NP-MRD: Showing NP-Card for Dicoumarol (NP0051443)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:30 UTC

Updated at

2022-04-27 22:48:30 UTC

NP-MRD ID

NP0051443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dicoumarol

Description

Dicumarol, also known as dicoumarin, 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. Dicumarol is a drug which is used for decreasing blood clotting. Often used along with heparin for treatment of deep vein thrombosis. Dicumarol is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, dicumarol is involved in dicumarol action pathway. Dicumarol is a bitter tasting compound. Outside of the human body, Dicumarol has been detected, but not quantified in, herbs and spices and pulses. This could make dicumarol a potential biomarker for the consumption of these foods. Dicumarol is a potentially toxic compound. Dicoumarol is found in Anthoxanthum spp., Melilotus alba, Melilotus spp. and Viola arvensis. Dicoumarol was first documented in 2003 (PMID: 12880296). A hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group (PMID: 14500388) (PMID: 15511084) (PMID: 15639223) (PMID: 16700548).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    0.3359    1.2163   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8496    0.7693   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490    1.6280   -0.1494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0887    1.2224   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1186    2.1198    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4490    1.7374    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7774    0.3870    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7540   -0.5272    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4207   -0.1210   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4316   -1.0380   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -2.3891   -0.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1126   -0.5769   -0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.6126   -0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2679   -1.0073   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -0.6275    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745   -0.8076    1.8343 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2327   -0.0598    0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8922    0.3077    1.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1536    0.8647    1.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7362    1.0467    0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0481    0.6665   -0.7546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777    0.1043   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1349   -0.2520   -1.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -0.7832   -1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141   -1.1285   -2.7893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622    3.1803    0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2460    2.4635    0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8045    0.0514    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9533   -1.6049    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -3.1112   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998   -2.1422   -1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1228   -2.4013    0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838   -1.1958    2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4457    0.1704    2.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6993    1.1665    2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7396    1.4890    0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4752    0.7948   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
 14 24  1  0
 24 25  2  0
 24 23  1  0
 23 22  1  0
 22 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 17 15  1  0
  2 12  1  0
 21 22  1  0
  8  9  1  0
 16 33  1  0
 13 31  1  0
 13 32  1  0
 11 30  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  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>
NP0051443

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

336.2950 Da

Monoisotopic Mass

336.06339 Da

IUPAC Name

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

Traditional Name

dicoumarol

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthoxanthum spp.	Plant	KNApSAcK
Melilotus alba	Plant	KNApSAcK
Melilotus spp.	Plant	KNApSAcK
Viola arvensis	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0014411

DrugBank ID

DB00266

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1023/a:1024474609667. [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. doi: 10.1078/0171-9335-00377. [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. doi: 10.1016/j.abb.2004.11.002. [PubMed:15639223 ]
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. doi: 10.1021/bi0600087. [PubMed:16700548 ]

Showing NP-Card for Dicoumarol (NP0051443)

MOL for NP0051443 (Dicoumarol)

3D MOL for NP0051443 (Dicoumarol)

3D SDF for NP0051443 (Dicoumarol)

3D-SDF for NP0051443 (Dicoumarol)

PDB for NP0051443 (Dicoumarol)

3D PDB for NP0051443 (Dicoumarol)

SMILES for NP0051443 (Dicoumarol)

INCHI for NP0051443 (Dicoumarol)

Structure for NP0051443 (Dicoumarol)

3D Structure for NP0051443 (Dicoumarol)