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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015394

Secondary Accession Numbers

HMDB15394

Metabolite Identification

Common Name

Telbivudine

Description

Telbivudine is only found in individuals that have used or taken this drug. It is a synthetic thymidine nucleoside analog with specific activity against the hepatitis B virus. Telbivudine is orally administered, with good tolerance, lack of toxicity and no dose-limiting side effects.Telbivudine 5'â€“triphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate, thymidine 5'â€“triphosphate. This leads to the chain termination of DNA synthesis, thereby inhibiting viral replication. Incorporation of telbivudine 5'â€“triphosphate into viral DNA also causes DNA chain termination, resulting in inhibition of HBV replication. Telbivudine inhibits anticompliment or second-strand DNA.

Structure

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

HMDB0015394
     RDKit          3D
Telbivudine
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.2630   -1.4550    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116   -0.4127    0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050   -0.6278   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271    0.2719    0.0800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858   -0.0223   -0.3547 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9893    0.9636   -1.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825    0.7624   -1.0606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1605    0.4194   -2.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644   -0.3664   -0.0564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6707   -0.3834    0.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -1.3438    1.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -0.0187    0.6998 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359    1.4235    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582    2.3250    0.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5088    1.6686    1.0860 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5008    0.7731    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    1.0036    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -2.4470    0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1200   -1.2928    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4842   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009   -1.5763   -0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4699   -1.0275   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703    1.9938   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791    0.6054   -2.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8773    1.7037   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651   -0.5654   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -1.3165   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5671   -0.6729    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355    0.5846    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1064   -2.0521    1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7734    2.5660    1.5614 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
  9 12  1  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
 12  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  7 25  1  1
  8 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
M  END

1265
  Mrv0541 02231215222D          

 17 18  0  0  1  0            999 V2000
    3.7462   -1.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814   -2.4546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7966   -2.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    0.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.3073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    1.5447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663   -1.7872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0789   -0.5177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4113   -1.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4913   -1.7872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9761   -2.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    0.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932    1.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5077    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 11  1  0  0  0  0
  8  2  1  6  0  0  0
  3 12  1  0  0  0  0
  4 14  2  0  0  0  0
  5 16  2  0  0  0  0
  9  6  1  1  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 14  1  0  0  0  0
  7 16  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  1  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015394

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m1/s1

> <INCHI_KEY>
IQFYYKKMVGJFEH-CSMHCCOUSA-N

> <FORMULA>
C10H14N2O5

> <MOLECULAR_WEIGHT>
242.2286

> <EXACT_MASS>
242.090271568

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.25380466939506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.32

> <JCHEM_LOGP>
-1.1190535893333329

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.907922676786033

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.960276156373078

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9780835894464888

> <JCHEM_POLAR_SURFACE_AREA>
99.09999999999998

> <JCHEM_REFRACTIVITY>
55.412000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
telbivudine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015394
     RDKit          3D
Telbivudine
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.2630   -1.4550    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116   -0.4127    0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050   -0.6278   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271    0.2719    0.0800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858   -0.0223   -0.3547 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9893    0.9636   -1.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825    0.7624   -1.0606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1605    0.4194   -2.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644   -0.3664   -0.0564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6707   -0.3834    0.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -1.3438    1.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -0.0187    0.6998 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359    1.4235    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582    2.3250    0.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5088    1.6686    1.0860 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5008    0.7731    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    1.0036    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -2.4470    0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1200   -1.2928    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4842   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009   -1.5763   -0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4699   -1.0275   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703    1.9938   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791    0.6054   -2.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8773    1.7037   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651   -0.5654   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -1.3165   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5671   -0.6729    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355    0.5846    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1064   -2.0521    1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7734    2.5660    1.5614 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
  9 12  1  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
 12  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  7 25  1  1
  8 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1265                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.993  -1.871   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.072  -4.582   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.954  -4.421   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   0.574   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.747   5.193   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.747   0.574   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.413   2.883   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.977  -3.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -0.966   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.501  -1.871   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.517  -3.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.422  -4.582   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   1.344   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.413   1.344   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   2.883   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.747   3.654   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.414   3.654   0.000  0.00  0.00           C+0
CONECT    1    9   11                                                       
CONECT    2    8                                                            
CONECT    3   12                                                            
CONECT    4   14                                                            
CONECT    5   16                                                            
CONECT    6    9   13   14                                                  
CONECT    7   14   16                                                       
CONECT    8    2   10   11                                                  
CONECT    9    1    6   10                                                  
CONECT   10    8    9                                                       
CONECT   11    1    8   12                                                  
CONECT   12    3   11                                                       
CONECT   13    6   15                                                       
CONECT   14    4    6    7                                                  
CONECT   15   13   16   17                                                  
CONECT   16    5    7   15                                                  
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015394
HETATM    1  C1  UNL     1       4.263  -1.455   0.040  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.212  -0.413   0.283  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.905  -0.628  -0.114  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.927   0.272   0.080  1.00  0.00           N  
HETATM    5  C4  UNL     1      -0.386  -0.022  -0.355  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.989   0.964  -1.306  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.482   0.762  -1.061  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.160   0.419  -2.209  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.464  -0.366  -0.056  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.671  -0.383   0.835  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.416  -1.344   1.834  1.00  0.00           O  
HETATM   12  O3  UNL     1      -1.329  -0.019   0.700  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.236   1.424   0.683  1.00  0.00           C  
HETATM   14  O4  UNL     1       0.358   2.325   0.901  1.00  0.00           O  
HETATM   15  N2  UNL     1       2.509   1.669   1.086  1.00  0.00           N  
HETATM   16  C10 UNL     1       3.501   0.773   0.897  1.00  0.00           C  
HETATM   17  O5  UNL     1       4.687   1.004   1.274  1.00  0.00           O  
HETATM   18  H1  UNL     1       3.782  -2.447   0.280  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.120  -1.293   0.703  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.507  -1.484  -1.030  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.701  -1.576  -0.599  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.470  -1.027  -0.813  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.670   1.994  -1.173  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.779   0.605  -2.350  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.877   1.704  -0.626  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.065  -0.565  -2.344  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.311  -1.316  -0.601  1.00  0.00           H  
HETATM   28  H11 UNL     1      -4.567  -0.673   0.289  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.736   0.585   1.353  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.106  -2.052   1.838  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.773   2.566   1.561  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   16
CONECT    3    4   21
CONECT    4    5   13
CONECT    5    6   12   22
CONECT    6    7   23   24
CONECT    7    8    9   25
CONECT    8   26
CONECT    9   10   12   27
CONECT   10   11   28   29
CONECT   11   30
CONECT   13   14   14   15
CONECT   15   16   31
CONECT   16   17   17
END

HMDB0015394
     RDKit          3D
Telbivudine
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.2630   -1.4550    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116   -0.4127    0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050   -0.6278   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271    0.2719    0.0800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858   -0.0223   -0.3547 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9893    0.9636   -1.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825    0.7624   -1.0606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1605    0.4194   -2.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644   -0.3664   -0.0564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6707   -0.3834    0.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -1.3438    1.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -0.0187    0.6998 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359    1.4235    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582    2.3250    0.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5088    1.6686    1.0860 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5008    0.7731    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    1.0036    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7819   -2.4470    0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1200   -1.2928    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4842   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009   -1.5763   -0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4699   -1.0275   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703    1.9938   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791    0.6054   -2.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8773    1.7037   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651   -0.5654   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -1.3165   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5671   -0.6729    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355    0.5846    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1064   -2.0521    1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7734    2.5660    1.5614 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
  9 12  1  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
 12  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  7 25  1  1
  8 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2-Deoxy-beta-L-ribofuranosyl)-5-methyluracil	ChEBI
2'-Deoxy-L-thymidine	ChEBI
beta-L-2'-Deoxythymidine	ChEBI
Beta-L-Thymidine	ChEBI
Epavudine	ChEBI
L-Deoxythymidine	ChEBI
L-DT	ChEBI
L-Thymidine	ChEBI
LDT	ChEBI
Tyzeka	Kegg
ABBR LDT	Kegg
1-(2-Deoxy-b-L-ribofuranosyl)-5-methyluracil	Generator
1-(2-Deoxy-β-L-ribofuranosyl)-5-methyluracil	Generator
b-L-2'-Deoxythymidine	Generator
Β-L-2'-deoxythymidine	Generator
b-L-Thymidine	Generator
Β-L-thymidine	Generator
Telbivudin	HMDB
1-(2-Deoxy-beta-L-erythropentafuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione	HMDB
beta L 2' Deoxythymidine	HMDB

Chemical Formula

C₁₀H₁₄N₂O₅

Average Molecular Weight

242.2286

Monoisotopic Molecular Weight

242.090271568

IUPAC Name

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

Traditional Name

telbivudine

CAS Registry Number

3424-98-4

SMILES

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

InChI Identifier

InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m1/s1

InChI Key

IQFYYKKMVGJFEH-CSMHCCOUSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Pyrimidone
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Vinylogous amide
Lactam
Secondary alcohol
Urea
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidine 2'-deoxyribonucleoside (CHEBI:63624 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015394)

Process

Not Available

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	66.8 g/L	Not Available
LogP	-1.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	66.8 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.1	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.41 m³·mol⁻¹	ChemAxon
Polarizability	23.25 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]+	155.081	31661259
DarkChem	[M-H]-	156.075	31661259
DeepCCS	[M+H]+	160.906	30932474
DeepCCS	[M-H]-	158.51	30932474
DeepCCS	[M-2H]-	191.396	30932474
DeepCCS	[M+Na]+	166.868	30932474
AllCCS	[M+H]+	154.3	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	157.8	32859911
AllCCS	[M+Na]+	158.9	32859911
AllCCS	[M-H]-	154.2	32859911
AllCCS	[M+Na-2H]-	154.3	32859911
AllCCS	[M+HCOO]-	154.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Telbivudine	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)NC1=O	3227.0	Standard polar	33892256
Telbivudine	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)NC1=O	2206.1	Standard non polar	33892256
Telbivudine	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)NC1=O	2390.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Telbivudine,1TMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO)O2)C(=O)[NH]C1=O	2332.5	Semi standard non polar	33892256
Telbivudine,1TMS,isomer #2	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C)O2)C(=O)[NH]C1=O	2281.7	Semi standard non polar	33892256
Telbivudine,1TMS,isomer #3	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)N([Si](C)(C)C)C1=O	2342.1	Semi standard non polar	33892256
Telbivudine,2TMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)[NH]C1=O	2312.0	Semi standard non polar	33892256
Telbivudine,2TMS,isomer #2	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO)O2)C(=O)N([Si](C)(C)C)C1=O	2397.2	Semi standard non polar	33892256
Telbivudine,2TMS,isomer #3	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2384.3	Semi standard non polar	33892256
Telbivudine,3TMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2403.0	Semi standard non polar	33892256
Telbivudine,3TMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2498.5	Standard non polar	33892256
Telbivudine,3TMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O	2732.2	Standard polar	33892256
Telbivudine,1TBDMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O2)C(=O)[NH]C1=O	2576.3	Semi standard non polar	33892256
Telbivudine,1TBDMS,isomer #2	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	2550.0	Semi standard non polar	33892256
Telbivudine,1TBDMS,isomer #3	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2574.8	Semi standard non polar	33892256
Telbivudine,2TBDMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O	2796.1	Semi standard non polar	33892256
Telbivudine,2TBDMS,isomer #2	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2843.8	Semi standard non polar	33892256
Telbivudine,2TBDMS,isomer #3	CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2815.4	Semi standard non polar	33892256
Telbivudine,3TBDMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3049.2	Semi standard non polar	33892256
Telbivudine,3TBDMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3118.0	Standard non polar	33892256
Telbivudine,3TBDMS,isomer #1	CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2994.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Telbivudine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9420000000-ebaddd47fbf973a127a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Telbivudine GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9522000000-ce76edd6f16ba8e724c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Telbivudine 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 - Telbivudine 10V, Positive-QTOF	splash10-004i-0900000000-9ad72ff6cb2e2dfab911	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 20V, Positive-QTOF	splash10-004i-4900000000-3b1e6c50c2450e123648	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 40V, Positive-QTOF	splash10-004i-6900000000-d30b05dfe1b6d25ebd2b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 10V, Negative-QTOF	splash10-052g-1940000000-ce16baa1ceb8a83565c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 20V, Negative-QTOF	splash10-0ufr-3920000000-c6ff3f238b6fed007635	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 40V, Negative-QTOF	splash10-0006-9200000000-104a4f5a4fe8a0ed5ca3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 10V, Positive-QTOF	splash10-004i-1900000000-ed2addc3268721b7d4d4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 20V, Positive-QTOF	splash10-004i-8900000000-447c3a769f2fc4753e53	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 40V, Positive-QTOF	splash10-056r-7900000000-ef6aea3f9c22b2f05174	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 10V, Negative-QTOF	splash10-002f-1980000000-d1c8e15ec36f5d6cd39e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 20V, Negative-QTOF	splash10-002f-9400000000-6ded983ef6b4abd0caa2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Telbivudine 40V, Negative-QTOF	splash10-0006-9400000000-157f5aad418618113102	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01265	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01265	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01265

