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Inherent Properties, Identifiers and References
ChemSpider ID: 62060
Empirical Formula: C15H22O5
Molecular Weight: 282.3322
Nominal Mass: 282 Da
Average Mass: 282.3322 Da
Monoisotopic Mass: 282.146724 Da
Systematic Name:
SMILES: O=C3O[C@@H]4O[C@@]1(OO[C@@]42[C@@H](CC1)[C@H](C)CC[C@H]2[C@H]3C)C
InChI: InChI=1/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,​18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m​1/s1
InChIKey: BLUAFEHZUWYNDE-NNWCWBAJBD
Std. InChI: InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3​,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/​m1/s1
Std. InChIKey: BLUAFEHZUWYNDE-NNWCWBAJSA-N
(Details...) Wikipedia Article(s)
Artemisinin () is a drug used to treat multi-drug resistant strains of falciparum malaria. The compound (a sesquiterpene lactone) is isolated from the plant Artemisia annua. Not all plants of this species contain artemisinin. Apparently it is only produced when the plant is subjected to certain conditions, most likely biotic or abiotic stress. It can be synthesized from artemisinic acid. The drug is derived from a herb used in Chinese traditional medicine, though it is usually chemically modified and combined with other medications. Use of the drug by itself as a monotherapy is explicitly discouraged by the World Health Organization as there have been signs that malarial parasites are developing resistance to the drug. Combination therapies that include artemisinin are the preferred treatment for malaria and are both effective and well tolerated in patients. The drug is also being studied as a treatment for cancer. Read more... or Edit at Wikipedia...
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User Data

  • miscellaneous
    • Source: Artemisia annua
    • Drug Status: INN
    • Chemical Class: sesquiterpene
Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(3R,5aS,6​R,8aS,9R,​12S,12aR)​-3,6,9-tr​imethyloc​tahydro-3​,12-epoxy​[1,2]diox​epino[4,3​-i]isochr​omen-10(3​H)-one

(4S,5R,8S​,9R,12S,1​3R)-1,5,9​-Trimethy​l-11,14,1​5,16-tetr​aoxatetra​cyclo[10.​3.1.0~4,1​3~.0~8,13​~]hexadec​an-10-on

(4S,5R,8S​,9R,12S,1​3R)-1,5,9​-Trimethy​l-11,14,1​5,16-tetr​aoxatetra​cyclo[10.​3.1.0~4,1​3~.0~8,13​~]hexadec​an-10-one

(4S,5R,8S​,9R,12S,1​3R)-1,5,9​-Triméthy​l-11,14,1​5,16-tétr​aoxatétra​cyclo[10.​3.1.0~4,1​3~.0~8,13​~]hexadéc​an-10-one

(5aS,6R,8​aS,9R,12S​,12aR)-3,​6,9-trime​thyloctah​ydro-3,12​-epoxy[1,​2]dioxepi​no[4,3-i]​isochrome​n-10(3H)-​one

[3R-(3a,5​ab,6b,8ab​,9a,12b,1​2aR*)]-Oc​tahydro-3​,6,9-trim​ethyl-3,1​2-epoxy-1​2H-pyrano​[4,3-j]-1​,2-benzod​ioxepin-1​0(3H)-one

3,12-epox​y-12H-pyr​ano[4,3-j​]-1,2-ben​zodioxepi​n-10(3H)-​one, octa​hydro-3,6​,9-trimet​hyl-, (3R​,5aS,6R,8​aS,9R,12S​,12aR)-

3,12-epox​y-12H-pyr​ano[4,3-j​]-1,2-ben​zodioxepi​n-10(3H)-​one, octa​hydro-3,6​,9-trimet​hyl-, (5a​S,6R,8aS,​9R,12S,12​aR)-

Artemisin​in [INN]

QHS

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Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(Details...) ACD/Labs Predicted Properties
ACD/LogP: 2.27 # of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 2.27 ACD/LogD (pH 7.4): 2.27
ACD/BCF (pH 5.5): 31.21 ACD/BCF (pH 7.4): 31.21
ACD/KOC (pH 5.5): 408.53 ACD/KOC (pH 7.4): 408.53
#H bond acceptors: 5 #H bond donors: 0
#Freely Rotating Bonds: 0 Polar Surface Area: 53.99 Å2
Index of Refraction: 1.533 Molar Refractivity: 70.31 cm3
Molar Volume: 226.4 cm3 Polarizability: 27.87 10-24cm3
Surface Tension: 43.5 dyne/cm Density: 1.24 g/cm3
Flash Point: 172 °C Enthalpy of Vaporization: 63.93 kJ/mol
Boiling Point: 389.9 °C at 760 mmHg Vapour Pressure: 2.76E-06 mmHg at 25°C
(Details...) EPI Summary 
            
 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
(Details...) SimBioSys LASSO
Descriptors: 0, 0, 0, 0, 0, 0, 0, 8, 1, 0, 0, 0, 21, 0, 1, 0, 0, 2, 1, 0, 0, 0, 0, 0
CategoryTargetPDB CodeLASSO Score
MetalloenzymesACE, angiotensin-converting enzyme1o860.03
Nuclear Hormone ReceptorsPPARg, peroxisome proliferator activated receptor1fm90.03
KinasesSRC, tyrosine kinase SRC2src0.01
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase1hw80.01
Other EnzymesHIVPR, HIV protease1hpx0.01
MetalloenzymesPDE5, phosphodiesterase 51xp00.01
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor2aa20.01
KinasesTK, thymidine kinase1kim0.01
Other EnzymesCOX-1, cyclooxygenase-11p4g0.01
Other EnzymesPARP, poly(ADP-ribose) polymerase1efy0.01
Other EnzymesPNP, purine nucleoside phosphorylase1b8o0.00
Other EnzymesAmpC, AmpC beta-lactamase1xgj0.00
Other EnzymesALR2, aldose reductase1ah30.00
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.00
Serine ProteasesThrombin1ba80.00
Nuclear Hormone ReceptorsPR, progesterone receptor1sr70.00
Folate EnzymesDHFR, dihydrofolate reductase3dfr0.00
Other EnzymesHIVRT, HIV reverse transcriptase1rt10.00
KinasesVEGFr2, vascular endothelial growth factor receptor1vr20.00
Other EnzymesGPB, glycogen phosphorylase1a8i0.00
Nuclear Hormone ReceptorsRXRa, retinoic X receptor R1mvc0.00
Other EnzymesSAHH, S-adenosyl-homocysteine hydrolase1a7a0.00
KinasesFGFr1, fibroblast growth factor receptor kinase1agw0.00
Other EnzymesNA, neuraminidase1a4g0.00
KinasesCDK2, cyclindependent kinase 21ckp0.00
Nuclear Hormone ReceptorsAR, androgen receptor1xq20.00
KinasesP38 MAP, P38 mitogen activated protein1kv20.00
Other EnzymesAChE, acetylcholinesterase1eve0.00
Nuclear Hormone ReceptorsGR, glucocorticoid receptor1m2z0.00
KinasesPDGFrb, platelet derived growth factor receptor kinaseN/A0.00
Folate EnzymesGART, glycinamide ribonucleotide transformylase1c2t0.00
Nuclear Hormone ReceptorsER, estrogen receptor; antagonist3ert0.00
KinasesHSP90, human heat shock protein 901uy60.00
MetalloenzymesCOMT, catechol O-methyltransferase1h1d0.00
Serine ProteasesTrypsin1bju0.00
Other EnzymesCOX-2, cyclooxygenase-21cx20.00
MetalloenzymesADA, adenosine deaminase1stw0.00
KinasesEGFr, epidermal growth factor receptor1m170.00
Serine ProteasesFXa, factor Xa1f0r0.00
Other EnzymesInhA, enoyl ACP reductase1p440.00