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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015139

Secondary Accession Numbers

HMDB15139

Metabolite Identification

Common Name

Ganciclovir

Description

Ganciclovir is only found in individuals that have used or taken this drug. It is an acyclovir analog that is a potent inhibitor of the Herpesvirus family including cytomegalovirus. Ganciclovir is used to treat complications from AIDS-associated cytomegalovirus infections. [PubChem]Ganciclovir's antiviral activity inhibits virus replication. This inhibitory action is highly selective as the drug must be converted to the active form by a virus-encoded cellular enzyme, thymidine kinase (TK). TK catalyzes phosphorylation of ganciclovir to the monophosphate, which is then subsequently converted into the diphosphate by cellular guanylate kinase and into the triphosphate by a number of cellular enzymes. In vitro, ganciclovir triphosphate stops replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, ganciclovir triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where ganciclovir triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand. Ganciclovir inhibits viral DNA polymerases more effectively than it does cellular polymerase, and chain elongation resumes when ganciclovir is removed.

Structure

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

HMDB0015139
     RDKit          3D
Ganciclovir
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.0540    2.2182   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    1.0217    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    0.7327   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5829   -0.4140   -0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.2924    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -2.3070    0.7299 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703   -2.0965   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -0.9409   -0.7627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -0.3542   -1.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    0.5272   -1.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916    0.1036   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7016    0.4634   -0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0688   -0.0586   -2.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0640    0.8528    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0303    0.4569    1.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.9758    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6503   -1.7724    2.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    0.1661    0.9795 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0774    2.3036   -0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562    3.0184   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.7696   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    0.2299   -2.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -1.2098   -2.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -0.9482   -0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381    1.5631   -0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.0003   -0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369   -1.0284   -2.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0342    0.6633    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    1.9318    0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -0.5106    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7389    0.4258    1.4609 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
  8  4  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END


  Mrv0541 04111413432D          

 18 19  0  0  0  0            999 V2000
    2.8150   -1.0862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0681    0.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613    0.2481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3228   -0.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2699   -1.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113   -0.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6399    0.0699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3553    1.2726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.1451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150   -1.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -2.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2368   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -2.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9364   -0.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6356   -1.8995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015139

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)

> <INCHI_KEY>
IRSCQMHQWWYFCW-UHFFFAOYSA-N

> <FORMULA>
C9H13N5O4

> <MOLECULAR_WEIGHT>
255.2306

> <EXACT_MASS>
255.096753929

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
24.154164573887854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-1.83

> <JCHEM_LOGP>
-2.179902508666667

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.298583858244307

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.159807017663518

> <JCHEM_PKA_STRONGEST_BASIC>
1.7601277428844484

> <JCHEM_POLAR_SURFACE_AREA>
134.99

> <JCHEM_REFRACTIVITY>
61.029300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gancyclovir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015139
     RDKit          3D
Ganciclovir
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.0540    2.2182   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    1.0217    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    0.7327   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5829   -0.4140   -0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.2924    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -2.3070    0.7299 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703   -2.0965   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -0.9409   -0.7627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -0.3542   -1.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    0.5272   -1.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916    0.1036   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7016    0.4634   -0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0688   -0.0586   -2.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0640    0.8528    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0303    0.4569    1.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.9758    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6503   -1.7724    2.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    0.1661    0.9795 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0774    2.3036   -0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562    3.0184   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.7696   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    0.2299   -2.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -1.2098   -2.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -0.9482   -0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381    1.5631   -0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.0003   -0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369   -1.0284   -2.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0342    0.6633    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    1.9318    0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -0.5106    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7389    0.4258    1.4609 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
  8  4  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 11-APR-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-APR-14         0                                  
HETATM    1  N   UNK     0       5.255  -2.028   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.884  -1.501   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.860   0.038   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       5.341   0.463   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.203  -0.814   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.370  -2.225   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.141  -1.409   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.194   0.130   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.554   0.854   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.530   2.376   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.230  -2.138   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.255  -3.567   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.574  -4.329   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.909  -3.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.205  -4.305   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.909  -1.996   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.215  -1.242   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.520  -3.546   0.000  0.00  0.00           O+0
CONECT    1    2    5   12                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1                                                       
CONECT    6    2    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   18                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015139
HETATM    1  N1  UNL     1       4.054   2.218  -0.296  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.396   1.022   0.053  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.260   0.733  -0.583  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.583  -0.414  -0.283  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.042  -1.292   0.669  1.00  0.00           C  
HETATM    6  N3  UNL     1       1.164  -2.307   0.730  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.170  -2.096  -0.151  1.00  0.00           C  
HETATM    8  N4  UNL     1       0.434  -0.941  -0.763  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.389  -0.354  -1.799  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.333   0.527  -1.374  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.292   0.104  -0.515  1.00  0.00           C  
HETATM   12  C7  UNL     1      -3.702   0.463  -0.931  1.00  0.00           C  
HETATM   13  O2  UNL     1      -4.069  -0.059  -2.145  1.00  0.00           O  
HETATM   14  C8  UNL     1      -2.064   0.853   0.810  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.030   0.457   1.747  1.00  0.00           O  
HETATM   16  C9  UNL     1       3.219  -0.976   1.318  1.00  0.00           C  
HETATM   17  O4  UNL     1       3.650  -1.772   2.192  1.00  0.00           O  
HETATM   18  N5  UNL     1       3.841   0.166   0.980  1.00  0.00           N  
HETATM   19  H1  UNL     1       5.077   2.304  -0.133  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.556   3.018  -0.712  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.692  -2.770  -0.327  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.320   0.230  -2.459  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.809  -1.210  -2.394  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.174  -0.948  -0.270  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.838   1.563  -0.934  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.380   0.000  -0.155  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.237  -1.028  -2.129  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.034   0.663   1.180  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.237   1.932   0.625  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.228  -0.511   1.672  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.739   0.426   1.461  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3   18
CONECT    3    4
CONECT    4    5    5    8
CONECT    5    6   16
CONECT    6    7    7
CONECT    7    8   21
CONECT    8    9
CONECT    9   10   22   23
CONECT   10   11
CONECT   11   12   14   24
CONECT   12   13   25   26
CONECT   13   27
CONECT   14   15   28   29
CONECT   15   30
CONECT   16   17   17   18
CONECT   18   31
END

HMDB0015139
     RDKit          3D
Ganciclovir
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.0540    2.2182   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    1.0217    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    0.7327   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5829   -0.4140   -0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.2924    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -2.3070    0.7299 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703   -2.0965   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -0.9409   -0.7627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -0.3542   -1.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    0.5272   -1.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916    0.1036   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7016    0.4634   -0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0688   -0.0586   -2.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0640    0.8528    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0303    0.4569    1.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.9758    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6503   -1.7724    2.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    0.1661    0.9795 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0774    2.3036   -0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562    3.0184   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.7696   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    0.2299   -2.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -1.2098   -2.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -0.9482   -0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381    1.5631   -0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    0.0003   -0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369   -1.0284   -2.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0342    0.6633    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    1.9318    0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -0.5106    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7389    0.4258    1.4609 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
  8  4  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(6-Amino-purin-9-ylmethoxy)-propane-1,3-diol	ChEBI
2-Amino-9-((1,3-dihydroxypropan-2-yloxy)methyl)-1H-purin-6(9H)-one	ChEBI
2-Amino-9-((1,3-dihydroxypropan-2-yloxy)methyl)-3H-purin-6(9H)-one	ChEBI
2-Amino-9-((1,3-dihydroxypropan-2-yloxy)methyl)-9H-purin-6-ol	ChEBI
2-Amino-9-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-1,9-dihydro-purin-6-one	ChEBI
2-Amino-9-(2-hydroxy-1-hydroxymethylethoxymethyl)-6,9-dihydro-1H-6-purinone	ChEBI
9-((2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl)guanine	ChEBI
9-(1,3-DIHYDROXY-propoxymethane)guanine	ChEBI
9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine	ChEBI
GA2	ChEBI
Ganciclovirum	ChEBI
Gancyclovir	ChEBI
Cytovene	Kegg
Vitrasert	Kegg
Zirgan	Kegg
Ganciclovir sodium	HMDB
BIOLF-62	HMDB
Ganciclovir, monosodium salt	HMDB

Chemical Formula

C₉H₁₃N₅O₄

Average Molecular Weight

255.2306

Monoisotopic Molecular Weight

255.096753929

IUPAC Name

2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one

Traditional Name

gancyclovir

CAS Registry Number

82410-32-0

SMILES

NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1

InChI Identifier

InChI=1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)

InChI Key

IRSCQMHQWWYFCW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. 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

Hypoxanthines

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Aminopyrimidine
Pyrimidone
Glycerolipid
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Azacycle
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:465284 )
2-aminopurines (CHEBI:465284 )

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: HMDB0015139)
Membrane (HMDB: HMDB0015139)

Source

Exogenous

Exogenous (HMDB: HMDB0015139)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.6 g/L	Not Available
LogP	-1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.16	ChemAxon
pKa (Strongest Basic)	1.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.03 m³·mol⁻¹	ChemAxon
Polarizability	24.15 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]+	157.579	31661259
DarkChem	[M-H]-	154.564	31661259
DeepCCS	[M+H]+	157.414	30932474
DeepCCS	[M-H]-	155.056	30932474
DeepCCS	[M-2H]-	189.257	30932474
DeepCCS	[M+Na]+	164.716	30932474
AllCCS	[M+H]+	155.4	32859911
AllCCS	[M+H-H2O]+	151.9	32859911
AllCCS	[M+NH4]+	158.7	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	155.4	32859911
AllCCS	[M+Na-2H]-	155.3	32859911
AllCCS	[M+HCOO]-	155.3	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.	1.56 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8594 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	233.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	612.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	30.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.5 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	271.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	867.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	637.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	55.1 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	870.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	780.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	387.2 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	346.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ganciclovir	NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1	3479.6	Standard polar	33892256
Ganciclovir	NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1	2291.6	Standard non polar	33892256
Ganciclovir	NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1	2951.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ganciclovir,1TMS,isomer #1	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N)[NH]C2=O	2543.6	Semi standard non polar	33892256
Ganciclovir,1TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO)C(=O)[NH]1	2640.8	Semi standard non polar	33892256
Ganciclovir,1TMS,isomer #3	C[Si](C)(C)N1C(N)=NC2=C(N=CN2COC(CO)CO)C1=O	2690.4	Semi standard non polar	33892256
Ganciclovir,2TMS,isomer #1	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N)[NH]C2=O	2502.6	Semi standard non polar	33892256
Ganciclovir,2TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C)C(=O)[NH]1	2524.6	Semi standard non polar	33892256
Ganciclovir,2TMS,isomer #3	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O	2597.0	Semi standard non polar	33892256
Ganciclovir,2TMS,isomer #4	C[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)[NH]1)[Si](C)(C)C	2570.2	Semi standard non polar	33892256
Ganciclovir,2TMS,isomer #5	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C	2664.2	Semi standard non polar	33892256
Ganciclovir,3TMS,isomer #1	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C)CO[Si](C)(C)C)C(=O)[NH]1	2505.5	Semi standard non polar	33892256
Ganciclovir,3TMS,isomer #1	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C)CO[Si](C)(C)C)C(=O)[NH]1	2708.3	Standard non polar	33892256
Ganciclovir,3TMS,isomer #1	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C)CO[Si](C)(C)C)C(=O)[NH]1	3765.1	Standard polar	33892256
Ganciclovir,3TMS,isomer #2	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O	2551.7	Semi standard non polar	33892256
Ganciclovir,3TMS,isomer #2	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O	2635.6	Standard non polar	33892256
Ganciclovir,3TMS,isomer #2	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C)C2=O	3892.8	Standard polar	33892256
Ganciclovir,3TMS,isomer #3	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O	2532.9	Semi standard non polar	33892256
Ganciclovir,3TMS,isomer #3	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O	2848.8	Standard non polar	33892256
Ganciclovir,3TMS,isomer #3	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O	3665.6	Standard polar	33892256
Ganciclovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C)C(=O)N1[Si](C)(C)C	2608.0	Semi standard non polar	33892256
Ganciclovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C)C(=O)N1[Si](C)(C)C	2753.6	Standard non polar	33892256
Ganciclovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C)C(=O)N1[Si](C)(C)C	3730.2	Standard polar	33892256
Ganciclovir,3TMS,isomer #5	C[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C)[Si](C)(C)C	2685.2	Semi standard non polar	33892256
Ganciclovir,3TMS,isomer #5	C[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C)[Si](C)(C)C	2865.8	Standard non polar	33892256
Ganciclovir,3TMS,isomer #5	C[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C)[Si](C)(C)C	3693.3	Standard polar	33892256
Ganciclovir,4TMS,isomer #1	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O	2549.2	Semi standard non polar	33892256
Ganciclovir,4TMS,isomer #1	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O	2787.6	Standard non polar	33892256
Ganciclovir,4TMS,isomer #1	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C2=O	3332.6	Standard polar	33892256
Ganciclovir,4TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C)CO[Si](C)(C)C)C(=O)N1[Si](C)(C)C	2601.0	Semi standard non polar	33892256
Ganciclovir,4TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C)CO[Si](C)(C)C)C(=O)N1[Si](C)(C)C	2703.6	Standard non polar	33892256
Ganciclovir,4TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C)CO[Si](C)(C)C)C(=O)N1[Si](C)(C)C	3399.8	Standard polar	33892256
Ganciclovir,4TMS,isomer #3	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O	2652.4	Semi standard non polar	33892256
Ganciclovir,4TMS,isomer #3	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O	2862.9	Standard non polar	33892256
Ganciclovir,4TMS,isomer #3	C[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O	3327.6	Standard polar	33892256
Ganciclovir,5TMS,isomer #1	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O	2645.6	Semi standard non polar	33892256
Ganciclovir,5TMS,isomer #1	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O	2823.2	Standard non polar	33892256
Ganciclovir,5TMS,isomer #1	C[Si](C)(C)OCC(CO[Si](C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C2=O	3064.3	Standard polar	33892256
Ganciclovir,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N)[NH]C2=O	2785.9	Semi standard non polar	33892256
Ganciclovir,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO)C(=O)[NH]1	2868.3	Semi standard non polar	33892256
Ganciclovir,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(N=CN2COC(CO)CO)C1=O	2883.3	Semi standard non polar	33892256
Ganciclovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N)[NH]C2=O	2949.5	Semi standard non polar	33892256
Ganciclovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C(C)(C)C)C(=O)[NH]1	2970.4	Semi standard non polar	33892256
Ganciclovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O	3042.4	Semi standard non polar	33892256
Ganciclovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)[NH]1)[Si](C)(C)C(C)(C)C	3002.2	Semi standard non polar	33892256
Ganciclovir,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C(C)(C)C	3083.8	Semi standard non polar	33892256
Ganciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C(=O)[NH]1	3159.2	Semi standard non polar	33892256
Ganciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C(=O)[NH]1	3288.7	Standard non polar	33892256
Ganciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C(=O)[NH]1	3796.1	Standard polar	33892256
Ganciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O	3235.4	Semi standard non polar	33892256
Ganciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O	3245.3	Standard non polar	33892256
Ganciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N)N([Si](C)(C)C(C)(C)C)C2=O	3884.8	Standard polar	33892256
Ganciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O	3130.4	Semi standard non polar	33892256
Ganciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O	3417.9	Standard non polar	33892256
Ganciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O	3679.9	Standard polar	33892256
Ganciclovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	3237.1	Semi standard non polar	33892256
Ganciclovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	3324.3	Standard non polar	33892256
Ganciclovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO)CO[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	3713.7	Standard polar	33892256
Ganciclovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3254.5	Semi standard non polar	33892256
Ganciclovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3408.2	Standard non polar	33892256
Ganciclovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2COC(CO)CO)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3651.3	Standard polar	33892256
Ganciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O	3306.7	Semi standard non polar	33892256
Ganciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O	3557.3	Standard non polar	33892256
Ganciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C2=O	3536.9	Standard polar	33892256
Ganciclovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	3415.1	Semi standard non polar	33892256
Ganciclovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	3466.6	Standard non polar	33892256
Ganciclovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2COC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	3575.0	Standard polar	33892256
Ganciclovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3400.7	Semi standard non polar	33892256
Ganciclovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3582.9	Standard non polar	33892256
Ganciclovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3514.3	Standard polar	33892256
Ganciclovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3565.1	Semi standard non polar	33892256
Ganciclovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3688.7	Standard non polar	33892256
Ganciclovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)OCN1C=NC2=C1N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=O	3408.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ganciclovir GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9650000000-8833f26b2a4a485cc527	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ganciclovir GC-MS (2 TMS) - 70eV, Positive	splash10-0uea-4944000000-abdc13da6e0d228949c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ganciclovir 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 - Ganciclovir LC-ESI-QQ , negative-QTOF	splash10-0gb9-0090000000-b4bf1558f31e6cd80503	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , negative-QTOF	splash10-014i-1090000000-80a7b4d22e1375eb8a4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , negative-QTOF	splash10-000j-9610000000-c3053bd735d9f92930bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , negative-QTOF	splash10-007a-9300000000-392c976e03c2a82984cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , negative-QTOF	splash10-00di-9000000000-168468ed262e2df62267	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , positive-QTOF	splash10-0a4r-0490000000-0a16ac79577fd707fd15	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , positive-QTOF	splash10-0udi-0920000000-16d50b83e7be32f4db70	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , positive-QTOF	splash10-0udi-1900000000-2eca31ed3c60988970dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , positive-QTOF	splash10-0udu-2900000000-fd85740333fbb29714c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-QQ , positive-QTOF	splash10-01pc-3900000000-81b422bf6764161bcb0f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ganciclovir LC-ESI-IT , positive-QTOF	splash10-0udi-0900000000-618946bbba03bdf5db19	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 10V, Positive-QTOF	splash10-0udi-0930000000-70cd640f0189ec01f99e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 20V, Positive-QTOF	splash10-0udi-0900000000-fc49c7f073ae10ab487c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 40V, Positive-QTOF	splash10-0udr-0900000000-d80c22cdcb2574987d4f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 10V, Negative-QTOF	splash10-0udi-1590000000-0f6062547f6f0b5361fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 20V, Negative-QTOF	splash10-0udi-1950000000-44b53e03563a8182d288	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 40V, Negative-QTOF	splash10-0pbc-4900000000-7a563bb9b702e9ef5287	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 10V, Positive-QTOF	splash10-0udi-0930000000-8591208e148c4533f09f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 20V, Positive-QTOF	splash10-0udi-0900000000-f2cc24b91d79a58f5388	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 40V, Positive-QTOF	splash10-000i-1900000000-ca0f90024b546ecff4a6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 10V, Negative-QTOF	splash10-0udi-1290000000-33f6d44fd5c47d6bd926	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 20V, Negative-QTOF	splash10-0udi-0900000000-5e48c6b7e667862711a5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ganciclovir 40V, Negative-QTOF	splash10-053u-5900000000-168c679102de3c71bc14	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)	2021-09-29	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

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 DB01004	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01004	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01004

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ganciclovir

METLIN ID

Not Available

PubChem Compound

3454

PDB ID

Not Available

ChEBI ID

465284

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

Transporters

Enzyme Details

1. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798 ]

Enzyme Details

2. 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

Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798 ]

Enzyme Details

3. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798 ]

Showing metabocard for Ganciclovir (HMDB0015139)

MOL for HMDB0015139 (Ganciclovir)

3D MOL for HMDB0015139 (Ganciclovir)

3D SDF for HMDB0015139 (Ganciclovir)

3D-SDF for HMDB0015139 (Ganciclovir)

PDB for HMDB0015139 (Ganciclovir)

3D PDB for HMDB0015139 (Ganciclovir)

SMILES for HMDB0015139 (Ganciclovir)

INCHI for HMDB0015139 (Ganciclovir)

Structure for HMDB0015139 (Ganciclovir)

3D Structure for HMDB0015139 (Ganciclovir)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Transporters

References

References

References