NP-MRD: Showing NP-Card for artemisinin (NP0051956)

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Record Information

Version

2.0

Created at

2022-04-27 23:10:01 UTC

Updated at

2024-09-03 04:16:47 UTC

NP-MRD ID

NP0051956

Natural Product DOI

https://doi.org/10.57994/0806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

artemisinin

Description

Artemisinin, also known as quing hau sau or arteannuin, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Thus, artemisinin is considered to be an isoprenoid lipid molecule. 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. Artemisinin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. artemisinin is found in Apis cerana, Artemisia annua , Artemisia caerulescens, Artemisia carvifolia, Artemisia herba-alba, Artemisia lancea, Artemisia tenuisecta, Artemisia vallesiaca, Microliabum polymnioides and Tessaria integrifolia. artemisinin was first documented in 1995 (PMID: 7877142). In humans, artemisinin is involved in artemether metabolism pathway (PMID: 15330155) (PMID: 18008167) (PMID: 19090980) (PMID: 22174561) (PMID: 8544181).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -0.3654    3.3964    0.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4461    2.0478   -0.3218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8960    1.7161   -0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.2444   -0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4950   -0.5424    0.3567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7576   -2.0204    0.2636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1823   -2.3821    0.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -2.4470   -1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9888   -3.3869   -1.6983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094   -1.8057   -1.7071 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345   -0.8616   -1.0701 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7513   -1.5428   -0.8413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645   -0.8750    0.1223 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8088   -1.5563    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6310    0.5596   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601    1.4324    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3241    1.0665    0.5298 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0197   -0.3596    0.2218 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5769   -1.1392    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8424   -0.8923    1.3802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3178    3.9783    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5019    3.9836    0.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297    3.2257    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423    2.2171   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920    2.2889   -1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087    2.0552    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2336    0.1039   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312    0.0492   -1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285   -0.1309    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0530   -2.5281    0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8349   -1.7992   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885   -3.4760    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675   -2.1804    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -0.0222   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -1.4585    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5781   -1.0592   -0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7858   -2.6160    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5366    0.6883   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000    0.8287   -0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017    1.4644    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919    2.4893    0.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    1.2460    1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 17  2  1  0
 18  5  1  0
 18 11  1  0
 20 13  1  0
  2 24  1  6
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  1
  7 31  1  0
  7 32  1  0
  7 33  1  0
 11 34  1  6
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  1
M  END

  Mrv1572004221604042D          

 25 28  0  0  1  0            999 V2000
    4.5141   -0.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4880    2.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064   -0.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5429   -0.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7995    0.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.4493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8064    0.8267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9421    0.3980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6391    0.5940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5179    1.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    1.8038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8026    1.7960    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3814    1.0934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7354    1.8782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2230    2.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9705    1.5831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462    2.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6200    2.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5771   -0.1089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0311    0.0328    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932    1.1446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5077    1.4085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0085    2.6283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  6  0  0  0
  8  4  1  0  0  0  0
  9  2  1  1  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 14  3  1  1  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 14  1  0  0  0  0
 15 20  1  6  0  0  0
 20 19  1  0  0  0  0
  8 21  1  1  0  0  0
  9 22  1  6  0  0  0
 10 23  1  6  0  0  0
 11 24  1  6  0  0  0
 13 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
BLUAFEHZUWYNDE-NNWCWBAJSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.433175836688754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,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

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
3.114058047333332

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.427808040586903

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
68.6817

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-artemisinin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       8.426  -1.687   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.326   0.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.244   4.210   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.799  -1.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.747  -0.487   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.959   0.764   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.872   2.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.141  -0.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.372   1.543   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.359   0.743   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.926   1.109   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.833   3.018   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.671   3.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.965   3.353   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.312   2.041   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.373   3.506   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.150   3.872   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.412   2.955   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.113   4.675   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.757   3.816   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       8.544  -0.203   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.791   0.061   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       8.014   2.137   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.681   2.629   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.616   4.906   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    7   10                                                       
CONECT    7    6   14                                                       
CONECT    8    1    4   10   21                                             
CONECT    9    2   11   12   22                                             
CONECT   10    6    8   15   23                                             
CONECT   11    5    9   15   24                                             
CONECT   12    9   16   17                                                  
CONECT   13   15   17   18   25                                             
CONECT   14    3    7   18   19                                             
CONECT   15   10   11   13   20                                             
CONECT   16   12                                                            
CONECT   17   12   13                                                       
CONECT   18   13   14                                                       
CONECT   19   14   20                                                       
CONECT   20   15   19                                                       
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
1,5,9-Trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one	ChEBI
Arteannuin	ChEBI
Artemisinina	ChEBI
Artemisinine	ChEBI
Artemisininum	ChEBI
Huanghuahaosu	ChEBI
Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-J)-1,2-benzodioxepin-10(3H)-one	ChEBI
QHS	ChEBI
Qing hau sau	ChEBI
Qinghaosu	ChEBI
Quing hau sau	ChEBI
Quinghaosu	MeSH
Artemisinin	ChEBI

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

(1R,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

Traditional Name

(+)-artemisinin

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4

InChI Identifier

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

InChI Key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Artemisia annua	Plant	KNApSAcK
Artemisia caerulescens	LOTUS Database	35616633
Artemisia carvifolia	LOTUS Database	35616633
Artemisia herba-alba	LOTUS Database	35616633
Artemisia lancea	LOTUS Database	35616633
Artemisia tenuisecta	LOTUS Database	35616633
Artemisia vallesiaca	LOTUS Database	35616633
Microliabum polymnioides	LOTUS Database	35616633
Tessaria integrifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Artemisinin skeleton
Terpene lactone
Sesquiterpenoid
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
1,2,4-trioxane
Carboxylic acid ester
Lactone
Dialkyl peroxide
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic peroxide (CHEBI:223316 )
sesquiterpene lactone (CHEBI:223316 )
Eudesmane sesquiterpenoids (C09538 )
Sesquiterpenoids (C15) (C09538 )
Eudesmane sesquiterpenoids (LMPR0103190003 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.52	ALOGPS
logP	3.11	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.68 m³·mol⁻¹	ChemAxon
Polarizability	29.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB13132

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003359

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-7561

BiGG ID

Not Available

Wikipedia Link

Artemisinin

METLIN ID

Not Available

PubChem Compound

68827

PDB ID

Not Available

ChEBI ID

223316

Good Scents ID

Not Available

References

General References

Yamachika E, Habte T, Oda D: Artemisinin: an alternative treatment for oral squamous cell carcinoma. Anticancer Res. 2004 Jul-Aug;24(4):2153-60. [PubMed:15330155 ]
Zeng Q, Qiu F, Yuan L: Production of artemisinin by genetically-modified microbes. Biotechnol Lett. 2008 Apr;30(4):581-92. doi: 10.1007/s10529-007-9596-y. Epub 2007 Nov 16. [PubMed:18008167 ]
Hommel M: The future of artemisinins: natural, synthetic or recombinant? J Biol. 2008 Dec 15;7(10):38. doi: 10.1186/jbiol101. [PubMed:19090980 ]
Crespo-Ortiz MP, Wei MQ: Antitumor activity of artemisinin and its derivatives: from a well-known antimalarial agent to a potential anticancer drug. J Biomed Biotechnol. 2012;2012:247597. doi: 10.1155/2012/247597. Epub 2011 Nov 22. [PubMed:22174561 ]
Lin AJ, Miller RE: Antimalarial activity of new dihydroartemisinin derivatives. 6. alpha-Alkylbenzylic ethers. J Med Chem. 1995 Mar 3;38(5):764-70. doi: 10.1021/jm00005a004. [PubMed:7877142 ]
Torok DS, Ziffer H, Meshnick SR, Pan XQ, Ager A: Syntheses and antimalarial activities of N-substituted 11-azaartemisinins. J Med Chem. 1995 Dec 22;38(26):5045-50. doi: 10.1021/jm00026a012. [PubMed:8544181 ]

Showing NP-Card for artemisinin (NP0051956)

MOL for NP0051956 (artemisinin)

3D MOL for NP0051956 (artemisinin)

3D SDF for NP0051956 (artemisinin)

3D-SDF for NP0051956 (artemisinin)

PDB for NP0051956 (artemisinin)

3D PDB for NP0051956 (artemisinin)

SMILES for NP0051956 (artemisinin)

INCHI for NP0051956 (artemisinin)

Structure for NP0051956 (artemisinin)

3D Structure for NP0051956 (artemisinin)