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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (1) Show 4 proteins XML

enzymes (3)transporters (1) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014576

Secondary Accession Numbers

HMDB14576

Metabolite Identification

Common Name

Trifluridine

Description

Trifluridine is only found in individuals that have used or taken this drug. It is an antiviral derivative of thymidine used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to herpes simplex virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557)The mechanism of action of trifluridine has not been fully determined, but appears to involve the inhibition of viral replication. Trifluridine does this by incorporating into viral DNA during replication, which leads to the formation of defective proteins and an increased mutation rate. This drug also reversibly inhibits thymidylate synthetase, an enzyme that is necessary for DNA synthesis.

Structure

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

HMDB0014576
     RDKit          3D
Trifluridine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.7444    0.1106    0.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5163   -0.2378    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -1.4164   -0.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.7662   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619   -2.8773   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573   -0.9499    0.3202 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -1.3892    0.3041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0019   -1.2398   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8942    0.0016   -0.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8454    0.0706   -1.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4808   -0.3106    0.3747 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2382    0.8513    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    2.0142    0.9853 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3443   -0.6272    1.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429    0.2176    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5791    0.6022    0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    1.9096    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199    1.6566    2.4020 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254    2.5854    1.8081 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    2.6530    0.4311 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8422   -2.0399   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -2.4372    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.0748   -1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.0893   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    0.9213   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7121    0.8578   -2.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -1.2123    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325    1.0077    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    0.5549    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526    2.7792    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    0.8744    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 16  2  1  0
 14  7  1  0
  3 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
M  END

432
  Mrv0541 02231214402D          

 20 21  0  0  1  0            999 V2000
    4.9205    1.2428    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.3699    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    2.6718    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465   -1.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816   -2.4548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970   -2.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.7824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.3073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.5448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6665   -1.7873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4115   -1.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.7873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9764   -2.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 20  1  0  0  0  0
  3 20  1  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
 12  5  1  1  0  0  0
  6 15  1  0  0  0  0
  7 17  2  0  0  0  0
  8 19  2  0  0  0  0
 11  9  1  6  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 17  1  0  0  0  0
 10 19  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014576

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(C(=O)NC1=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1

> <INCHI_KEY>
VSQQQLOSPVPRAZ-RRKCRQDMSA-N

> <FORMULA>
C10H11F3N2O5

> <MOLECULAR_WEIGHT>
296.1999

> <EXACT_MASS>
296.062006087

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.074149718395166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-0.7546264969999998

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.907878998150686

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.59857689451916

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9780835895525817

> <JCHEM_POLAR_SURFACE_AREA>
99.09999999999998

> <JCHEM_REFRACTIVITY>
56.3445

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifluridine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014576
     RDKit          3D
Trifluridine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.7444    0.1106    0.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5163   -0.2378    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -1.4164   -0.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.7662   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619   -2.8773   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573   -0.9499    0.3202 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -1.3892    0.3041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0019   -1.2398   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8942    0.0016   -0.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8454    0.0706   -1.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4808   -0.3106    0.3747 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2382    0.8513    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    2.0142    0.9853 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3443   -0.6272    1.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429    0.2176    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5791    0.6022    0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    1.9096    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199    1.6566    2.4020 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254    2.5854    1.8081 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    2.6530    0.4311 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8422   -2.0399   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -2.4372    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.0748   -1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.0893   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    0.9213   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7121    0.8578   -2.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -1.2123    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325    1.0077    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    0.5549    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526    2.7792    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    0.8744    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 16  2  1  0
 14  7  1  0
  3 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 432                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       9.185   2.320   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       9.748   4.424   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       7.645   4.987   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       6.993  -1.872   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.072  -4.582   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.954  -4.421   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.080   0.574   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.748   5.194   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       5.748   0.574   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       4.414   2.884   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.748  -0.966   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.977  -3.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.501  -1.872   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.518  -3.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.423  -4.582   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   1.344   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   1.344   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   2.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748   3.654   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   3.654   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   11   14                                                       
CONECT    5   12                                                            
CONECT    6   15                                                            
CONECT    7   17                                                            
CONECT    8   19                                                            
CONECT    9   11   16   17                                                  
CONECT   10   17   19                                                       
CONECT   11    4    9   13                                                  
CONECT   12    5   13   14                                                  
CONECT   13   11   12                                                       
CONECT   14    4   12   15                                                  
CONECT   15    6   14                                                       
CONECT   16    9   18                                                       
CONECT   17    7    9   10                                                  
CONECT   18   16   19   20                                                  
CONECT   19    8   10   18                                                  
CONECT   20    1    2    3   18                                             
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0014576
HETATM    1  O1  UNL     1      -4.744   0.111   0.283  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.516  -0.238   0.289  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.106  -1.416  -0.215  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.789  -1.766  -0.198  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.462  -2.877  -0.681  1.00  0.00           O  
HETATM    6  N2  UNL     1      -0.857  -0.950   0.320  1.00  0.00           N  
HETATM    7  C3  UNL     1       0.528  -1.389   0.304  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.002  -1.240  -1.138  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.894   0.002  -0.998  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.845   0.071  -1.983  1.00  0.00           O  
HETATM   11  C6  UNL     1       2.481  -0.311   0.375  1.00  0.00           C  
HETATM   12  C7  UNL     1       3.238   0.851   0.940  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.515   2.014   0.985  1.00  0.00           O  
HETATM   14  O5  UNL     1       1.344  -0.627   1.088  1.00  0.00           O  
HETATM   15  C8  UNL     1      -1.243   0.218   0.822  1.00  0.00           C  
HETATM   16  C9  UNL     1      -2.579   0.602   0.819  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.028   1.910   1.378  1.00  0.00           C  
HETATM   18  F1  UNL     1      -3.920   1.657   2.402  1.00  0.00           F  
HETATM   19  F2  UNL     1      -1.925   2.585   1.808  1.00  0.00           F  
HETATM   20  F3  UNL     1      -3.710   2.653   0.431  1.00  0.00           F  
HETATM   21  H1  UNL     1      -3.842  -2.040  -0.614  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.539  -2.437   0.642  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.179  -1.075  -1.832  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.651  -2.089  -1.360  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.274   0.921  -0.897  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.712   0.858  -2.579  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.103  -1.212   0.240  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.133   1.008   0.286  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.629   0.555   1.932  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.153   2.779   0.925  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.497   0.874   1.238  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7   15
CONECT    7    8   14   22
CONECT    8    9   23   24
CONECT    9   10   11   25
CONECT   10   26
CONECT   11   12   14   27
CONECT   12   13   28   29
CONECT   13   30
CONECT   15   16   16   31
CONECT   16   17
CONECT   17   18   19   20
END

HMDB0014576
     RDKit          3D
Trifluridine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.7444    0.1106    0.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5163   -0.2378    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -1.4164   -0.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.7662   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619   -2.8773   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573   -0.9499    0.3202 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -1.3892    0.3041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0019   -1.2398   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8942    0.0016   -0.9977 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8454    0.0706   -1.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4808   -0.3106    0.3747 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2382    0.8513    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    2.0142    0.9853 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3443   -0.6272    1.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429    0.2176    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5791    0.6022    0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    1.9096    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199    1.6566    2.4020 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254    2.5854    1.8081 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    2.6530    0.4311 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8422   -2.0399   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -2.4372    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.0748   -1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.0893   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    0.9213   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7121    0.8578   -2.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034   -1.2123    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1325    1.0077    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    0.5549    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526    2.7792    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    0.8744    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 16  2  1  0
 14  7  1  0
  3 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-(Trifluoromethyl)deoxyuridine	ChEBI
5-Trifluoromethyl-2-deoxyuridine	ChEBI
Trifluoromethyldeoxyuridine	ChEBI
Trifluorothymidine	ChEBI
Trifluorothymine deoxyriboside	ChEBI
Trifluridina	ChEBI
Trifluridinum	ChEBI
Viroptic	ChEBI
Elcon brand OF trifluridine	HMDB
Viromidin	HMDB
5-Trifluoromethyl-2'-deoxyuridine	HMDB
Allergan brand OF trifluridine	HMDB
Mann brand OF trifluridine	HMDB
Monarch brand OF trifluridine	HMDB
Tramedico brand OF trifluridine	HMDB
Trifluoridine	HMDB
2'-Deoxy-5-(trifluoromethyl)uridine	HMDB
5 Trifluoromethyl 2' deoxyuridine	HMDB
TFT Ophtiole	HMDB
Triflumann	HMDB
Virophta	HMDB

