NP-MRD: Showing NP-Card for Artesunate (NP0137143)

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Record Information

Version

2.0

Created at

2022-05-30 16:42:58 UTC

Updated at

2022-05-30 16:42:58 UTC

NP-MRD ID

NP0137143

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Artesunate

Description

Artesunate, also known as artesunic acid or AS, belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins. Artesunate is a drug which is used for the treatment of severe malaria caused by *plasmodium falciparum* in adults and children [l891]. Artesunate is found in Artemisia carvifolia. Artesunate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

      
  Mrv1652304091822502D          

 30 33  0  0  1  0            999 V2000
    7.5769   -8.0553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8629   -8.4686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2909   -8.4686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8629   -9.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5769   -9.7087    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5373   -7.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613   -8.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5393   -7.1993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7106   -7.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2909   -9.2954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4747   -7.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9255   -7.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8838   -6.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5727  -10.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2282   -6.7359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9296   -7.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738   -6.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0048   -9.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2240   -5.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1490   -8.8820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5143   -6.3143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0068   -8.8820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2896  -10.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2896  -11.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0028  -10.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7184  -10.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4317  -10.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1473  -10.9346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4290   -9.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  2  4  1  6  0  0  0
  5 10  1  0  0  0  0
  1  6  1  6  0  0  0
  7  2  1  0  0  0  0
  8  1  1  0  0  0  0
  9 11  1  6  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  3  1  0  0  0  0
 13  8  1  0  0  0  0
  5 14  1  6  0  0  0
 15  8  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 10 19  1  1  0  0  0
 15 20  1  6  0  0  0
  2 21  1  1  0  0  0
  8 22  1  6  0  0  0
 16 12  1  0  0  0  0
  9 17  1  0  0  0  0
  9  7  1  0  0  0  0
  5  4  1  0  0  0  0
  3 23  1  6  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.5454   -1.5756   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293   -1.3551   -0.4257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3473   -2.5133    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2164   -2.2336    1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651   -0.9618    0.8521 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7069   -1.1426   -0.0868 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3574   -1.7687   -1.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    0.1357   -0.2707 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7562    0.1413    0.2389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8174    0.4316   -0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5730    0.6660   -1.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2205    0.4704   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7872   -0.9184    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1906   -0.7980    0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1340   -0.7754   -0.2676 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4615   -0.7093    1.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692    1.1915    0.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277    1.2494   -0.2233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9460    2.5410    0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    2.6222    0.5204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4459    4.0475    0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553    2.3712   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822    0.9585   -1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6802   -0.0083    0.0556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3249    0.2225    0.6027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4948    0.9388    1.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    1.7807    1.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006   -2.6332   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7871   -1.1492    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1205   -1.0658   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8742   -1.4048   -1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738   -3.1743    0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735   -3.2335   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4481   -3.0602    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5642   -2.2969    2.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -0.7825    1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980   -1.8727    0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3022   -2.8797   -1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349   -1.6084   -2.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058   -1.3401   -1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513    0.3985   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8741    0.9554   -0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940    1.0675    0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -1.4260    0.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7786   -1.4774   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7297    0.2343    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4012    0.9633   -1.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3837    4.1421    2.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579    4.7296    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4186    4.4640    0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7590    3.0224   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812    2.6984   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9874    0.6141   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2984    0.8237   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4802    0.2829    0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  1
 20 27  1  0
 27 26  1  0
 25 26  1  1
 25 18  1  0
 18 17  1  0
 17  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  8  6  1  0
  6  7  1  0
 18 19  1  0
 25  5  1  0
  6  5  1  0
 25 24  1  0
 19 20  1  0
  5 36  1  1
  4 34  1  0
  4 35  1  0
  3 32  1  0
  3 33  1  0
  2 31  1  6
  1 28  1  0
  1 29  1  0
  1 30  1  0
 24 55  1  1
 23 53  1  0
 23 54  1  0
 22 51  1  0
 22 52  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 18 47  1  6
  8 41  1  6
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  0
  6 37  1  1
  7 38  1  0
  7 39  1  0
  7 40  1  0
M  END

      
  Mrv1652304091822502D          

 30 33  0  0  1  0            999 V2000
    7.5769   -8.0553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8629   -8.4686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2909   -8.4686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8629   -9.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5769   -9.7087    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5373   -7.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613   -8.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5393   -7.1993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7106   -7.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2909   -9.2954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4747   -7.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9255   -7.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8838   -6.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5727  -10.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2282   -6.7359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9296   -7.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738   -6.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0048   -9.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2240   -5.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1490   -8.8820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5143   -6.3143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0068   -8.8820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2896  -10.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2896  -11.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0028  -10.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7184  -10.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4317  -10.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1473  -10.9346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4290   -9.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  2  4  1  6  0  0  0
  5 10  1  0  0  0  0
  1  6  1  6  0  0  0
  7  2  1  0  0  0  0
  8  1  1  0  0  0  0
  9 11  1  6  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  3  1  0  0  0  0
 13  8  1  0  0  0  0
  5 14  1  6  0  0  0
 15  8  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 10 19  1  1  0  0  0
 15 20  1  6  0  0  0
  2 21  1  1  0  0  0
  8 22  1  6  0  0  0
 16 12  1  0  0  0  0
  9 17  1  0  0  0  0
  9  7  1  0  0  0  0
  5  4  1  0  0  0  0
  3 23  1  6  0  0  0
 14 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137143

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O4

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1

> <INCHI_KEY>
FIHJKUPKCHIPAT-AHIGJZGOSA-N

> <FORMULA>
C19H28O8

> <MOLECULAR_WEIGHT>
384.425

> <EXACT_MASS>
384.178417862

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.48017281404418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
3.104253674

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.768142988199547

> <JCHEM_PKA_STRONGEST_BASIC>
-4.177948164471451

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000001

> <JCHEM_REFRACTIVITY>
89.95409999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-APR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-18         0                                  
HETATM    1  C   UNK     0      14.144 -15.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.811 -15.808   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.476 -15.808   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.811 -17.351   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.144 -18.123   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.203 -14.546   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      11.314 -15.457   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.073 -13.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.660 -14.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.476 -17.351   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.086 -13.322   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.661 -14.873   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.850 -12.348   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.136 -19.666   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.359 -12.574   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.669 -13.353   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.338 -12.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.117 -14.055   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.809 -18.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.351 -11.031   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      11.478 -16.580   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      14.027 -11.787   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      16.813 -16.580   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      15.474 -20.428   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.474 -21.968   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.805 -19.654   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.141 -20.419   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.473 -19.645   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.808 -20.411   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      19.467 -18.105   0.000  0.00  0.00           O+0
CONECT    1    2    3    6    8                                             
CONECT    2    1    4    7   21                                             
CONECT    3    1   10   12   23                                             
CONECT    4    2    5                                                       
CONECT    5   10   14    4                                                  
CONECT    6    1   11                                                       
CONECT    7    2    9                                                       
CONECT    8    1   13   15   22                                             
CONECT    9   11   18   17    7                                             
CONECT   10    5    3   19                                                  
CONECT   11    9    6                                                       
CONECT   12    3   16                                                       
CONECT   13    8   17                                                       
CONECT   14    5   24                                                       
CONECT   15    8   16   20                                                  
CONECT   16   15   12                                                       
CONECT   17   13    9                                                       
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   15                                                            
CONECT   21    2                                                            
CONECT   22    8                                                            
CONECT   23    3                                                            
CONECT   24   14   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Artesunato	ChEBI
Artesunatum	ChEBI
Artesunic acid	ChEBI
AS	ChEBI
Butanedioic acid, 1-[(3R,5as,6R,8as,9R,10S,12R,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-J]-1,2-benzodioxepin-10-yl] ester	ChEBI
Dihydroqinghasu hemsuccinate	ChEBI
Butanedioate, 1-[(3R,5as,6R,8as,9R,10S,12R,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-J]-1,2-benzodioxepin-10-yl] ester	Generator
Dihydroqinghasu hemsuccinic acid	Generator
Malartin	MeSH
Dihydroartemisinine-12-alpha-succinate	MeSH
Dihydroartemisinin, succinyl	MeSH
Succinyl dihydroartemisinin	MeSH
Malacef	MeSH
Sodium artesunate	MeSH
Dihydroartemisinine 12 alpha succinate	MeSH

Chemical Formula

C₁₉H₂₈O₈

Average Mass

384.4250 Da

Monoisotopic Mass

384.17842 Da

IUPAC Name

4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid

Traditional Name

4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O4

InChI Identifier

InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1

InChI Key

FIHJKUPKCHIPAT-AHIGJZGOSA-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 carvifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Artemisinins

Alternative Parents

Substituents

Artemisinin skeleton
Fatty acid ester
Heterocyclic fatty acid
Oxepane
Dicarboxylic acid or derivatives
Oxane
Fatty acyl
1,2,4-trioxane
Carboxylic acid ester
Dialkyl peroxide
Oxacycle
Carboxylic acid
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:63918 )
semisynthetic derivative (CHEBI:63918 )
sesquiterpenoid (CHEBI:63918 )
artemisinin derivative (CHEBI:63918 )
cyclic acetal (CHEBI:63918 )

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	2.35	ALOGPS
logP	3.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.95 m³·mol⁻¹	ChemAxon
Polarizability	39.48 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

HMDB0240267

DrugBank ID

DB09274

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Artesunate

METLIN ID

Not Available

PubChem Compound

6917864

PDB ID

Not Available

ChEBI ID

63918

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Artesunate (NP0137143)

MOL for NP0137143 (Artesunate)

3D MOL for NP0137143 (Artesunate)

3D SDF for NP0137143 (Artesunate)

3D-SDF for NP0137143 (Artesunate)

PDB for NP0137143 (Artesunate)

3D PDB for NP0137143 (Artesunate)

SMILES for NP0137143 (Artesunate)

INCHI for NP0137143 (Artesunate)

Structure for NP0137143 (Artesunate)

3D Structure for NP0137143 (Artesunate)