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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:24:02 UTC

Update Date

2021-09-14 15:19:35 UTC

HMDB ID

HMDB0060593

Secondary Accession Numbers

HMDB60593

Metabolite Identification

Common Name

Alpha-dihydroartemisinin

Description

Alpha-dihydroartemisinin is a metabolite of artemisinin. Artemisinin, also known as Qinghaosu, and its derivatives are a group of drugs that possess the most rapid action of all current drugs against Plasmodium falciparum malaria. Treatments containing an artemisinin derivative (artemisinin-combination therapies, ACTs) are now standard treatment worldwide for P. falciparum malaria. The starting compound artemisinin is isolated from the plant Artemisia annua, sweet wormwood, an herb employed in Chinese traditional medicine. (Wikipedia)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0060593
     RDKit          3D
Alpha-dihydroartemisinin
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.4905   -0.7814    0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9874   -0.6925    0.5527 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4730   -2.1181    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.1676    0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5308   -1.3704   -0.8234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0096   -1.5133   -0.9349 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5209   -2.7339   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6562   -0.3061   -0.2566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9559   -0.7015    0.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784   -0.0987    0.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7284    0.5230    0.6909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0195    1.9070    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352    2.5537   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125    4.0378   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2063    2.4529    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.4891   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3933    0.0919   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1004    0.0828   -0.5810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5382    0.8393   -1.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987    2.1079   -1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0005    0.1749    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -1.3736   -0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606   -1.4009    1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8107   -0.2653    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -2.4656   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805   -2.7917    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085   -3.2315    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4076   -1.7820    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080   -1.7230   -1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3481   -1.6396   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178   -2.7240   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513   -3.6715   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -2.5938    0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338    0.5586   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194   -0.8237   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    0.3399    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715    4.6811   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    4.2654    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4389    4.2527   -0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    2.1491    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7197    3.4453    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    1.8530   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    1.6059   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7151   -0.4415   -1.5293 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 19 20  1  0
 17  2  1  0
 18  5  1  0
 18 11  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  6
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  6
  9 35  1  0
 11 36  1  1
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
M  END


  Mrv0541 06151310242D          

 20 23  0  0  1  0            999 V2000
    4.4084   -0.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360   -0.4388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0337   -0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4834   -0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    0.5801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7641    0.8073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2170    0.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4824    1.5790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7182    1.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710    2.0258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668    1.7616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8776    1.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902    1.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3595    2.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1645    1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6871    0.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8498    0.3887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3022    1.0678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5353    1.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2445    2.4460    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  1  1  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  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
  5 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060593

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14?,15-/m1/s1

> <INCHI_KEY>
BJDCWCLMFKKGEE-KXTPALSWSA-N

> <FORMULA>
C15H24O5

> <MOLECULAR_WEIGHT>
284.3481

> <EXACT_MASS>
284.162373878

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.080427888832986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-ol

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.8382655166666666

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.114969558644466

> <JCHEM_PKA_STRONGEST_BASIC>
-4.060712315048911

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
69.9093

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artenimol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060593
     RDKit          3D
Alpha-dihydroartemisinin
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.4905   -0.7814    0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9874   -0.6925    0.5527 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4730   -2.1181    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.1676    0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5308   -1.3704   -0.8234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0096   -1.5133   -0.9349 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5209   -2.7339   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6562   -0.3061   -0.2566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9559   -0.7015    0.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784   -0.0987    0.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7284    0.5230    0.6909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0195    1.9070    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352    2.5537   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125    4.0378   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2063    2.4529    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.4891   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3933    0.0919   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1004    0.0828   -0.5810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5382    0.8393   -1.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987    2.1079   -1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0005    0.1749    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -1.3736   -0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606   -1.4009    1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8107   -0.2653    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -2.4656   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805   -2.7917    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085   -3.2315    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4076   -1.7820    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080   -1.7230   -1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3481   -1.6396   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178   -2.7240   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513   -3.6715   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -2.5938    0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338    0.5586   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194   -0.8237   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    0.3399    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715    4.6811   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    4.2654    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4389    4.2527   -0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    2.1491    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7197    3.4453    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    1.8530   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    1.6059   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7151   -0.4415   -1.5293 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 19 20  1  0
 17  2  1  0
 18  5  1  0
 18 11  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  6
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  6
  9 35  1  0
 11 36  1  1
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       8.229  -1.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.974  -0.819   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.663  -1.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.636  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.811   1.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.293   1.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.272   0.403   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.767   2.947   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.341   3.424   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.052   3.782   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.538   3.288   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.238   2.886   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.755   3.274   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.004   4.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.640   2.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.749   0.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.186   0.726   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.164   1.993   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.599   3.727   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.923   4.566   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   20                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17    5   11   19                                             
CONECT   19   18   20                                                       
CONECT   20   19   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0060593
HETATM    1  C1  UNL     1       3.491  -0.781   0.363  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.987  -0.692   0.553  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.473  -2.118   0.419  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.031  -2.168   0.360  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.531  -1.370  -0.823  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.010  -1.513  -0.935  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.521  -2.734  -0.157  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.656  -0.306  -0.257  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.956  -0.701   0.069  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.978  -0.099   0.923  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.728   0.523   0.691  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.019   1.907   0.700  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.235   2.554  -0.232  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.613   4.038  -0.165  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.206   2.453   0.251  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.903   1.489  -0.693  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.393   0.092  -0.585  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.100   0.083  -0.581  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.538   0.839  -1.662  1.00  0.00           O  
HETATM   20  O5  UNL     1      -0.399   2.108  -1.512  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.001   0.175   0.435  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.684  -1.374  -0.530  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.861  -1.401   1.232  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.811  -0.265   1.539  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.840  -2.466  -0.591  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.881  -2.792   1.169  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.309  -3.232   0.213  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.408  -1.782   1.326  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.008  -1.723  -1.714  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.348  -1.640  -1.963  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.618  -2.724  -0.224  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.151  -3.672  -0.568  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.275  -2.594   0.926  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.734   0.559  -0.912  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.419  -0.824  -0.816  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.136   0.340   1.599  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.272   4.681  -0.295  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.995   4.265   0.873  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.439   4.253  -0.845  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.282   2.149   1.297  1.00  0.00           H  
HETATM   41  H21 UNL     1       1.720   3.445   0.095  1.00  0.00           H  
HETATM   42  H22 UNL     1       1.638   1.853  -1.730  1.00  0.00           H  
HETATM   43  H23 UNL     1       2.983   1.606  -0.603  1.00  0.00           H  
HETATM   44  H24 UNL     1       1.715  -0.441  -1.529  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   17   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   18   29
CONECT    6    7    8   30
CONECT    7   31   32   33
CONECT    8    9   10   34
CONECT    9   35
CONECT   10   11
CONECT   11   12   18   36
CONECT   12   13
CONECT   13   14   15   20
CONECT   14   37   38   39
CONECT   15   16   40   41
CONECT   16   17   42   43
CONECT   17   18   44
CONECT   18   19
CONECT   19   20
END

HMDB0060593
     RDKit          3D
Alpha-dihydroartemisinin
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.4905   -0.7814    0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9874   -0.6925    0.5527 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4730   -2.1181    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.1676    0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5308   -1.3704   -0.8234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0096   -1.5133   -0.9349 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5209   -2.7339   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6562   -0.3061   -0.2566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9559   -0.7015    0.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784   -0.0987    0.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7284    0.5230    0.6909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0195    1.9070    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352    2.5537   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125    4.0378   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2063    2.4529    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.4891   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3933    0.0919   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1004    0.0828   -0.5810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5382    0.8393   -1.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987    2.1079   -1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0005    0.1749    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -1.3736   -0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606   -1.4009    1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8107   -0.2653    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -2.4656   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805   -2.7917    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085   -3.2315    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4076   -1.7820    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080   -1.7230   -1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3481   -1.6396   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178   -2.7240   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513   -3.6715   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -2.5938    0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338    0.5586   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194   -0.8237   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    0.3399    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715    4.6811   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945    4.2654    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4389    4.2527   -0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    2.1491    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7197    3.4453    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    1.8530   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    1.6059   -0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7151   -0.4415   -1.5293 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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 19 20  1  0
 17  2  1  0
 18  5  1  0
 18 11  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  6
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  6
  9 35  1  0
 11 36  1  1
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
a-Dihydroartemisinin	Generator
Α-dihydroartemisinin	Generator
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12ar*))-isomer	HMDB
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12ar*))-isomer	HMDB
Dihydroartemisinine	HMDB
Dihydroqinghaosu	HMDB
Dihydroquinghaosu	HMDB
Dihydroartemisinin	HMDB
3alpha-Hydroxydeoxydihydroartemisinin	MeSH
9alpha-Hydroxydeoxyartemisinin	MeSH
8alpha-Hydroxydeoxyartemisinin	MeSH

Chemical Formula

C₁₅H₂₄O₅

Average Molecular Weight

284.3481

Monoisotopic Molecular Weight

284.162373878

IUPAC Name

(4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-ol

Traditional Name

artenimol

CAS Registry Number

81496-81-3

SMILES

C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

InChI Identifier

InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14?,15-/m1/s1

InChI Key

BJDCWCLMFKKGEE-KXTPALSWSA-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
Oxepane
1,2,4-trioxane
Oxane
Dialkyl peroxide
Hemiacetal
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060593)
Liver (HMDB: HMDB0060593)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060593)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060593)

Cellular substructure

Cytoplasm (HMDB: HMDB0060593)
Membrane (HMDB: HMDB0060593)

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
Water Solubility	3.16 g/L	ALOGPS
logP	2.25	ALOGPS
logP	2.84	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.91 m³·mol⁻¹	ChemAxon
Polarizability	30.08 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
DarkChem	[M+H]+	166.594	31661259
DarkChem	[M-H]-	158.462	31661259
DeepCCS	[M-2H]-	203.255	30932474
DeepCCS	[M+Na]+	178.183	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.4	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	173.9	32859911
AllCCS	[M+Na-2H]-	173.8	32859911
AllCCS	[M+HCOO]-	173.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alpha-dihydroartemisinin	C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4	3034.8	Standard polar	33892256
Alpha-dihydroartemisinin	C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4	1964.9	Standard non polar	33892256
Alpha-dihydroartemisinin	C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4	1966.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alpha-dihydroartemisinin,1TMS,isomer #1	C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O[Si](C)(C)C)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4	2076.0	Semi standard non polar	33892256
Alpha-dihydroartemisinin,1TBDMS,isomer #1	C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4	2338.9	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 - Alpha-dihydroartemisinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-05r0-5090000000-2c3d5f82fba0d14e9a07	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-dihydroartemisinin GC-MS (1 TMS) - 70eV, Positive	splash10-009l-9044000000-2064a50503f409cfea9d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-dihydroartemisinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Alpha-dihydroartemisinin 10V, Positive-QTOF	splash10-000i-0090000000-957508038617389e634a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Positive-QTOF	splash10-000i-0090000000-2f125a25192ab9dac3ff	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Positive-QTOF	splash10-00kf-9120000000-c175280a233f4849aab7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 10V, Negative-QTOF	splash10-0019-0090000000-73c4d85a7f84863d34b5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Negative-QTOF	splash10-0019-0090000000-03701af12b5b9b5f19d1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Negative-QTOF	splash10-004i-2930000000-61834bfa8e89873f8831	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 10V, Positive-QTOF	splash10-000i-0090000000-dac20fbea8167508deeb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Positive-QTOF	splash10-000i-0090000000-844f91982253be80d135	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Positive-QTOF	splash10-056r-2090000000-acb28e00350215015bd3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 10V, Negative-QTOF	splash10-001i-0090000000-1345a6d7d83d2353d1d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 20V, Negative-QTOF	splash10-001i-0090000000-4ecf30250c7b7c1b4824	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-dihydroartemisinin 40V, Negative-QTOF	splash10-053r-1090000000-987e60b5c92178e5b805	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Not Available

METLIN ID

Not Available

PubChem Compound

456410

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Alpha-dihydroartemisinin (HMDB0060593)

MOL for HMDB0060593 (Alpha-dihydroartemisinin)

3D MOL for HMDB0060593 (Alpha-dihydroartemisinin)

3D SDF for HMDB0060593 (Alpha-dihydroartemisinin)

3D-SDF for HMDB0060593 (Alpha-dihydroartemisinin)

PDB for HMDB0060593 (Alpha-dihydroartemisinin)

3D PDB for HMDB0060593 (Alpha-dihydroartemisinin)

SMILES for HMDB0060593 (Alpha-dihydroartemisinin)

INCHI for HMDB0060593 (Alpha-dihydroartemisinin)

Structure for HMDB0060593 (Alpha-dihydroartemisinin)

3D Structure for HMDB0060593 (Alpha-dihydroartemisinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra