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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 19:51:27 UTC

Update Date

2021-09-26 22:48:54 UTC

HMDB ID

HMDB0242246

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Arteannuin

Description

1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on 1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+)-arteannuin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+)-Arteannuin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0242653
     RDKit          3D
artemisinin
 42 45  0  0  0  0  0  0  0  0999 V2000
   -0.3519    3.3963   -0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    2.0867    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542    2.0934    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644    0.7092    0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -0.2491   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1723   -1.6286   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -1.6298   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104   -2.1032    1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823   -2.9291    1.9469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -1.6378    1.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4510   -0.9420    1.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536   -1.8749    0.7648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -1.4007   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -2.3265   -0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7067   -0.0193    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686    1.0547   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4921    0.9695   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644   -0.3721   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -1.2632   -1.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5210   -1.2730   -1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145    3.7870   -0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    3.2085   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4041    4.1860   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    2.0912    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    2.8888    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9094    2.2359   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0488    0.7577    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.5227    1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490    0.1935   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730   -2.2647   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -1.6347   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234   -2.5784    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1665   -0.8104    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7994   -0.1164    1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441   -1.6902   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553   -2.9820   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -2.9304    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.0402   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    0.1429    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    1.0547   -1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.0370   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1080    1.2004   -1.6164 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  2  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  0
 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  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
M  END


  Mrv1533004251516232D          

 20 23  0  0  0  0            999 V2000
    4.5141   -0.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064   -0.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5429   -0.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    0.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8064    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    1.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7354    1.8782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2230    2.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    1.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9705    1.5831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8026    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4880    2.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7995    0.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421    0.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814    1.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6200    2.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462    2.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  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
 16 17  1  0  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  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242246

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(C)C(=O)OC3OC4(C)CCC1C23OO4

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3

> <INCHI_KEY>
BLUAFEHZUWYNDE-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.39943671661829

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
3.114058047333332

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.427808040586903

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
68.6817

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artemisinin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242653
     RDKit          3D
artemisinin
 42 45  0  0  0  0  0  0  0  0999 V2000
   -0.3519    3.3963   -0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    2.0867    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542    2.0934    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644    0.7092    0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -0.2491   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1723   -1.6286   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -1.6298   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104   -2.1032    1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823   -2.9291    1.9469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -1.6378    1.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4510   -0.9420    1.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536   -1.8749    0.7648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -1.4007   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -2.3265   -0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7067   -0.0193    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686    1.0547   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4921    0.9695   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644   -0.3721   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -1.2632   -1.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5210   -1.2730   -1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145    3.7870   -0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    3.2085   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4041    4.1860   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    2.0912    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    2.8888    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9094    2.2359   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0488    0.7577    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.5227    1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490    0.1935   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730   -2.2647   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -1.6347   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234   -2.5784    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1665   -0.8104    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7994   -0.1164    1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441   -1.6902   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553   -2.9820   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -2.9304    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.0402   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    0.1429    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    1.0547   -1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.0370   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1080    1.2004   -1.6164 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  2  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  0
 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  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       8.426  -1.687   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.141  -0.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.799  -1.643   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.747  -0.487   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.926   1.109   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.372   1.543   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.326   0.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.833   3.018   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.373   3.506   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.150   3.872   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.671   3.367   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.412   2.955   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.965   3.353   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.244   4.210   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.872   2.050   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.959   0.764   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.359   0.743   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.312   2.041   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.757   3.816   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.113   4.675   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    HMDB0248623
HETATM    1  C1  UNL     1       1.200  -3.081  -0.703  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.473  -1.908  -0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.999  -2.328  -0.020  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.853  -1.213   0.501  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.707   0.027  -0.395  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.652   1.099  -0.004  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.646   0.687   1.061  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.980   2.382   0.365  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.402   3.104   1.325  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.882   2.720  -0.403  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.092   1.754  -0.751  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.294   2.190  -0.256  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.965   1.317   0.544  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.022   2.114   1.315  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.719   0.341  -0.327  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.877  -0.253  -1.406  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.517  -0.682  -0.972  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.245   0.405  -0.233  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.005   0.376   1.139  1.00  0.00           O  
HETATM   20  O5  UNL     1       1.219   0.641   1.465  1.00  0.00           O  
HETATM   21  H1  UNL     1       2.273  -2.894  -0.892  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.665  -3.470  -1.582  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.172  -3.893   0.073  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.819  -1.751   0.905  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.119  -3.203   0.624  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.351  -2.591  -1.038  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.876  -1.558   0.574  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.501  -0.884   1.507  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.868  -0.338  -1.431  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.274   1.351  -0.913  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.163   0.398   1.996  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.296  -0.093   0.616  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.299   1.575   1.245  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.145   1.772  -1.874  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.589   3.079   1.620  1.00  0.00           H  
HETATM   36  H16 UNL     1       3.291   1.546   2.241  1.00  0.00           H  
HETATM   37  H17 UNL     1       3.946   2.197   0.725  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.238  -0.411   0.299  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.533   0.941  -0.826  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.386  -1.090  -1.872  1.00  0.00           H  
HETATM   41  H21 UNL     1       1.744   0.530  -2.195  1.00  0.00           H  
HETATM   42  H22 UNL     1      -0.069  -0.902  -1.913  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    9   10
CONECT   10   11
CONECT   11   12   18   34
CONECT   12   13
CONECT   13   14   15   20
CONECT   14   35   36   37
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   18   42
CONECT   18   19
CONECT   19   20
END

HMDB0242653
     RDKit          3D
artemisinin
 42 45  0  0  0  0  0  0  0  0999 V2000
   -0.3519    3.3963   -0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    2.0867    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542    2.0934    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644    0.7092    0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -0.2491   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1723   -1.6286   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -1.6298   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104   -2.1032    1.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823   -2.9291    1.9469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -1.6378    1.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4510   -0.9420    1.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536   -1.8749    0.7648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -1.4007   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -2.3265   -0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7067   -0.0193    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686    1.0547   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4921    0.9695   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644   -0.3721   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -1.2632   -1.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5210   -1.2730   -1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145    3.7870   -0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    3.2085   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4041    4.1860   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    2.0912    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    2.8888    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9094    2.2359   -0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0488    0.7577    1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.5227    1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490    0.1935   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730   -2.2647   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -1.6347   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234   -2.5784    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1665   -0.8104    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7994   -0.1164    1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441   -1.6902   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553   -2.9820   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -2.9304    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.0402   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    0.1429    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    1.0547   -1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474    2.0370   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1080    1.2004   -1.6164 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  2  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  0
 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  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
GNF-PF-5671SID26754245	ChEMBL, HMDB
Artemisinine	MeSH, HMDB
Quing hau sau	MeSH, HMDB
Quinghaosu	MeSH, HMDB
Arteannuin	MeSH, HMDB
Qinghaosu	MeSH, HMDB

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Weight

282.336

Monoisotopic Molecular Weight

282.146723808

IUPAC Name

1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one

Traditional Name

artemisinin

CAS Registry Number

Not Available

SMILES

CC1CCC2C(C)C(=O)OC3OC4(C)CCC1C23OO4

InChI Identifier

InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3

InChI Key

BLUAFEHZUWYNDE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Artemisinin skeleton
Terpene lactone
Sesquiterpenoid
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
1,2,4-trioxane
Carboxylic acid ester
Lactone
Dialkyl peroxide
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

a sesquiterpenoid (CPD-7561 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.52	ALOGPS
logP	3.11	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.68 m³·mol⁻¹	ChemAxon
Polarizability	29.4 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
DeepCCS	[M-2H]-	196.268	30932474
DeepCCS	[M+Na]+	171.495	30932474
AllCCS	[M+H]+	165.0	32859911
AllCCS	[M+H-H2O]+	161.4	32859911
AllCCS	[M+NH4]+	168.3	32859911
AllCCS	[M+Na]+	169.2	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	173.1	32859911
AllCCS	[M+HCOO]-	173.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	16.4428 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.57 minutes	32390414

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Arteannuin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-6090000000-fa2c44cc24cdf96f7d85	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Arteannuin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Arteannuin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Arteannuin 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 - (+)-Arteannuin 10V, Positive-QTOF	splash10-001i-0090000000-39382db646a7b40cef58	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Arteannuin 20V, Positive-QTOF	splash10-001i-0090000000-7485bc58f98d3df2c97f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Arteannuin 40V, Positive-QTOF	splash10-004i-1090000000-9f02f6789078f8027827	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Arteannuin 10V, Negative-QTOF	splash10-001i-0090000000-4206ab54dd729eeefe27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Arteannuin 20V, Negative-QTOF	splash10-001i-0090000000-c9a936da36573e24bd9c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Arteannuin 40V, Negative-QTOF	splash10-056r-2090000000-47e0a4ed47bd0b679df1	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

2153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2240

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (+)-Arteannuin (HMDB0242246)

MOL for HMDB0242246 ((+)-Arteannuin)

3D MOL for HMDB0242246 ((+)-Arteannuin)

3D SDF for HMDB0242246 ((+)-Arteannuin)

3D-SDF for HMDB0242246 ((+)-Arteannuin)

PDB for HMDB0242246 ((+)-Arteannuin)

3D PDB for HMDB0242246 ((+)-Arteannuin)

SMILES for HMDB0242246 ((+)-Arteannuin)

INCHI for HMDB0242246 ((+)-Arteannuin)

Structure for HMDB0242246 ((+)-Arteannuin)

3D Structure for HMDB0242246 ((+)-Arteannuin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra