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Showing metabocard for Dracunculin (HMDB0030789)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:02 UTC
Update Date2022-03-07 02:52:42 UTC
HMDB IDHMDB0030789
Secondary Accession Numbers
  • HMDB30789
Metabolite Identification
Common NameDracunculin
DescriptionDracunculin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Dracunculin has been detected, but not quantified in, mugworts (Artemisia vulgaris) and pulses. This could make dracunculin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Dracunculin.
Structure
Data?1563862038
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030789 (Dracunculin)

  Mrv0541 05061305302D          

 16 18  0  0  0  0            999 V2000
    0.7516   -0.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0947    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8355    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0109    0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    2.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555    1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739    2.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762   -0.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196    1.0699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    2.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147    2.2499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  2  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0030789 (Dracunculin)

HMDB0030789
     RDKit          3D
Dracunculin
 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.6979   -2.3703   -0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.9720   -0.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -0.3983   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2270   -1.1943   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -0.6067   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755   -1.3851   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -0.7512    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850    0.6185    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040    1.2022    0.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673    1.2987    0.2084 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0957    0.7624    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    1.5712    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2490    0.9660   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979    1.9792    0.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6040    3.1949    0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.9412    0.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997   -2.7196   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7286   -2.6895   -0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -2.8282    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413   -2.2631   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -2.4647   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -1.3235    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078    3.3733    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552    4.0591   -0.0993 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  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  3  1  0
 11  5  2  0
 16 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 15 23  1  0
 15 24  1  0
M  END
Download

3D SDF for HMDB0030789 (Dracunculin)

  Mrv0541 05061305302D          

 16 18  0  0  0  0            999 V2000
    0.7516   -0.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0947    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8355    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0109    0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    2.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555    1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739    2.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762   -0.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196    1.0699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    2.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147    2.2499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  2  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030789

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OCOC2=C2OC(=O)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O5/c1-13-7-4-6-2-3-8(12)16-9(6)11-10(7)14-5-15-11/h2-4H,5H2,1H3

> <INCHI_KEY>
GHIKZCCKJTXOGO-UHFFFAOYSA-N

> <FORMULA>
C11H8O5

> <MOLECULAR_WEIGHT>
220.1782

> <EXACT_MASS>
220.037173366

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.67896357569576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-2H,8H-[1,3]dioxolo[4,5-h]chromen-8-one

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.2489218173333332

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.559537235991328

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
53.77870000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-2H-[1,3]dioxolo[4,5-h]chromen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0030789 (Dracunculin)

HMDB0030789
     RDKit          3D
Dracunculin
 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.6979   -2.3703   -0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.9720   -0.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -0.3983   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2270   -1.1943   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -0.6067   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755   -1.3851   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -0.7512    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850    0.6185    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040    1.2022    0.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673    1.2987    0.2084 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0957    0.7624    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    1.5712    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2490    0.9660   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979    1.9792    0.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6040    3.1949    0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.9412    0.2743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997   -2.7196   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7286   -2.6895   -0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -2.8282    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413   -2.2631   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -2.4647   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -1.3235    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078    3.3733    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552    4.0591   -0.0993 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  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  3  1  0
 11  5  2  0
 16 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 15 23  1  0
 15 24  1  0
M  END
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PDB for HMDB0030789 (Dracunculin)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.403  -0.988   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.643   1.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.455   2.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.293   0.225   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.417   3.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.104   1.534   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.754   0.273   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.727   4.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.376   2.891   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.026   1.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.837   2.939   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.538   5.461   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.942  -1.036   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.530   1.997   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.843   4.115   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.187   4.200   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    6                                                       
CONECT    3    2    8                                                       
CONECT    4    6    7                                                       
CONECT    5   14   15                                                       
CONECT    6    2    4    9                                                  
CONECT    7    4   10   13                                                  
CONECT    8    3   12   16                                                  
CONECT    9    6   11   16                                                  
CONECT   10    7   11   14                                                  
CONECT   11    9   10   15                                                  
CONECT   12    8                                                            
CONECT   13    1    7                                                       
CONECT   14    5   10                                                       
CONECT   15    5   11                                                       
CONECT   16    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END
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3D PDB for HMDB0030789 (Dracunculin)

COMPND    HMDB0030789
HETATM    1  C1  UNL     1      -2.698  -2.370  -0.457  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.592  -0.972  -0.292  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.346  -0.398  -0.164  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.227  -1.194  -0.200  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.038  -0.607  -0.071  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.175  -1.385  -0.104  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.392  -0.751   0.029  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.385   0.618   0.186  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.504   1.202   0.308  1.00  0.00           O  
HETATM   10  O3  UNL     1       2.267   1.299   0.208  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.096   0.762   0.089  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.030   1.571   0.126  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.249   0.966  -0.003  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.198   1.979   0.066  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.604   3.195   0.481  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.206   2.941   0.274  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.000  -2.720  -1.261  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.729  -2.689  -0.680  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.408  -2.828   0.534  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.241  -2.263  -0.323  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.113  -2.465  -0.230  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.320  -1.323   0.009  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.808   3.373   1.574  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.955   4.059  -0.099  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   20
CONECT    5    6   11   11
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   16
CONECT   13   14
CONECT   14   15
CONECT   15   16   23   24
END
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SMILES for HMDB0030789 (Dracunculin)

COC1=C2OCOC2=C2OC(=O)C=CC2=C1
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INCHI for HMDB0030789 (Dracunculin)

InChI=1S/C11H8O5/c1-13-7-4-6-2-3-8(12)16-9(6)11-10(7)14-5-15-11/h2-4H,5H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-Methoxy-8H-1,3-dioxolo[4,5-H][1]benzopyran-8-oneHMDB
6-Methoxy-7,8-methylenedioxycoumarinHMDB
Chemical FormulaC11H8O5
Average Molecular Weight220.1782
Monoisotopic Molecular Weight220.037173366
IUPAC Name4-methoxy-2H,8H-[1,3]dioxolo[4,5-h]chromen-8-one
Traditional Name4-methoxy-2H-[1,3]dioxolo[4,5-h]chromen-8-one
CAS Registry Number28843-40-5
SMILES
COC1=C2OCOC2=C2OC(=O)C=CC2=C1
InChI Identifier
InChI=1S/C11H8O5/c1-13-7-4-6-2-3-8(12)16-9(6)11-10(7)14-5-15-11/h2-4H,5H2,1H3
InChI KeyGHIKZCCKJTXOGO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Acetal
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point219 - 221 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1324 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002727
KNApSAcK IDC00050744
Chemspider ID4477766
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319474
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1822761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .