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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 16:57:59 UTC

Update Date

2021-09-14 15:19:35 UTC

HMDB ID

HMDB0060570

Secondary Accession Numbers

HMDB60570

Metabolite Identification

Common Name

Deoxydihydro-artemisinin

Description

Deoxydihydro-artemisinin 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

HMDB0060570
     RDKit          3D
Deoxydihydro-artemisinin
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.9453   -2.1708   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6138   -1.5631   -0.5824 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5541   -2.5889   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285   -2.0094   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.7793    0.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3444   -0.2604    0.4900 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3139   -1.4438    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6130    0.6058   -0.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710    1.4711   -0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    1.3563   -1.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.8987   -1.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4794    2.0493   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    2.2915    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    3.7203    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1944    2.0081    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623    0.7067   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4268   -0.2806    0.1723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0328    0.2450    0.1558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0072    1.3700    0.9998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0267   -3.2350   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -2.1533    1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7794   -1.6054   -0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -1.4144   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116   -3.3910   -1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7824   -3.0510    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919   -1.8764   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024   -2.7846    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -1.0672    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5737    0.2505    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -0.9941    0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2031   -1.9586   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681   -2.1296    1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -0.0142   -1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082    1.7937    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.2673   -1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    3.9438    0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132    3.8658    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256    4.4076    0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    1.8684    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    2.8405    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3395    0.9763   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4637    0.3479   -0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6649   -0.5134    1.2532 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  1
 17  2  1  0
 18  5  1  0
 18 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  1
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  6
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
M  END


  Mrv0541 06151309572D          

 19 22  0  0  0  0            999 V2000
    0.3917    2.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1236    1.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901   -0.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8147    2.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5787    2.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4389    0.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1448    2.2088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5354    1.2614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2475    1.4198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7217    1.5075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7624    0.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.0975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1790   -0.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    0.9734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5650    0.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -0.1380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738   -0.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222    0.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  6  0  0  0
  8  4  1  0  0  0  0
  9  2  1  1  0  0  0
 10  6  1  1  0  0  0
 10  8  1  0  0  0  0
 11  5  1  1  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 13 18  1  6  0  0  0
 18 14  1  0  0  0  0
 19 14  1  0  0  0  0
 15 19  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0060570

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12?,13-,14?,15-/m1/s1

> <INCHI_KEY>
JQGOBHOUYKYFPD-YONALABKSA-N

> <FORMULA>
C15H24O4

> <MOLECULAR_WEIGHT>
268.3487

> <EXACT_MASS>
268.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.42341180778026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0⁴,¹³.0⁸,¹³]pentadecan-10-ol

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.654095920333333

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.115195908575728

> <JCHEM_PKA_STRONGEST_BASIC>
-4.019106698692424

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
68.828

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0⁴,¹³.0⁸,¹³]pentadecan-10-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060570
     RDKit          3D
Deoxydihydro-artemisinin
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.9453   -2.1708   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6138   -1.5631   -0.5824 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5541   -2.5889   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285   -2.0094   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.7793    0.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3444   -0.2604    0.4900 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3139   -1.4438    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6130    0.6058   -0.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710    1.4711   -0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    1.3563   -1.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.8987   -1.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4794    2.0493   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    2.2915    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    3.7203    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1944    2.0081    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623    0.7067   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4268   -0.2806    0.1723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0328    0.2450    0.1558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0072    1.3700    0.9998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0267   -3.2350   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -2.1533    1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7794   -1.6054   -0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -1.4144   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116   -3.3910   -1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7824   -3.0510    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919   -1.8764   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024   -2.7846    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -1.0672    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5737    0.2505    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -0.9941    0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2031   -1.9586   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681   -2.1296    1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -0.0142   -1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082    1.7937    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.2673   -1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    3.9438    0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132    3.8658    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256    4.4076    0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    1.8684    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    2.8405    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3395    0.9763   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4637    0.3479   -0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6649   -0.5134    1.2532 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  1
 17  2  1  0
 18  5  1  0
 18 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  1
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  6
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
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       0.731   4.752   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.697   3.434   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.475  -1.574   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.387   4.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.814   4.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.851   1.989   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.819   0.455   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.137   4.123   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.599   2.355   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.329   2.650   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.081   2.814   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.023   0.863   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.548   0.182   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.201  -0.216   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.926   1.817   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.521   0.508   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.993  -0.258   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.498  -0.975   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.028   1.077   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    7   10                                                       
CONECT    7    6   14                                                       
CONECT    8    1    4   10                                                  
CONECT    9    2   11   12                                                  
CONECT   10    6    8   15                                                  
CONECT   11    5    9   15                                                  
CONECT   12    9   16   17                                                  
CONECT   13   15   17   18                                                  
CONECT   14    3    7   18   19                                             
CONECT   15   10   11   13   19                                             
CONECT   16   12                                                            
CONECT   17   12   13                                                       
CONECT   18   13   14                                                       
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0060570
HETATM    1  C1  UNL     1      -2.945  -2.171  -0.123  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.614  -1.563  -0.582  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.554  -2.589  -0.258  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.829  -2.009  -0.258  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.944  -0.779   0.572  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.344  -0.260   0.490  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.314  -1.444   0.420  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.613   0.606  -0.692  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.671   1.471  -0.315  1.00  0.00           O  
HETATM   10  O2  UNL     1       1.614   1.356  -1.162  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.347   0.899  -1.153  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.479   2.049  -1.081  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.703   2.292   0.252  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.360   3.720   0.608  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.194   2.008   0.490  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.462   0.707  -0.279  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.427  -0.281   0.172  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.033   0.245   0.156  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.007   1.370   1.000  1.00  0.00           O  
HETATM   20  H1  UNL     1      -3.027  -3.235  -0.424  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.918  -2.153   1.001  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.779  -1.605  -0.533  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.677  -1.414  -1.666  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.612  -3.391  -1.019  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.782  -3.051   0.732  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.192  -1.876  -1.299  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.502  -2.785   0.195  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.735  -1.067   1.633  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.574   0.251   1.448  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.345  -0.994   0.397  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.203  -1.959  -0.574  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.168  -2.130   1.266  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.058  -0.014  -1.523  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.408   1.794   0.605  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.038   0.267  -1.999  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.614   3.944   0.115  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.213   3.866   1.680  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.126   4.408   0.239  1.00  0.00           H  
HETATM   39  H20 UNL     1      -2.388   1.868   1.563  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.744   2.841   0.029  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.340   0.976  -1.352  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.464   0.348  -0.024  1.00  0.00           H  
HETATM   43  H24 UNL     1      -1.665  -0.513   1.253  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   17   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   18   28
CONECT    6    7    8   29
CONECT    7   30   31   32
CONECT    8    9   10   33
CONECT    9   34
CONECT   10   11
CONECT   11   12   18   35
CONECT   12   13
CONECT   13   14   15   19
CONECT   14   36   37   38
CONECT   15   16   39   40
CONECT   16   17   41   42
CONECT   17   18   43
CONECT   18   19
END

HMDB0060570
     RDKit          3D
Deoxydihydro-artemisinin
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.9453   -2.1708   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6138   -1.5631   -0.5824 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5541   -2.5889   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285   -2.0094   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.7793    0.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3444   -0.2604    0.4900 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3139   -1.4438    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6130    0.6058   -0.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710    1.4711   -0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    1.3563   -1.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.8987   -1.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4794    2.0493   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030    2.2915    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    3.7203    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1944    2.0081    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623    0.7067   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4268   -0.2806    0.1723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0328    0.2450    0.1558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0072    1.3700    0.9998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0267   -3.2350   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -2.1533    1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7794   -1.6054   -0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -1.4144   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116   -3.3910   -1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7824   -3.0510    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919   -1.8764   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024   -2.7846    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -1.0672    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5737    0.2505    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -0.9941    0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2031   -1.9586   -0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681   -2.1296    1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -0.0142   -1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082    1.7937    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.2673   -1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    3.9438    0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132    3.8658    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256    4.4076    0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    1.8684    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7439    2.8405    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3395    0.9763   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4637    0.3479   -0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6649   -0.5134    1.2532 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  1
 17  2  1  0
 18  5  1  0
 18 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  1
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  6
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₄

Average Molecular Weight

268.3487

Monoisotopic Molecular Weight

268.167459256

IUPAC Name

(4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0⁴,¹³.0⁸,¹³]pentadecan-10-ol

Traditional Name

(4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.0⁴,¹³.0⁸,¹³]pentadecan-10-ol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4

InChI Identifier

InChI=1S/C15H24O4/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12?,13-,14?,15-/m1/s1

InChI Key

JQGOBHOUYKYFPD-YONALABKSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxolopyrans

Sub Class

Not Available

Direct Parent

Dioxolopyrans

Alternative Parents

Substituents

Dioxolopyran
Ketal
Oxepane
Oxane
Meta-dioxolane
Hemiacetal
Oxacycle
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: HMDB0060570)
Liver (HMDB: HMDB0060570)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060570)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060570)

Cellular substructure

Cytoplasm (HMDB: HMDB0060570)
Membrane (HMDB: HMDB0060570)

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	2.23 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.65	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.83 m³·mol⁻¹	ChemAxon
Polarizability	29.42 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]+	159.813	31661259
DarkChem	[M-H]-	159.823	31661259
DeepCCS	[M-2H]-	200.627	30932474
DeepCCS	[M+Na]+	175.413	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.5	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	171.4	32859911
AllCCS	[M+HCOO]-	171.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxydihydro-artemisinin	C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4	2772.7	Standard polar	33892256
Deoxydihydro-artemisinin	C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4	1882.6	Standard non polar	33892256
Deoxydihydro-artemisinin	C[C@@H]1CC[C@H]2[C@@H](C)C(O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4	1942.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deoxydihydro-artemisinin,1TMS,isomer #1	C[C@@H]1CC[C@H]2[C@@H](C)C(O[Si](C)(C)C)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4	1927.1	Semi standard non polar	33892256
Deoxydihydro-artemisinin,1TBDMS,isomer #1	C[C@@H]1CC[C@H]2[C@@H](C)C(O[Si](C)(C)C(C)(C)C)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23O4	2183.4	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 - Deoxydihydro-artemisinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zi0-6290000000-bd14a8d092a3bee64c65	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxydihydro-artemisinin GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-9223000000-7d969d6919602d3f4e3c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxydihydro-artemisinin 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 - Deoxydihydro-artemisinin 10V, Positive-QTOF	splash10-014i-0190000000-e455e0a72274f43bb7fc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 20V, Positive-QTOF	splash10-014i-1090000000-5ef1625041d20f32efda	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 40V, Positive-QTOF	splash10-00kf-9110000000-31dcde3255d244134837	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 10V, Negative-QTOF	splash10-00xr-0090000000-c3d5d3f5efc5c3db114f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 20V, Negative-QTOF	splash10-01ba-0290000000-dd4313ddfc322d5bd263	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 40V, Negative-QTOF	splash10-03xu-1900000000-1e26c3fb2ac2255ba21c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 10V, Positive-QTOF	splash10-014i-0090000000-6dad1a58afcfbbf57a53	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 20V, Positive-QTOF	splash10-014i-0090000000-082aa5454f2335a9e6ab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 40V, Positive-QTOF	splash10-014i-0090000000-002e35597a873c8c066f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 10V, Negative-QTOF	splash10-014i-0090000000-9699a607ea019e68b5c3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 20V, Negative-QTOF	splash10-014i-0090000000-4bf9a5034aa186a4a153	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxydihydro-artemisinin 40V, Negative-QTOF	splash10-014i-1090000000-a1b91a64300f5bec5254	2021-10-12	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

496630

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

Not Available

Showing metabocard for Deoxydihydro-artemisinin (HMDB0060570)

MOL for HMDB0060570 (Deoxydihydro-artemisinin)

3D MOL for HMDB0060570 (Deoxydihydro-artemisinin)

3D SDF for HMDB0060570 (Deoxydihydro-artemisinin)

3D-SDF for HMDB0060570 (Deoxydihydro-artemisinin)

PDB for HMDB0060570 (Deoxydihydro-artemisinin)

3D PDB for HMDB0060570 (Deoxydihydro-artemisinin)

SMILES for HMDB0060570 (Deoxydihydro-artemisinin)

INCHI for HMDB0060570 (Deoxydihydro-artemisinin)

Structure for HMDB0060570 (Deoxydihydro-artemisinin)

3D Structure for HMDB0060570 (Deoxydihydro-artemisinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra