ChemSpider 2D Image | Artemisinin | C15H22O5

Artemisinin

  • Molecular FormulaC15H22O5
  • Average mass282.332 Da
  • Monoisotopic mass282.146729 Da
  • ChemSpider ID62060

  • defined stereocentres - 7 of 7 defined stereocentres

More details:

Featured data source
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Artemisinin [INN]
(+)-artemisinin
(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0?,¹³.0?,¹³]hexadecan-10-one
(3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one
(4S,5R,8S,9R,12S,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-on [German] [ACD/IUPAC Name]
(4S,5R,8S,9R,12S,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one [ACD/IUPAC Name]
(4S,5R,8S,9R,12S,13R)-1,5,9-Triméthyl-11,14,15,16-tétraoxatétracyclo[10.3.1.04,13.08,13]hexadécan-10-one [French] [ACD/IUPAC Name]
[3R-(3a,5ab,6b,8ab,9a,12b,12aR*)]-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,12S,12aR)- [ACD/Index Name]
3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (5aS,6R,8aS,9R,12S,12aR)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5954 [DBID]
CHEBI:223316 [DBID]
361593_ALDRICH [DBID]
4194670 [DBID]
BRN 4194670 [DBID]
C09538 [DBID]
D02481 [DBID]
DivK1c_000656 [DBID]
KBio1_000656 [DBID]
KBio2_001831 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      Others TargetMol T0392

    • Chemical Class:

      A sesquiterpene lactone obtained from sweet wormwood, <ital>Artemisia annua</ital>, which is used as an antimalarial for the treatment of multi-drug resistant strains of <ital>falciparum</ital> malari a. ChEBI CHEBI:223316
      A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malari; a. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:223316
      A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria. ChEBI CHEBI:223316

    • Compound Source:

      artemisinin biosynthesis PlantCyc CPD-7561
      Linum usitatissimum PlantCyc CPD-7561

    • Bio Activity:

      Anti-infection MedChem Express HY-B0094
      Anti-infection; MedChem Express HY-B0094
      Antimalarial agent; interacts with heme to produce carbon-centred free radicals, causes protein alkylation and damages parasite microorganelles and membranes. Also selectively inhibits the P-type ATPa se (PfATP6) of Plasmodium falciparum (Ki ~ 150 nM). Displays antiangiogenic effects in mouse embryonic stem cell-derived embryoid bodies. Tocris Bioscience 2668
      Antimalarial agent; interacts with heme to produce carbon-centred free radicals, causes protein alkylation and damages parasite microorganelles and membranes. Also selectively inhibits the P-type ATPase (PfATP6) of Plasmodium falciparum (Ki ~ 150 nM). Displays antiangiogenic effects in mouse embryonic stem cell-derived embryoid bodies. Tocris Bioscience 2668
      Antimalarial; inhibits P-type ATPase (PfATP6) of P.falciparum Tocris Bioscience 2668
      artemisinate -> artemisinin PlantCyc CPD-7561
      Artemisinin (NSC 369397), a widely used anti-malarial drug, is an inhibitor of HCV subgenomic replicon replication. MedChem Express
      Artemisinin (NSC 369397), a widely used anti-malarial drug, is an inhibitor of HCV subgenomic replicon replication.; Target: HCV; Artemisinin (ART), a widely used anti-malarial drug, is an inhibitor of in vitro HCV subgenomic replicon replication. MedChem Express HY-B0094
      ATPase Tocris Bioscience 2668
      ATPases/GTPases Tocris Bioscience 2668
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB1115]
      Cell signaling/Ca<sup>2+</sup> signaling/Ca<sup>2+</sup>-ATPase (SERCA) Hello Bio [HB1115]
      dihydroartemisinic acid hydroperoxide + oxygen + H+ -> artemisinin + H2O PlantCyc CPD-7561
      Enzymes Tocris Bioscience 2668
      Enzymes/ATPase / GTPase/Ca<sup>2+</sup>-ATPase (SERCA) Hello Bio [HB1115]
      HCV MedChem Express HY-B0094
      Others TargetMol T0392
      Plasmodium falciparum SERCA orthologue (PfATP6) inhibitor (K<sub>i</sub> = 150 nM). Thought to generate cytotoxic C-radicals. Shows anti-malarial, anti-proliferative and anti-neoplastic actions. Hello Bio [HB1115]
      Plasmodium falciparum SERCA orthologue inhibitor Hello Bio [HB1115]
  • Gas Chromatography

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

Density: 1.2±0.1 g/cm3
Boiling Point: 389.9±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 63.9±3.0 kJ/mol
Flash Point: 172.0±27.9 °C
Index of Refraction: 1.533
Molar Refractivity: 70.3±0.4 cm3
#H bond acceptors: 5
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 2.27
ACD/LogD (pH 5.5): 2.79
ACD/BCF (pH 5.5): 78.24
ACD/KOC (pH 5.5): 788.70
ACD/LogD (pH 7.4): 2.79
ACD/BCF (pH 7.4): 78.24
ACD/KOC (pH 7.4): 788.70
Polar Surface Area: 54 Å2
Polarizability: 27.9±0.5 10-24cm3
Surface Tension: 43.5±5.0 dyne/cm
Molar Volume: 226.5±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) =  2.85
    Log Kow (Exper. database match) =  2.90
       Exper. Ref:  Avery, MA et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  379.33  (Adapted Stein & Brown method)
    Melting Pt (deg C):  132.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.18E-006  (Modified Grain method)
    Subcooled liquid VP: 2.63E-005 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):  51.85
       log Kow used: 2.90 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.8081 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.92E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.562E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.90  (exp database)
  Log Kaw used:  -6.696  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.596
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0721
   Biowin2 (Non-Linear Model)     :   0.0219
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2825  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3527  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4950
   Biowin6 (MITI Non-Linear Model):   0.1061
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4393
 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):  0.00351 Pa (2.63E-005 mm Hg)
  Log Koa (Koawin est  ): 9.596
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000856 
       Octanol/air (Koa) model:  0.000968 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.03 
       Mackay model           :  0.0641 
       Octanol/air (Koa) model:  0.0719 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  43.2548 E-12 cm3/molecule-sec
      Half-Life =     0.247 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.967 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.047 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1206
      Log Koc:  3.081 

 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 = 1.533 (BCF = 34.12)
       log Kow used: 2.90 (expkow database)

 Volatilization from Water:
    Henry LC:  4.92E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:     2E+005  hours   (8332 days)
    Half-Life from Model Lake : 2.182E+006  hours   (9.09E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               4.92  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.81  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       0.034           5.94         1000       
   Water     14.1            900          1000       
   Soil      85.6            1.8e+003     1000       
   Sediment  0.259           8.1e+003     0          
     Persistence Time: 1.6e+003 hr

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