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Showing metabocard for Cantharidin (HMDB0249592)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 04:06:30 UTC
Update Date2022-09-22 17:44:21 UTC
HMDB IDHMDB0249592
Secondary Accession NumbersNone
Metabolite Identification
Common NameCantharidin
Description2,6-dimethyl-4,10-dioxatricyclo[5.2.1.0²,⁶]decane-3,5-dione belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Based on a literature review very few articles have been published on 2,6-dimethyl-4,10-dioxatricyclo[5.2.1.0²,⁶]decane-3,5-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cantharidin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cantharidin 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0249592 (Cantharidin)

  Mrv1533004241518592D          

 14 16  0  0  0  0            999 V2000
    2.0043    1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7026   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1876    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7026    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0043   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4098    0.4125    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
  2  7  1  0  0  0  0
  7  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
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
  6 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
Download

3D MOL for HMDB0249592 (Cantharidin)

HMDB0249592
     RDKit          3D
Cantharidin
 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.1021    1.4990    1.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1898    0.7977    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535    1.5583   -0.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    2.6721   -1.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674    0.8585   -2.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199   -0.2696   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -0.9781   -2.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -0.4956   -0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -1.0739    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696   -1.4095   -0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -0.9331   -0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001    0.1978   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0776    0.3411    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8446   -1.0293    1.2013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    2.4999    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909    1.6026    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1285    0.9530    2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5909   -1.5583   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761   -1.9218    1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3599   -0.3781    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -2.4586   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -0.5939   -1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3679   -1.7402   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    1.1048   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0881   -0.1419    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630    0.8972    1.8305 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
  3  5  1  0
  5  6  1  0
  6  7  2  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
  8  2  1  0
 14 10  1  0
 13  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  9 18  1  0
  9 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
M  END
Download

3D SDF for HMDB0249592 (Cantharidin)

  Mrv1533004241518592D          

 14 16  0  0  0  0            999 V2000
    2.0043    1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7026   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1876    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7026    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0043   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4098    0.4125    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
  2  7  1  0  0  0  0
  7  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
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
  6 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249592

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12C3CCC(O3)C1(C)C(=O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3

> <INCHI_KEY>
DHZBEENLJMYSHQ-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.202

> <EXACT_MASS>
196.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.523486759492503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethyl-4,10-dioxatricyclo[5.2.1.0²,⁶]decane-3,5-dione

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.0591830693333333

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.181485683637536

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
45.40330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cantharidin

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0249592 (Cantharidin)

HMDB0249592
     RDKit          3D
Cantharidin
 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.1021    1.4990    1.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1898    0.7977    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535    1.5583   -0.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    2.6721   -1.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674    0.8585   -2.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199   -0.2696   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -0.9781   -2.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -0.4956   -0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -1.0739    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696   -1.4095   -0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -0.9331   -0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001    0.1978   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0776    0.3411    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8446   -1.0293    1.2013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    2.4999    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909    1.6026    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1285    0.9530    2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5909   -1.5583   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761   -1.9218    1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3599   -0.3781    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -2.4586   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623   -0.5939   -1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3679   -1.7402   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    1.1048   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0881   -0.1419    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630    0.8972    1.8305 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
  3  5  1  0
  5  6  1  0
  6  7  2  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
  8  2  1  0
 14 10  1  0
 13  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  9 18  1  0
  9 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
M  END
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PDB for HMDB0249592 (Cantharidin)

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       3.741   3.072   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.580   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.247   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.913   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.913  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.247  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.580   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.045  -0.476   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.521  -1.941   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.950   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.045   2.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.521   3.481   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.741  -1.532   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.632   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    2    8   13                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
CONECT   13    7                                                            
CONECT   14    6    3                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END
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3D PDB for HMDB0249592 (Cantharidin)

COMPND    HMDB0249592
HETATM    1  C1  UNL     1      -1.102   1.499   1.228  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.190   0.798   0.280  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.054   1.558  -0.966  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.629   2.672  -1.131  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.467   0.859  -2.071  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.120  -0.270  -1.651  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.892  -0.978  -2.345  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.755  -0.496  -0.254  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.837  -1.074   0.588  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.470  -1.410  -0.110  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.623  -0.933  -0.936  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.200   0.198  -0.076  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.078   0.341   0.946  1.00  0.00           C  
HETATM   14  O4  UNL     1       0.845  -1.029   1.201  1.00  0.00           O  
HETATM   15  H1  UNL     1      -0.674   2.500   1.436  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.091   1.603   0.739  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.128   0.953   2.173  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.591  -1.558  -0.092  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.476  -1.922   1.239  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.360  -0.378   1.238  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.228  -2.459  -0.195  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.362  -0.594  -1.939  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.368  -1.740  -0.981  1.00  0.00           H  
HETATM   24  H10 UNL     1       2.377   1.105  -0.644  1.00  0.00           H  
HETATM   25  H11 UNL     1       3.088  -0.142   0.492  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.363   0.897   1.830  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    8   13
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10
CONECT    9   18   19   20
CONECT   10   11   14   21
CONECT   11   12   22   23
CONECT   12   13   24   25
CONECT   13   14   26
END
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SMILES for HMDB0249592 (Cantharidin)

CC12C3CCC(O3)C1(C)C(=O)OC2=O
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INCHI for HMDB0249592 (Cantharidin)

InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
SynonymsNot Available
Chemical FormulaC10H12O4
Average Molecular Weight196.202
Monoisotopic Molecular Weight196.073558866
IUPAC Name2,6-dimethyl-4,10-dioxatricyclo[5.2.1.0²,⁶]decane-3,5-dione
Traditional Namecantharidin
CAS Registry NumberNot Available
SMILES
CC12C3CCC(O3)C1(C)C(=O)OC2=O
InChI Identifier
InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3
InChI KeyDHZBEENLJMYSHQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassNot Available
Direct ParentFurofurans
Alternative Parents
Substituents
  • Furofuran
  • Dicarboxylic acid or derivatives
  • Tetrahydrofuran
  • Carboxylic acid anhydride
  • Lactone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2449
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2545
PDB IDNot Available
ChEBI ID93862
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]