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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 16:57:55 UTC

Update Date

2021-09-14 15:19:36 UTC

HMDB ID

HMDB0060569

Secondary Accession Numbers

HMDB60569

Metabolite Identification

Common Name

Deoxyartemsinin

Description

Deoxyartemsinin 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

HMDB0060569
     RDKit          3D
Deoxyartemsinin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.2579    3.1058   -1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    2.4048   -0.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5397    2.4321   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2864    1.3756    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    0.0139    0.3649 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4370   -0.0495   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5290    1.0521   -0.1135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2351    0.8076    1.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035    0.1584    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009   -1.1458    0.2080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4577   -2.1702    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442   -0.9752   -1.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235   -1.5894    0.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1917   -1.3891   -0.4577 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7586   -2.4303   -0.3582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587   -2.1714   -0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384   -2.9121   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -0.9517   -0.2101 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6944   -1.4204    0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2358    4.0757   -1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0473    2.4574   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    3.1935   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663    3.0407    0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    3.3854   -0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641    1.4877    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270   -0.1882    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7648    0.1628   -1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3371    1.0109   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    0.2557    1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653    1.8153    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777    0.8438    0.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0265   -0.0564    1.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0522   -3.2008    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3201   -2.1283   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -1.9669    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322   -1.5358   -1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -1.5768   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -0.4772   -1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -2.2154    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -1.9227    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164   -0.6053    1.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18  5  1  0
 14  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  7 28  1  6
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  6
 18 38  1  6
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  END

  Mrv0541 06151309572D          

 19 21  0  0  0  0            999 V2000
    2.8768   -1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783    1.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2362    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0740   -0.5144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8783    1.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    1.3394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0740    1.3394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  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  6  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  3  1  1  0  0  0
 15  7  1  0  0  0  0
 16 13  2  0  0  0  0
 15 17  1  6  0  0  0
 18 13  1  0  0  0  0
 14 18  1  1  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060569

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C23

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8-4-5-11-9(2)13(16)18-14-12(11)10(8)6-7-15(3,17)19-14/h4-5,8-12,14,17H,6-7H2,1-3H3/t8-,9-,10+,11-,12?,14+,15+/m1/s1

> <INCHI_KEY>
ZHHCFKHSMKRNCX-CRBWWJEESA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.859712014866098

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.0⁵,¹⁴]tetradec-6-en-3-one

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
2.217351064

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.263174412330688

> <JCHEM_PKA_STRONGEST_BASIC>
-3.995887512046555

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
70.9852

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.0⁵,¹⁴]tetradec-6-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060569
     RDKit          3D
Deoxyartemsinin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.2579    3.1058   -1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    2.4048   -0.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5397    2.4321   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2864    1.3756    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    0.0139    0.3649 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4370   -0.0495   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5290    1.0521   -0.1135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2351    0.8076    1.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035    0.1584    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009   -1.1458    0.2080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4577   -2.1702    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442   -0.9752   -1.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235   -1.5894    0.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1917   -1.3891   -0.4577 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7586   -2.4303   -0.3582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587   -2.1714   -0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384   -2.9121   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -0.9517   -0.2101 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6944   -1.4204    0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2358    4.0757   -1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0473    2.4574   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    3.1935   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663    3.0407    0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    3.3854   -0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641    1.4877    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270   -0.1882    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7648    0.1628   -1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3371    1.0109   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    0.2557    1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653    1.8153    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777    0.8438    0.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0265   -0.0564    1.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0522   -3.2008    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3201   -2.1283   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -1.9669    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322   -1.5358   -1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -1.5768   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -0.4772   -1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -2.2154    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -1.9227    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164   -0.6053    1.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18  5  1  0
 14  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  7 28  1  6
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  6
 18 38  1  6
 19 39  1  0
 19 40  1  0
 19 41  1  0
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       5.370  -3.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.373   3.697   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.373  -0.617   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.041   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.871  -0.960   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.373   2.157   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.874   2.500   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.871   2.500   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    7   10                                                       
CONECT    7    6   15                                                       
CONECT    8    1    4   10                                                  
CONECT    9    2   11   13                                                  
CONECT   10    6    8   12                                                  
CONECT   11    5    9   12                                                  
CONECT   12   10   11   14                                                  
CONECT   13    9   16   18                                                  
CONECT   14   12   18   19                                                  
CONECT   15    3    7   17   19                                             
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18   13   14                                                       
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060569
HETATM    1  C1  UNL     1      -0.258   3.106  -1.513  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.079   2.405  -0.197  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.540   2.432  -0.026  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.286   1.376   0.226  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.702   0.014   0.365  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.437  -0.050  -0.464  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.529   1.052  -0.113  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.235   0.808   1.199  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.604   0.158   0.974  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.401  -1.146   0.208  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.458  -2.170   0.636  1.00  0.00           C  
HETATM   12  O1  UNL     1      -2.544  -0.975  -1.150  1.00  0.00           O  
HETATM   13  O2  UNL     1      -1.123  -1.589   0.547  1.00  0.00           O  
HETATM   14  C12 UNL     1      -0.192  -1.389  -0.458  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.759  -2.430  -0.358  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.059  -2.171  -0.740  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.738  -2.912  -1.520  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.710  -0.952  -0.210  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.694  -1.420   0.862  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.236   4.076  -1.544  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.047   2.457  -2.371  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.360   3.194  -1.547  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.366   3.041   0.599  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.041   3.385  -0.113  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.364   1.488   0.337  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.527  -0.188   1.433  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.765   0.163  -1.525  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.337   1.011  -0.903  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.647   0.256   1.929  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.465   1.815   1.633  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.278   0.844   0.448  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.027  -0.056   1.971  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.052  -3.201   0.555  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.320  -2.128  -0.088  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.851  -1.967   1.632  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.232  -1.536  -1.558  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.738  -1.577  -1.428  1.00  0.00           H  
HETATM   38  H19 UNL     1       3.331  -0.477  -1.008  1.00  0.00           H  
HETATM   39  H20 UNL     1       3.148  -2.215   1.440  1.00  0.00           H  
HETATM   40  H21 UNL     1       4.538  -1.923   0.327  1.00  0.00           H  
HETATM   41  H22 UNL     1       4.016  -0.605   1.517  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    7   23
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6   18   26
CONECT    6    7   14   27
CONECT    7    8   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   12   13
CONECT   11   33   34   35
CONECT   12   36
CONECT   13   14
CONECT   14   15   37
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   38
CONECT   19   39   40   41
END

HMDB0060569
     RDKit          3D
Deoxyartemsinin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.2579    3.1058   -1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    2.4048   -0.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5397    2.4321   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2864    1.3756    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    0.0139    0.3649 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4370   -0.0495   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5290    1.0521   -0.1135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2351    0.8076    1.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035    0.1584    0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009   -1.1458    0.2080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4577   -2.1702    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442   -0.9752   -1.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235   -1.5894    0.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1917   -1.3891   -0.4577 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7586   -2.4303   -0.3582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587   -2.1714   -0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384   -2.9121   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -0.9517   -0.2101 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6944   -1.4204    0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2358    4.0757   -1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0473    2.4574   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    3.1935   -1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663    3.0407    0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    3.3854   -0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641    1.4877    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270   -0.1882    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7648    0.1628   -1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3371    1.0109   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    0.2557    1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653    1.8153    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777    0.8438    0.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0265   -0.0564    1.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0522   -3.2008    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3201   -2.1283   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -1.9669    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322   -1.5358   -1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -1.5768   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -0.4772   -1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484   -2.2154    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -1.9227    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164   -0.6053    1.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18  5  1  0
 14  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  7 28  1  6
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  6
 18 38  1  6
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Molecular Weight

266.3328

Monoisotopic Molecular Weight

266.151809192

IUPAC Name

(1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.0⁵,¹⁴]tetradec-6-en-3-one

Traditional Name

(1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.0⁵,¹⁴]tetradec-6-en-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C23

InChI Identifier

InChI=1S/C15H22O4/c1-8-4-5-11-9(2)13(16)18-14-12(11)10(8)6-7-15(3,17)19-14/h4-5,8-12,14,17H,6-7H2,1-3H3/t8-,9-,10+,11-,12?,14+,15+/m1/s1

InChI Key

ZHHCFKHSMKRNCX-CRBWWJEESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060569)

Organ

Kidney (HMDB: HMDB0060569)
Liver (HMDB: HMDB0060569)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060569)

Cellular substructure

Cytoplasm (HMDB: HMDB0060569)
Membrane (HMDB: HMDB0060569)

Source

Endogenous

Endogenous (HMDB: HMDB0060569)

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	2.14 g/L	ALOGPS
logP	1.27	ALOGPS
logP	2.22	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.99 m³·mol⁻¹	ChemAxon
Polarizability	28.86 Å³	ChemAxon
Number of Rings	3	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]+	161.793	31661259
DarkChem	[M-H]-	158.242	31661259
DeepCCS	[M-2H]-	199.073	30932474
DeepCCS	[M+Na]+	173.734	30932474
AllCCS	[M+H]+	161.8	32859911
AllCCS	[M+H-H2O]+	158.1	32859911
AllCCS	[M+NH4]+	165.3	32859911
AllCCS	[M+Na]+	166.3	32859911
AllCCS	[M-H]-	168.9	32859911
AllCCS	[M+Na-2H]-	168.9	32859911
AllCCS	[M+HCOO]-	169.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxyartemsinin	C[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C23	3074.7	Standard polar	33892256
Deoxyartemsinin	C[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C23	1922.3	Standard non polar	33892256
Deoxyartemsinin	C[C@@H]1C=C[C@@H]2[C@@H](C)C(=O)O[C@H]3O[C@](C)(O)CC[C@@H]1C23	2089.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deoxyartemsinin,1TMS,isomer #1	C[C@@H]1C=C[C@H]2C3[C@H]1CC[C@@](C)(O[Si](C)(C)C)O[C@@H]3OC(=O)[C@@H]2C	2158.8	Semi standard non polar	33892256
Deoxyartemsinin,1TBDMS,isomer #1	C[C@@H]1C=C[C@H]2C3[C@H]1CC[C@@](C)(O[Si](C)(C)C(C)(C)C)O[C@@H]3OC(=O)[C@@H]2C	2405.5	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 - Deoxyartemsinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zi0-5690000000-c472fade044113c82540	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyartemsinin GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9141000000-65583165d952d95370fa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyartemsinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyartemsinin 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 - Deoxyartemsinin 10V, Positive-QTOF	splash10-014i-0190000000-83bd23db6874cc2486a3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Positive-QTOF	splash10-014j-1190000000-396aac6abf9880cf85be	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Positive-QTOF	splash10-0kai-9570000000-3ae434b265a650116f02	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 10V, Negative-QTOF	splash10-0aor-0090000000-22ef8eccc2e0800cc1f7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Negative-QTOF	splash10-06di-0090000000-5a12eed7d2b358da3a74	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Negative-QTOF	splash10-056r-6920000000-2ed359e26af8536f0b9c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 10V, Positive-QTOF	splash10-014i-0090000000-338ee9c9746d3716bbb8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Positive-QTOF	splash10-014i-0190000000-6681a1cebefda6e746a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Positive-QTOF	splash10-05r3-3930000000-a78a8acb6468c93befa0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 10V, Negative-QTOF	splash10-014i-0090000000-c6cc318d73093d112373	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 20V, Negative-QTOF	splash10-014i-0090000000-9fda6044b1dccf2e8e96	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyartemsinin 40V, Negative-QTOF	splash10-06r6-5290000000-4e336d79e9468e52d37d	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

137470

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156094

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 Deoxyartemsinin (HMDB0060569)

MOL for HMDB0060569 (Deoxyartemsinin)

3D MOL for HMDB0060569 (Deoxyartemsinin)

3D SDF for HMDB0060569 (Deoxyartemsinin)

3D-SDF for HMDB0060569 (Deoxyartemsinin)

PDB for HMDB0060569 (Deoxyartemsinin)

3D PDB for HMDB0060569 (Deoxyartemsinin)

SMILES for HMDB0060569 (Deoxyartemsinin)

INCHI for HMDB0060569 (Deoxyartemsinin)

Structure for HMDB0060569 (Deoxyartemsinin)

3D Structure for HMDB0060569 (Deoxyartemsinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra