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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-18 08:58:42 UTC

Update Date

2022-03-25 18:55:00 UTC

HMDB ID

HMDB0001935

Secondary Accession Numbers

HMDB01935

Metabolite Identification

Common Name

Warfarin

Description

Warfarin is an anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.

Structure

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

HMDB0001935
     RDKit          3D
Warfarin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.0043    3.8370   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990    2.5872   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0096    2.6650   -0.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.2375   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    0.3168    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8729   -1.0603    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -1.8369    1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176   -3.1020    1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8857   -3.6636   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6381   -2.9029   -1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1373   -1.6131   -1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864    0.3889    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656   -0.0725   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678   -0.5811   -1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920    0.0085    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -0.4330   -0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.3449   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.1814    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545    0.6285    1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.5422    1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7981    0.9655    2.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5453    0.8911    1.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.3091    2.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    4.4306   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451    4.4960    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    3.5933   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089    0.9172   -1.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727    1.2864   -1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8900    0.7220    1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9169   -1.3904    2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960   -3.6639    2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2778   -4.6781   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551   -3.3651   -2.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -1.0746   -2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1899   -0.9414   -2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1160   -0.8437   -1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -0.7053   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649    0.2282    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067    1.0405    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 11  6  1  0
 22 12  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

  Mrv1652305271900322D          

 23 25  0  0  0  0            999 V2000
    1.0993   -0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586   -0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    1.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875   -0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874    1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875   -0.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730   -2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  6  1  0  0  0  0
 11  5  1  0  0  0  0
  6  5  2  0  0  0  0
  6 13  1  0  0  0  0
 11  7  2  0  0  0  0
 13 14  1  0  0  0  0
 14  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8 16  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 17  1  0  0  0  0
 20 16  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001935

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3

> <INCHI_KEY>
PJVWKTKQMONHTI-UHFFFAOYSA-N

> <FORMULA>
C19H16O4

> <MOLECULAR_WEIGHT>
308.3279

> <EXACT_MASS>
308.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.895032290513946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.744707362333333

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.427730728397098

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.559616389561608

> <JCHEM_PKA_STRONGEST_BASIC>
-6.903837402787224

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
86.86010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
warfarin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001935
     RDKit          3D
Warfarin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.0043    3.8370   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990    2.5872   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0096    2.6650   -0.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.2375   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    0.3168    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8729   -1.0603    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -1.8369    1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176   -3.1020    1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8857   -3.6636   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6381   -2.9029   -1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1373   -1.6131   -1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864    0.3889    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656   -0.0725   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678   -0.5811   -1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920    0.0085    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -0.4330   -0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.3449   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.1814    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545    0.6285    1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.5422    1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7981    0.9655    2.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5453    0.8911    1.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.3091    2.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    4.4306   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451    4.4960    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    3.5933   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089    0.9172   -1.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727    1.2864   -1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8900    0.7220    1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9169   -1.3904    2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960   -3.6639    2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2778   -4.6781   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551   -3.3651   -2.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -1.0746   -2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1899   -0.9414   -2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1160   -0.8437   -1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -0.7053   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649    0.2282    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067    1.0405    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 11  6  1  0
 22 12  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       2.052  -0.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.386   0.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.386   2.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.052   3.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.718   0.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.718   2.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.949   0.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.616   0.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.283  -0.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.283  -1.610   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.615  -0.070   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.615  -1.610   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.615   3.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.949   2.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.283   3.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.950  -0.070   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.616   2.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.950   3.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.284   2.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.284   0.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.616  -2.380   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.950  -1.610   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.616  -3.920   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    1   11    6                                                  
CONECT    6    4    5   13                                                  
CONECT    7   11   14    9                                                  
CONECT    8    9   16   17                                                  
CONECT    9    7    8   10                                                  
CONECT   10    9   21                                                       
CONECT   11    5    7   12                                                  
CONECT   12   11                                                            
CONECT   13    6   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14                                                            
CONECT   16    8   20                                                       
CONECT   17   18    8                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   10   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0243748
HETATM    1  C1  UNL     1      -0.479   3.115   1.083  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.955   2.952  -0.293  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.920   3.912  -1.042  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.493   1.693  -0.890  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.463   0.514   0.021  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.034  -0.661  -0.687  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.644  -1.614   0.102  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.208  -2.738  -0.443  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.166  -2.924  -1.806  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.562  -1.982  -2.601  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.996  -0.849  -2.038  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.148   0.226   0.608  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.981   0.133  -0.204  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.908   0.317  -1.560  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.196  -0.154   0.397  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.355  -0.260  -0.355  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.552  -0.543   0.241  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.595  -0.724   1.605  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.445  -0.620   2.356  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.235  -0.337   1.785  1.00  0.00           C  
HETATM   21  O3  UNL     1       1.134  -0.235   2.482  1.00  0.00           O  
HETATM   22  C19 UNL     1      -0.029   0.033   1.962  1.00  0.00           C  
HETATM   23  O4  UNL     1      -1.039   0.108   2.743  1.00  0.00           O  
HETATM   24  H1  UNL     1       0.546   2.766   1.259  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.445   4.221   1.305  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.161   2.687   1.845  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.562   1.967  -1.166  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.999   1.545  -1.850  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.166   0.708   0.896  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.710  -1.526   1.180  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.697  -3.503   0.181  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.612  -3.817  -2.259  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.509  -2.095  -3.696  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.521  -0.113  -2.703  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.685   0.258  -2.157  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.375  -0.125  -1.445  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.482  -0.630  -0.340  1.00  0.00           H  
HETATM   38  H15 UNL     1       5.555  -0.945   2.043  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.470  -0.762   3.441  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   27   28
CONECT    5    6   12   29
CONECT    6    7    7   11
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   34
CONECT   12   13   13   22
CONECT   13   14   15
CONECT   14   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   20   21
CONECT   21   22
CONECT   22   23   23
END

HMDB0001935
     RDKit          3D
Warfarin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.0043    3.8370   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990    2.5872   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0096    2.6650   -0.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.2375   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    0.3168    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8729   -1.0603    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -1.8369    1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176   -3.1020    1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8857   -3.6636   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6381   -2.9029   -1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1373   -1.6131   -1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864    0.3889    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656   -0.0725   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678   -0.5811   -1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920    0.0085    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -0.4330   -0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.3449   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.1814    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545    0.6285    1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.5422    1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7981    0.9655    2.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5453    0.8911    1.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.3091    2.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    4.4306   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451    4.4960    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    3.5933   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089    0.9172   -1.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727    1.2864   -1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8900    0.7220    1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9169   -1.3904    2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960   -3.6639    2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2778   -4.6781   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551   -3.3651   -2.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -1.0746   -2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1899   -0.9414   -2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1160   -0.8437   -1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -0.7053   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649    0.2282    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067    1.0405    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 11  6  1  0
 22 12  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Warfarine	Kegg
Choice	Kegg
(Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarin	HMDB
(Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarine	HMDB
(S)-4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2-benzopyrone	HMDB
1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone	HMDB
200 Coumarin	HMDB
3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin	HMDB
3-(Acetonylbenzyl)-4-hydroxycoumarin	HMDB
3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin	HMDB
3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarin	HMDB
3-(alpha-Phenyl-beta-acetylethyl)-4-hydroxycoumarin	HMDB
4-Hydroxy-3- (3-oxo-1-fenyl-butyl) cumarine	HMDB
4-Hydroxy-3- (3-oxo-1-phenyl-butyl)-cumarin	HMDB
4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarine	HMDB
4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarin	HMDB
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one	HMDB, MeSH
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one	HMDB
4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin	HMDB
4-Idrossi-3- (3-oxo-)-fenil-butil)-cumarine	HMDB
4-Idrossi-3-(3-oxo-)-fenil-butil)-cumarine	HMDB
4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarine	HMDB
4oh-Coumarin deriv.	HMDB
Arab rat death	HMDB
Arab rat deth	HMDB
Athrombin-K	HMDB
Athrombine-K	HMDB
Brumolin	HMDB
CO-Rax	HMDB
Compound 42	HMDB
Coumadin	HMDB, MeSH
Coumafen	HMDB
Coumafene	HMDB
Coumaphen	HMDB
Coumaphene	HMDB
Coumarins	HMDB
Coumefene	HMDB
Cov-R-tox	HMDB
D-CON	HMDB
delta-CON	HMDB
Dethmor	HMDB
Dethnel	HMDB
Dicusat e	HMDB
DL-3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin	HMDB
Eastern states duocide	HMDB
fasco Fascrat powder	HMDB
Frass-ratron	HMDB
Killgerm sewarin P	HMDB
Kumader	HMDB
Kumadu	HMDB
Kumatox	HMDB
Kypfarin	HMDB
Latka 42	HMDB
Liqua-tox	HMDB
Maag rattentod cum	HMDB
Mar-frin	HMDB
Martin'S mar-frin	HMDB
Maveran	HMDB
Mouse pak	HMDB
Place-pax	HMDB
Prothromadin	HMDB
Rat & mice bait	HMDB
Rat and mice bait	HMDB
Rat-a-way	HMDB
Rat-alpha-way	HMDB
Rat-b-gon	HMDB
Rat-beta-gon	HMDB
Rat-gard	HMDB
Rat-kill	HMDB
Rat-mix	HMDB
Rat-O-cide #2	HMDB
Rat-O-cide no. 2	HMDB
Rat-ola	HMDB
Rat-trol	HMDB
Ratorex	HMDB
Ratox	HMDB
Ratoxin	HMDB
Ratron	HMDB
Ratron g	HMDB
Rats-NO-more	HMDB
Ratten-koederrohr	HMDB
Rattenstreupulver neu schacht	HMDB
Rattenstreupulver new schacht	HMDB
Rattentraenke	HMDB
Rattunal	HMDB
RAX	HMDB
RCR Grey squirrel killer concentrate	HMDB
ro-Deth	HMDB
Rodafarin	HMDB
Rodafarin c	HMDB
Rodex	HMDB
Rodex blox	HMDB
Rosex	HMDB
Rough & ready mouse mix	HMDB
Rough and ready mouse mix	HMDB
Sakarat	HMDB
Sewarin	HMDB
Solfarin	HMDB
Sorexa plus	HMDB
Spray-trol brand roden-trol	HMDB
Temus W	HMDB
Tox-hid	HMDB
Twin light rat away	HMDB
Vampirinip II	HMDB
Vampirinip III	HMDB
Waran	HMDB
Warfarin sodium	HMDB, MeSH
Zoocoumarin	HMDB
aldo Brand OF warfarin sodium	MeSH, HMDB
apo-Warfarin	MeSH, HMDB
Apotex brand OF warfarin sodium	MeSH, HMDB
Bailly brand OF warfarin sodium	MeSH, HMDB
Boots brand OF warfarin sodium	MeSH, HMDB
Marevan	MeSH, HMDB
Aldocumar	MeSH, HMDB
Coumadine	MeSH, HMDB
Warfant	MeSH, HMDB
Bristol-myers squibb brand OF warfarin sodium	MeSH, HMDB
Genpharm brand OF warfarin sodium	MeSH, HMDB
Goldshield brand OF warfarin sodium	MeSH, HMDB
Sodium, warfarin	MeSH, HMDB
Tedicumar	MeSH, HMDB
Warfarin potassium	MeSH, HMDB
Antigen brand OF warfarin sodium	MeSH, HMDB
Estedi brand OF warfarin sodium	MeSH, HMDB
Gen-warfarin	MeSH, HMDB
Potassium, warfarin	MeSH, HMDB

Chemical Formula

C₁₉H₁₆O₄

Average Molecular Weight

308.3279

Monoisotopic Molecular Weight

308.104859

IUPAC Name

4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one

Traditional Name

warfarin

CAS Registry Number

81-81-2

SMILES

CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2

InChI Identifier

InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3

InChI Key

PJVWKTKQMONHTI-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
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl ketone (CHEBI:87732 )
hydroxycoumarin (CHEBI:87732 )
Coumarin rodenticides (C01541 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0001935)

Source

Exogenous

Exogenous (HMDB: HMDB0001935)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Warfarin Action Pathway (PathBank: SMP0000268)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 °C	Not Available
Boiling Point	515.15 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.017 mg/mL at 20 °C	Not Available
LogP	2.70	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	166.8	30932474
[M+H]+	Not Available	165.872	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001390

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.74	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.56	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.86 m³·mol⁻¹	ChemAxon
Polarizability	31.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.81	31661259
DarkChem	[M-H]-	171.567	31661259
AllCCS	[M+H]+	172.291	32859911
AllCCS	[M-H]-	176.332	32859911
DeepCCS	[M+H]+	172.867	30932474
DeepCCS	[M-H]-	170.509	30932474
DeepCCS	[M-2H]-	203.659	30932474
DeepCCS	[M+Na]+	178.96	30932474
AllCCS	[M+H]+	172.3	32859911
AllCCS	[M+H-H2O]+	168.7	32859911
AllCCS	[M+NH4]+	175.6	32859911
AllCCS	[M+Na]+	176.6	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Warfarin,1TMS,isomer #1	CC(=O)CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O	2723.3	Semi standard non polar	33892256
Warfarin,1TMS,isomer #1	CC(=O)CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O	2504.9	Standard non polar	33892256
Warfarin,1TMS,isomer #1	CC(=O)CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O	3314.5	Standard polar	33892256
Warfarin,1TMS,isomer #2	CC(=CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2834.0	Semi standard non polar	33892256
Warfarin,1TMS,isomer #2	CC(=CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2674.0	Standard non polar	33892256
Warfarin,1TMS,isomer #2	CC(=CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3516.3	Standard polar	33892256
Warfarin,1TMS,isomer #3	C=C(CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2710.8	Semi standard non polar	33892256
Warfarin,1TMS,isomer #3	C=C(CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2592.4	Standard non polar	33892256
Warfarin,1TMS,isomer #3	C=C(CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3510.8	Standard polar	33892256
Warfarin,2TMS,isomer #1	CC(=CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2864.1	Semi standard non polar	33892256
Warfarin,2TMS,isomer #1	CC(=CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2699.0	Standard non polar	33892256
Warfarin,2TMS,isomer #1	CC(=CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3191.8	Standard polar	33892256
Warfarin,2TMS,isomer #2	C=C(CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2759.7	Semi standard non polar	33892256
Warfarin,2TMS,isomer #2	C=C(CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2598.9	Standard non polar	33892256
Warfarin,2TMS,isomer #2	C=C(CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3200.1	Standard polar	33892256
Warfarin,1TBDMS,isomer #1	CC(=O)CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O	2973.3	Semi standard non polar	33892256
Warfarin,1TBDMS,isomer #1	CC(=O)CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O	2708.4	Standard non polar	33892256
Warfarin,1TBDMS,isomer #1	CC(=O)CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O	3409.3	Standard polar	33892256
Warfarin,1TBDMS,isomer #2	CC(=CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3119.2	Semi standard non polar	33892256
Warfarin,1TBDMS,isomer #2	CC(=CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	2890.7	Standard non polar	33892256
Warfarin,1TBDMS,isomer #2	CC(=CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3557.8	Standard polar	33892256
Warfarin,1TBDMS,isomer #3	C=C(CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	2996.9	Semi standard non polar	33892256
Warfarin,1TBDMS,isomer #3	C=C(CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	2798.4	Standard non polar	33892256
Warfarin,1TBDMS,isomer #3	C=C(CC(C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3561.6	Standard polar	33892256
Warfarin,2TBDMS,isomer #1	CC(=CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3296.4	Semi standard non polar	33892256
Warfarin,2TBDMS,isomer #1	CC(=CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3118.0	Standard non polar	33892256
Warfarin,2TBDMS,isomer #1	CC(=CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3369.2	Standard polar	33892256
Warfarin,2TBDMS,isomer #2	C=C(CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3216.7	Semi standard non polar	33892256
Warfarin,2TBDMS,isomer #2	C=C(CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3002.7	Standard non polar	33892256
Warfarin,2TBDMS,isomer #2	C=C(CC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3384.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Warfarin EI-B (Non-derivatized)	splash10-014i-0293000000-848341bcbd6a3f0a2c6b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Warfarin EI-B (Non-derivatized)	splash10-014i-0293000000-848341bcbd6a3f0a2c6b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Warfarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-3190000000-b963cb54bb6abedefbe3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Warfarin GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-7195000000-ca3a892fd51e0eac1242	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Warfarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Warfarin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Warfarin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Warfarin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-7692000000-6e3993fee62d7eb7438e	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0429000000-1e818b579dc7a0fade2d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , negative-QTOF	splash10-03di-0900000000-f568338c06cd9b4762ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , negative-QTOF	splash10-03di-0900000000-acdd0ed19e403aa73c77	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-QFT , negative-QTOF	splash10-0bt9-0539000000-5b1c7c6c812ba72325e3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0009000000-e461e1aca7977a2838ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , positive-QTOF	splash10-0w29-0960000000-9fa099190280529cd891	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , positive-QTOF	splash10-00di-0910000000-d7dbaf6e7b34ee85e1f7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , positive-QTOF	splash10-03di-0920000000-4fb886a5c160afa86df9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-ITFT , positive-QTOF	splash10-03di-0920000000-ad608fe7680a2adf9d90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin LC-ESI-QFT , positive-QTOF	splash10-0ik9-0942000000-5864f2d15892753d6a8b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 55V, Negative-QTOF	splash10-03di-0900000000-acdd0ed19e403aa73c77	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 55V, Positive-QTOF	splash10-0w29-0960000000-b5bc3614bc1379df068c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 35V, Negative-QTOF	splash10-0bt9-0539000000-3554db4e3651d4691cbb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 75V, Positive-QTOF	splash10-0229-2900000000-022920b191a958c73833	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 60V, Positive-QTOF	splash10-07vi-5920000000-0506f7adccf44b63822a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 55V, Negative-QTOF	splash10-0a4i-0009000000-e461e1aca7977a2838ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 80V, Negative-QTOF	splash10-0a4i-0429000000-1e818b579dc7a0fade2d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 75V, Positive-QTOF	splash10-0229-2900000000-6909a3446398afc7d421	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Warfarin 60V, Positive-QTOF	splash10-03kc-0910000000-b4521bf9a45fcfff36ac	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Warfarin 10V, Positive-QTOF	splash10-0a4l-0197000000-a98e039dbdc8da6c3b7c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Warfarin 20V, Positive-QTOF	splash10-052f-0292000000-d9a969b41fe312282de6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Warfarin 40V, Positive-QTOF	splash10-00di-2690000000-f20b105406ab790d37f0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Warfarin 10V, Negative-QTOF	splash10-0a4i-1149000000-4072cf2742b0e6164f82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Warfarin 20V, Negative-QTOF	splash10-0bt9-5988000000-eb075587f79ddb4af966	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Warfarin 40V, Negative-QTOF	splash10-052f-9350000000-47075e4967528dede6f3	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Warfarin 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 DB00682	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00682	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10442445

KEGG Compound ID

C01541

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

87732

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1136391

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rost S, Fregin A, Ivaskevicius V, Conzelmann E, Hortnagel K, Pelz HJ, Lappegard K, Seifried E, Scharrer I, Tuddenham EG, Muller CR, Strom TM, Oldenburg J: Mutations in VKORC1 cause warfarin resistance and multiple coagulation factor deficiency type 2. Nature. 2004 Feb 5;427(6974):537-41. [PubMed:14765194 ]
Li T, Chang CY, Jin DY, Lin PJ, Khvorova A, Stafford DW: Identification of the gene for vitamin K epoxide reductase. Nature. 2004 Feb 5;427(6974):541-4. [PubMed:14765195 ]
Whitlon DS, Sadowski JA, Suttie JW: Mechanism of coumarin action: significance of vitamin K epoxide reductase inhibition. Biochemistry. 1978 Apr 18;17(8):1371-7. [PubMed:646989 ]
Freedman MD: Oral anticoagulants: pharmacodynamics, clinical indications and adverse effects. J Clin Pharmacol. 1992 Mar;32(3):196-209. [PubMed:1564123 ]
Hirsh J, Fuster V, Ansell J, Halperin JL: American Heart Association/American College of Cardiology Foundation guide to warfarin therapy. J Am Coll Cardiol. 2003 May 7;41(9):1633-52. [PubMed:12742309 ]
Ansell J, Hirsh J, Poller L, Bussey H, Jacobson A, Hylek E: The pharmacology and management of the vitamin K antagonists: the Seventh ACCP Conference on Antithrombotic and Thrombolytic Therapy. Chest. 2004 Sep;126(3 Suppl):204S-233S. [PubMed:15383473 ]
Holbrook AM, Pereira JA, Labiris R, McDonald H, Douketis JD, Crowther M, Wells PS: Systematic overview of warfarin and its drug and food interactions. Arch Intern Med. 2005 May 23;165(10):1095-106. [PubMed:15911722 ]
Ansell J, Hirsh J, Hylek E, Jacobson A, Crowther M, Palareti G: Pharmacology and management of the vitamin K antagonists: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):160S-198S. doi: 10.1378/chest.08-0670. [PubMed:18574265 ]
(). Loftus, Christopher M. (1995). Fetal toxicity of common neurosurgical drugs. Neurosurgical Aspects of Pregnancy. Park Ridge, Ill: American Association of Neurological Surgeons. pp. 11-3.. .
(). Macina, Orest T.; Schardein, James L. (2007). Warfarin. Human Developmental Toxicants. Boca Raton: CRC Taylor & Francis. pp. 193-4. .

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

Warfarin → 3,4,5-trihydroxy-6-{[2-oxo-3-(3-oxo-1-phenylbutyl)-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

Enzyme Details

3. Activin receptor type-1

General function:: Involved in receptor signaling protein serine/threonine kinase activity
Specific function:: On ligand binding, forms a receptor complex consisting of two type II and two type I transmembrane serine/threonine kinases. Type II receptors phosphorylate and activate type I receptors which autophosphorylate, then bind and activate SMAD transcriptional regulators. Receptor for activin. May be involved for left-right pattern formation during embryogenesis
Gene Name:: ACVR1
Uniprot ID:: Q04771
Molecular weight:: 57152.4

Enzyme Details

4. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

Enzyme Details

5. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

Enzyme Details

6. 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

Enzyme Details

7. Vitamin K epoxide reductase complex subunit 1-like protein 1

General function:: Not Available
Specific function:: Not Available
Gene Name:: VKORC1L1
Uniprot ID:: Q8N0U8
Molecular weight:: 19835.4

Showing metabocard for Warfarin (HMDB0001935)

MOL for HMDB0001935 (Warfarin)

3D MOL for HMDB0001935 (Warfarin)

3D SDF for HMDB0001935 (Warfarin)

3D-SDF for HMDB0001935 (Warfarin)

PDB for HMDB0001935 (Warfarin)

3D PDB for HMDB0001935 (Warfarin)

SMILES for HMDB0001935 (Warfarin)

INCHI for HMDB0001935 (Warfarin)

Structure for HMDB0001935 (Warfarin)

3D Structure for HMDB0001935 (Warfarin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions