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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014411

Secondary Accession Numbers

HMDB14411

Metabolite Identification

Common Name

Dicumarol

Description

Dicumarol is only found in individuals that have used or taken this drug. It is an oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem]Dicumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.

Structure

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

HMDB0014411
     RDKit          3D
Dicumarol
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.0571    2.7620    0.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905    1.7678    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7763    1.4212    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5196    0.4102    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6633    0.0588    1.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -1.0158    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978   -1.7813    0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557   -1.4260   -0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976   -0.3486   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495    0.0016   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.8022   -2.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688    1.0732   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0874    1.4288   -1.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156    1.1583   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7650   -0.1036   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437   -1.1979   -1.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0291   -0.2755   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.5018    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8956   -1.6202    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.5126    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.7209    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.8294    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    2.0064    0.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    2.2051   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419    3.3804   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510    0.6182    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2991   -1.2663    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6802   -2.6269   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6751   -2.0157   -1.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -0.7482   -2.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756    1.0025   -2.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796    2.5410   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396   -2.1374   -0.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837   -2.3807   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378   -2.6000    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -0.6356    1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    1.6104    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 12  2  1  0
 24 14  1  0
  9  4  1  0
 22 17  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv0541 04191212112D          

 25 28  0  0  0  0            999 V2000
    3.7294   -3.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -3.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7294   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7048   -3.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -5.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111   -3.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440   -5.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -2.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -3.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -5.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818   -3.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6802   -3.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949   -3.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6802   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949   -5.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0985   -3.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0985   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9655   -5.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949   -2.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8132   -3.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8132   -5.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5279   -3.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5279   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  2  1  0  0  0  0
  9  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  3  2  0  0  0  0
  7  5  1  0  0  0  0
 10  6  1  0  0  0  0
  7  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
  4 14  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 18 15  1  0  0  0  0
 21 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 16  2  0  0  0  0
 19 17  1  0  0  0  0
 22 18  1  0  0  0  0
 19 18  2  0  0  0  0
 23 19  1  0  0  0  0
 24 22  2  0  0  0  0
 25 23  2  0  0  0  0
 25 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014411

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2

> <INCHI_KEY>
DOBMPNYZJYQDGZ-UHFFFAOYSA-N

> <FORMULA>
C19H12O6

> <MOLECULAR_WEIGHT>
336.295

> <EXACT_MASS>
336.063388116

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.31505969606336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
-1.5927893718444859

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.35400343846115

> <JCHEM_PKA_STRONGEST_ACIDIC>
-11.942615868512426

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1001245556623425

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
89.19280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dicoumarol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014411
     RDKit          3D
Dicumarol
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.0571    2.7620    0.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905    1.7678    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7763    1.4212    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5196    0.4102    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6633    0.0588    1.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -1.0158    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978   -1.7813    0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557   -1.4260   -0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976   -0.3486   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495    0.0016   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.8022   -2.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688    1.0732   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0874    1.4288   -1.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156    1.1583   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7650   -0.1036   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437   -1.1979   -1.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0291   -0.2755   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.5018    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8956   -1.6202    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.5126    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.7209    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.8294    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    2.0064    0.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    2.2051   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419    3.3804   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510    0.6182    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2991   -1.2663    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6802   -2.6269   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6751   -2.0157   -1.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -0.7482   -2.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756    1.0025   -2.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796    2.5410   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396   -2.1374   -0.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837   -2.3807   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378   -2.6000    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -0.6356    1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    1.6104    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 12  2  1  0
 24 14  1  0
  9  4  1  0
 22 17  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       6.962  -7.325   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.627  -6.556   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.962  -8.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.782  -6.285   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.627  -9.624   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.314  -7.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.314  -8.855   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.295  -9.634   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.627  -5.016   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.980  -6.556   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.980  -9.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.646  -7.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.646  -8.855   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.603  -7.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.937  -6.556   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.603  -8.855   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.937  -9.624   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.251  -7.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.251  -8.855   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.269  -9.634   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.937  -5.016   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.585  -6.556   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.585  -9.624   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.919  -7.325   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.919  -8.855   0.000  0.00  0.00           C+0
CONECT    1    4    2    3                                                  
CONECT    2    1    6    9                                                  
CONECT    3    1    5    8                                                  
CONECT    4    1   14                                                       
CONECT    5    3    7                                                       
CONECT    6    2   10    7                                                  
CONECT    7    5    6   11                                                  
CONECT    8    3                                                            
CONECT    9    2                                                            
CONECT   10    6   12                                                       
CONECT   11    7   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
CONECT   14    4   15   16                                                  
CONECT   15   14   18   21                                                  
CONECT   16   14   17   20                                                  
CONECT   17   16   19                                                       
CONECT   18   15   22   19                                                  
CONECT   19   17   18   23                                                  
CONECT   20   16                                                            
CONECT   21   15                                                            
CONECT   22   18   24                                                       
CONECT   23   19   25                                                       
CONECT   24   22   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0014411
HETATM    1  O1  UNL     1      -1.057   2.762   0.988  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.690   1.768   0.549  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.776   1.421   1.211  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.520   0.410   0.858  1.00  0.00           C  
HETATM    5  C3  UNL     1      -4.663   0.059   1.570  1.00  0.00           C  
HETATM    6  C4  UNL     1      -5.416  -1.016   1.159  1.00  0.00           C  
HETATM    7  C5  UNL     1      -5.098  -1.781   0.061  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.956  -1.426  -0.646  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.198  -0.349  -0.237  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.049   0.002  -0.955  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.782  -0.802  -2.051  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.269   1.073  -0.573  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.087   1.429  -1.347  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.216   1.158  -0.747  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.765  -0.104  -0.590  1.00  0.00           C  
HETATM   16  O4  UNL     1       1.044  -1.198  -1.004  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.029  -0.276  -0.023  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.624  -1.502   0.158  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.896  -1.620   0.733  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.601  -0.513   1.140  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.019   0.721   0.967  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.746   0.829   0.390  1.00  0.00           C  
HETATM   23  O5  UNL     1       3.192   2.006   0.224  1.00  0.00           O  
HETATM   24  C19 UNL     1       2.008   2.205  -0.304  1.00  0.00           C  
HETATM   25  O6  UNL     1       1.542   3.380  -0.433  1.00  0.00           O  
HETATM   26  H1  UNL     1      -4.951   0.618   2.425  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.299  -1.266   1.731  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.680  -2.627  -0.272  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.675  -2.016  -1.526  1.00  0.00           H  
HETATM   30  H5  UNL     1      -1.044  -0.748  -2.696  1.00  0.00           H  
HETATM   31  H6  UNL     1      -0.176   1.002  -2.387  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.180   2.541  -1.543  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.340  -2.137  -0.939  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.084  -2.381  -0.157  1.00  0.00           H  
HETATM   35  H10 UNL     1       5.338  -2.600   0.862  1.00  0.00           H  
HETATM   36  H11 UNL     1       6.579  -0.636   1.580  1.00  0.00           H  
HETATM   37  H12 UNL     1       5.545   1.610   1.275  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4
CONECT    4    5    5    9
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   10
CONECT   10   11   12   12
CONECT   11   30
CONECT   12   13
CONECT   13   14   31   32
CONECT   14   15   15   24
CONECT   15   16   17
CONECT   16   33
CONECT   17   18   18   22
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   20   21   36
CONECT   21   22   22   37
CONECT   22   23
CONECT   23   24
CONECT   24   25   25
END

HMDB0014411
     RDKit          3D
Dicumarol
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.0571    2.7620    0.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905    1.7678    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7763    1.4212    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5196    0.4102    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6633    0.0588    1.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -1.0158    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978   -1.7813    0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557   -1.4260   -0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976   -0.3486   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495    0.0016   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.8022   -2.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688    1.0732   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0874    1.4288   -1.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156    1.1583   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7650   -0.1036   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437   -1.1979   -1.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0291   -0.2755   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.5018    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8956   -1.6202    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.5126    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.7209    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.8294    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    2.0064    0.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    2.2051   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419    3.3804   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510    0.6182    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2991   -1.2663    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6802   -2.6269   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6751   -2.0157   -1.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -0.7482   -2.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756    1.0025   -2.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796    2.5410   -1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3396   -2.1374   -0.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837   -2.3807   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378   -2.6000    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -0.6356    1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    1.6104    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 12  2  1  0
 24 14  1  0
  9  4  1  0
 22 17  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,3'-Methylen-bis(4-hydroxy-cumarin)	ChEBI
3,3'-Methylene-bis(4-hydroxycoumarine)	ChEBI
3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)	ChEBI
3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)	ChEBI
3,3'-Methylenebis(4-hydroxycoumarin)	ChEBI
Bis(4-hydroxycoumarin-3-yl)methane	ChEBI
Bis-3,3'-(4-hydroxycoumarinyl)methane	ChEBI
Bis-hydroxycoumarin	ChEBI
Di-(4-hydroxy-3-coumarinyl)methane	ChEBI
Dicoumarolum	ChEBI
Dicoumarol	Kegg
Bishydroxycoumarin	HMDB
Dicoumarin	HMDB

Chemical Formula

C₁₉H₁₂O₆

Average Molecular Weight

336.295

Monoisotopic Molecular Weight

336.063388116

IUPAC Name

4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one

Traditional Name

dicoumarol

CAS Registry Number

66-76-2

SMILES

OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2

InChI Identifier

InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2

InChI Key

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
Benzopyran
1-benzopyran
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:4513 )
coumarins (C00796 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.066 g/L	Not Available
LogP	3.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	181.981	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001392

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	1.54	ALOGPS
logP	-1.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	-12	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.19 m³·mol⁻¹	ChemAxon
Polarizability	32.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	173.886	31661259
DarkChem	[M-H]-	176.5	31661259
DeepCCS	[M+H]+	175.174	30932474
DeepCCS	[M-H]-	172.723	30932474
DeepCCS	[M-2H]-	207.108	30932474
DeepCCS	[M+Na]+	182.679	30932474
AllCCS	[M+H]+	178.8	32859911
AllCCS	[M+H-H2O]+	175.3	32859911
AllCCS	[M+NH4]+	182.0	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	176.6	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.69 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9903 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2167.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	416.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	592.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	720.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1316.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	476.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1555.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	370.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	240.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	34.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dicumarol	OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2	4239.1	Standard polar	33892256
Dicumarol	OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2	2746.3	Standard non polar	33892256
Dicumarol	OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2	3259.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dicumarol,1TMS,isomer #1	C[Si](C)(C)OC1=C(CC2=C(O)C3=CC=CC=C3OC2=O)C(=O)OC2=CC=CC=C12	3313.0	Semi standard non polar	33892256
Dicumarol,2TMS,isomer #1	C[Si](C)(C)OC1=C(CC2=C(O[Si](C)(C)C)C3=CC=CC=C3OC2=O)C(=O)OC2=CC=CC=C12	3270.7	Semi standard non polar	33892256
Dicumarol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(CC2=C(O)C3=CC=CC=C3OC2=O)C(=O)OC2=CC=CC=C12	3552.6	Semi standard non polar	33892256
Dicumarol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(CC2=C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3OC2=O)C(=O)OC2=CC=CC=C12	3795.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dicumarol EI-B (Non-derivatized)	splash10-0079-6914000000-95659ff5087535a07662	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dicumarol EI-B (Non-derivatized)	splash10-0079-6914000000-95659ff5087535a07662	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dicumarol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abi-1429000000-b3b5b41c6d8058aa0750	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dicumarol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6111900000-373caca34eb4c76ecec6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dicumarol 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 - Dicumarol 10V, Positive-QTOF	splash10-000i-0109000000-3c885b6fd0411c0ff106	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 20V, Positive-QTOF	splash10-002r-0719000000-9268ef0a7aa4edc0f242	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 40V, Positive-QTOF	splash10-00di-2911000000-04685f91d611459131c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 10V, Negative-QTOF	splash10-000i-0129000000-e46a63fb14d246913958	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 20V, Negative-QTOF	splash10-03di-0924000000-3d4892a9013fb818db2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 40V, Negative-QTOF	splash10-052f-8941000000-5d292f12289cd60d251e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 10V, Negative-QTOF	splash10-000i-0009000000-cf75db3fcf76086bc0a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 20V, Negative-QTOF	splash10-000i-0529000000-7a6f916db51a10874a5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 40V, Negative-QTOF	splash10-00du-3910000000-e6d48e72ac9f9dddf912	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 10V, Positive-QTOF	splash10-000i-0009000000-a487dc1a344a66353635	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 20V, Positive-QTOF	splash10-01t9-0901000000-74ccf5992000b52087f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dicumarol 40V, Positive-QTOF	splash10-00ku-0392000000-56dee6c1117cdcc0532d	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Dicumarol Action Pathway		Not Available
Dicoumarol Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00266	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00266	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00266

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dicumarol

METLIN ID

Not Available

PubChem Compound

54676038

PDB ID

Not Available

ChEBI ID

4513

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

Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride. Pharm Res. 2003 Jul;20(7):1093-100. [PubMed:12880296 ]
Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, Weydert CJ, Domann FE, Oberley LW: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism. Cancer Res. 2003 Sep 1;63(17):5513-20. [PubMed:14500388 ]
Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA Jr, Fusella A, Di Tullio G, Silletta MG, Corda D, De Matteis MA, Luini A: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport. Eur J Cell Biol. 2004 Jul;83(6):263-79. [PubMed:15511084 ]
Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. [PubMed:15639223 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Dicumarol → 3,4,5-trihydroxy-6-({3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2-oxo-2H-chromen-4-yl}oxy)oxane-2-carboxylic acid	details

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Quinone oxidoreductase

General function:: Involved in zinc ion binding
Specific function:: Does not have alcohol dehydrogenase activity. Binds NADP and acts through a one-electron transfer process. Orthoquinones, such as 1,2-naphthoquinone or 9,10-phenanthrenequinone, are the best substrates (in vitro). May act in the detoxification of xenobiotics. Interacts with (AU)-rich elements (ARE) in the 3'-UTR of target mRNA species. Enhances the stability of mRNA coding for BCL2. NADPH binding interferes with mRNA binding.
Gene Name:: CRYZ
Uniprot ID:: Q08257
Molecular weight:: 35206.36

References

Evans PJ: Decreased intracellular proteolysis correlates with the maintenance of a specific isoenzyme of cytochrome P-450. Cell Biol Int. 1999;23(2):117-24. [PubMed:10561120 ]
Audi SH, Bongard RD, Dawson CA, Siegel D, Roerig DL, Merker MP: Duroquinone reduction during passage through the pulmonary circulation. Am J Physiol Lung Cell Mol Physiol. 2003 Nov;285(5):L1116-31. Epub 2003 Jul 25. [PubMed:12882764 ]
Asher G, Dym O, Tsvetkov P, Adler J, Shaul Y: The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol. Biochemistry. 2006 May 23;45(20):6372-8. [PubMed:16700548 ]
Maser E, Gebel T, Netter KJ: Carbonyl reduction of metyrapone in human liver. Biochem Pharmacol. 1991 Dec 11;42 Suppl:S93-8. [PubMed:1722672 ]
Hao H, Wang G, Cui N, Li J, Xie L, Ding Z: Identification of a novel intestinal first pass metabolic pathway: NQO1 mediated quinone reduction and subsequent glucuronidation. Curr Drug Metab. 2007 Feb;8(2):137-49. [PubMed:17305492 ]

Enzyme Details

4. NAD(P)H dehydrogenase [quinone] 1

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO1
Uniprot ID:: P15559
Molecular weight:: 30867.405

References

Chen S, Wu K, Zhang D, Sherman M, Knox R, Yang CS: Molecular characterization of binding of substrates and inhibitors to DT-diaphorase: combined approach involving site-directed mutagenesis, inhibitor-binding analysis, and computer modeling. Mol Pharmacol. 1999 Aug;56(2):272-8. [PubMed:10419545 ]
Jaiswal AK: Characterization and partial purification of microsomal NAD(P)H:quinone oxidoreductases. Arch Biochem Biophys. 2000 Mar 1;375(1):62-8. [PubMed:10683249 ]
Joseph P, Jaiswal AK: A unique cytosolic activity related but distinct from NQO1 catalyses metabolic activation of mitomycin C. Br J Cancer. 2000 Apr;82(7):1305-11. [PubMed:10755406 ]
Floreani M, Napoli E, Palatini P: Protective action of cardiac DT-diaphorase against menadione toxicity in guinea pig isolated atria. Biochem Pharmacol. 2000 Aug 15;60(4):601-5. [PubMed:10874136 ]
Arriagada C, Dagnino-Subiabre A, Caviedes P, Armero JM, Caviedes R, Segura-Aguilar J: Studies of aminochrome toxicity in a mouse derived neuronal cell line: is this toxicity mediated via glutamate transmission? Amino Acids. 2000;18(4):363-73. [PubMed:10949919 ]
Preusch PC, Smalley DM: Vitamin K1 2,3-epoxide and quinone reduction: mechanism and inhibition. Free Radic Res Commun. 1990;8(4-6):401-15. [PubMed:2113031 ]

Enzyme Details

5. Vitamin K epoxide reductase complex subunit 1

General function:: Involved in vitamin-K-epoxide reductase (warfarin-sensi
Specific function:: Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K.
Gene Name:: VKORC1
Uniprot ID:: Q9BQB6
Molecular weight:: 18234.3

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Wallin R, Patrick SD, Ballard JO: Vitamin K antagonism of coumarin intoxication in the rat. Thromb Haemost. 1986 Apr 30;55(2):235-9. [PubMed:2424118 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Dicumarol (HMDB0014411)

MOL for HMDB0014411 (Dicumarol)

3D MOL for HMDB0014411 (Dicumarol)

3D SDF for HMDB0014411 (Dicumarol)

3D-SDF for HMDB0014411 (Dicumarol)

PDB for HMDB0014411 (Dicumarol)

3D PDB for HMDB0014411 (Dicumarol)

SMILES for HMDB0014411 (Dicumarol)

INCHI for HMDB0014411 (Dicumarol)

Structure for HMDB0014411 (Dicumarol)

3D Structure for HMDB0014411 (Dicumarol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

References

References

References

References