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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2018-04-09 20:47:50 UTC

Update Date

2022-03-07 03:18:15 UTC

HMDB ID

HMDB0240267

Secondary Accession Numbers

None

Metabolite 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. Based on a literature review a significant number of articles have been published on Artesunate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

HMDB0240267
     RDKit          3D
Artesunate
 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.6615   -0.2049    1.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3426   -0.3676    0.2369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1275   -1.7635   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -2.4376    0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604   -1.6282    0.3134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3604   -1.9016   -0.7490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1808   -2.5892   -1.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100   -0.6417   -1.1545 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0930   -0.4136   -0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671   -0.5414   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151   -0.8789   -1.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657   -0.2644    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149   -0.4094    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    0.5248   -0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0873    0.3330   -1.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    1.7346   -0.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3197    0.4127   -1.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    0.4635   -0.8947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2807    1.8326   -0.8379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    2.3782    0.3584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4205    3.8146    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0786    2.4972    1.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    1.2498    1.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361   -0.0127    1.2002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9387   -0.1270    0.4688 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0389    0.5007    1.2284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    1.7517    0.9506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5581   -0.5022    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0230    0.8606    0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518   -0.8200    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4102    0.3626   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175   -2.3653    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2630   -1.7584   -1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1267   -2.9936    1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -3.2768   -0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689   -1.8909    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -2.5933   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -2.2166   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740   -2.4150   -2.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081   -3.7019   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641   -0.9308   -2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1657   -0.9791    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1945    0.7706    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4402   -0.2606    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9949   -1.4694    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2658    2.6099   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6586    0.0089   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    4.5046    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223    3.7711   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211    4.1750    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209    2.8131    0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637    3.3168    1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202    1.3025    2.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838    1.2103    2.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -0.8439    1.9703 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  8 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 26 27  1  0
 24  2  1  0
 25  5  1  0
 25 18  1  0
 27 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  1
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  6
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  0
 18 47  1  6
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  1
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>
HMDB0240267

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0240267
     RDKit          3D
Artesunate
 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.6615   -0.2049    1.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3426   -0.3676    0.2369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1275   -1.7635   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -2.4376    0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604   -1.6282    0.3134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3604   -1.9016   -0.7490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1808   -2.5892   -1.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100   -0.6417   -1.1545 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0930   -0.4136   -0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671   -0.5414   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151   -0.8789   -1.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657   -0.2644    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149   -0.4094    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    0.5248   -0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0873    0.3330   -1.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    1.7346   -0.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3197    0.4127   -1.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    0.4635   -0.8947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2807    1.8326   -0.8379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    2.3782    0.3584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4205    3.8146    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0786    2.4972    1.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    1.2498    1.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361   -0.0127    1.2002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9387   -0.1270    0.4688 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0389    0.5007    1.2284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    1.7517    0.9506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5581   -0.5022    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0230    0.8606    0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518   -0.8200    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4102    0.3626   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175   -2.3653    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2630   -1.7584   -1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1267   -2.9936    1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -3.2768   -0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689   -1.8909    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -2.5933   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -2.2166   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740   -2.4150   -2.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081   -3.7019   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641   -0.9308   -2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1657   -0.9791    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1945    0.7706    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4402   -0.2606    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9949   -1.4694    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2658    2.6099   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6586    0.0089   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    4.5046    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223    3.7711   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211    4.1750    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209    2.8131    0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637    3.3168    1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202    1.3025    2.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838    1.2103    2.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -0.8439    1.9703 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  8 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 26 27  1  0
 24  2  1  0
 25  5  1  0
 25 18  1  0
 27 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  1
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  6
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  0
 18 47  1  6
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  1
M  END

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

COMPND    HMDB0240267
HETATM    1  C1  UNL     1      -4.662  -0.205   1.006  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.343  -0.368   0.237  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.128  -1.764  -0.230  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.900  -2.438   0.215  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.660  -1.628   0.313  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.360  -1.902  -0.749  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.181  -2.589  -1.966  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.110  -0.642  -1.154  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.093  -0.414  -0.185  1.00  0.00           O  
HETATM   10  C9  UNL     1       3.467  -0.541  -0.420  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.815  -0.879  -1.566  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.366  -0.264   0.710  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.815  -0.409   0.343  1.00  0.00           C  
HETATM   14  C12 UNL     1       6.208   0.525  -0.731  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.087   0.333  -1.952  1.00  0.00           O  
HETATM   16  O4  UNL     1       6.767   1.735  -0.325  1.00  0.00           O  
HETATM   17  O5  UNL     1       0.320   0.413  -1.448  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.924   0.463  -0.895  1.00  0.00           C  
HETATM   19  O6  UNL     1      -1.281   1.833  -0.838  1.00  0.00           O  
HETATM   20  C14 UNL     1      -0.864   2.378   0.358  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.421   3.815   0.047  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.079   2.497   1.245  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.450   1.250   1.940  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.236  -0.013   1.200  1.00  0.00           C  
HETATM   25  C19 UNL     1      -0.939  -0.127   0.469  1.00  0.00           C  
HETATM   26  O7  UNL     1       0.039   0.501   1.228  1.00  0.00           O  
HETATM   27  O8  UNL     1       0.194   1.752   0.951  1.00  0.00           O  
HETATM   28  H1  UNL     1      -4.558  -0.502   2.057  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.023   0.861   0.906  1.00  0.00           H  
HETATM   30  H3  UNL     1      -5.452  -0.820   0.529  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.410   0.363  -0.603  1.00  0.00           H  
HETATM   32  H5  UNL     1      -4.017  -2.365   0.127  1.00  0.00           H  
HETATM   33  H6  UNL     1      -3.263  -1.758  -1.352  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.127  -2.994   1.174  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.684  -3.277  -0.514  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.169  -1.891   1.300  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.172  -2.593  -0.365  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.125  -2.217  -2.335  1.00  0.00           H  
HETATM   39  H12 UNL     1       0.574  -2.415  -2.788  1.00  0.00           H  
HETATM   40  H13 UNL     1      -0.208  -3.702  -1.855  1.00  0.00           H  
HETATM   41  H14 UNL     1       1.664  -0.931  -2.097  1.00  0.00           H  
HETATM   42  H15 UNL     1       4.166  -0.979   1.537  1.00  0.00           H  
HETATM   43  H16 UNL     1       4.195   0.771   1.117  1.00  0.00           H  
HETATM   44  H17 UNL     1       6.440  -0.261   1.259  1.00  0.00           H  
HETATM   45  H18 UNL     1       5.995  -1.469   0.048  1.00  0.00           H  
HETATM   46  H19 UNL     1       6.266   2.610  -0.519  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.659   0.009  -1.592  1.00  0.00           H  
HETATM   48  H21 UNL     1      -1.268   4.505   0.024  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.122   3.771  -0.928  1.00  0.00           H  
HETATM   50  H23 UNL     1       0.321   4.175   0.788  1.00  0.00           H  
HETATM   51  H24 UNL     1      -2.921   2.813   0.586  1.00  0.00           H  
HETATM   52  H25 UNL     1      -1.964   3.317   1.991  1.00  0.00           H  
HETATM   53  H26 UNL     1      -3.520   1.303   2.241  1.00  0.00           H  
HETATM   54  H27 UNL     1      -1.884   1.210   2.911  1.00  0.00           H  
HETATM   55  H28 UNL     1      -2.237  -0.844   1.970  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   24   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   25   36
CONECT    6    7    8   37
CONECT    7   38   39   40
CONECT    8    9   17   41
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   15   16
CONECT   16   46
CONECT   17   18
CONECT   18   19   25   47
CONECT   19   20
CONECT   20   21   22   27
CONECT   21   48   49   50
CONECT   22   23   51   52
CONECT   23   24   53   54
CONECT   24   25   55
CONECT   25   26
CONECT   26   27
END

HMDB0240267
     RDKit          3D
Artesunate
 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.6615   -0.2049    1.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3426   -0.3676    0.2369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1275   -1.7635   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -2.4376    0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604   -1.6282    0.3134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3604   -1.9016   -0.7490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1808   -2.5892   -1.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100   -0.6417   -1.1545 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0930   -0.4136   -0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671   -0.5414   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151   -0.8789   -1.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657   -0.2644    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149   -0.4094    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    0.5248   -0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0873    0.3330   -1.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    1.7346   -0.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3197    0.4127   -1.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    0.4635   -0.8947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2807    1.8326   -0.8379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    2.3782    0.3584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4205    3.8146    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0786    2.4972    1.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    1.2498    1.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361   -0.0127    1.2002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9387   -0.1270    0.4688 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0389    0.5007    1.2284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    1.7517    0.9506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5581   -0.5022    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0230    0.8606    0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518   -0.8200    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4102    0.3626   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175   -2.3653    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2630   -1.7584   -1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1267   -2.9936    1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -3.2768   -0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689   -1.8909    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -2.5933   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -2.2166   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740   -2.4150   -2.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081   -3.7019   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641   -0.9308   -2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1657   -0.9791    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1945    0.7706    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4402   -0.2606    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9949   -1.4694    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2658    2.6099   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6586    0.0089   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    4.5046    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223    3.7711   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211    4.1750    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209    2.8131    0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637    3.3168    1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202    1.3025    2.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838    1.2103    2.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -0.8439    1.9703 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  8 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 26 27  1  0
 24  2  1  0
 25  5  1  0
 25 18  1  0
 27 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  1
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  6
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  0
 18 47  1  6
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  1
M  END

View in JSmol View Stereo Labels

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	HMDB
Dihydroartemisinine-12-alpha-succinate	HMDB
Dihydroartemisinin, succinyl	HMDB
Succinyl dihydroartemisinin	HMDB
Malacef	HMDB
Sodium artesunate	HMDB
Dihydroartemisinine 12 alpha succinate	HMDB

Chemical Formula

C₁₉H₂₈O₈

Average Molecular Weight

384.425

Monoisotopic Molecular Weight

384.178417862

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

88495-63-0

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

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 )

Ontology

Not Available

Exogenous (HMDB: HMDB0240267)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	191.812	31661259
AllCCS	[M+H]+	189.512	31661259
DeepCCS	[M-2H]-	220.814	30932474
DeepCCS	[M+Na]+	194.834	30932474
AllCCS	[M+H]+	189.5	32859911
AllCCS	[M+H-H2O]+	187.0	32859911
AllCCS	[M+NH4]+	191.8	32859911
AllCCS	[M+Na]+	192.5	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	192.2	32859911
AllCCS	[M+HCOO]-	192.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.69 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0549 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2578.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	232.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	179.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	583.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	538.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1101.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	471.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1283.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	219.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	231.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	40.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artesunate	[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	4159.3	Standard polar	33892256
Artesunate	[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	2591.2	Standard non polar	33892256
Artesunate	[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	2695.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artesunate,1TMS,isomer #1	C[C@@H]1CC[C@H]2[C@@H](C)[C@H](OC(=O)CCC(=O)O[Si](C)(C)C)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO4	2722.7	Semi standard non polar	33892256
Artesunate,1TBDMS,isomer #1	C[C@@H]1CC[C@H]2[C@@H](C)[C@H](OC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO4	2968.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Artesunate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artesunate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artesunate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artesunate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artesunate GC-MS ("Artesunate,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 10V, Positive-QTOF	splash10-00kr-2459000000-709f5cba7340e7cb0802	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 20V, Positive-QTOF	splash10-014i-7392000000-6aade85a0d3ce77db50e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 40V, Positive-QTOF	splash10-0a4l-9050000000-c432eeabf339e3f7593b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 10V, Negative-QTOF	splash10-000t-9034000000-4fd3316b534c1c9695e5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 20V, Negative-QTOF	splash10-00m0-4191000000-c1b630ac82bbe1ed3eec	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 40V, Negative-QTOF	splash10-0a4i-8590000000-1aec7778a60c3c83b96f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 10V, Positive-QTOF	splash10-000i-0059000000-c401777b25dc78e3e3d6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 20V, Positive-QTOF	splash10-014r-5091000000-a70049f2a7891ca11fda	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 40V, Positive-QTOF	splash10-0a4u-9040000000-7170837027905000882c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 10V, Negative-QTOF	splash10-001i-0094000000-8eadce9bbd79f8190164	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 20V, Negative-QTOF	splash10-0089-9072000000-f24fb27ab8342500be33	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artesunate 40V, Negative-QTOF	splash10-0ab9-9010000000-bde61be07af13e719ef6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09274

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293084

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1481341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Artesunate (HMDB0240267)

MOL for HMDB0240267 (Artesunate)

3D MOL for HMDB0240267 (Artesunate)

3D SDF for HMDB0240267 (Artesunate)

3D-SDF for HMDB0240267 (Artesunate)

PDB for HMDB0240267 (Artesunate)

3D PDB for HMDB0240267 (Artesunate)

SMILES for HMDB0240267 (Artesunate)

INCHI for HMDB0240267 (Artesunate)

Structure for HMDB0240267 (Artesunate)

3D Structure for HMDB0240267 (Artesunate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra