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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014445

Secondary Accession Numbers

HMDB14445

Metabolite Identification

Common Name

Tenofovir

Description

Tenofovir is only found in individuals that have used or taken this drug. Tenofovir, marketed by Gilead Sciences under the trade name Viread®, belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (nRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. [Wikipedia ]Tenofovir inhibits the activity of HIV reverse transcriptase by competing with the natural substrate deoxyadenosine 5’-triphosphate and, after incorporation into DNA, by DNA chain termination. Specifically, the drugs are analogues of the naturally occurring deoxynucleotides needed to synthesize the viral DNA and they compete with the natural deoxynucleotides for incorporation into the growing viral DNA chain. However, unlike the natural deoxynucleotides substrates, NRTIs and NtRTIs (nucleoside/tide reverse transcriptase inhibitors) lack a 3'-hydroxyl group on the deoxyribose moiety. As a result, following incorporation of an NRTI or an NtRTI, the next incoming deoxynucleotide cannot form the next 5'-3' phosphodiester bond needed to extend the DNA chain. Thus, when an NRTI or NtRTI is incorporated, viral DNA synthesis is halted, a process known as chain termination. All NRTIs and NtRTIs are classified as competitive substrate inhibitors.

Structure

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

HMDB0014445
     RDKit          3D
Tenofovir
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.8926    1.0041   -2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -0.0913   -1.0216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2422   -1.2692   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1372   -0.8598   -0.9615 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512   -0.4148   -1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1554   -1.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -0.4352    0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -0.3299    1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2399    0.1353    0.9040 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4630   -0.6869    2.3528 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -1.1272    2.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.2189    1.4892 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -0.8778    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.5226   -1.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148   -0.4407    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    1.2721    0.6669 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.2893    2.1714    0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3648    1.3590    2.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8631    1.9036    0.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    0.5424   -2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413    1.4326   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256    1.7786   -1.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720    0.2885    0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859   -1.6568   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5635   -2.0537   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -0.2851   -2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875    0.5204    1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6233    0.0765   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -1.4037    3.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2469   -0.8433   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -1.1020    0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6101    0.4584    2.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5567    1.7310    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 13  4  1  0
 13  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
M  END

464205
  Mrv0541 02231214352D          

 19 20  0  0  1  0            999 V2000
    6.2432   -2.1865    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795   -1.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4994   -2.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0273   -1.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4590   -2.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.5064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    1.8343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.5829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.8204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -0.4479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1159   -0.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742    0.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    1.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  1 17  1  0  0  0  0
 11  2  1  1  0  0  0
  2 17  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 16  1  0  0  0  0
  7 15  1  0  0  0  0
  7 16  2  0  0  0  0
  8 13  1  0  0  0  0
  8 19  2  0  0  0  0
  9 18  2  0  0  0  0
  9 19  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014445

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1

> <INCHI_KEY>
SGOIRFVFHAKUTI-ZCFIWIBFSA-N

> <FORMULA>
C9H14N5O4P

> <MOLECULAR_WEIGHT>
287.2123

> <EXACT_MASS>
287.078340473

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
25.54019716118723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid

> <ALOGPS_LOGP>
-1.51

> <JCHEM_LOGP>
-3.656297687793935

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.905973811236994

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3533237119111554

> <JCHEM_PKA_STRONGEST_BASIC>
5.123811764568992

> <JCHEM_POLAR_SURFACE_AREA>
136.38

> <JCHEM_REFRACTIVITY>
67.535

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tenofovir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014445
     RDKit          3D
Tenofovir
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.8926    1.0041   -2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -0.0913   -1.0216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2422   -1.2692   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1372   -0.8598   -0.9615 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512   -0.4148   -1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1554   -1.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -0.4352    0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -0.3299    1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2399    0.1353    0.9040 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4630   -0.6869    2.3528 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -1.1272    2.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.2189    1.4892 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -0.8778    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.5226   -1.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148   -0.4407    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    1.2721    0.6669 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.2893    2.1714    0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3648    1.3590    2.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8631    1.9036    0.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    0.5424   -2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413    1.4326   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256    1.7786   -1.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720    0.2885    0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859   -1.6568   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5635   -2.0537   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -0.2851   -2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875    0.5204    1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6233    0.0765   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -1.4037    3.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2469   -0.8433   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -1.1020    0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6101    0.4584    2.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5567    1.7310    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 13  4  1  0
 13  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 464205                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      11.654  -4.081   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       9.668  -2.300   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.132  -5.545   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.118  -3.603   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.190  -4.560   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.205   0.945   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.205   3.424   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414   0.645   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       3.080   2.955   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       4.414   5.265   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.190  -0.836   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.683  -0.519   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747   1.415   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.219   0.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747   2.955   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.104   2.185   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.175  -2.618   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414   3.725   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080   1.415   0.000  0.00  0.00           C+0
CONECT    1    3    4    5   17                                             
CONECT    2   11   17                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6   12   13   16                                                  
CONECT    7   15   16                                                       
CONECT    8   13   19                                                       
CONECT    9   18   19                                                       
CONECT   10   18                                                            
CONECT   11    2   12   14                                                  
CONECT   12    6   11                                                       
CONECT   13    6    8   15                                                  
CONECT   14   11                                                            
CONECT   15    7   13   18                                                  
CONECT   16    6    7                                                       
CONECT   17    1    2                                                       
CONECT   18    9   10   15                                                  
CONECT   19    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014445
HETATM    1  C1  UNL     1      -0.893   1.004  -2.001  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.205  -0.091  -1.022  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.242  -1.269  -1.186  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.137  -0.860  -0.961  1.00  0.00           N  
HETATM    5  C4  UNL     1       2.051  -0.415  -1.835  1.00  0.00           C  
HETATM    6  N2  UNL     1       3.194  -0.155  -1.212  1.00  0.00           N  
HETATM    7  C5  UNL     1       3.020  -0.435   0.079  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.922  -0.330   1.144  1.00  0.00           C  
HETATM    9  N3  UNL     1       5.240   0.135   0.904  1.00  0.00           N  
HETATM   10  N4  UNL     1       3.463  -0.687   2.353  1.00  0.00           N  
HETATM   11  C7  UNL     1       2.188  -1.127   2.529  1.00  0.00           C  
HETATM   12  N5  UNL     1       1.342  -1.219   1.489  1.00  0.00           N  
HETATM   13  C8  UNL     1       1.731  -0.878   0.244  1.00  0.00           C  
HETATM   14  O1  UNL     1      -2.497  -0.523  -1.027  1.00  0.00           O  
HETATM   15  C9  UNL     1      -3.215  -0.441   0.121  1.00  0.00           C  
HETATM   16  P1  UNL     1      -3.366   1.272   0.667  1.00  0.00           P  
HETATM   17  O2  UNL     1      -2.289   2.171   0.159  1.00  0.00           O  
HETATM   18  O3  UNL     1      -3.365   1.359   2.374  1.00  0.00           O  
HETATM   19  O4  UNL     1      -4.863   1.904   0.169  1.00  0.00           O  
HETATM   20  H1  UNL     1      -0.349   0.542  -2.880  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.841   1.433  -2.426  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.226   1.779  -1.606  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.972   0.288   0.017  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.286  -1.657  -2.219  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.564  -2.054  -0.483  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.881  -0.285  -2.913  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.787   0.520   1.693  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.623   0.077  -0.064  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.864  -1.404   3.525  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.247  -0.843  -0.109  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.858  -1.102   0.939  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.610   0.458   2.697  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.557   1.731   0.842  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   14   23
CONECT    3    4   24   25
CONECT    4    5   13
CONECT    5    6    6   26
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   10
CONECT    9   27   28
CONECT   10   11   11
CONECT   11   12   29
CONECT   12   13   13
CONECT   14   15
CONECT   15   16   30   31
CONECT   16   17   17   18   19
CONECT   18   32
CONECT   19   33
END

HMDB0014445
     RDKit          3D
Tenofovir
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.8926    1.0041   -2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -0.0913   -1.0216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2422   -1.2692   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1372   -0.8598   -0.9615 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512   -0.4148   -1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1554   -1.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -0.4352    0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -0.3299    1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2399    0.1353    0.9040 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4630   -0.6869    2.3528 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -1.1272    2.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.2189    1.4892 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -0.8778    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.5226   -1.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148   -0.4407    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    1.2721    0.6669 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.2893    2.1714    0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3648    1.3590    2.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8631    1.9036    0.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    0.5424   -2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413    1.4326   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256    1.7786   -1.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720    0.2885    0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859   -1.6568   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5635   -2.0537   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -0.2851   -2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875    0.5204    1.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6233    0.0765   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -1.4037    3.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2469   -0.8433   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -1.1020    0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6101    0.4584    2.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5567    1.7310    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 13  4  1  0
 13  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-PMPA	ChEBI
Anh. tenofovir	ChEBI
Anhydrous tenofovir	ChEBI
Tenofovir (anh.)	ChEBI
D,L-Tenofovir	HMDB
PMPA	HMDB
TDF	HMDB
Tenofovir disoproxil	HMDB
Tenofovir disoproxil fumarate	HMDB
(R)-9-(2-Phosphonylmethoxypropyl)adenine	HMDB
Fumarate, tenofovir disoproxil	HMDB
9-(2-Phosphonylmethoxypropyl)adenine, (R)-isomer - T357098	HMDB
9-(2-Phosphonylmethoxypropyl)adenine, (+-)-isomer	HMDB
9-(2-Phosphonylmethoxypropyl)adenine, (S)-isomer	HMDB
9-(2-Phosphonylmethoxypropyl)adenine	HMDB
9-(2-Phosphonomethoxypropyl)adenine	HMDB
9-PMPA (tenofovir)	HMDB
Disoproxil fumarate, tenofovir	HMDB
Disoproxil, tenofovir	HMDB
Viread	HMDB

Chemical Formula

C₉H₁₄N₅O₄P

Average Molecular Weight

287.2123

Monoisotopic Molecular Weight

287.078340473

IUPAC Name

({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid

Traditional Name

tenofovir

CAS Registry Number

147127-20-6

SMILES

C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O

InChI Identifier

InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1

InChI Key

SGOIRFVFHAKUTI-ZCFIWIBFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Aminopyrimidine
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Imidazole
Organophosphonic acid
Organophosphonic acid derivative
Heteroaromatic compound
Azacycle
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Amine
Primary amine
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phosphonic acids (CHEBI:63625 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014445)
Membrane (HMDB: HMDB0014445)

Source

Exogenous

Exogenous (HMDB: HMDB0014445)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tenofovir Metabolism Pathway (PathBank: SMP0000630)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	276 - 280 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.87 g/L	Not Available
LogP	-1.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.87 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-3.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	5.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	136.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.54 m³·mol⁻¹	ChemAxon
Polarizability	25.54 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]+	164.336	31661259
DarkChem	[M-H]-	163.282	31661259
DeepCCS	[M+H]+	151.691	30932474
DeepCCS	[M-H]-	149.295	30932474
DeepCCS	[M-2H]-	182.18	30932474
DeepCCS	[M+Na]+	157.694	30932474
AllCCS	[M+H]+	163.5	32859911
AllCCS	[M+H-H2O]+	160.2	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	160.0	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	160.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.24 minutes	32390414
Predicted by Siyang on May 30, 2022	9.101 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.08 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	265.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	940.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	64.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	148.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	324.6 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	268.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	540.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	577.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	90.0 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	620.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	159.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	162.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	500.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	417.6 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	114.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tenofovir	C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O	3295.0	Standard polar	33892256
Tenofovir	C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O	2273.5	Standard non polar	33892256
Tenofovir	C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O	2699.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tenofovir,1TMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	2661.2	Semi standard non polar	33892256
Tenofovir,1TMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	2594.0	Standard non polar	33892256
Tenofovir,1TMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	4381.0	Standard polar	33892256
Tenofovir,1TMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O	2691.8	Semi standard non polar	33892256
Tenofovir,1TMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O	2668.2	Standard non polar	33892256
Tenofovir,1TMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O	4713.9	Standard polar	33892256
Tenofovir,2TMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2612.8	Semi standard non polar	33892256
Tenofovir,2TMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2629.8	Standard non polar	33892256
Tenofovir,2TMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3995.3	Standard polar	33892256
Tenofovir,2TMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	2659.4	Semi standard non polar	33892256
Tenofovir,2TMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	2710.2	Standard non polar	33892256
Tenofovir,2TMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	4023.4	Standard polar	33892256
Tenofovir,2TMS,isomer #3	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O	2633.7	Semi standard non polar	33892256
Tenofovir,2TMS,isomer #3	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O	2823.5	Standard non polar	33892256
Tenofovir,2TMS,isomer #3	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O	4184.1	Standard polar	33892256
Tenofovir,3TMS,isomer #1	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2660.9	Semi standard non polar	33892256
Tenofovir,3TMS,isomer #1	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2718.1	Standard non polar	33892256
Tenofovir,3TMS,isomer #1	C[C@H](CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3623.6	Standard polar	33892256
Tenofovir,3TMS,isomer #2	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	2648.6	Semi standard non polar	33892256
Tenofovir,3TMS,isomer #2	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	2776.2	Standard non polar	33892256
Tenofovir,3TMS,isomer #2	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C	3587.0	Standard polar	33892256
Tenofovir,4TMS,isomer #1	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2682.6	Semi standard non polar	33892256
Tenofovir,4TMS,isomer #1	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2782.3	Standard non polar	33892256
Tenofovir,4TMS,isomer #1	C[C@H](CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3210.2	Standard polar	33892256
Tenofovir,1TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	2901.6	Semi standard non polar	33892256
Tenofovir,1TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	2795.0	Standard non polar	33892256
Tenofovir,1TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	4427.7	Standard polar	33892256
Tenofovir,1TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O	2893.9	Semi standard non polar	33892256
Tenofovir,1TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O	2906.6	Standard non polar	33892256
Tenofovir,1TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O	4648.1	Standard polar	33892256
Tenofovir,2TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3077.0	Semi standard non polar	33892256
Tenofovir,2TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3002.2	Standard non polar	33892256
Tenofovir,2TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4087.1	Standard polar	33892256
Tenofovir,2TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3069.3	Semi standard non polar	33892256
Tenofovir,2TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3108.0	Standard non polar	33892256
Tenofovir,2TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	4105.4	Standard polar	33892256
Tenofovir,2TBDMS,isomer #3	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O	3067.8	Semi standard non polar	33892256
Tenofovir,2TBDMS,isomer #3	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O	3222.2	Standard non polar	33892256
Tenofovir,2TBDMS,isomer #3	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O	4140.1	Standard polar	33892256
Tenofovir,3TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3251.8	Semi standard non polar	33892256
Tenofovir,3TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3237.1	Standard non polar	33892256
Tenofovir,3TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3829.2	Standard polar	33892256
Tenofovir,3TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3230.6	Semi standard non polar	33892256
Tenofovir,3TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3319.7	Standard non polar	33892256
Tenofovir,3TBDMS,isomer #2	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3708.6	Standard polar	33892256
Tenofovir,4TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3403.5	Semi standard non polar	33892256
Tenofovir,4TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3407.4	Standard non polar	33892256
Tenofovir,4TBDMS,isomer #1	C[C@H](CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3491.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tenofovir GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2920000000-93fa3e16e2deed5b1e92	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tenofovir GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tenofovir 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 - Tenofovir LC-ESI-QFT , negative-QTOF	splash10-000i-0290000000-3e1938b3d02b375e35df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , negative-QTOF	splash10-001r-1930000000-d365f36771addeb5b51c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , negative-QTOF	splash10-001i-2900000000-c8f91e6bb9d4588f055d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , negative-QTOF	splash10-001i-2900000000-099f967e8f8229f1fb82	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , negative-QTOF	splash10-001i-3900000000-521761795a56429a8f51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , negative-QTOF	splash10-06si-5900000000-b88fc7e5619f18889624	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , positive-QTOF	splash10-000i-0090000000-e85e6b9ea88e6c214687	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , positive-QTOF	splash10-000i-0190000000-405fbe60309faffed10c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , positive-QTOF	splash10-004r-0950000000-d7cec4ba580879c76061	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , positive-QTOF	splash10-004i-0910000000-f2abf612e945d8c69371	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , positive-QTOF	splash10-056r-1900000000-c48435c099065334ef3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir LC-ESI-QFT , positive-QTOF	splash10-0570-1900000000-7b90db7cba32420df6d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir 75V, Positive-QTOF	splash10-056r-0900000000-de4511ad1a86f8a69306	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir 90V, Positive-QTOF	splash10-0570-1900000000-735f5903582c7fb18e93	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir 15V, Positive-QTOF	splash10-000i-0090000000-a439fd9f7f987e4575fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir 15V, Negative-QTOF	splash10-000i-0290000000-6b581f541a52be20d9bb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir 30V, Negative-QTOF	splash10-001r-1930000000-ebfded6e5a124700a539	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir 30V, Positive-QTOF	splash10-000i-0190000000-7587229ffd658c035ccc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tenofovir 60V, Negative-QTOF	splash10-001i-2900000000-fc948e8fa5f1eff04475	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenofovir 10V, Positive-QTOF	splash10-002r-0980000000-52e67b818d6f67ebe46b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenofovir 20V, Positive-QTOF	splash10-0040-6910000000-fa7c104ef806824be3de	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenofovir 40V, Positive-QTOF	splash10-000i-2900000000-514c8cf39cc5d2610f23	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenofovir 10V, Negative-QTOF	splash10-000i-1290000000-cfa0589d123306000d96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenofovir 20V, Negative-QTOF	splash10-001i-2910000000-a76d01fa8fb2fbb25203	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenofovir 40V, Negative-QTOF	splash10-053r-4900000000-5eb36b143c3108e10d0c	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	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

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tenofovir Action Pathway		Not Available
Tenofovir Metabolism Pathway		Not Available

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 DB00300	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00300	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

408154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tenofovir

METLIN ID

Not Available

PubChem Compound

464205

PDB ID

TFO

ChEBI ID

63625

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

(). FDA label . .

Enzymes

Enzyme Details

1. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Tenofovir (HMDB0014445)

MOL for HMDB0014445 (Tenofovir)

3D MOL for HMDB0014445 (Tenofovir)

3D SDF for HMDB0014445 (Tenofovir)

3D-SDF for HMDB0014445 (Tenofovir)

PDB for HMDB0014445 (Tenofovir)

3D PDB for HMDB0014445 (Tenofovir)

SMILES for HMDB0014445 (Tenofovir)

INCHI for HMDB0014445 (Tenofovir)

Structure for HMDB0014445 (Tenofovir)

3D Structure for HMDB0014445 (Tenofovir)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References