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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:59:31 UTC

Update Date

2021-09-14 15:39:00 UTC

HMDB ID

HMDB0060397

Secondary Accession Numbers

HMDB60397

Metabolite Identification

Common Name

5-Fluorouridine monophosphate

Description

5-Fluorouridine monophosphate is a metabolite of fluorouracil. Fluorouracil (5-FU or f5U) (sold under the brand names Adrucil, Carac, Efudix, Efudex and Fluoroplex) is a drug that is a pyrimidine analog which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. (Wikipedia)

Structure

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

HMDB0060397
     RDKit          3D
5-Fluorouridine monophosphate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.0729    1.6013   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.4487   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021    0.0940   -0.4348 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355   -1.1033    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2856   -1.4311    0.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -1.9580    0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2249   -3.1692    0.9475 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.5648    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -0.3606   -0.2514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.1203   -0.4608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0086   -0.7147    0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331    0.1104    0.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3597   -0.5013    0.6163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3976    0.4240    0.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478   -0.1152    1.0788 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9387    0.0448    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1564    0.6714    0.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -1.7730    0.6873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597    1.3348    0.7516 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4738    2.4223    0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    1.4968    0.1237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5638    2.4147   -0.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7087   -2.2080   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989   -2.2297    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    0.1409   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    0.3712   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597   -1.4428    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.6872    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8731    1.3228   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403   -1.9237   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    1.1634    1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    3.2899    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    1.8033    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    1.9074   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  2  1  0
 21 10  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  6
 12 26  1  6
 13 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  1
 20 32  1  0
 21 33  1  1
 22 34  1  0
M  END


  Mrv1652305101918142D          

 22 23  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937   -0.4056    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4784   -0.1506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -1.1902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    0.3790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378   -3.6695    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -4.5956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4559   -4.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
  5 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060397

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H12FN2O9P/c10-3-1-12(9(16)11-7(3)15)8-6(14)5(13)4(21-8)2-20-22(17,18)19/h1,4-6,8,13-14H,2H2,(H,11,15,16)(H2,17,18,19)/t4-,5-,6-,8-/m1/s1

> <INCHI_KEY>
RNBMPPYRHNWTMA-UAKXSSHOSA-N

> <FORMULA>
C9H12FN2O9P

> <MOLECULAR_WEIGHT>
342.1717

> <EXACT_MASS>
342.026444709

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.760300970324785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.33

> <JCHEM_LOGP>
-2.339365263

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.2448400223089395

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2255022463552159

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6645442283702954

> <JCHEM_POLAR_SURFACE_AREA>
165.86

> <JCHEM_REFRACTIVITY>
63.64140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060397
     RDKit          3D
5-Fluorouridine monophosphate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.0729    1.6013   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.4487   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021    0.0940   -0.4348 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355   -1.1033    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2856   -1.4311    0.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -1.9580    0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2249   -3.1692    0.9475 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.5648    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -0.3606   -0.2514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.1203   -0.4608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0086   -0.7147    0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331    0.1104    0.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3597   -0.5013    0.6163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3976    0.4240    0.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478   -0.1152    1.0788 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9387    0.0448    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1564    0.6714    0.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -1.7730    0.6873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597    1.3348    0.7516 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4738    2.4223    0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    1.4968    0.1237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5638    2.4147   -0.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7087   -2.2080   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989   -2.2297    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    0.1409   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    0.3712   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597   -1.4428    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.6872    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8731    1.3228   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403   -1.9237   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    1.1634    1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    3.2899    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    1.8033    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    1.9074   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  2  1  0
 21 10  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  6
 12 26  1  6
 13 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  1
 20 32  1  0
 21 33  1  1
 22 34  1  0
M  END

HEADER    PROTEIN                                 10-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAY-19         0                                  
HETATM    1  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.044  -2.739   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.564  -4.680   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.697  -1.233   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0      -3.162  -0.757   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0      -4.626  -0.281   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.638  -2.222   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.686   0.708   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       3.009  -5.926   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   17  F   UNK     0       6.977  -6.850   0.000  0.00  0.00           F+0
HETATM   18  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.724  -9.663   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       3.288  -8.578   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.851  -7.494   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    5   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0060397
HETATM    1  O1  UNL     1      -3.073   1.601  -1.080  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.308   0.449  -0.590  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.602   0.094  -0.435  1.00  0.00           N  
HETATM    4  C2  UNL     1      -4.936  -1.103   0.074  1.00  0.00           C  
HETATM    5  O2  UNL     1      -6.286  -1.431   0.219  1.00  0.00           O  
HETATM    6  C3  UNL     1      -3.928  -1.958   0.433  1.00  0.00           C  
HETATM    7  F1  UNL     1      -4.225  -3.169   0.947  1.00  0.00           F  
HETATM    8  C4  UNL     1      -2.600  -1.565   0.260  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.292  -0.361  -0.251  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.958   0.120  -0.461  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.009  -0.715   0.106  1.00  0.00           O  
HETATM   12  C6  UNL     1       1.133   0.110   0.006  1.00  0.00           C  
HETATM   13  C7  UNL     1       2.360  -0.501   0.616  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.398   0.424   0.445  1.00  0.00           O  
HETATM   15  P1  UNL     1       4.848  -0.115   1.079  1.00  0.00           P  
HETATM   16  O5  UNL     1       4.939   0.045   2.562  1.00  0.00           O  
HETATM   17  O6  UNL     1       6.156   0.671   0.354  1.00  0.00           O  
HETATM   18  O7  UNL     1       4.986  -1.773   0.687  1.00  0.00           O  
HETATM   19  C8  UNL     1       0.660   1.335   0.752  1.00  0.00           C  
HETATM   20  O8  UNL     1       1.474   2.422   0.452  1.00  0.00           O  
HETATM   21  C9  UNL     1      -0.730   1.497   0.124  1.00  0.00           C  
HETATM   22  O9  UNL     1      -0.564   2.415  -0.927  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.709  -2.208  -0.268  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.799  -2.230   0.539  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.730   0.141  -1.561  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.260   0.371  -1.048  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.660  -1.443   0.117  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.241  -0.687   1.682  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.873   1.323  -0.324  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.740  -1.924  -0.267  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.570   1.163   1.842  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.003   3.290   0.612  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.479   1.803   0.846  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.090   1.907  -1.660  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    9
CONECT    3    4    4
CONECT    4    5    6
CONECT    5   23
CONECT    6    7    8    8
CONECT    8    9   24
CONECT    9   10
CONECT   10   11   21   25
CONECT   11   12
CONECT   12   13   19   26
CONECT   13   14   27   28
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   29
CONECT   18   30
CONECT   19   20   21   31
CONECT   20   32
CONECT   21   22   33
CONECT   22   34
END

HMDB0060397
     RDKit          3D
5-Fluorouridine monophosphate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.0729    1.6013   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085    0.4487   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021    0.0940   -0.4348 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355   -1.1033    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2856   -1.4311    0.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -1.9580    0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2249   -3.1692    0.9475 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.5648    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -0.3606   -0.2514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578    0.1203   -0.4608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0086   -0.7147    0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331    0.1104    0.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3597   -0.5013    0.6163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3976    0.4240    0.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478   -0.1152    1.0788 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9387    0.0448    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1564    0.6714    0.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -1.7730    0.6873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597    1.3348    0.7516 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4738    2.4223    0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    1.4968    0.1237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5638    2.4147   -0.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7087   -2.2080   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989   -2.2297    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    0.1409   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    0.3712   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597   -1.4428    0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.6872    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8731    1.3228   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403   -1.9237   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    1.1634    1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    3.2899    0.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    1.8033    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    1.9074   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  2  1  0
 21 10  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  6
 12 26  1  6
 13 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  1
 20 32  1  0
 21 33  1  1
 22 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-F-UMP	ChEBI
5-Fluorouridylic acid	ChEBI
Fosfluoridine	ChEBI
Fump-5'	ChEBI
5-Fluorouridylate	Generator
5-Fluorouridine monophosphoric acid	Generator
5-Fluorouridine 5'-monophosphoric acid	HMDB
5-Fluorouridine 5'-phosphate	HMDB
5-Fluorouridine 5'-phosphate, 18F-labeled	HMDB
5'-FUMP	HMDB
5-Fluorouridine 5'-phosphate, disodium salt	HMDB
5-Fluorouridine 5'-phosphate, calcium salt	HMDB
5-Fluorouridine monophosphate	ChEBI

Chemical Formula

C₉H₁₂FN₂O₉P

Average Molecular Weight

342.1717

Monoisotopic Molecular Weight

342.026444709

IUPAC Name

{[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H12FN2O9P/c10-3-1-12(9(16)11-7(3)15)8-6(14)5(13)4(21-8)2-20-22(17,18)19/h1,4-6,8,13-14H,2H2,(H,11,15,16)(H2,17,18,19)/t4-,5-,6-,8-/m1/s1

InChI Key

RNBMPPYRHNWTMA-UAKXSSHOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside monophosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Halopyrimidine
Pyrimidone
Monoalkyl phosphate
Alkyl phosphate
Aryl fluoride
Pyrimidine
Aryl halide
Phosphoric acid ester
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Vinylogous amide
Tetrahydrofuran
Heteroaromatic compound
Urea
Secondary alcohol
1,2-diol
Lactam
Azacycle
Organoheterocyclic compound
Oxacycle
Organopnictogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organonitrogen compound
Organohalogen compound
Organofluoride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:40101 )
pyrimidine ribonucleoside 5'-monophosphate (CHEBI:40101 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060397)

Organ

Liver (HMDB: HMDB0060397)
Kidney (HMDB: HMDB0060397)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060397)

Source

Endogenous

Endogenous (HMDB: HMDB0060397)

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	12.4 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	165.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.64 m³·mol⁻¹	ChemAxon
Polarizability	26.76 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]+	169.166	30932474
DeepCCS	[M-H]-	166.771	30932474
DeepCCS	[M-2H]-	200.304	30932474
DeepCCS	[M+Na]+	175.253	30932474
AllCCS	[M+H]+	171.5	32859911
AllCCS	[M+H-H2O]+	168.5	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.1	32859911
AllCCS	[M-H]-	165.2	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	164.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.22 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1738 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	425.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	45.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	300.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	259.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	811.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	565.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	59.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	588.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	160.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	749.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	389.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	409.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Fluorouridine monophosphate	O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O	3803.7	Standard polar	33892256
5-Fluorouridine monophosphate	O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O	2160.7	Standard non polar	33892256
5-Fluorouridine monophosphate	O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O	2941.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Fluorouridine monophosphate,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O	2590.7	Semi standard non polar	33892256
5-Fluorouridine monophosphate,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=C(F)C(O)=NC1=O	2577.7	Semi standard non polar	33892256
5-Fluorouridine monophosphate,1TMS,isomer #3	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1F	2626.8	Semi standard non polar	33892256
5-Fluorouridine monophosphate,1TMS,isomer #4	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O	2745.5	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F	2581.8	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C	2540.9	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O	2698.9	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TMS,isomer #4	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F	2565.3	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O	2692.6	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TMS,isomer #6	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=C1F	2707.3	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TMS,isomer #7	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C	2751.0	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F	2548.0	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TMS,isomer #2	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F	2691.3	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C	2667.8	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O	2727.6	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TMS,isomer #5	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F	2685.5	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O	2728.3	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TMS,isomer #7	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=C1F	2736.9	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F	2688.1	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F	2669.6	Standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F	3333.4	Standard polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #2	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F	2733.6	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #2	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F	2674.0	Standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #2	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F	3173.6	Standard polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C	2721.0	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C	2605.5	Standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C	3168.3	Standard polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #4	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F	2727.0	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #4	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F	2679.3	Standard non polar	33892256
5-Fluorouridine monophosphate,4TMS,isomer #4	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F	3203.2	Standard polar	33892256
5-Fluorouridine monophosphate,5TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F	2732.1	Semi standard non polar	33892256
5-Fluorouridine monophosphate,5TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F	2659.9	Standard non polar	33892256
5-Fluorouridine monophosphate,5TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F	3034.0	Standard polar	33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O	2875.1	Semi standard non polar	33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=C(F)C(O)=NC1=O	2859.4	Semi standard non polar	33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1F	2864.1	Semi standard non polar	33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O	2988.8	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F	3059.1	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3047.4	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O	3167.2	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3040.4	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O	3155.4	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C1F	3159.5	Semi standard non polar	33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3211.1	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3271.5	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F	3358.4	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3336.6	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O	3384.9	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3343.2	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O	3374.2	Semi standard non polar	33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C1F	3384.2	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3546.9	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3400.4	Standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3563.0	Standard polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F	3583.2	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F	3370.9	Standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F	3453.2	Standard polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3560.9	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3333.1	Standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3466.7	Standard polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3568.8	Semi standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3372.8	Standard non polar	33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F	3482.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Fluorouridine monophosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9501000000-6e3e3f07071a4b3fe25b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Fluorouridine monophosphate GC-MS (3 TMS) - 70eV, Positive	splash10-000b-9422320000-a9309e7224043db6e96e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Fluorouridine monophosphate 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 - 5-Fluorouridine monophosphate 10V, Positive-QTOF	splash10-001i-0901000000-3b46c2e15a4da2f0d7ba	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Positive-QTOF	splash10-001i-1900000000-5e082b9fb7ff4e4a3bef	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Positive-QTOF	splash10-0f89-3900000000-95bf4479fa01e01b5fd9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 10V, Negative-QTOF	splash10-004i-6932000000-83f85ee655c0c86555da	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Negative-QTOF	splash10-004i-9200000000-3d9058daaa7d559c901e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Negative-QTOF	splash10-004i-9000000000-4b472f80502ae0db304e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 10V, Positive-QTOF	splash10-00ke-0896000000-36a39434e942710b455a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Positive-QTOF	splash10-0032-0790000000-7f1ccf28f980f99eaf64	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Positive-QTOF	splash10-000t-8910000000-eea690d5bc86a0096c85	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 10V, Negative-QTOF	splash10-0006-3309000000-dd2203c1062e091c9f1f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Negative-QTOF	splash10-004i-9300000000-1b995bb274a6141e33b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Negative-QTOF	splash10-004i-9200000000-ec60836b4f0880754527	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

C16634

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

150856

PDB ID

5FU

ChEBI ID

40101

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Uridine-cytidine kinase 1

General function:: Involved in ATP binding
Specific function:: Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:: UCK1
Uniprot ID:: Q9HA47
Molecular weight:: 22760.43

Reactions

5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADP	details

Enzyme Details

2. Uridine 5'-monophosphate synthase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: UMPS
Uniprot ID:: P11172
Molecular weight:: 52221.075

Reactions

Fluorouracil + Phosphoribosyl pyrophosphate → 5-Fluorouridine monophosphate + Pyrophosphate	details

Enzyme Details

3. Uridine-cytidine kinase 2

General function:: Involved in ATP binding
Specific function:: Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:: UCK2
Uniprot ID:: Q9BZX2
Molecular weight:: 29298.92

Reactions

5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADP	details

Enzyme Details

4. Uridine-cytidine kinase-like 1

General function:: Involved in ATP binding
Specific function:: May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name:: UCKL1
Uniprot ID:: Q9NWZ5
Molecular weight:: 59465.77

Reactions

5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADP	details

Showing metabocard for 5-Fluorouridine monophosphate (HMDB0060397)

MOL for HMDB0060397 (5-Fluorouridine monophosphate)

3D MOL for HMDB0060397 (5-Fluorouridine monophosphate)

3D SDF for HMDB0060397 (5-Fluorouridine monophosphate)

3D-SDF for HMDB0060397 (5-Fluorouridine monophosphate)

PDB for HMDB0060397 (5-Fluorouridine monophosphate)

3D PDB for HMDB0060397 (5-Fluorouridine monophosphate)

SMILES for HMDB0060397 (5-Fluorouridine monophosphate)

INCHI for HMDB0060397 (5-Fluorouridine monophosphate)

Structure for HMDB0060397 (5-Fluorouridine monophosphate)

3D Structure for HMDB0060397 (5-Fluorouridine monophosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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