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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:01:31 UTC

Update Date

2019-07-23 07:14:37 UTC

HMDB ID

HMDB0060575

Secondary Accession Numbers

HMDB60575

Metabolite Identification

Common Name

Dehydrowarfarin

Description

Dehydrowarfarin is a metabolite of warfarin. Warfarin (also known under the brand names Coumadin, Jantoven, Marevan, Lawarin, Waran, and Warfant) is an anticoagulant normally used in the prevention of thrombosis and thromboembolism, the formation of blood clots in the blood vessels and their migration elsewhere in the body respectively. It was initially introduced in 1948 as a pesticide against rats and mice and is still used for this purpose, although more potent poisons such as brodifacoum have since been developed. (Wikipedia)

Structure

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

HMDB0060575
     RDKit          3D
Dehydrowarfarin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.3680   -3.0396   -2.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -1.8048   -1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290   -1.1612   -0.8416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -1.5992   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -0.6745   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630    0.3269    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.1380    1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852    1.1657    1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194    2.4610    1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    2.7115    0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077    1.6713    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5644   -0.5764   -0.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    0.0904    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5541    0.5723    1.6050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055    0.2551    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552    0.9245    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7274    1.0753    1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3303    0.5451    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6187   -0.1146   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607   -0.2644   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799   -0.8821   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566   -1.0643   -1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.6860   -2.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -3.8965   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634   -3.0215   -2.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890   -2.9588   -2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745   -2.3480   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0784   -0.8663    1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    0.9549    2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085    3.2520    1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    3.7522    0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    1.9202   -0.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    1.0590    2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.3355    2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837    1.5979    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3955    0.6621    0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.5126   -1.6481 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  2  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
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv0541 06151310012D          

 23 25  0  0  0  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12  1  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 20 12  2  0  0  0  0
 21 18  1  0  0  0  0
 22 19  2  0  0  0  0
 23 16  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060575

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)\C=C(/C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O4/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/h2-11,21H,1H3/b15-11+

> <INCHI_KEY>
SWIPQYPHTPMNLK-RVDMUPIBSA-N

> <FORMULA>
C19H14O4

> <MOLECULAR_WEIGHT>
306.3121

> <EXACT_MASS>
306.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.706457511759755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-[(1E)-3-oxo-1-phenylbut-1-en-1-yl]-2H-chromen-2-one

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.837606360666666

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.6449625978103875

> <JCHEM_PKA_STRONGEST_BASIC>
-6.097068196346397

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
87.68679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-[(1E)-3-oxo-1-phenylbut-1-en-1-yl]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060575
     RDKit          3D
Dehydrowarfarin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.3680   -3.0396   -2.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -1.8048   -1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290   -1.1612   -0.8416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -1.5992   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -0.6745   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630    0.3269    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.1380    1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852    1.1657    1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194    2.4610    1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    2.7115    0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077    1.6713    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5644   -0.5764   -0.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    0.0904    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5541    0.5723    1.6050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055    0.2551    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552    0.9245    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7274    1.0753    1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3303    0.5451    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6187   -0.1146   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607   -0.2644   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799   -0.8821   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566   -1.0643   -1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.6860   -2.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -3.8965   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634   -3.0215   -2.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890   -2.9588   -2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745   -2.3480   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0784   -0.8663    1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    0.9549    2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085    3.2520    1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    3.7522    0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    1.9202   -0.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    1.0590    2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.3355    2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837    1.5979    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3955    0.6621    0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.5126   -1.6481 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  2  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
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    3   13                                                       
CONECT    8    4   13                                                       
CONECT    9    5   14                                                       
CONECT   10    6   16                                                       
CONECT   11   12   15                                                       
CONECT   12    1   11   20                                                  
CONECT   13    7    8   15                                                  
CONECT   14    9   16   18                                                  
CONECT   15   11   13   17                                                  
CONECT   16   10   14   23                                                  
CONECT   17   15   18   19                                                  
CONECT   18   14   17   21                                                  
CONECT   19   17   22   23                                                  
CONECT   20   12                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0060575
HETATM    1  C1  UNL     1      -3.368  -3.040  -2.052  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.984  -1.805  -1.242  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.929  -1.161  -0.842  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.572  -1.599  -1.080  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.927  -0.674  -0.415  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.663   0.327   0.323  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.751   0.138   1.106  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.485   1.166   1.667  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.119   2.461   1.442  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.023   2.712   0.658  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.308   1.671   0.108  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.564  -0.576  -0.457  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.251   0.090   0.535  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.554   0.572   1.605  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.606   0.255   0.438  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.355   0.924   1.414  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.727   1.075   1.290  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.330   0.545   0.174  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.619  -0.115  -0.795  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.261  -0.264  -0.673  1.00  0.00           C  
HETATM   21  O3  UNL     1       2.580  -0.882  -1.577  1.00  0.00           O  
HETATM   22  C19 UNL     1       1.257  -1.064  -1.524  1.00  0.00           C  
HETATM   23  O4  UNL     1       0.776  -1.686  -2.503  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.155  -3.896  -1.398  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.663  -3.022  -2.924  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.389  -2.959  -2.415  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.875  -2.348  -1.547  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.078  -0.866   1.399  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.348   0.955   2.283  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.708   3.252   1.892  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.762   3.752   0.503  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.458   1.920  -0.508  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.994   1.059   2.347  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.888   1.336   2.279  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.284   1.598   2.060  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.395   0.662   0.078  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.126  -0.513  -1.648  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5    5   27
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   32
CONECT   12   13   13   22
CONECT   13   14   15
CONECT   14   33
CONECT   15   16   16   20
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   21
CONECT   21   22
CONECT   22   23   23
END

HMDB0060575
     RDKit          3D
Dehydrowarfarin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.3680   -3.0396   -2.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -1.8048   -1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290   -1.1612   -0.8416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -1.5992   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -0.6745   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630    0.3269    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511    0.1380    1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852    1.1657    1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194    2.4610    1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    2.7115    0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077    1.6713    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5644   -0.5764   -0.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    0.0904    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5541    0.5723    1.6050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055    0.2551    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552    0.9245    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7274    1.0753    1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3303    0.5451    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6187   -0.1146   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607   -0.2644   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799   -0.8821   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566   -1.0643   -1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.6860   -2.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -3.8965   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634   -3.0215   -2.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890   -2.9588   -2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745   -2.3480   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0784   -0.8663    1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    0.9549    2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085    3.2520    1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    3.7522    0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    1.9202   -0.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    1.0590    2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.3355    2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2837    1.5979    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3955    0.6621    0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1259   -0.5126   -1.6481 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  2  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
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₄

Average Molecular Weight

306.3121

Monoisotopic Molecular Weight

306.089208936

IUPAC Name

4-hydroxy-3-[(1E)-3-oxo-1-phenylbut-1-en-1-yl]-2H-chromen-2-one

Traditional Name

4-hydroxy-3-[(1E)-3-oxo-1-phenylbut-1-en-1-yl]chromen-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)\C=C(/C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O

InChI Identifier

InChI=1S/C19H14O4/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/h2-11,21H,1H3/b15-11+

InChI Key

SWIPQYPHTPMNLK-RVDMUPIBSA-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
Styrene
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Acryloyl-group
Enone
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated ketone
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060575)
Liver (HMDB: HMDB0060575)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060575)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060575)

Cellular substructure

Cytoplasm (HMDB: HMDB0060575)
Membrane (HMDB: HMDB0060575)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.84	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.64	ChemAxon
pKa (Strongest Basic)	-6.1	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	3	ChemAxon
Refractivity	87.69 m³·mol⁻¹	ChemAxon
Polarizability	31.71 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
DeepCCS	[M+H]+	165.891	30932474
DeepCCS	[M-H]-	163.533	30932474
DeepCCS	[M-2H]-	196.488	30932474
DeepCCS	[M+Na]+	171.984	30932474
AllCCS	[M+H]+	171.2	32859911
AllCCS	[M+H-H2O]+	167.6	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	174.1	32859911
AllCCS	[M+Na-2H]-	173.4	32859911
AllCCS	[M+HCOO]-	172.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrowarfarin	CC(=O)\C=C(/C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O	3985.0	Standard polar	33892256
Dehydrowarfarin	CC(=O)\C=C(/C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O	2628.7	Standard non polar	33892256
Dehydrowarfarin	CC(=O)\C=C(/C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O	2743.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydrowarfarin,1TMS,isomer #1	CC(=O)/C=C(\C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O	2883.7	Semi standard non polar	33892256
Dehydrowarfarin,1TMS,isomer #2	C=C(/C=C(\C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2826.4	Semi standard non polar	33892256
Dehydrowarfarin,2TMS,isomer #1	C=C(/C=C(\C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2875.8	Semi standard non polar	33892256
Dehydrowarfarin,2TMS,isomer #1	C=C(/C=C(\C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	2673.1	Standard non polar	33892256
Dehydrowarfarin,2TMS,isomer #1	C=C(/C=C(\C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O)O[Si](C)(C)C	3266.8	Standard polar	33892256
Dehydrowarfarin,1TBDMS,isomer #1	CC(=O)/C=C(\C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O	3145.0	Semi standard non polar	33892256
Dehydrowarfarin,1TBDMS,isomer #2	C=C(/C=C(\C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O)O[Si](C)(C)C(C)(C)C	3083.6	Semi standard non polar	33892256
Dehydrowarfarin,2TBDMS,isomer #1	C=C(/C=C(\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	3321.4	Semi standard non polar	33892256
Dehydrowarfarin,2TBDMS,isomer #1	C=C(/C=C(\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	3105.8	Standard non polar	33892256
Dehydrowarfarin,2TBDMS,isomer #1	C=C(/C=C(\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	3451.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrowarfarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-1290000000-222fc87ce597a97e8975	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrowarfarin GC-MS (1 TMS) - 70eV, Positive	splash10-01w0-2109000000-cd0774d270afea53d466	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrowarfarin 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 - Dehydrowarfarin 10V, Positive-QTOF	splash10-0a4r-0197000000-afe4afb55686e751ccd3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 20V, Positive-QTOF	splash10-052s-0292000000-3dec1a2ecc1544f48dd0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 40V, Positive-QTOF	splash10-0fi0-0930000000-c4e9386942940fe3d973	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 10V, Negative-QTOF	splash10-0a4i-0219000000-0685b8fa188689c1ec09	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 20V, Negative-QTOF	splash10-03di-0945000000-aed0023afd785cd5593b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 40V, Negative-QTOF	splash10-000f-6920000000-a97e072f12b7d4520e78	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 10V, Positive-QTOF	splash10-0a4i-0009000000-fddbcb59439fb349a196	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 20V, Positive-QTOF	splash10-0a4i-0059000000-effadf06c5754cd2cd3b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 40V, Positive-QTOF	splash10-0r94-3920000000-30a8eafaea3fad8e07a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 10V, Negative-QTOF	splash10-0a4i-0009000000-42ed0a7901a822b9c40e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 20V, Negative-QTOF	splash10-0a4i-0129000000-cd5d3e8c3b5b1d581079	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrowarfarin 40V, Negative-QTOF	splash10-01pc-3960000000-5cafcd85f1b0cdad3660	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54684422

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Dehydrowarfarin (HMDB0060575)

MOL for HMDB0060575 (Dehydrowarfarin)

3D MOL for HMDB0060575 (Dehydrowarfarin)

3D SDF for HMDB0060575 (Dehydrowarfarin)

3D-SDF for HMDB0060575 (Dehydrowarfarin)

PDB for HMDB0060575 (Dehydrowarfarin)

3D PDB for HMDB0060575 (Dehydrowarfarin)

SMILES for HMDB0060575 (Dehydrowarfarin)

INCHI for HMDB0060575 (Dehydrowarfarin)

Structure for HMDB0060575 (Dehydrowarfarin)

3D Structure for HMDB0060575 (Dehydrowarfarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra