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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (1) Show 2 proteins XML

enzymes (1)transporters (1) Show 2 proteins

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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 02:51:39 UTC

HMDB ID

HMDB0014513

Secondary Accession Numbers

HMDB14513

Metabolite Identification

Common Name

Cidofovir

Description

Cidofovir is only found in individuals that have used or taken this drug. It is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA synthesis. [Wikipedia ]Cidofovir acts through the selective inhibition of viral DNA polymerase.Biochemical data support selective inhibition of CMV DNA polymerase by cidofovir diphosphate, the active intracellular metabolite of cidofovir. Cidofovir diphosphate inhibits herpesvirus polymerases at concentrations that are 8- to 600-fold lower than those needed to inhibit human cellular DNA polymerase alpha, beta, and gamma(1,2,3). Incorporation of cidofovir into the growing viral DNA chain results in reductions in the rate of viral DNA synthesis.

Structure

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

HMDB0014513
     RDKit          3D
Cidofovir
 32 32  0  0  0  0  0  0  0  0999 V2000
   -5.5948    0.8348   -0.1396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803    0.7715   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269    1.4094    0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    1.3224    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    0.6195   -0.5917 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    0.5081   -0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -0.5790   -0.0373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2375   -1.9772   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -2.2587    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495   -0.5484   -0.5287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.3432    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.2894    0.0181 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3268   -1.5143    0.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771   -0.0958   -1.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3686    1.0502    0.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    0.0106   -1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8018   -0.6537   -2.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6035    0.0838   -1.2800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.0246   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203    1.6812    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7751    1.9693    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    1.8100    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060    0.3696   -1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950    1.4737   -0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293   -0.4303    1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -2.1455   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259   -2.6641    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125   -2.4944    1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    0.6143    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -1.1726    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.8595   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    1.8033    0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
M  END

369
  Mrv0541 02231214382D          

 18 18  0  0  1  0            999 V2000
    4.5080   -2.4751    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6830   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0791    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1 14  1  0  0  0  0
 11  2  1  1  0  0  0
  2 14  1  0  0  0  0
  3 13  1  0  0  0  0
  7 16  2  0  0  0  0
  8 12  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  9 16  1  0  0  0  0
  9 18  2  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014513

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1

> <INCHI_KEY>
VWFCHDSQECPREK-LURJTMIESA-N

> <FORMULA>
C8H14N3O6P

> <MOLECULAR_WEIGHT>
279.187

> <EXACT_MASS>
279.062021707

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
24.443744856111607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid

> <ALOGPS_LOGP>
-2.12

> <JCHEM_LOGP>
-3.413351889658639

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.904873659261004

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1871568476753072

> <JCHEM_PKA_STRONGEST_BASIC>
2.1509040654505562

> <JCHEM_POLAR_SURFACE_AREA>
145.68

> <JCHEM_REFRACTIVITY>
60.4279

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cidofovir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014513
     RDKit          3D
Cidofovir
 32 32  0  0  0  0  0  0  0  0999 V2000
   -5.5948    0.8348   -0.1396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803    0.7715   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269    1.4094    0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    1.3224    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    0.6195   -0.5917 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    0.5081   -0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -0.5790   -0.0373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2375   -1.9772   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -2.2587    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495   -0.5484   -0.5287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.3432    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.2894    0.0181 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3268   -1.5143    0.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771   -0.0958   -1.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3686    1.0502    0.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    0.0106   -1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8018   -0.6537   -2.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6035    0.0838   -1.2800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.0246   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203    1.6812    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7751    1.9693    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    1.8100    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060    0.3696   -1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950    1.4737   -0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293   -0.4303    1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -2.1455   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259   -2.6641    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125   -2.4944    1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    0.6143    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -1.1726    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.8595   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    1.8033    0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 369                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0       8.415  -4.620   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       7.081  -2.310   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748  -0.770   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.415  -6.160   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.955  -4.620   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.875  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.080   1.540   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       5.748   1.540   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       4.414   3.850   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       5.748   6.160   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   4.620   0.000  0.00  0.00           C+0
CONECT    1    4    5    6   14                                             
CONECT    2   11   14                                                       
CONECT    3   13                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7   16                                                            
CONECT    8   12   15   16                                                  
CONECT    9   16   18                                                       
CONECT   10   18                                                            
CONECT   11    2   12   13                                                  
CONECT   12    8   11                                                       
CONECT   13    3   11                                                       
CONECT   14    1    2                                                       
CONECT   15    8   17                                                       
CONECT   16    7    8    9                                                  
CONECT   17   15   18                                                       
CONECT   18    9   10   17                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0014513
HETATM    1  N1  UNL     1      -5.595   0.835  -0.140  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.180   0.772  -0.279  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.327   1.409   0.601  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.961   1.322   0.430  1.00  0.00           C  
HETATM    5  N2  UNL     1      -1.396   0.620  -0.592  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.011   0.508  -0.771  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.711  -0.579  -0.037  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.237  -1.977  -0.352  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.038  -2.259   0.066  1.00  0.00           O  
HETATM   10  O2  UNL     1       2.050  -0.548  -0.529  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.904  -0.343   0.539  1.00  0.00           C  
HETATM   12  P1  UNL     1       4.616  -0.289   0.018  1.00  0.00           P  
HETATM   13  O3  UNL     1       5.327  -1.514   0.507  1.00  0.00           O  
HETATM   14  O4  UNL     1       4.777  -0.096  -1.652  1.00  0.00           O  
HETATM   15  O5  UNL     1       5.369   1.050   0.765  1.00  0.00           O  
HETATM   16  C8  UNL     1      -2.248   0.011  -1.432  1.00  0.00           C  
HETATM   17  O6  UNL     1      -1.802  -0.654  -2.399  1.00  0.00           O  
HETATM   18  N3  UNL     1      -3.604   0.084  -1.280  1.00  0.00           N  
HETATM   19  H1  UNL     1      -6.141  -0.025  -0.345  1.00  0.00           H  
HETATM   20  H2  UNL     1      -6.120   1.681   0.154  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.775   1.969   1.415  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.282   1.810   1.102  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.206   0.370  -1.854  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.495   1.474  -0.442  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.729  -0.430   1.058  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.357  -2.145  -1.452  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.926  -2.664   0.210  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.113  -2.494   1.003  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.575   0.614   1.025  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.741  -1.173   1.253  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.831   0.859  -1.842  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.720   1.803   0.867  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3   18   18
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6   16
CONECT    6    7   23   24
CONECT    7    8   10   25
CONECT    8    9   26   27
CONECT    9   28
CONECT   10   11
CONECT   11   12   29   30
CONECT   12   13   13   14   15
CONECT   14   31
CONECT   15   32
CONECT   16   17   17   18
END

HMDB0014513
     RDKit          3D
Cidofovir
 32 32  0  0  0  0  0  0  0  0999 V2000
   -5.5948    0.8348   -0.1396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803    0.7715   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269    1.4094    0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    1.3224    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    0.6195   -0.5917 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    0.5081   -0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -0.5790   -0.0373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2375   -1.9772   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -2.2587    0.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495   -0.5484   -0.5287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.3432    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.2894    0.0181 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3268   -1.5143    0.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771   -0.0958   -1.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3686    1.0502    0.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    0.0106   -1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8018   -0.6537   -2.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6035    0.0838   -1.2800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.0246   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203    1.6812    0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7751    1.9693    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    1.8100    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060    0.3696   -1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950    1.4737   -0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293   -0.4303    1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -2.1455   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259   -2.6641    0.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125   -2.4944    1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    0.6143    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -1.1726    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.8595   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    1.8033    0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-(3-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1-hydroxypropan-2-yloxy)methylphosphonic acid	ChEBI
(S)-1-(3-Hydroxy-2-phosphonomethoxypropyl)cytosine	ChEBI
(S)-1-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine	ChEBI
(S)-1-[3-Hydroxy-2-(phosphonylmethoxy)propyl]cytosine	ChEBI
(S)-HPMPC	ChEBI
1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine	ChEBI
1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine	ChEBI
[(S)-2-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonic acid	ChEBI
CDV	ChEBI
(S)-(3-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1-hydroxypropan-2-yloxy)methylphosphonate	Generator
[(S)-2-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonate	Generator
Cidofovir anhydrous	HMDB
HPMPC	HMDB
Cidofovir, (R)-isomer	HMDB
Cidofovir, sodium salt	HMDB
1-((3-Hydroxy-2-phosphonylmethoxy)propyl)cytosine	HMDB
Cidofovir sodium	HMDB
Vistide	HMDB
1-(3-Hydroxy-2-phosphonylmethoxypropyl)cytosine	HMDB
Cidofovir, (+-)-isomer	HMDB
Cidofovir	ChEBI

Chemical Formula

C₈H₁₄N₃O₆P

Average Molecular Weight

279.187

Monoisotopic Molecular Weight

279.062021707

IUPAC Name

({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid

Traditional Name

cidofovir

CAS Registry Number

113852-37-2

SMILES

NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1

InChI Identifier

InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1

InChI Key

VWFCHDSQECPREK-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Aminopyrimidine
Pyrimidone
Hydropyrimidine
Imidolactam
Organophosphonic acid
Organophosphonic acid derivative
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidone (CHEBI:3696 )
phosphonic acids (CHEBI:3696 )

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: HMDB0014513)

Source

Exogenous

Exogenous (HMDB: HMDB0014513)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	480 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.5 g/L	Not Available
LogP	-3.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	2.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.43 m³·mol⁻¹	ChemAxon
Polarizability	24.44 Å³	ChemAxon
Number of Rings	1	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]+	160.963	31661259
DarkChem	[M-H]-	158.687	31661259
DeepCCS	[M+H]+	158.997	30932474
DeepCCS	[M-H]-	156.639	30932474
DeepCCS	[M-2H]-	189.525	30932474
DeepCCS	[M+Na]+	165.09	30932474
AllCCS	[M+H]+	159.1	32859911
AllCCS	[M+H-H2O]+	155.8	32859911
AllCCS	[M+NH4]+	162.1	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	156.3	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cidofovir	NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1	3618.2	Standard polar	33892256
Cidofovir	NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1	2449.5	Standard non polar	33892256
Cidofovir	NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1	2854.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cidofovir,1TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O	2590.9	Semi standard non polar	33892256
Cidofovir,1TMS,isomer #2	C[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N)=NC1=O	2631.1	Semi standard non polar	33892256
Cidofovir,1TMS,isomer #3	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1	2693.4	Semi standard non polar	33892256
Cidofovir,2TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O[Si](C)(C)C	2600.3	Semi standard non polar	33892256
Cidofovir,2TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O[Si](C)(C)C	2610.2	Standard non polar	33892256
Cidofovir,2TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O[Si](C)(C)C	3921.5	Standard polar	33892256
Cidofovir,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O)O)C=C1	2697.5	Semi standard non polar	33892256
Cidofovir,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O)O)C=C1	2723.6	Standard non polar	33892256
Cidofovir,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O)O)C=C1	4110.6	Standard polar	33892256
Cidofovir,2TMS,isomer #3	C[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N)=NC1=O)O[Si](C)(C)C	2617.7	Semi standard non polar	33892256
Cidofovir,2TMS,isomer #3	C[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N)=NC1=O)O[Si](C)(C)C	2600.8	Standard non polar	33892256
Cidofovir,2TMS,isomer #3	C[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N)=NC1=O)O[Si](C)(C)C	3778.4	Standard polar	33892256
Cidofovir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O[Si](C)(C)C)C=C1	2715.8	Semi standard non polar	33892256
Cidofovir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O[Si](C)(C)C)C=C1	2663.4	Standard non polar	33892256
Cidofovir,2TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O[Si](C)(C)C)C=C1	3768.2	Standard polar	33892256
Cidofovir,2TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1)[Si](C)(C)C	2602.8	Semi standard non polar	33892256
Cidofovir,2TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1)[Si](C)(C)C	2762.0	Standard non polar	33892256
Cidofovir,2TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1)[Si](C)(C)C	4041.5	Standard polar	33892256
Cidofovir,3TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2610.8	Semi standard non polar	33892256
Cidofovir,3TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2658.4	Standard non polar	33892256
Cidofovir,3TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3619.2	Standard polar	33892256
Cidofovir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O)O[Si](C)(C)C)C=C1	2698.6	Semi standard non polar	33892256
Cidofovir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O)O[Si](C)(C)C)C=C1	2705.8	Standard non polar	33892256
Cidofovir,3TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O)O[Si](C)(C)C)C=C1	3558.8	Standard polar	33892256
Cidofovir,3TMS,isomer #3	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O)O	2574.3	Semi standard non polar	33892256
Cidofovir,3TMS,isomer #3	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O)O	2795.5	Standard non polar	33892256
Cidofovir,3TMS,isomer #3	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O)O	3709.6	Standard polar	33892256
Cidofovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	2703.4	Semi standard non polar	33892256
Cidofovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	2725.2	Standard non polar	33892256
Cidofovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	3351.7	Standard polar	33892256
Cidofovir,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O	2623.6	Semi standard non polar	33892256
Cidofovir,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O	2731.4	Standard non polar	33892256
Cidofovir,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O	3444.7	Standard polar	33892256
Cidofovir,4TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	2713.2	Semi standard non polar	33892256
Cidofovir,4TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	2736.4	Standard non polar	33892256
Cidofovir,4TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C1	3193.7	Standard polar	33892256
Cidofovir,4TMS,isomer #2	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O)O[Si](C)(C)C	2619.0	Semi standard non polar	33892256
Cidofovir,4TMS,isomer #2	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O)O[Si](C)(C)C	2737.4	Standard non polar	33892256
Cidofovir,4TMS,isomer #2	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O)O[Si](C)(C)C	3219.5	Standard polar	33892256
Cidofovir,4TMS,isomer #3	C[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)O[Si](C)(C)C	2648.4	Semi standard non polar	33892256
Cidofovir,4TMS,isomer #3	C[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)O[Si](C)(C)C	2771.5	Standard non polar	33892256
Cidofovir,4TMS,isomer #3	C[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)O[Si](C)(C)C	3058.9	Standard polar	33892256
Cidofovir,5TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2666.0	Semi standard non polar	33892256
Cidofovir,5TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2742.3	Standard non polar	33892256
Cidofovir,5TMS,isomer #1	C[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O)OCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2933.3	Standard polar	33892256
Cidofovir,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O	2871.0	Semi standard non polar	33892256
Cidofovir,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N)=NC1=O	2871.0	Semi standard non polar	33892256
Cidofovir,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1	2944.5	Semi standard non polar	33892256
Cidofovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3076.9	Semi standard non polar	33892256
Cidofovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3039.0	Standard non polar	33892256
Cidofovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3994.9	Standard polar	33892256
Cidofovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O)O)C=C1	3146.1	Semi standard non polar	33892256
Cidofovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O)O)C=C1	3132.3	Standard non polar	33892256
Cidofovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O)O)C=C1	4114.2	Standard polar	33892256
Cidofovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N)=NC1=O)O[Si](C)(C)C(C)(C)C	3085.2	Semi standard non polar	33892256
Cidofovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N)=NC1=O)O[Si](C)(C)C(C)(C)C	2997.1	Standard non polar	33892256
Cidofovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N)=NC1=O)O[Si](C)(C)C(C)(C)C	3852.5	Standard polar	33892256
Cidofovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	3163.5	Semi standard non polar	33892256
Cidofovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	3070.1	Standard non polar	33892256
Cidofovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	3836.8	Standard polar	33892256
Cidofovir,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1)[Si](C)(C)C(C)(C)C	3062.0	Semi standard non polar	33892256
Cidofovir,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1)[Si](C)(C)C(C)(C)C	3147.9	Standard non polar	33892256
Cidofovir,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)N(C[C@@H](CO)OCP(=O)(O)O)C=C1)[Si](C)(C)C(C)(C)C	3992.7	Standard polar	33892256
Cidofovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3297.5	Semi standard non polar	33892256
Cidofovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3185.6	Standard non polar	33892256
Cidofovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N)=NC1=O)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3744.1	Standard polar	33892256
Cidofovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	3366.2	Semi standard non polar	33892256
Cidofovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	3284.7	Standard non polar	33892256
Cidofovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O)O[Si](C)(C)C(C)(C)C)C=C1	3706.2	Standard polar	33892256
Cidofovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O)O	3266.9	Semi standard non polar	33892256
Cidofovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O)O	3351.5	Standard non polar	33892256
Cidofovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O)O	3771.5	Standard polar	33892256
Cidofovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3364.7	Semi standard non polar	33892256
Cidofovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3250.8	Standard non polar	33892256
Cidofovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3549.8	Standard polar	33892256
Cidofovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O	3292.0	Semi standard non polar	33892256
Cidofovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O	3285.0	Standard non polar	33892256
Cidofovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OP(=O)(O)CO[C@H](CO)CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O	3563.0	Standard polar	33892256
Cidofovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3549.8	Semi standard non polar	33892256
Cidofovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3375.6	Standard non polar	33892256
Cidofovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C[C@@H](CO[Si](C)(C)C(C)(C)C)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3492.9	Standard polar	33892256
Cidofovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3489.5	Semi standard non polar	33892256
Cidofovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3441.5	Standard non polar	33892256
Cidofovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O)O[Si](C)(C)C(C)(C)C	3427.8	Standard polar	33892256
Cidofovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)O[Si](C)(C)C(C)(C)C	3481.4	Semi standard non polar	33892256
Cidofovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)O[Si](C)(C)C(C)(C)C	3410.7	Standard non polar	33892256
Cidofovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(CO[C@H](CO)CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)O[Si](C)(C)C(C)(C)C	3334.1	Standard polar	33892256
Cidofovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3668.6	Semi standard non polar	33892256
Cidofovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3503.0	Standard non polar	33892256
Cidofovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CN1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O)OCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3302.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cidofovir GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9820000000-aa7cf1e5b61efad3d0f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cidofovir GC-MS (1 TMS) - 70eV, Positive	splash10-008c-7944000000-f609f0eec561142266d6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cidofovir 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 - Cidofovir 10V, Positive-QTOF	splash10-001i-0290000000-038de61e1070c6bf959e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 20V, Positive-QTOF	splash10-001i-9530000000-e84e35d965622e5b208a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 40V, Positive-QTOF	splash10-0j4i-9700000000-0a34ce1648d60bc6bc11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 10V, Negative-QTOF	splash10-004i-2290000000-7c97d41d12fa58e21a13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 20V, Negative-QTOF	splash10-02ci-9480000000-c2815452e80e1a83b618	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 40V, Negative-QTOF	splash10-01ox-9200000000-6321e41040f16d71637a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 10V, Positive-QTOF	splash10-001i-0290000000-7d98ba2e3a98c2228dae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 20V, Positive-QTOF	splash10-0159-0910000000-6524ca93000937bb1113	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 40V, Positive-QTOF	splash10-02u0-9300000000-843eaedb395204ad0128	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 10V, Negative-QTOF	splash10-004i-0090000000-da9719fb0cbd12dc3e52	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 20V, Negative-QTOF	splash10-03fr-5950000000-b7fb54b7fe21f1e0e346	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cidofovir 40V, Negative-QTOF	splash10-0006-9100000000-cca88b97e143183784da	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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 DB00369	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00369	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00369

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54636

KEGG Compound ID

C06909

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cidofovir

METLIN ID

Not Available

PubChem Compound

60613

PDB ID

Not Available

ChEBI ID

3696

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

Not Available

Enzymes

Enzyme Details

1. Thymidine phosphorylase

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro. Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:: TYMP
Uniprot ID:: P19971
Molecular weight:: 49954.965

References

De Clercq E: The next ten stories on antiviral drug discovery (part E): advents, advances, and adventures. Med Res Rev. 2011 Jan;31(1):118-60. doi: 10.1002/med.20179. [PubMed:19844936 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [PubMed:10929807 ]
Cihlar T, Lin DC, Pritchard JB, Fuller MD, Mendel DB, Sweet DH: The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1. Mol Pharmacol. 1999 Sep;56(3):570-80. [PubMed:10462545 ]
Ho ES, Lin DC, Mendel DB, Cihlar T: Cytotoxicity of antiviral nucleotides adefovir and cidofovir is induced by the expression of human renal organic anion transporter 1. J Am Soc Nephrol. 2000 Mar;11(3):383-93. [PubMed:10703662 ]

Showing metabocard for Cidofovir (HMDB0014513)

MOL for HMDB0014513 (Cidofovir)

3D MOL for HMDB0014513 (Cidofovir)

3D SDF for HMDB0014513 (Cidofovir)

3D-SDF for HMDB0014513 (Cidofovir)

PDB for HMDB0014513 (Cidofovir)

3D PDB for HMDB0014513 (Cidofovir)

SMILES for HMDB0014513 (Cidofovir)

INCHI for HMDB0014513 (Cidofovir)

Structure for HMDB0014513 (Cidofovir)

3D Structure for HMDB0014513 (Cidofovir)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References