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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (16) Show 16 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:46:10 UTC

HMDB ID

HMDB0001227

Secondary Accession Numbers

HMDB01227

Metabolite Identification

Common Name

5-Thymidylic acid

Description

5-Thymidylic acid (conjugate base thymidylate), also known as thymidine monophosphate (TMP), deoxythymidine monophosphate (dTMP), or deoxythymidylic acid (conjugate base deoxythymidylate), is a nucleotide that is used as a monomer in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. dTMP consists of a phosphate group, the pentose sugar deoxyribose, and the nucleobase thymine. Unlike the other deoxyribonucleotides, thymidine monophosphate often does not contain the "deoxy" prefix in its name; nevertheless, its symbol often includes a "d" ("dTMP"). 5-Thymidylic acid belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. The neutral species of 5-Thymidylic acid (2'-deoxythymidine 5'-monophosphate). 5-Thymidylic acid exists in all living species, ranging from bacteria to humans. Within humans, 5-thymidylic acid participates in a number of enzymatic reactions. In particular, 5-thymidylic acid and dihydrofolic acid can be biosynthesized from dUMP and 5,10-methylene-THF by the enzyme thymidylate synthase. In addition, 5-thymidylic acid can be converted into dTDP; which is catalyzed by the enzyme thymidylate synthase. In humans, 5-thymidylic acid is involved in pyrimidine metabolism. Outside of the human body, 5-Thymidylic acid has been detected, but not quantified in several different foods, such as common buckwheats, corn salad, garden cress, squashberries, and star fruits.

Structure

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

HMDB0001227
     RDKit          3D
5-Thymidylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.5110   -0.2377    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    0.3720   -0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0045   -0.3925   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.1494   -0.1029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483   -0.7408   -0.1628 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1392   -0.6286   -1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271   -1.4877   -1.0685 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8963   -2.8100   -1.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -1.0549    0.3732 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6019   -0.0032    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753   -0.6425   -0.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0854    0.3914   -0.0969 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.0747   -0.1365   -1.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.9259   -0.5579 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8989    0.5023    1.3812 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -0.4546    0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402    1.4751   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    1.9547   -0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    2.2412   -0.0224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9902    1.7381    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9896    2.4744    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2611    0.4585   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6690   -0.5273    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4856   -1.2067   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -1.4768   -0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394   -1.7879   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -1.0109   -2.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940    0.4165   -1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -1.2945   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8325   -3.2224   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.9139    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.7755   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    0.4785    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2930    2.5709   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449   -0.1798    2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5909    3.2851   -0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  9 16  1  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20  2  1  0
 16  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  7 29  1  6
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
 14 34  1  0
 15 35  1  0
 19 36  1  0
M  END


  Mrv1652309042000192D          

 21 22  0  0  0  0            999 V2000
10002.1188 9998.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.548510001.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.118810001.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6364 9999.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1067 9998.0222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9228 9999.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2071 9999.8723    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.619610000.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4914 9999.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.792510000.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1188 9999.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8333 9999.8734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.833310000.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.118810001.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.404310000.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4043 9999.8734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0178 9999.9550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6852 9999.4700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.4303 9998.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6053 9998.6854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3504 9999.4700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 16  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 21  4  1  1  0  0  0
 20  5  1  6  0  0  0
  1 11  2  0  0  0  0
 18 16  1  1  0  0  0
 13  2  2  0  0  0  0
 14  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001227

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1

> <INCHI_KEY>
GYOZYWVXFNDGLU-XLPZGREQSA-N

> <FORMULA>
C10H15N2O8P

> <MOLECULAR_WEIGHT>
322.2085

> <EXACT_MASS>
322.056601978

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.459022719953495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.37

> <JCHEM_LOGP>
-1.242619620666666

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.258488240760722

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2327578601680882

> <JCHEM_PKA_STRONGEST_BASIC>
-3.240344046121354

> <JCHEM_POLAR_SURFACE_AREA>
145.63000000000002

> <JCHEM_REFRACTIVITY>
66.2849

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thymidylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001227
     RDKit          3D
5-Thymidylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.5110   -0.2377    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    0.3720   -0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0045   -0.3925   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.1494   -0.1029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483   -0.7408   -0.1628 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1392   -0.6286   -1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271   -1.4877   -1.0685 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8963   -2.8100   -1.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -1.0549    0.3732 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6019   -0.0032    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753   -0.6425   -0.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0854    0.3914   -0.0969 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.0747   -0.1365   -1.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.9259   -0.5579 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8989    0.5023    1.3812 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -0.4546    0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402    1.4751   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    1.9547   -0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    2.2412   -0.0224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9902    1.7381    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9896    2.4744    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2611    0.4585   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6690   -0.5273    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4856   -1.2067   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -1.4768   -0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394   -1.7879   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -1.0109   -2.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940    0.4165   -1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -1.2945   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8325   -3.2224   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.9139    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.7755   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    0.4785    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2930    2.5709   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449   -0.1798    2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5909    3.2851   -0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  9 16  1  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20  2  1  0
 16  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  7 29  1  6
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
 14 34  1  0
 15 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8670.6228664.122   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8673.2918668.743   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8670.6228670.284   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.1218666.428   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8664.9998662.975   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.7898665.662   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0    8661.4538666.428   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0    8662.2238667.764   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8660.1178665.662   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8660.6798667.764   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8670.6228665.660   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8671.9558666.430   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8671.9558667.971   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.6228668.740   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.2888667.971   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8669.2888666.430   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0    8666.7008666.583   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8667.9468665.677   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8667.4708664.213   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.9308664.213   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.4548665.677   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    6   21                                                       
CONECT    5   20                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11   12   16    1                                                  
CONECT   12   11   13                                                       
CONECT   13   14   12    2                                                  
CONECT   14   13   15    3                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15   18                                                  
CONECT   17   18   21                                                       
CONECT   18   19   17   16                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21    5                                                  
CONECT   21   20   17    4                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0001227
HETATM    1  C1  UNL     1      -5.511  -0.238   0.028  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.145   0.372  -0.010  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.004  -0.393  -0.068  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.761   0.149  -0.103  1.00  0.00           N  
HETATM    5  C4  UNL     1      -0.648  -0.741  -0.163  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.139  -0.629  -1.460  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.327  -1.488  -1.068  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.896  -2.810  -1.109  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.496  -1.055   0.373  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.602  -0.003   0.370  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.775  -0.643  -0.044  1.00  0.00           O  
HETATM   12  P1  UNL     1       5.085   0.391  -0.097  1.00  0.00           P  
HETATM   13  O3  UNL     1       6.075  -0.136  -1.139  1.00  0.00           O  
HETATM   14  O4  UNL     1       4.547   1.926  -0.558  1.00  0.00           O  
HETATM   15  O5  UNL     1       5.899   0.502   1.381  1.00  0.00           O  
HETATM   16  O6  UNL     1       0.335  -0.455   0.775  1.00  0.00           O  
HETATM   17  C9  UNL     1      -1.640   1.475  -0.079  1.00  0.00           C  
HETATM   18  O7  UNL     1      -0.475   1.955  -0.112  1.00  0.00           O  
HETATM   19  N2  UNL     1      -2.737   2.241  -0.022  1.00  0.00           N  
HETATM   20  C10 UNL     1      -3.990   1.738   0.013  1.00  0.00           C  
HETATM   21  O8  UNL     1      -4.990   2.474   0.066  1.00  0.00           O  
HETATM   22  H1  UNL     1      -6.261   0.458  -0.345  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.669  -0.527   1.104  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.486  -1.207  -0.539  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.158  -1.477  -0.086  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.939  -1.788  -0.026  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.403  -1.011  -2.326  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.494   0.417  -1.583  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.213  -1.295  -1.685  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.833  -3.222  -0.224  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.795  -1.914   1.022  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.330   0.776  -0.371  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.730   0.478   1.344  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.293   2.571  -0.447  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.545  -0.180   2.014  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.591   3.285  -0.006  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   20
CONECT    3    4   25
CONECT    4    5   17
CONECT    5    6   16   26
CONECT    6    7   27   28
CONECT    7    8    9   29
CONECT    8   30
CONECT    9   10   16   31
CONECT   10   11   32   33
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   34
CONECT   15   35
CONECT   17   18   18   19
CONECT   19   20   36
CONECT   20   21   21
END

HMDB0001227
     RDKit          3D
5-Thymidylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.5110   -0.2377    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    0.3720   -0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0045   -0.3925   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.1494   -0.1029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483   -0.7408   -0.1628 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1392   -0.6286   -1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271   -1.4877   -1.0685 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8963   -2.8100   -1.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -1.0549    0.3732 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6019   -0.0032    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753   -0.6425   -0.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0854    0.3914   -0.0969 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.0747   -0.1365   -1.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.9259   -0.5579 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8989    0.5023    1.3812 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -0.4546    0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402    1.4751   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    1.9547   -0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    2.2412   -0.0224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9902    1.7381    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9896    2.4744    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2611    0.4585   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6690   -0.5273    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4856   -1.2067   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -1.4768   -0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394   -1.7879   -0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -1.0109   -2.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940    0.4165   -1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -1.2945   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8325   -3.2224   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.9139    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.7755   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    0.4785    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2930    2.5709   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449   -0.1798    2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5909    3.2851   -0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  9 16  1  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20  2  1  0
 16  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  7 29  1  6
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
 14 34  1  0
 15 35  1  0
 19 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(DT)1	ChEBI
5'-Thymidylic acid	ChEBI
5'-TMP	ChEBI
5-Methyl-dUMP	ChEBI
Deoxyribosylthymine monophosphate	ChEBI
Ribothymidine 5'-monophosphate	ChEBI
Thymidine 5'-(dihydrogen phosphate)	ChEBI
Thymidine 5'-phosphate	ChEBI
Thymidine 5'-phosphoric acid	ChEBI
Thymidine monophosphate	ChEBI
Thymidine-5'-monophosphoric acid	ChEBI
THYMIDINE-5'-phosphATE	ChEBI
Thymidylate	ChEBI
Thymidylic acid	ChEBI
TMP	ChEBI
Deoxythymidine 5'-phosphate	Kegg
Deoxythymidylic acid	Kegg
5'-Thymidylate	Generator
Deoxyribosylthymine monophosphoric acid	Generator
Ribothymidine 5'-monophosphoric acid	Generator
Thymidine 5'-(dihydrogen phosphoric acid)	Generator
Thymidine monophosphoric acid	Generator
Thymidine-5'-monophosphate	Generator
THYMIDINE-5'-phosphoric acid	Generator
Deoxythymidine 5'-phosphoric acid	Generator
Deoxythymidylate	Generator
5-Thymidylate	Generator
2'-Deoxythymidine 5'-monophosphate	HMDB
5'-dTMP	HMDB
Deoxy TMP	HMDB
Deoxythymidine 5'-monophosphate	HMDB
Deoxythymidine monophosphate	HMDB
Deoxythymydilate	HMDB
Deoxythymydilic acid	HMDB
dTMP	HMDB
Thymidine 5'-monophosphate	HMDB
Thymidine 5'-phosphorate	HMDB
Thymidine 5'MP	HMDB
Thymidine mononucleotide	HMDB
Thymidine phosphate	HMDB
Thymidine-5'-monophosphorate	HMDB
Thymidylic acids	HMDB
Acids, thymidylic	HMDB
Acid, thymidylic	HMDB
monoPhosphate, thymidine	HMDB

Chemical Formula

C₁₀H₁₅N₂O₈P

Average Molecular Weight

322.2085

Monoisotopic Molecular Weight

322.056601978

IUPAC Name

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

Traditional Name

thymidylate

CAS Registry Number

365-07-1

SMILES

CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O

InChI Identifier

InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1

InChI Key

GYOZYWVXFNDGLU-XLPZGREQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine deoxyribonucleotides

Direct Parent

Pyrimidine 2'-deoxyribonucleoside monophosphates

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside monophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Lactam
Secondary alcohol
Urea
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thymidine 5'-monophosphate (CHEBI:17013 )
Deoxyribonucleotides (C00364 )

Ontology

Not Available

Fibroblasts (HMDB: HMDB0001227)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Cellular substructure

Organelle

Lysosome (HMDB: HMDB0001227)
Mitochondrion (HMDB: HMDB0001227)

Source

Exogenous

Exogenous (HMDB: HMDB0001227)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0001227)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyrimidine Metabolism (PathBank: SMP0121324)
Pyrimidine Metabolism (PathBank: SMP0002370)
One Carbon Pool by Folate (PathBank: SMP0122040)
Salvage Pathways of Pyrimidine Deoxyribonucleotides (PathBank: SMP0002073)
One Carbon Pool by Folate I (PathBank: SMP0002369)
Pyrimidine Deoxyribonucleosides Salvage (PathBank: SMP0012077)

Disease pathway

Beta-Ureidopropionase Deficiency (PathBank: SMP0120678)
UMP Synthase Deficiency (Orotic Aciduria) (PathBank: SMP0120507)
Dihydropyrimidinase Deficiency (PathBank: SMP0120473)
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy) (PathBank: SMP0120530)

Role

Not Available

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	164.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000163
[M+H]+	Not Available	163.843	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000163

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.78 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.2	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.28 m³·mol⁻¹	ChemAxon
Polarizability	27.46 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
DarkChem	[M+H]+	169.474	31661259
DarkChem	[M-H]-	165.643	31661259
AllCCS	[M+H]+	169.664	32859911
AllCCS	[M-H]-	166.102	32859911
DeepCCS	[M+H]+	172.465	30932474
DeepCCS	[M-H]-	170.107	30932474
DeepCCS	[M-2H]-	204.235	30932474
DeepCCS	[M+Na]+	180.126	30932474
AllCCS	[M+H]+	169.7	32859911
AllCCS	[M+H-H2O]+	166.6	32859911
AllCCS	[M+NH4]+	172.5	32859911
AllCCS	[M+Na]+	173.3	32859911
AllCCS	[M-H]-	166.1	32859911
AllCCS	[M+Na-2H]-	166.1	32859911
AllCCS	[M+HCOO]-	166.2	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.	3.11 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0891 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.29 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	323.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	439.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	224.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	299.3 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	281.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	711.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	583.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	80.3 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	636.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	646.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	305.0 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	375.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Thymidylic acid	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O	3717.8	Standard polar	33892256
5-Thymidylic acid	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O	2150.8	Standard non polar	33892256
5-Thymidylic acid	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O	2996.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Thymidylic acid,1TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)[NH]C1=O	2556.1	Semi standard non polar	33892256
5-Thymidylic acid,1TMS,isomer #2	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	2714.3	Semi standard non polar	33892256
5-Thymidylic acid,1TMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O	2692.9	Semi standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	2701.8	Semi standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	2826.8	Standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	3835.8	Standard polar	33892256
5-Thymidylic acid,2TMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O	2639.9	Semi standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O	2894.0	Standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C)C1=O	4280.9	Standard polar	33892256
5-Thymidylic acid,2TMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	2756.2	Semi standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	2859.7	Standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	3546.0	Standard polar	33892256
5-Thymidylic acid,2TMS,isomer #4	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2744.1	Semi standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #4	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2861.4	Standard non polar	33892256
5-Thymidylic acid,2TMS,isomer #4	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	3879.2	Standard polar	33892256
5-Thymidylic acid,3TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	2752.9	Semi standard non polar	33892256
5-Thymidylic acid,3TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	2880.2	Standard non polar	33892256
5-Thymidylic acid,3TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)[NH]C1=O	3335.6	Standard polar	33892256
5-Thymidylic acid,3TMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2722.4	Semi standard non polar	33892256
5-Thymidylic acid,3TMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2892.5	Standard non polar	33892256
5-Thymidylic acid,3TMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	3579.1	Standard polar	33892256
5-Thymidylic acid,3TMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2755.7	Semi standard non polar	33892256
5-Thymidylic acid,3TMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2907.4	Standard non polar	33892256
5-Thymidylic acid,3TMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	3345.0	Standard polar	33892256
5-Thymidylic acid,4TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2774.2	Semi standard non polar	33892256
5-Thymidylic acid,4TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2919.5	Standard non polar	33892256
5-Thymidylic acid,4TMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	3165.1	Standard polar	33892256
5-Thymidylic acid,1TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)[NH]C1=O	2851.9	Semi standard non polar	33892256
5-Thymidylic acid,1TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	2974.4	Semi standard non polar	33892256
5-Thymidylic acid,1TBDMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2917.4	Semi standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3183.5	Semi standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3287.5	Standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3929.4	Standard polar	33892256
5-Thymidylic acid,2TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3121.6	Semi standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3350.5	Standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	4200.4	Standard polar	33892256
5-Thymidylic acid,2TBDMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3208.1	Semi standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3273.1	Standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3725.7	Standard polar	33892256
5-Thymidylic acid,2TBDMS,isomer #4	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3198.8	Semi standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #4	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3278.2	Standard non polar	33892256
5-Thymidylic acid,2TBDMS,isomer #4	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3916.9	Standard polar	33892256
5-Thymidylic acid,3TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3407.3	Semi standard non polar	33892256
5-Thymidylic acid,3TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3486.5	Standard non polar	33892256
5-Thymidylic acid,3TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	3595.1	Standard polar	33892256
5-Thymidylic acid,3TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3404.8	Semi standard non polar	33892256
5-Thymidylic acid,3TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3503.6	Standard non polar	33892256
5-Thymidylic acid,3TBDMS,isomer #2	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3708.1	Standard polar	33892256
5-Thymidylic acid,3TBDMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3428.4	Semi standard non polar	33892256
5-Thymidylic acid,3TBDMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3484.4	Standard non polar	33892256
5-Thymidylic acid,3TBDMS,isomer #3	CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3567.9	Standard polar	33892256
5-Thymidylic acid,4TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3615.1	Semi standard non polar	33892256
5-Thymidylic acid,4TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3627.3	Standard non polar	33892256
5-Thymidylic acid,4TBDMS,isomer #1	CC1=CN([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3460.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)	splash10-01u0-0961000000-4380a23f8bec3c2dd015	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)	splash10-03k9-0940000000-6238904f1b1f293aaf3a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)	splash10-01u0-0961000000-4380a23f8bec3c2dd015	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Thymidylic acid GC-EI-TOF (Non-derivatized)	splash10-03k9-0940000000-6238904f1b1f293aaf3a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Thymidylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9500000000-ca4d82d816839360b115	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Thymidylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9621000000-1a0c588cd8f192b77565	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Thymidylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Thymidylic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-9110000000-a45c0d5a58cdb0e5fee4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9000000000-624fe22ca203d0e6430e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9000000000-0c23943cc868acaaeda4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-004i-9703000000-452b674ca61adb40209b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid LC-ESI-QTOF , negative-QTOF	splash10-004i-9703000000-452b674ca61adb40209b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 40V, Positive-QTOF	splash10-001i-9000000000-2233c579a23110abe895	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 40V, Positive-QTOF	splash10-001i-9000000000-9af792986db292f0d8d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 10V, Positive-QTOF	splash10-001i-9010000000-9936ff7b595382418b7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOF	splash10-001i-9200000000-5c7a9e2c6c970eec2d92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOF	splash10-001i-9000000000-edfd7498bf3ebaedbb4b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 10V, Positive-QTOF	splash10-001i-9000000000-9dafb0586b1aadb8475d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 35V, Positive-QTOF	splash10-001i-9100000000-b286ae95b38725486f5b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOF	splash10-001i-9000000000-c716e9bc2009f1adb3ae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 40V, Negative-QTOF	splash10-004i-9000000000-ec3ffc3673cc769d3a0e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 35V, Negative-QTOF	splash10-004i-8900000000-90b7e520ce562f39a280	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 35V, Negative-QTOF	splash10-004i-7900000000-a01024a3e21d2de7f133	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 10V, Negative-QTOF	splash10-004j-5900000000-57620f7a2b0abf78c220	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Negative-QTOF	splash10-004i-8900000000-b0b0ac82c08ccb2ea84e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Thymidylic acid 35V, Negative-QTOF	splash10-006t-0905000000-49f5a9d8a112c369032d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Thymidylic acid 10V, Positive-QTOF	splash10-004i-0900000000-b932c025cbc139ba930b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Positive-QTOF	splash10-004i-4900000000-ae144ce0df705b85f237	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Thymidylic acid 40V, Positive-QTOF	splash10-004i-5900000000-9f2e5ba96fb24ff28b7f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Thymidylic acid 10V, Negative-QTOF	splash10-004i-9766000000-855dcb81a8d160218e77	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Thymidylic acid 20V, Negative-QTOF	splash10-004i-9200000000-f9116de370dd3211ece6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Thymidylic acid 40V, Negative-QTOF	splash10-004i-9000000000-0953b010bfa0e123afa7	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria
Lysosome

Biospecimen Locations

Feces

Tissue Locations

Fibroblasts

Pathways

Name	SMPDB/PathBank	KEGG
Pyrimidine metabolism	Not Available
Beta Ureidopropionase Deficiency		Not Available
UMP Synthase Deficiency (Orotic Aciduria)		Not Available
Dihydropyrimidinase Deficiency		Not Available
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB01643

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Thymidine_monophosphate

METLIN ID

6092

PubChem Compound

9700

PDB ID

Not Available

ChEBI ID

17013

Food Biomarker Ontology

Not Available

VMH ID

DTMP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Scarano, E. Enzymic formation of thymidylic acid from 5-methyl-5'-deoxycytidylic acid. Bollettino - Societa Italiana di Biologia Sperimentale (1958), 34 945.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Gribaudo G, Riera L, Caposio P, Maley F, Landolfo S: Human cytomegalovirus requires cellular deoxycytidylate deaminase for replication in quiescent cells. J Gen Virol. 2003 Jun;84(Pt 6):1437-41. [PubMed:12771412 ]
Seno T, Ayusawa D, Shimizu K, Koyama H, Takeishi K, Hori T: Thymineless death and genetic events in mammalian cells. Basic Life Sci. 1985;31:241-63. [PubMed:3888175 ]
Terai C, Carson DA: Pyrimidine nucleotide and nucleic acid synthesis in human monocytes and macrophages. Exp Cell Res. 1991 Apr;193(2):375-81. [PubMed:1706277 ]
Gribaudo G, Riera L, Lembo D, De Andrea M, Gariglio M, Rudge TL, Johnson LF, Landolfo S: Murine cytomegalovirus stimulates cellular thymidylate synthase gene expression in quiescent cells and requires the enzyme for replication. J Virol. 2000 Jun;74(11):4979-87. [PubMed:10799571 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

Reactions

5-Thymidylic acid + Water → Thymidine + Phosphate	details

Enzyme Details

2. Cytosolic 5'-nucleotidase 1B

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:: NT5C1B
Uniprot ID:: Q96P26
Molecular weight:: 68803.055

Reactions

5-Thymidylic acid + Water → Thymidine + Phosphate	details

Enzyme Details

3. Cytosolic 5'-nucleotidase 1A

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:: NT5C1A
Uniprot ID:: Q9BXI3
Molecular weight:: 41020.145

Reactions

5-Thymidylic acid + Water → Thymidine + Phosphate	details

Enzyme Details

4. 5'(3')-deoxyribonucleotidase, cytosolic type

General function:: Involved in metal ion binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:: NT5C
Uniprot ID:: Q8TCD5
Molecular weight:: Not Available

Reactions

5-Thymidylic acid + Water → Thymidine + Phosphate	details

Enzyme Details

5. 5'(3')-deoxyribonucleotidase, mitochondrial

General function:: Involved in phosphatase activity
Specific function:: Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:: NT5M
Uniprot ID:: Q9NPB1
Molecular weight:: Not Available

Reactions

5-Thymidylic acid + Water → Thymidine + Phosphate	details

Enzyme Details

6. Thymidylate kinase

General function:: Involved in thymidylate kinase activity
Specific function:: Catalyzes the conversion of dTMP to dTDP.
Gene Name:: DTYMK
Uniprot ID:: P23919
Molecular weight:: 23819.105

Reactions

Adenosine triphosphate + 5-Thymidylic acid → ADP + dTDP	details

Enzyme Details

7. Ectonucleoside triphosphate diphosphohydrolase 1

General function:: Involved in hydrolase activity
Specific function:: In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:: ENTPD1
Uniprot ID:: P49961
Molecular weight:: 58706.0

Reactions

dTDP + Water → 5-Thymidylic acid + Phosphate	details

Enzyme Details

8. Soluble calcium-activated nucleotidase 1

General function:: Involved in calcium ion binding
Specific function:: Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:: CANT1
Uniprot ID:: Q8WVQ1
Molecular weight:: 44839.24

Enzyme Details

9. Ectonucleoside triphosphate diphosphohydrolase 3

General function:: Involved in hydrolase activity
Specific function:: Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:: ENTPD3
Uniprot ID:: O75355
Molecular weight:: 59104.76

Reactions

dTDP + Water → 5-Thymidylic acid + Phosphate	details

Enzyme Details

10. Cytosolic 5'-nucleotidase 3

General function:: Involved in magnesium ion binding
Specific function:: Can act both as nucleotidase and as phosphotransferase.
Gene Name:: NT5C3
Uniprot ID:: Q9H0P0
Molecular weight:: 33914.91

Reactions

5-Thymidylic acid + Water → Thymidine + Phosphate	details

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Showing metabocard for 5-Thymidylic acid (HMDB0001227)

MOL for HMDB0001227 (5-Thymidylic acid)

3D MOL for HMDB0001227 (5-Thymidylic acid)

3D SDF for HMDB0001227 (5-Thymidylic acid)

3D-SDF for HMDB0001227 (5-Thymidylic acid)

PDB for HMDB0001227 (5-Thymidylic acid)

3D PDB for HMDB0001227 (5-Thymidylic acid)

SMILES for HMDB0001227 (5-Thymidylic acid)

INCHI for HMDB0001227 (5-Thymidylic acid)

Structure for HMDB0001227 (5-Thymidylic acid)

3D Structure for HMDB0001227 (5-Thymidylic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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