Chemical Formula

C₁₀H₁₁F₃N₂O₅

Average Molecular Weight

296.1999

Monoisotopic Molecular Weight

296.062006087

IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

trifluridine

CAS Registry Number

70-00-8

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(C(=O)NC1=O)C(F)(F)F

InChI Identifier

InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1

InChI Key

VSQQQLOSPVPRAZ-RRKCRQDMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Pyrimidone
Hydroxypyrimidine
Hydropyrimidine
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Alkyl fluoride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:75179 )
nucleoside analogue (CHEBI:75179 )
pyrimidine 2'-deoxyribonucleoside (CHEBI:75179 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014576)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	186 - 189 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.69 g/L	Not Available
LogP	-0.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.69 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.75	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.34 m³·mol⁻¹	ChemAxon
Polarizability	23.07 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	168.092	30932474
DeepCCS	[M-H]-	165.696	30932474
DeepCCS	[M-2H]-	199.346	30932474
DeepCCS	[M+Na]+	174.313	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	165.7	32859911
AllCCS	[M+Na]+	166.6	32859911
AllCCS	[M-H]-	158.6	32859911
AllCCS	[M+Na-2H]-	158.3	32859911
AllCCS	[M+HCOO]-	158.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trifluridine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(C(=O)NC1=O)C(F)(F)F	2493.9	Standard polar	33892256
Trifluridine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(C(=O)NC1=O)C(F)(F)F	1929.4	Standard non polar	33892256
Trifluridine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(C(=O)NC1=O)C(F)(F)F	2274.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trifluridine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)[NH]C2=O)C[C@@H]1O	2033.2	Semi standard non polar	33892256
Trifluridine,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=C(C(F)(F)F)C(=O)[NH]C2=O)O[C@@H]1CO	2068.1	Semi standard non polar	33892256
Trifluridine,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C(C(F)(F)F)=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2160.2	Semi standard non polar	33892256
Trifluridine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)[NH]C2=O)C[C@@H]1O[Si](C)(C)C	2082.5	Semi standard non polar	33892256
Trifluridine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O	2206.4	Semi standard non polar	33892256
Trifluridine,2TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C)C2=O)O[C@@H]1CO	2226.4	Semi standard non polar	33892256
Trifluridine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C	2208.3	Semi standard non polar	33892256
Trifluridine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C	2342.0	Standard non polar	33892256
Trifluridine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C	2242.7	Standard polar	33892256
Trifluridine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)[NH]C2=O)C[C@@H]1O	2280.6	Semi standard non polar	33892256
Trifluridine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=C(C(F)(F)F)C(=O)[NH]C2=O)O[C@@H]1CO	2301.7	Semi standard non polar	33892256
Trifluridine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C(C(F)(F)F)=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2372.5	Semi standard non polar	33892256
Trifluridine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)[NH]C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2548.5	Semi standard non polar	33892256
Trifluridine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O	2624.2	Semi standard non polar	33892256
Trifluridine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)O[C@@H]1CO	2637.1	Semi standard non polar	33892256
Trifluridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2858.6	Semi standard non polar	33892256
Trifluridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2940.3	Standard non polar	33892256
Trifluridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(C(F)(F)F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2551.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trifluridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9070000000-5b0bc8f23d4e75143939	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifluridine GC-MS (2 TMS) - 70eV, Positive	splash10-0v70-9845200000-37084cd9faa19fab8cdd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifluridine 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 - Trifluridine 10V, Positive-QTOF	splash10-001i-0900000000-98b3bdac019c141f7f2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 20V, Positive-QTOF	splash10-001i-0910000000-88c39b37d01c15092d5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 40V, Positive-QTOF	splash10-001r-1900000000-6af805305211581c822e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 10V, Negative-QTOF	splash10-0w2a-1490000000-06d5a9ab5df20c112030	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 20V, Negative-QTOF	splash10-0a6r-0790000000-aca1588a5498c0e36172	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 40V, Negative-QTOF	splash10-0006-5900000000-3142b258f9393903ca54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 10V, Negative-QTOF	splash10-002b-0090000000-9941fbdce182b1697ae3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 20V, Negative-QTOF	splash10-0ufr-1920000000-0b7d290fcb81239751b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 40V, Negative-QTOF	splash10-0006-9500000000-c59f899250e30f03cf63	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 10V, Positive-QTOF	splash10-0002-0290000000-d2c6f13535b38e719f66	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 20V, Positive-QTOF	splash10-001i-0910000000-2f204a289423b2c2048d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifluridine 40V, Positive-QTOF	splash10-053r-2960000000-d74ea6cb75e5abd92cdb	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00432	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00432	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00432

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trifluridine

METLIN ID

Not Available

PubChem Compound

6256

PDB ID

Not Available

ChEBI ID

75179

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

Overman MJ, Kopetz S, Varadhachary G, Fukushima M, Kuwata K, Mita A, Wolff RA, Hoff P, Xiong H, Abbruzzese JL: Phase I clinical study of three times a day oral administration of TAS-102 in patients with solid tumors. Cancer Invest. 2008 Oct;26(8):794-9. doi: 10.1080/07357900802087242. [PubMed:18798063 ]
Hong DS, Abbruzzese JL, Bogaard K, Lassere Y, Fukushima M, Mita A, Kuwata K, Hoff PM: Phase I study to determine the safety and pharmacokinetics of oral administration of TAS-102 in patients with solid tumors. Cancer. 2006 Sep 15;107(6):1383-90. [PubMed:16902987 ]
Temmink OH, Prins HJ, van Gelderop E, Peters GJ: The Hollow Fibre Assay as a model for in vivo pharmacodynamics of fluoropyrimidines in colon cancer cells. Br J Cancer. 2007 Jan 15;96(1):61-6. Epub 2006 Dec 19. [PubMed:17179993 ]
O'Brien WJ, Taylor JL: Therapeutic response of herpes simplex virus-induced corneal edema to trifluridine in combination with immunosuppressive agents. Invest Ophthalmol Vis Sci. 1991 Aug;32(9):2455-61. [PubMed:1907950 ]
Kuster P, Taravella M, Gelinas M, Stepp P: Delivery of trifluridine to human cornea and aqueous using collagen shields. CLAO J. 1998 Apr;24(2):122-4. [PubMed:9571274 ]
Costin D, Dogaru M, Popa AS, Cijevschi I: [Trifluridine therapy in herpetic in keratitis]. Rev Med Chir Soc Med Nat Iasi. 2004 Apr-Jun;108(2):409-12. [PubMed:15688823 ]

Enzymes

Enzyme Details

1. Thymidine kinase, cytosolic

General function:: Nucleotide transport and metabolism
Specific function:: Not Available
Gene Name:: TK1
Uniprot ID:: P04183
Molecular weight:: 25468.455

References

Temmink OH, Comijn EM, Fukushima M, Peters GJ: Intracellular thymidylate synthase inhibition by trifluorothymidine in FM3A cells. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1491-4. [PubMed:15571283 ]
Shintani M, Urano M, Takakuwa Y, Kuroda M, Kamoshida S: Immunohistochemical characterization of pyrimidine synthetic enzymes, thymidine kinase-1 and thymidylate synthase, in various types of cancer. Oncol Rep. 2010 May;23(5):1345-50. [PubMed:20372850 ]
Emura T, Nakagawa F, Fujioka A, Ohshimo H, Yokogawa T, Okabe H, Kitazato K: An optimal dosing schedule for a novel combination antimetabolite, TAS-102, based on its intracellular metabolism and its incorporation into DNA. Int J Mol Med. 2004 Feb;13(2):249-55. [PubMed:14719131 ]
Emura T, Nakagawa F, Fujioka A, Ohshimo H, Kitazato K: Thymidine kinase and thymidine phosphorylase level as the main predictive parameter for sensitivity to TAS-102 in a mouse model. Oncol Rep. 2004 Feb;11(2):381-7. [PubMed:14719072 ]

Enzyme Details

2. Thymidine phosphorylase

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro. Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:: TYMP
Uniprot ID:: P19971
Molecular weight:: 49954.965

References

Temmink OH, Comijn EM, Fukushima M, Peters GJ: Intracellular thymidylate synthase inhibition by trifluorothymidine in FM3A cells. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1491-4. [PubMed:15571283 ]
Emura T, Nakagawa F, Fujioka A, Ohshimo H, Kitazato K: Thymidine kinase and thymidine phosphorylase level as the main predictive parameter for sensitivity to TAS-102 in a mouse model. Oncol Rep. 2004 Feb;11(2):381-7. [PubMed:14719072 ]
Overman MJ, Kopetz S, Varadhachary G, Fukushima M, Kuwata K, Mita A, Wolff RA, Hoff P, Xiong H, Abbruzzese JL: Phase I clinical study of three times a day oral administration of TAS-102 in patients with solid tumors. Cancer Invest. 2008 Oct;26(8):794-9. doi: 10.1080/07357900802087242. [PubMed:18798063 ]
Hong DS, Abbruzzese JL, Bogaard K, Lassere Y, Fukushima M, Mita A, Kuwata K, Hoff PM: Phase I study to determine the safety and pharmacokinetics of oral administration of TAS-102 in patients with solid tumors. Cancer. 2006 Sep 15;107(6):1383-90. [PubMed:16902987 ]
Temmink OH, Prins HJ, van Gelderop E, Peters GJ: The Hollow Fibre Assay as a model for in vivo pharmacodynamics of fluoropyrimidines in colon cancer cells. Br J Cancer. 2007 Jan 15;96(1):61-6. Epub 2006 Dec 19. [PubMed:17179993 ]
Bassler R, Buchwald W: [Experimental inflammation and fibrosis of the lung framework caused by ionizing rays. Light and electron microscopic studies]. Fortschr Geb Rontgenstr Nuklearmed. 1966 Feb;104(2):192-206. [PubMed:6010427 ]

Enzyme Details

3. Thymidylate synthase

General function:: Involved in thymidylate synthase activity
Specific function:: Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:: TYMS
Uniprot ID:: P04818
Molecular weight:: 35715.65

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
De Clercq E: Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33. [PubMed:15125867 ]
Bijnsdorp IV, Kruyt FA, Fukushima M, Smid K, Gokoel S, Peters GJ: Molecular mechanism underlying the synergistic interaction between trifluorothymidine and the epidermal growth factor receptor inhibitor erlotinib in human colorectal cancer cell lines. Cancer Sci. 2010 Feb;101(2):440-7. doi: 10.1111/j.1349-7006.2009.01375.x. Epub 2009 Sep 29. [PubMed:19886911 ]
Bijnsdorp IV, Peters GJ, Temmink OH, Fukushima M, Kruyt FA: Differential activation of cell death and autophagy results in an increased cytotoxic potential for trifluorothymidine compared to 5-fluorouracil in colon cancer cells. Int J Cancer. 2010 May 15;126(10):2457-68. doi: 10.1002/ijc.24943. [PubMed:19816940 ]
Bijnsdorp IV, Kruyt FA, Fukushima M, Peters GJ: Trifluorothymidine induces cell death independently of p53. Nucleosides Nucleotides Nucleic Acids. 2008 Jun;27(6):699-703. doi: 10.1080/15257770802145017. [PubMed:18600528 ]
Madeira VM, Antunes-Madeira MC: Chemical composition of sarcolemma isolated from rabbit skeletal muscle. Biochim Biophys Acta. 1973 Mar 16;298(2):230-8. [PubMed:4719131 ]
Temmink OH, Hoogeland MF, Fukushima M, Peters GJ: Low folate conditions may enhance the interaction of trifluorothymidine with antifolates in colon cancer cells. Cancer Chemother Pharmacol. 2006 Jan;57(2):171-9. Epub 2005 Jul 12. [PubMed:16010590 ]
Oberg B, Johansson NG: The relative merits and drawbacks of new nucleoside analogues with clinical potential. J Antimicrob Chemother. 1984 Aug;14 Suppl A:5-26. [PubMed:6436227 ]
Temmink OH, Comijn EM, Fukushima M, Peters GJ: Intracellular thymidylate synthase inhibition by trifluorothymidine in FM3A cells. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1491-4. [PubMed:15571283 ]
Shintani M, Urano M, Takakuwa Y, Kuroda M, Kamoshida S: Immunohistochemical characterization of pyrimidine synthetic enzymes, thymidine kinase-1 and thymidylate synthase, in various types of cancer. Oncol Rep. 2010 May;23(5):1345-50. [PubMed:20372850 ]
Emura T, Nakagawa F, Fujioka A, Ohshimo H, Kitazato K: Thymidine kinase and thymidine phosphorylase level as the main predictive parameter for sensitivity to TAS-102 in a mouse model. Oncol Rep. 2004 Feb;11(2):381-7. [PubMed:14719072 ]
Overman MJ, Kopetz S, Varadhachary G, Fukushima M, Kuwata K, Mita A, Wolff RA, Hoff P, Xiong H, Abbruzzese JL: Phase I clinical study of three times a day oral administration of TAS-102 in patients with solid tumors. Cancer Invest. 2008 Oct;26(8):794-9. doi: 10.1080/07357900802087242. [PubMed:18798063 ]
Hong DS, Abbruzzese JL, Bogaard K, Lassere Y, Fukushima M, Mita A, Kuwata K, Hoff PM: Phase I study to determine the safety and pharmacokinetics of oral administration of TAS-102 in patients with solid tumors. Cancer. 2006 Sep 15;107(6):1383-90. [PubMed:16902987 ]
Temmink OH, Prins HJ, van Gelderop E, Peters GJ: The Hollow Fibre Assay as a model for in vivo pharmacodynamics of fluoropyrimidines in colon cancer cells. Br J Cancer. 2007 Jan 15;96(1):61-6. Epub 2006 Dec 19. [PubMed:17179993 ]
Bassler R, Buchwald W: [Experimental inflammation and fibrosis of the lung framework caused by ionizing rays. Light and electron microscopic studies]. Fortschr Geb Rontgenstr Nuklearmed. 1966 Feb;104(2):192-206. [PubMed:6010427 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832 ]

Showing metabocard for Trifluridine (HMDB0014576)

MOL for HMDB0014576 (Trifluridine)

3D MOL for HMDB0014576 (Trifluridine)

3D SDF for HMDB0014576 (Trifluridine)

3D-SDF for HMDB0014576 (Trifluridine)

PDB for HMDB0014576 (Trifluridine)

3D PDB for HMDB0014576 (Trifluridine)

SMILES for HMDB0014576 (Trifluridine)

INCHI for HMDB0014576 (Trifluridine)

Structure for HMDB0014576 (Trifluridine)

3D Structure for HMDB0014576 (Trifluridine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

Transporters

References