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

140081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Telbivudine

METLIN ID

Not Available

PubChem Compound

159269

PDB ID

LLT

ChEBI ID

63624

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

Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. [PubMed:15882124 ]
Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [PubMed:15985003 ]
Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [PubMed:16981973 ]
Ruiz-Sancho A, Sheldon J, Soriano V: Telbivudine: a new option for the treatment of chronic hepatitis B. Expert Opin Biol Ther. 2007 May;7(5):751-61. [PubMed:17477811 ]
Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [PubMed:17722961 ]
Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [PubMed:17724496 ]
Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [PubMed:18069753 ]
Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. doi: 10.1016/j.clinthera.2007.12.032. [PubMed:18201580 ]
Cieslak J, Ausin C, Grajkowski A, Beaucage SL: Convenient and efficient approach to the permanent or reversible conjugation of RNA and DNA sequences with functional groups. Curr Protoc Nucleic Acid Chem. 2012 Sep;Chapter 4:Unit4.52. doi: 10.1002/0471142700.nc0452s50. [PubMed:22956458 ]
Standring DN, Bridges EG, Placidi L, Faraj A, Loi AG, Pierra C, Dukhan D, Gosselin G, Imbach JL, Hernandez B, Juodawlkis A, Tennant B, Korba B, Cote P, Cretton-Scott E, Schinazi RF, Myers M, Bryant ML, Sommadossi JP: Antiviral beta-L-nucleosides specific for hepatitis B virus infection. Antivir Chem Chemother. 2001;12 Suppl 1:119-29. [PubMed:11594678 ]

Showing metabocard for Telbivudine (HMDB0015394)

MOL for HMDB0015394 (Telbivudine)

3D MOL for HMDB0015394 (Telbivudine)

3D SDF for HMDB0015394 (Telbivudine)

3D-SDF for HMDB0015394 (Telbivudine)

PDB for HMDB0015394 (Telbivudine)

3D PDB for HMDB0015394 (Telbivudine)

SMILES for HMDB0015394 (Telbivudine)

INCHI for HMDB0015394 (Telbivudine)

Structure for HMDB0015394 (Telbivudine)

3D Structure for HMDB0015394 (Telbivudine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra