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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015081

Secondary Accession Numbers

HMDB15081

Metabolite Identification

Common Name

Phenprocoumon

Description

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

Structure

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

HMDB0015081
     RDKit          3D
Phenprocoumon
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.3950   -2.7648   -0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382   -2.1730    1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218   -0.9076    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.2411    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    1.1070    1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1700    2.1774    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3689    2.3719   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    1.5348   -1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137    0.4683   -0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3736   -0.8363    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642    0.3124    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230    1.2625    1.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4025    0.4160    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    1.5099    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.6158   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    0.6322   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435   -0.4778   -1.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741   -0.5633   -0.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -1.5997   -1.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -1.7766   -0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337   -2.7967   -0.8153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1493   -3.8616   -0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -2.8191    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760   -2.2831   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.0433    1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -2.9235    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742   -0.5928    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021    0.9236    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6197    2.8430    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9868    3.2036   -0.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.6857   -2.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669   -0.1785   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    2.0927    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8752    2.3198    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0851    2.4802   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    0.6641   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034   -1.2642   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 20 10  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

  Mrv0541 04191212152D          

 21 23  0  0  0  0            999 V2000
   -3.1527    0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8671    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8671   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1527   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237    0.6777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1341    0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1341   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948   -1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237   -1.7973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948    0.6777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 14 12  2  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 20  1  0  0  0  0
 10 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015081

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3

> <INCHI_KEY>
DQDAYGNAKTZFIW-UHFFFAOYSA-N

> <FORMULA>
C18H16O3

> <MOLECULAR_WEIGHT>
280.3178

> <EXACT_MASS>
280.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.918673803084125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.735323604666666

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.438633009678774

> <JCHEM_PKA_STRONGEST_BASIC>
-6.543541921575128

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
81.6436

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenprocoumon

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015081
     RDKit          3D
Phenprocoumon
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.3950   -2.7648   -0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382   -2.1730    1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218   -0.9076    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.2411    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    1.1070    1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1700    2.1774    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3689    2.3719   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    1.5348   -1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137    0.4683   -0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3736   -0.8363    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642    0.3124    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230    1.2625    1.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4025    0.4160    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    1.5099    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.6158   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    0.6322   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435   -0.4778   -1.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741   -0.5633   -0.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -1.5997   -1.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -1.7766   -0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337   -2.7967   -0.8153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1493   -3.8616   -0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -2.8191    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760   -2.2831   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.0433    1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -2.9235    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742   -0.5928    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021    0.9236    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6197    2.8430    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9868    3.2036   -0.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.6857   -2.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669   -0.1785   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    2.0927    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8752    2.3198    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0851    2.4802   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    0.6641   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034   -1.2642   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 20 10  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -5.885   1.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.219   0.495   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.219  -1.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.885  -1.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.551  -1.045   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.551   0.495   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.218   1.265   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.218  -1.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.884  -1.045   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.884   0.495   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.550  -1.815   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.783  -1.045   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.117   1.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.783   0.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.117  -1.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.451  -1.045   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.451   0.495   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.550  -3.355   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.783  -4.125   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.218  -3.355   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.550   1.265   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    7    9   21                                                  
CONECT   11    9   12   18                                                  
CONECT   12   11   14   15                                                  
CONECT   13   14   17                                                       
CONECT   14   12   13                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18   11   19                                                       
CONECT   19   18                                                            
CONECT   20    8                                                            
CONECT   21   10                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0015081
HETATM    1  C1  UNL     1      -2.395  -2.765  -0.033  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.638  -2.173   1.089  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.922  -0.908   0.913  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.792   0.241   0.480  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.380   1.107   1.378  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.170   2.177   1.021  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.369   2.372  -0.328  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.803   1.535  -1.261  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.014   0.468  -0.862  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.374  -0.836   0.282  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.164   0.312   0.568  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.623   1.263   1.411  1.00  0.00           O  
HETATM   13  C12 UNL     1       2.402   0.416   0.001  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.186   1.510   0.256  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.454   1.616  -0.324  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.909   0.632  -1.144  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.143  -0.478  -1.418  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.874  -0.563  -0.824  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.118  -1.600  -1.060  1.00  0.00           O  
HETATM   20  C18 UNL     1       0.908  -1.777  -0.550  1.00  0.00           C  
HETATM   21  O3  UNL     1       0.234  -2.797  -0.815  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.149  -3.862  -0.176  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.515  -2.819   0.215  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.376  -2.283  -0.999  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.379  -2.043   1.947  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.920  -2.923   1.562  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.674  -0.593   2.024  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.202   0.924   2.437  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.620   2.843   1.766  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.987   3.204  -0.692  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.959   1.686  -2.339  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.567  -0.178  -1.637  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.083   2.093   1.673  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.875   2.320   0.899  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.085   2.480  -0.128  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.894   0.664  -1.625  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.503  -1.264  -2.071  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   10   27
CONECT    4    5    5    9
CONECT    5    6   28
CONECT    6    7    7   29
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   32
CONECT   10   11   11   20
CONECT   11   12   13
CONECT   12   33
CONECT   13   14   14   18
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19
CONECT   19   20
CONECT   20   21   21
END

HMDB0015081
     RDKit          3D
Phenprocoumon
 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.3950   -2.7648   -0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382   -2.1730    1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218   -0.9076    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921    0.2411    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    1.1070    1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1700    2.1774    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3689    2.3719   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031    1.5348   -1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137    0.4683   -0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3736   -0.8363    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642    0.3124    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230    1.2625    1.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4025    0.4160    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    1.5099    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.6158   -0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    0.6322   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435   -0.4778   -1.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741   -0.5633   -0.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -1.5997   -1.0597 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -1.7766   -0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337   -2.7967   -0.8153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1493   -3.8616   -0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -2.8191    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760   -2.2831   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.0433    1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -2.9235    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742   -0.5928    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021    0.9236    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6197    2.8430    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9868    3.2036   -0.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.6857   -2.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669   -0.1785   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    2.0927    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8752    2.3198    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0851    2.4802   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8943    0.6641   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034   -1.2642   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 20 10  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(1'-Phenyl-propyl)-4-oxycoumarin	ChEBI
3-(1-Phenylpropyl)-4-hydroxycoumarin	ChEBI
3-(alpha-Ethylbenzyl)-4-hydroxycoumarin	ChEBI
3-(alpha-Phenylpropyl)-4-hydroxycoumarin	ChEBI
4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one	ChEBI
4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one	ChEBI
Fenprocumon	ChEBI
Fenprocumone	ChEBI
Phenprocoumarol	ChEBI
Phenprocoumarole	ChEBI
Phenprocoumone	ChEBI
Phenprocoumonum	ChEBI
Phenprocumone	ChEBI
Liquamar	Kegg
3-(a-Ethylbenzyl)-4-hydroxycoumarin	Generator
3-(Α-ethylbenzyl)-4-hydroxycoumarin	Generator
3-(a-Phenylpropyl)-4-hydroxycoumarin	Generator
3-(Α-phenylpropyl)-4-hydroxycoumarin	Generator
Falithrom	MeSH, HMDB
Marcoumar	MeSH, HMDB
Phenprocoumalol	MeSH, HMDB
Phenylpropylhydroxycumarinum	MeSH, HMDB
Marcumar	MeSH, HMDB
Phenprogramma	MeSH, HMDB
Hexal brand OF phenprocoumon	MeSH, HMDB
Wörwag brand OF phenprocoumon	MeSH, HMDB
Roche brand OF phenprocoumon	MeSH, HMDB

Chemical Formula

C₁₈H₁₆O₃

Average Molecular Weight

280.3178

Monoisotopic Molecular Weight

280.109944378

IUPAC Name

4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one

Traditional Name

phenprocoumon

CAS Registry Number

435-97-2

SMILES

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

InChI Identifier

InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3

InChI Key

DQDAYGNAKTZFIW-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
Phenylpropane
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:50438 )

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

Extracellular (HMDB: HMDB0015081)
Membrane (HMDB: HMDB0015081)

Source

Exogenous

Exogenous (HMDB: HMDB0015081)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Phenprocoumon Action Pathway (PathBank: SMP0000271)

Role

Industrial application

Anticoagulant (HMDB: HMDB0015081)

Biological role

Modulator

Inhibitor

EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor (HMDB: HMDB0015081)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	179.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.049 g/L	Not Available
LogP	4.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	160.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	3.81	ALOGPS
logP	3.74	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.64 m³·mol⁻¹	ChemAxon
Polarizability	29.92 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]+	165.77	31661259
DarkChem	[M-H]-	164.837	31661259
DeepCCS	[M+H]+	167.43	30932474
DeepCCS	[M-H]-	165.072	30932474
DeepCCS	[M-2H]-	197.959	30932474
DeepCCS	[M+Na]+	173.524	30932474
AllCCS	[M+H]+	165.8	32859911
AllCCS	[M+H-H2O]+	162.0	32859911
AllCCS	[M+NH4]+	169.4	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	170.7	32859911
AllCCS	[M+Na-2H]-	170.1	32859911
AllCCS	[M+HCOO]-	169.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenprocoumon	CCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2	3536.7	Standard polar	33892256
Phenprocoumon	CCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2	2363.0	Standard non polar	33892256
Phenprocoumon	CCC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2	2439.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenprocoumon,1TMS,isomer #1	CCC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C)C2=CC=CC=C2OC1=O	2460.1	Semi standard non polar	33892256
Phenprocoumon,1TBDMS,isomer #1	CCC(C1=CC=CC=C1)C1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2OC1=O	2724.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gk9-1390000000-b8adf6e29e27ba0e0032	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenprocoumon GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-6659000000-d206d323114210822b66	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenprocoumon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenprocoumon GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Phenprocoumon 10V, Positive-QTOF	splash10-001i-0190000000-3363e5ab875f54ecfdbe	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 20V, Positive-QTOF	splash10-001i-0390000000-5d8ad9702c75c69b0036	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 40V, Positive-QTOF	splash10-06di-4940000000-8a3c1778a9c418538afb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 10V, Negative-QTOF	splash10-004i-0090000000-b940e8a82db8a93a6124	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 20V, Negative-QTOF	splash10-01t9-0490000000-9f94c9b5f041d6204096	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 40V, Negative-QTOF	splash10-054o-8960000000-ce2be44f7678a353e146	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 10V, Positive-QTOF	splash10-001i-0190000000-e4c63991e04960d28471	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 20V, Positive-QTOF	splash10-001i-2390000000-7d5deb49a774d3652362	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 40V, Positive-QTOF	splash10-00b9-7940000000-2379ac94fd9f7accb460	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 10V, Negative-QTOF	splash10-004i-0090000000-095b46a5a952085bd428	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 20V, Negative-QTOF	splash10-03fr-1980000000-5cc9eb499f441aa93168	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenprocoumon 40V, Negative-QTOF	splash10-056r-4970000000-d20cae73879a28552702	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Phenprocoumon 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 DB00946	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00946	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

10441592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenprocoumon

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

50438

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

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [PubMed:17192772 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. 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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Vitamin K epoxide reductase complex subunit 1

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

References

Schalekamp T, Brasse BP, Roijers JF, van Meegen E, van der Meer FJ, van Wijk EM, Egberts AC, de Boer A: VKORC1 and CYP2C9 genotypes and phenprocoumon anticoagulation status: interaction between both genotypes affects dose requirement. Clin Pharmacol Ther. 2007 Feb;81(2):185-93. Epub 2006 Dec 27. [PubMed:17192772 ]
Reitsma PH, van der Heijden JF, Groot AP, Rosendaal FR, Buller HR: A C1173T dimorphism in the VKORC1 gene determines coumarin sensitivity and bleeding risk. PLoS Med. 2005 Oct;2(10):e312. Epub 2005 Oct 11. [PubMed:16201835 ]
Thijssen HH, Baars LG: Microsomal warfarin binding and vitamin K 2,3-epoxide reductase. Biochem Pharmacol. 1989 Apr 1;38(7):1115-20. [PubMed:2706010 ]
Thijssen HH, Baars LG, Vervoort-Peters HT: Vitamin K 2,3-epoxide reductase: the basis for stereoselectivity of 4-hydroxycoumarin anticoagulant activity. Br J Pharmacol. 1988 Nov;95(3):675-82. [PubMed:3207986 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Phenprocoumon (HMDB0015081)

MOL for HMDB0015081 (Phenprocoumon)

3D MOL for HMDB0015081 (Phenprocoumon)

3D SDF for HMDB0015081 (Phenprocoumon)

3D-SDF for HMDB0015081 (Phenprocoumon)

PDB for HMDB0015081 (Phenprocoumon)

3D PDB for HMDB0015081 (Phenprocoumon)

SMILES for HMDB0015081 (Phenprocoumon)

INCHI for HMDB0015081 (Phenprocoumon)

Structure for HMDB0015081 (Phenprocoumon)

3D Structure for HMDB0015081 (Phenprocoumon)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

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