NP-MRD: Showing NP-Card for 2-deoxyartemisinin (NP0203884)

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Record Information

Version

2.0

Created at

2022-09-04 23:27:10 UTC

Updated at

2022-09-04 23:27:10 UTC

NP-MRD ID

NP0203884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-deoxyartemisinin

Description

Deoxyartemisinin, also known as artemisinin, deoxy, belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring. 2-deoxyartemisinin is found in Artemisia annua. 2-deoxyartemisinin was first documented in 2021 (PMID: 34021777). Based on a literature review a small amount of articles have been published on Deoxyartemisinin (PMID: 34023721) (PMID: 35355096) (PMID: 35451509) (PMID: 35432559).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
   -0.3945    3.3259   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910    2.1246    0.7428 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9877    1.9300    1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    1.1140    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2036    0.2398   -0.6161 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1088   -0.8857   -1.0397 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4755   -0.8053   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -2.1549   -0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149   -3.1431   -1.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -2.1495    0.7165 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -1.1836    1.0581 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2245   -1.8785    0.9934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7558   -1.6178   -0.2666 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3004   -2.8363   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8835   -0.6099   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596    0.4584    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.9232    0.1229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1159   -0.2295   -0.0963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7458   -1.0675   -1.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4553    3.9911   -0.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658    3.8700   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577    2.9132   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0437    2.4271    1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9225    1.5524    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4597    2.9491    1.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    0.4823    1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174    1.7527   -0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    0.8586   -1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2489   -0.9074   -2.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413   -1.4654   -0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102    0.1887   -0.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4476   -1.2810    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1664   -0.7082    2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5492   -3.3075   -1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1533   -2.5339   -1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7345   -3.5796   -0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6798   -1.1507    0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -0.1289   -0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9692    1.2848    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995   -0.0040    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    1.2425   -0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 17  2  1  0
 18  5  1  0
 18 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  6
  7 30  1  0
  7 31  1  0
  7 32  1  0
 11 33  1  1
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  6
M  END


  Mrv1652309052201272D          

 19 22  0  0  1  0            999 V2000
    4.2550   -1.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217   -0.9813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8224   -1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0826   -1.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371   -0.1956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2302   -0.0050    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6624   -0.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1923    0.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358    1.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    1.1976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9196    1.8483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6711    1.4517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1095    2.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3599    0.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837    0.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -0.1587    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6911    0.3558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1886    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 13 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23O4

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

> <INCHI_KEY>
ZQGMLVQZBIKKMP-NNWCWBAJSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.601129365088475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^{4,13}.0^{8,13}]pentadecan-10-one

> <JCHEM_LOGP>
2.929888450999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.17858048431283

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
67.60040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^{4,13}.0^{8,13}]pentadecan-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.943  -2.538   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.574  -1.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.268  -2.606   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.888  -1.917   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.803  -0.365   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.296  -0.009   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.237  -1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.863   1.470   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.359   1.801   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.867   2.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.354   2.235   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.450   3.450   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.853   2.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.671   4.014   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.138   1.763   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.996   0.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.446  -0.296   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.023   0.664   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.952   1.580   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17   11    5   19                                             
CONECT   19   18   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
Artemisinin, deoxy	MeSH

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^{4,13}.0^{8,13}]pentadecan-10-one

Traditional Name

(1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0^{4,13}.0^{8,13}]pentadecan-10-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23O4

InChI Identifier

InChI=1S/C15H22O4/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

InChI Key

ZQGMLVQZBIKKMP-NNWCWBAJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Artemisia annua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxolopyrans

Sub Class

Not Available

Direct Parent

Dioxolopyrans

Alternative Parents

Substituents

Dioxolopyran
Ketal
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Meta-dioxolane
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.93	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.6 m³·mol⁻¹	ChemAxon
Polarizability	28.6 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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10261096

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12814879

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kadioglu O, Klauck SM, Fleischer E, Shan L, Efferth T: Selection of safe artemisinin derivatives using a machine learning-based cardiotoxicity platform and in vitro and in vivo validation. Arch Toxicol. 2021 Jul;95(7):2485-2495. doi: 10.1007/s00204-021-03058-4. Epub 2021 May 22. [PubMed:34021777 ]
Nagy C, Pesti A, Andrasi M, Vasas G, Gaspar A: Determination of artemisinin and its analogs in Artemisia annua extracts by capillary electrophoresis - Mass spectrometry. J Pharm Biomed Anal. 2021 Aug 5;202:114131. doi: 10.1016/j.jpba.2021.114131. Epub 2021 May 12. [PubMed:34023721 ]
Luo J, Mobley R, Woodfine S, Drijfhout F, Horrocks P, Ren XD, Li WW: Biotransformation of artemisinin to a novel derivative via ring rearrangement by Aspergillus niger. Appl Microbiol Biotechnol. 2022 Apr;106(7):2433-2444. doi: 10.1007/s00253-022-11888-0. Epub 2022 Mar 31. [PubMed:35355096 ]
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LOTUS database [Link]

Showing NP-Card for 2-deoxyartemisinin (NP0203884)

MOL for NP0203884 (2-deoxyartemisinin)

3D MOL for NP0203884 (2-deoxyartemisinin)

3D SDF for NP0203884 (2-deoxyartemisinin)

3D-SDF for NP0203884 (2-deoxyartemisinin)

PDB for NP0203884 (2-deoxyartemisinin)

3D PDB for NP0203884 (2-deoxyartemisinin)

SMILES for NP0203884 (2-deoxyartemisinin)

INCHI for NP0203884 (2-deoxyartemisinin)

Structure for NP0203884 (2-deoxyartemisinin)

3D Structure for NP0203884 (2-deoxyartemisinin)