log Kow used: 3.53 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4.4472 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.88E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.301E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.53  (exp database)
  Log Kaw used:  -7.114  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.644
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.8044
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0895  (months      )
   Biowin4 (Primary Survey Model) :   3.0811  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1193
   Biowin6 (MITI Non-Linear Model):   0.0047
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1658
 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):  0.0464 Pa (0.000348 mm Hg)
  Log Koa (Koawin est  ): 10.644
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.47E-005 
       Octanol/air (Koa) model:  0.0108 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00233 
       Mackay model           :  0.00515 
       Octanol/air (Koa) model:  0.464 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  40.4574 E-12 cm3/molecule-sec
      Half-Life =     0.264 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.173 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00374 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  140.5
      Log Koc:  2.148 

 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 = 2.018 (BCF = 104.3)
       log Kow used: 3.53 (expkow database)

 Volatilization from Water:
    Henry LC:  1.88E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  5.38E+005  hours   (2.241E+004 days)
    Half-Life from Model Lake : 5.869E+006  hours   (2.445E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              13.73  percent
    Total biodegradation:        0.19  percent
    Total sludge adsorption:    13.54  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       0.0086          6.35         1000       
   Water     9.41            1.44e+003    1000       
   Soil      89.7            2.88e+003    1000       
   Sediment  0.873           1.3e+004     0          
     Persistence Time: 2.73e+003 hr




                    

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