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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:59:27 UTC

Update Date

2021-09-14 15:44:40 UTC

HMDB ID

HMDB0060396

Secondary Accession Numbers

HMDB60396

Metabolite Identification

Common Name

5-Fluorouridine

Description

5-Fluorouridine 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

HMDB0060396
     RDKit          3D
5-Fluorouridine
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.3946   -0.1402    0.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -0.0858    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2689   -0.8235    1.2501 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497   -0.7349    0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1874   -1.4481    1.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    0.0565    0.0629 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529    0.1576   -0.2159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7234    0.5520    0.8903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    0.5928    0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0971    0.5693    1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.6124    0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -0.6500   -0.5613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4082   -0.2938   -1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -1.1191   -0.5906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2833   -1.5729   -1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141    0.8120   -0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    0.7597   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    1.5206   -1.1594 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -1.4531    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    0.8998   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    1.5287   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0670    1.4101    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613   -0.3950    1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909    1.3984    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531   -1.4169   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727    0.6797   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -1.8978    0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3494   -0.9960   -2.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567    1.4777   -1.4285 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
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  2  1  0
 14  7  1  0
  3 19  1  0
  7 20  1  6
  9 21  1  6
 10 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  1
 13 26  1  0
 14 27  1  1
 15 28  1  0
 16 29  1  0
M  END


  Mrv1652305101918242D          

 18 19  0  0  1  0            999 V2000
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    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 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
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  6  0  0  0
  5 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060396

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1

> <INCHI_KEY>
FHIDNBAQOFJWCA-UAKXSSHOSA-N

> <FORMULA>
C9H11FN2O6

> <MOLECULAR_WEIGHT>
262.1918

> <EXACT_MASS>
262.060114299

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.921241391842877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.35

> <JCHEM_LOGP>
-2.2157992316666664

> <ALOGPS_LOGS>
-0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.61945518318634

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.074206157117867

> <JCHEM_PKA_STRONGEST_BASIC>
-2.980299648796752

> <JCHEM_POLAR_SURFACE_AREA>
119.32999999999998

> <JCHEM_REFRACTIVITY>
52.768499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-fluorouridine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060396
     RDKit          3D
5-Fluorouridine
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.3946   -0.1402    0.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -0.0858    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2689   -0.8235    1.2501 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497   -0.7349    0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1874   -1.4481    1.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    0.0565    0.0629 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529    0.1576   -0.2159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7234    0.5520    0.8903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    0.5928    0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0971    0.5693    1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.6124    0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -0.6500   -0.5613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4082   -0.2938   -1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -1.1191   -0.5906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2833   -1.5729   -1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141    0.8120   -0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    0.7597   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    1.5206   -1.1594 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -1.4531    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    0.8998   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    1.5287   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0670    1.4101    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613   -0.3950    1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909    1.3984    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531   -1.4169   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727    0.6797   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -1.8978    0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3494   -0.9960   -2.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567    1.4777   -1.4285 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
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  2  1  0
 14  7  1  0
  3 19  1  0
  7 20  1  6
  9 21  1  6
 10 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  1
 13 26  1  0
 14 27  1  1
 15 28  1  0
 16 29  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       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.580  -3.215   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  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.342  -5.926   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.377  -2.739   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       3.009  -5.926   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   13  F   UNK     0       6.977  -6.850   0.000  0.00  0.00           F+0
HETATM   14  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.724  -9.663   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       3.288  -8.578   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.851  -7.494   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060396
HETATM    1  O1  UNL     1       5.395  -0.140   0.761  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.138  -0.086   0.549  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.269  -0.824   1.250  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.950  -0.735   0.992  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.187  -1.448   1.680  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.432   0.057   0.063  1.00  0.00           N  
HETATM    7  C3  UNL     1       0.053   0.158  -0.216  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.723   0.552   0.890  1.00  0.00           O  
HETATM    9  C4  UNL     1      -1.996   0.593   0.295  1.00  0.00           C  
HETATM   10  C5  UNL     1      -3.097   0.569   1.325  1.00  0.00           C  
HETATM   11  O4  UNL     1      -4.304   0.612   0.648  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.090  -0.650  -0.561  1.00  0.00           C  
HETATM   13  O5  UNL     1      -2.408  -0.294  -1.864  1.00  0.00           O  
HETATM   14  C7  UNL     1      -0.628  -1.119  -0.591  1.00  0.00           C  
HETATM   15  O6  UNL     1      -0.283  -1.573  -1.857  1.00  0.00           O  
HETATM   16  C8  UNL     1       2.314   0.812  -0.656  1.00  0.00           C  
HETATM   17  C9  UNL     1       3.669   0.760  -0.434  1.00  0.00           C  
HETATM   18  F1  UNL     1       4.548   1.521  -1.159  1.00  0.00           F  
HETATM   19  H1  UNL     1       3.649  -1.453   1.985  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.155   0.900  -1.007  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.028   1.529  -0.299  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.067   1.410   2.018  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.061  -0.395   1.870  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.391   1.398   0.048  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.753  -1.417  -0.137  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.373   0.680  -2.027  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.549  -1.898   0.180  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.349  -0.996  -2.318  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.957   1.478  -1.428  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4   19
CONECT    4    5    5    6
CONECT    6    7   16
CONECT    7    8   14   20
CONECT    8    9
CONECT    9   10   12   21
CONECT   10   11   22   23
CONECT   11   24
CONECT   12   13   14   25
CONECT   13   26
CONECT   14   15   27
CONECT   15   28
CONECT   16   17   17   29
CONECT   17   18
END

HMDB0060396
     RDKit          3D
5-Fluorouridine
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.3946   -0.1402    0.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -0.0858    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2689   -0.8235    1.2501 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497   -0.7349    0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1874   -1.4481    1.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    0.0565    0.0629 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529    0.1576   -0.2159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7234    0.5520    0.8903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    0.5928    0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0971    0.5693    1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.6124    0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -0.6500   -0.5613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4082   -0.2938   -1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -1.1191   -0.5906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2833   -1.5729   -1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3141    0.8120   -0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    0.7597   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    1.5206   -1.1594 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -1.4531    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    0.8998   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    1.5287   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0670    1.4101    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613   -0.3950    1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909    1.3984    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531   -1.4169   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727    0.6797   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -1.8978    0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3494   -0.9960   -2.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567    1.4777   -1.4285 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
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  2  1  0
 14  7  1  0
  3 19  1  0
  7 20  1  6
  9 21  1  6
 10 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  1
 13 26  1  0
 14 27  1  1
 15 28  1  0
 16 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Fluoro-uridine	ChEBI
5-Fluorouracil 1beta-D-ribofuranoside	ChEBI
5-Fluorouracil 1b-D-ribofuranoside	Generator
5-Fluorouracil 1β-D-ribofuranoside	Generator
5-Fluorouridine, 18F-labeled	HMDB

Chemical Formula

C₉H₁₁FN₂O₆

Average Molecular Weight

262.1918

Monoisotopic Molecular Weight

262.060114299

IUPAC Name

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

Traditional Name

5-fluorouridine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1

InChI Key

FHIDNBAQOFJWCA-UAKXSSHOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Not Available

Direct Parent

Pyrimidine nucleosides

Alternative Parents

Substituents

Pyrimidine nucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Halopyrimidine
Pyrimidone
Aryl fluoride
Aryl halide
Hydropyrimidine
Monosaccharide
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Lactam
Urea
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:40154 )
uridines (CHEBI:40154 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060396)

Organ

Liver (HMDB: HMDB0060396)
Kidney (HMDB: HMDB0060396)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060396)

Source

Endogenous

Endogenous (HMDB: HMDB0060396)

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	10.7 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2.2	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.77 m³·mol⁻¹	ChemAxon
Polarizability	21.92 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]+	162.161	30932474
DeepCCS	[M-H]-	159.765	30932474
DeepCCS	[M-2H]-	193.55	30932474
DeepCCS	[M+Na]+	168.677	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.7	32859911
AllCCS	[M+NH4]+	160.8	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	153.6	32859911
AllCCS	[M+Na-2H]-	153.4	32859911
AllCCS	[M+HCOO]-	153.4	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.	1.83 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2416 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	610.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	250.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	61.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	44.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.2 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	255.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	509.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	582.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	90.9 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	845.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	171.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	523.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	296.3 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	287.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Fluorouridine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(F)C(=O)NC1=O	3478.0	Standard polar	33892256
5-Fluorouridine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(F)C(=O)NC1=O	1842.0	Standard non polar	33892256
5-Fluorouridine	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(F)C(=O)NC1=O	2496.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Fluorouridine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O)[C@@H]1O	2207.5	Semi standard non polar	33892256
5-Fluorouridine,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=C(F)C(=O)[NH]C1=O	2215.0	Semi standard non polar	33892256
5-Fluorouridine,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@@H]1O	2238.8	Semi standard non polar	33892256
5-Fluorouridine,1TMS,isomer #4	C[Si](C)(C)N1C(=O)C(F)=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O	2265.5	Semi standard non polar	33892256
5-Fluorouridine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O	2262.7	Semi standard non polar	33892256
5-Fluorouridine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C	2270.7	Semi standard non polar	33892256
5-Fluorouridine,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@H](O)[C@@H]1O	2317.8	Semi standard non polar	33892256
5-Fluorouridine,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@@H]1O[Si](C)(C)C	2275.2	Semi standard non polar	33892256
5-Fluorouridine,2TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=C(F)C(=O)N([Si](C)(C)C)C1=O	2323.9	Semi standard non polar	33892256
5-Fluorouridine,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@@H]1O	2327.9	Semi standard non polar	33892256
5-Fluorouridine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2273.5	Semi standard non polar	33892256
5-Fluorouridine,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O	2346.2	Semi standard non polar	33892256
5-Fluorouridine,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C	2345.5	Semi standard non polar	33892256
5-Fluorouridine,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@@H]1O[Si](C)(C)C	2346.2	Semi standard non polar	33892256
5-Fluorouridine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2358.1	Semi standard non polar	33892256
5-Fluorouridine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2397.8	Standard non polar	33892256
5-Fluorouridine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2446.3	Standard polar	33892256
5-Fluorouridine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O)[C@@H]1O	2488.0	Semi standard non polar	33892256
5-Fluorouridine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=C(F)C(=O)[NH]C1=O	2487.3	Semi standard non polar	33892256
5-Fluorouridine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@@H]1O	2503.2	Semi standard non polar	33892256
5-Fluorouridine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(=O)C(F)=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O	2512.6	Semi standard non polar	33892256
5-Fluorouridine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2758.1	Semi standard non polar	33892256
5-Fluorouridine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2763.0	Semi standard non polar	33892256
5-Fluorouridine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O)[C@@H]1O	2787.7	Semi standard non polar	33892256
5-Fluorouridine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	2743.6	Semi standard non polar	33892256
5-Fluorouridine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2784.5	Semi standard non polar	33892256
5-Fluorouridine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@@H]1O	2794.5	Semi standard non polar	33892256
5-Fluorouridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2983.4	Semi standard non polar	33892256
5-Fluorouridine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3012.3	Semi standard non polar	33892256
5-Fluorouridine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3009.8	Semi standard non polar	33892256
5-Fluorouridine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@@H]1O[Si](C)(C)C(C)(C)C	3003.1	Semi standard non polar	33892256
5-Fluorouridine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3226.9	Semi standard non polar	33892256
5-Fluorouridine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3183.5	Standard non polar	33892256
5-Fluorouridine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2886.4	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 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-9440000000-95cd5ad111dfa003f286	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Fluorouridine GC-MS (3 TMS) - 70eV, Positive	splash10-0fg9-9768500000-a1c8281940ad831ed2b6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Fluorouridine 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 10V, Positive-QTOF	splash10-001i-0920000000-02290d153dc9edadb175	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 20V, Positive-QTOF	splash10-001i-2900000000-70ac2ce48a79ae07735b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 40V, Positive-QTOF	splash10-01q9-9700000000-e518659df5820d88280b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 10V, Negative-QTOF	splash10-004l-5960000000-e010cff5b3db3ca93151	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 20V, Negative-QTOF	splash10-004l-4930000000-87f22990bef1abaa65fd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 40V, Negative-QTOF	splash10-0006-9100000000-28c02b9cb08506945f37	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 10V, Positive-QTOF	splash10-02ai-0950000000-104cde7c527b1d9ad380	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 20V, Positive-QTOF	splash10-03e9-1970000000-18e44fc0b01191fe8368	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 40V, Positive-QTOF	splash10-0a5c-9810000000-b3c0713cf9a1c6f90182	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 10V, Negative-QTOF	splash10-03dl-0390000000-2b94b3d551b6cf6e1779	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 20V, Negative-QTOF	splash10-002f-6970000000-2a53d10554d18aa7375b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Fluorouridine 40V, Negative-QTOF	splash10-0006-9100000000-aede0be6f7ac960f7167	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

DB01629

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9056

KEGG Compound ID

C16633

BioCyc ID

CPD0-2367

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9427

PDB ID

Not Available

ChEBI ID

40154

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-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

3. Uridine phosphorylase 1

General function:: Involved in transferase activity, transferring pentosyl groups
Specific function:: Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:: UPP1
Uniprot ID:: Q16831
Molecular weight:: 33934.005

Reactions

Fluorouracil + Ribose 1-phosphate → 5-Fluorouridine + Phosphate	details

Enzyme Details

4. Uridine phosphorylase 2

General function:: Involved in transferase activity, transferring pentosyl groups
Specific function:: Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis. Shows substrate specificity and accept uridine, deoxyuridine, and thymidine as well as the two pyrimidine nucleoside analogs 5-fluorouridine and 5-fluoro-2(')-deoxyuridine as substrates.
Gene Name:: UPP2
Uniprot ID:: O95045
Molecular weight:: 41601.795

Reactions

Fluorouracil + Ribose 1-phosphate → 5-Fluorouridine + Phosphate	details

Enzyme Details

5. 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 (HMDB0060396)

MOL for HMDB0060396 (5-Fluorouridine)

3D MOL for HMDB0060396 (5-Fluorouridine)

3D SDF for HMDB0060396 (5-Fluorouridine)

3D-SDF for HMDB0060396 (5-Fluorouridine)

PDB for HMDB0060396 (5-Fluorouridine)

3D PDB for HMDB0060396 (5-Fluorouridine)

SMILES for HMDB0060396 (5-Fluorouridine)

INCHI for HMDB0060396 (5-Fluorouridine)

Structure for HMDB0060396 (5-Fluorouridine)

3D Structure for HMDB0060396 (5-Fluorouridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions