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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014444

Secondary Accession Numbers

HMDB14444

Metabolite Identification

Common Name

Penciclovir

Description

Penciclovir is only found in individuals that have used or taken this drug. It is a guanine analogue antiviral drug used for the treatment of various herpesvirus infections. It is a nucleoside analogue which exhibits low toxicity and good selectivity. [Wikipedia ]Penciclovir has in vitro activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). In cells infected with HSV-1 or HSV-2, viral thymidine kinase phosphorylates penciclovir to a monophosphate form. The monophosphate form of the drug is then converted to penciclovir triphosphate by cellular kinases. The intracellular triphosphate of penciclovir is retained in vitro inside HSV-infected cells for 10-20 hours, compared with 0.7-1 hour for acyclovir. in vitro studies show that penciclovir triphosphate selectively inhibits viral DNA polymerase by competing with deoxyguanosine triphosphate. Inhibition of DNA synthesis of virus-infected cells inhibits viral replication. In cells not infected with HSV, DNA synthesis is unaltered. Resistant mutants of HSV can occur from qualitative changes in viral thymidine kinase or DNA polymerase. The most commonly encountered acyclovir-resistant mutants that are deficient in viral thymidine kinase are also resistant to penciclovir.

Structure

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

HMDB0014444
     RDKit          3D
Penciclovir
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.9334    2.4367   -0.6189 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    1.0358   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5230    0.0999   -0.9229 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2265   -1.2147   -0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869   -2.0650   -1.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.5914   -0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -2.7859   -0.1920 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -2.5678    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -1.2348    0.4183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -0.5287    0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -0.2197   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615    0.5103    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1212   -0.2659    1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994    0.5587    1.7427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833    0.9435   -0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7507   -0.1364   -1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -0.6260    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.6723   -0.0932 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487    2.9764    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    2.9356   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -3.2911    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -1.1042    1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384    0.4096    1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.2949   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350   -1.2127   -0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0246    1.4638    0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592   -0.4626    2.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -1.1864    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9133    1.5123    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.4745   -0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682    1.6431   -1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    0.0946   -2.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    1.4312    0.1979 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18  2  1  0
 17  6  2  0
  1 19  1  0
  1 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END

299
  Mrv0541 02231214352D          

 18 19  0  0  0  0            999 V2000
    6.0424    2.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4006    2.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -0.6018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.4406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.9296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.6782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370    1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0807    0.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    0.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860    1.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1443    1.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -1.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3 17  2  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
  4 16  1  0  0  0  0
  5 14  1  0  0  0  0
  5 18  1  0  0  0  0
  6 15  1  0  0  0  0
  6 16  2  0  0  0  0
  7 17  1  0  0  0  0
  7 18  2  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 14 15  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014444

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)C2=C(N1)N(CCC(CO)CO)C=N2

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17/h5-6,16-17H,1-4H2,(H3,11,13,14,18)

> <INCHI_KEY>
JNTOCHDNEULJHD-UHFFFAOYSA-N

> <FORMULA>
C10H15N5O3

> <MOLECULAR_WEIGHT>
253.2578

> <EXACT_MASS>
253.117489371

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.106083786739198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6,9-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-0.86

> <JCHEM_LOGP>
-1.5479088533333338

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.095575891007815

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.010394283090589

> <JCHEM_PKA_STRONGEST_BASIC>
2.835791198749247

> <JCHEM_POLAR_SURFACE_AREA>
125.75999999999999

> <JCHEM_REFRACTIVITY>
64.59190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
denavir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014444
     RDKit          3D
Penciclovir
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.9334    2.4367   -0.6189 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    1.0358   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5230    0.0999   -0.9229 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2265   -1.2147   -0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869   -2.0650   -1.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.5914   -0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -2.7859   -0.1920 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -2.5678    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -1.2348    0.4183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -0.5287    0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -0.2197   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615    0.5103    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1212   -0.2659    1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994    0.5587    1.7427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833    0.9435   -0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7507   -0.1364   -1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -0.6260    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.6723   -0.0932 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487    2.9764    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    2.9356   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -3.2911    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -1.1042    1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384    0.4096    1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.2949   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350   -1.2127   -0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0246    1.4638    0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592   -0.4626    2.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -1.1864    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9133    1.5123    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.4745   -0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682    1.6431   -1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    0.0946   -2.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    1.4312    0.1979 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18  2  1  0
 17  6  2  0
  1 19  1  0
  1 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 299                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.279   4.732   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.814   3.903   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574  -5.443   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.365  -1.123   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.574  -0.822   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.365  -3.602   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.241  -3.133   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.907  -0.822   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      11.829   2.122   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.351   0.658   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.844   0.340   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.801   3.268   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.336   2.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908  -1.593   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -3.133   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.264  -2.363   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574  -3.903   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.241  -1.593   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   17                                                            
CONECT    4   11   14   16                                                  
CONECT    5   14   18                                                       
CONECT    6   15   16                                                       
CONECT    7   17   18                                                       
CONECT    8   18                                                            
CONECT    9   10   12   13                                                  
CONECT   10    9   11                                                       
CONECT   11    4   10                                                       
CONECT   12    1    9                                                       
CONECT   13    2    9                                                       
CONECT   14    4    5   15                                                  
CONECT   15    6   14   17                                                  
CONECT   16    4    6                                                       
CONECT   17    3    7   15                                                  
CONECT   18    5    7    8                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0014444
HETATM    1  N1  UNL     1       3.933   2.437  -0.619  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.648   1.036  -0.553  1.00  0.00           C  
HETATM    3  N2  UNL     1       4.523   0.100  -0.923  1.00  0.00           N  
HETATM    4  C2  UNL     1       4.226  -1.215  -0.850  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.087  -2.065  -1.211  1.00  0.00           O  
HETATM    6  C3  UNL     1       2.981  -1.591  -0.377  1.00  0.00           C  
HETATM    7  N3  UNL     1       2.406  -2.786  -0.192  1.00  0.00           N  
HETATM    8  C4  UNL     1       1.160  -2.568   0.299  1.00  0.00           C  
HETATM    9  N4  UNL     1       0.964  -1.235   0.418  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.214  -0.529   0.899  1.00  0.00           C  
HETATM   11  C6  UNL     1      -1.167  -0.220  -0.235  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.361   0.510   0.313  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.121  -0.266   1.340  1.00  0.00           C  
HETATM   14  O2  UNL     1      -4.199   0.559   1.743  1.00  0.00           O  
HETATM   15  C9  UNL     1      -3.283   0.944  -0.799  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.751  -0.136  -1.526  1.00  0.00           O  
HETATM   17  C10 UNL     1       2.088  -0.626   0.001  1.00  0.00           C  
HETATM   18  N5  UNL     1       2.436   0.672  -0.093  1.00  0.00           N  
HETATM   19  H1  UNL     1       3.849   2.976   0.269  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.211   2.936  -1.469  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.410  -3.291   0.568  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.715  -1.104   1.708  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.138   0.410   1.374  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.682   0.295  -1.063  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.535  -1.213  -0.610  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.025   1.464   0.819  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.559  -0.463   2.259  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.584  -1.186   0.935  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.913   1.512   1.687  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.155   1.475  -0.350  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.768   1.643  -1.484  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.779   0.095  -2.476  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.750   1.431   0.198  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3   18
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   17   17
CONECT    7    8    8
CONECT    8    9   21
CONECT    9   10   17
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   12   13   15   26
CONECT   13   14   27   28
CONECT   14   29
CONECT   15   16   30   31
CONECT   16   32
CONECT   17   18
CONECT   18   33
END

HMDB0014444
     RDKit          3D
Penciclovir
 33 34  0  0  0  0  0  0  0  0999 V2000
    3.9334    2.4367   -0.6189 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    1.0358   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5230    0.0999   -0.9229 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2265   -1.2147   -0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869   -2.0650   -1.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -1.5914   -0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -2.7859   -0.1920 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -2.5678    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -1.2348    0.4183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -0.5287    0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -0.2197   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615    0.5103    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1212   -0.2659    1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994    0.5587    1.7427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833    0.9435   -0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7507   -0.1364   -1.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -0.6260    0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.6723   -0.0932 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487    2.9764    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    2.9356   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -3.2911    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -1.1042    1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384    0.4096    1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    0.2949   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350   -1.2127   -0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0246    1.4638    0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5592   -0.4626    2.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -1.1864    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9133    1.5123    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553    1.4745   -0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682    1.6431   -1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    0.0946   -2.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    1.4312    0.1979 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18  2  1  0
 17  6  2  0
  1 19  1  0
  1 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
9-(4-Hydroxy-3-(hydroxymethyl)butyl)guanine	ChEBI
9-(4-Hydroxy-3-hydroxymethylbut-1-yl)-guanine	ChEBI
9-[2-Hydroxy-1-(hydroxymethyl)-ethoxymethyl]guanine	ChEBI
9-[4-Hydroxy-3-(hydroxymethyl)but-1-yl]guanine	ChEBI
PCV	ChEBI
PE2	ChEBI
Penciclovirum	ChEBI
Denavir	Kegg
Novartis brand OF penciclovir	HMDB
Penciclovir visfarm	HMDB
SB-CH Brand OF penciclovir	HMDB
9-(4-Hydroxy-3-hydroxymethylbut-1-yl)guanine	HMDB
Vectavir	HMDB
Visfarm brand OF penciclovir	HMDB
Penciclovir, monosodium salt	HMDB
Penciclovir, monosodium salt, monohydrate	HMDB

Chemical Formula

C₁₀H₁₅N₅O₃

Average Molecular Weight

253.2578

Monoisotopic Molecular Weight

253.117489371

IUPAC Name

2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6,9-dihydro-3H-purin-6-one

Traditional Name

denavir

CAS Registry Number

39809-25-1

SMILES

NC1=NC(=O)C2=C(N1)N(CCC(CO)CO)C=N2

InChI Identifier

InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17/h5-6,16-17H,1-4H2,(H3,11,13,14,18)

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2-aminopurines (CHEBI:7956 )
propane-1,3-diols (CHEBI:7956 )

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: HMDB0014444)

Source

Exogenous

Exogenous (HMDB: HMDB0014444)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	275 - 277 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7.45 g/L	Not Available
LogP	-1.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.45 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-1.5	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	2.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.59 m³·mol⁻¹	ChemAxon
Polarizability	25.11 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]+	158.724	31661259
DarkChem	[M-H]-	156.502	31661259
DeepCCS	[M+H]+	162.678	30932474
DeepCCS	[M-H]-	160.32	30932474
DeepCCS	[M-2H]-	193.206	30932474
DeepCCS	[M+Na]+	168.771	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	151.3	32859911
AllCCS	[M+NH4]+	158.1	32859911
AllCCS	[M+Na]+	159.0	32859911
AllCCS	[M-H]-	157.0	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	156.9	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.	1.83 minutes	32390414
Predicted by Siyang on May 30, 2022	9.448 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.24 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	182.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	731.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	54.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	293.7 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	263.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	765.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	584.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	71.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	789.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	691.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	307.5 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	262.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Penciclovir	NC1=NC(=O)C2=C(N1)N(CCC(CO)CO)C=N2	3529.0	Standard polar	33892256
Penciclovir	NC1=NC(=O)C2=C(N1)N(CCC(CO)CO)C=N2	2087.6	Standard non polar	33892256
Penciclovir	NC1=NC(=O)C2=C(N1)N(CCC(CO)CO)C=N2	3020.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Penciclovir,1TMS,isomer #1	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N)=NC2=O	2635.5	Semi standard non polar	33892256
Penciclovir,1TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO)CO)C=N2	2780.2	Semi standard non polar	33892256
Penciclovir,1TMS,isomer #3	C[Si](C)(C)N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2	2740.1	Semi standard non polar	33892256
Penciclovir,2TMS,isomer #1	C[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N)=NC2=O)CO[Si](C)(C)C	2553.6	Semi standard non polar	33892256
Penciclovir,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO)CO[Si](C)(C)C)C=N2	2610.1	Semi standard non polar	33892256
Penciclovir,2TMS,isomer #3	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O	2609.0	Semi standard non polar	33892256
Penciclovir,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(CCC(CO)CO)C=N2)[Si](C)(C)C	2674.4	Semi standard non polar	33892256
Penciclovir,2TMS,isomer #5	C[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C	2706.5	Semi standard non polar	33892256
Penciclovir,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO[Si](C)(C)C)CO[Si](C)(C)C)C=N2	2559.5	Semi standard non polar	33892256
Penciclovir,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO[Si](C)(C)C)CO[Si](C)(C)C)C=N2	2808.8	Standard non polar	33892256
Penciclovir,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO[Si](C)(C)C)CO[Si](C)(C)C)C=N2	3693.0	Standard polar	33892256
Penciclovir,3TMS,isomer #2	C[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O)CO[Si](C)(C)C	2545.6	Semi standard non polar	33892256
Penciclovir,3TMS,isomer #2	C[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O)CO[Si](C)(C)C	2727.0	Standard non polar	33892256
Penciclovir,3TMS,isomer #2	C[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O)CO[Si](C)(C)C	3770.0	Standard polar	33892256
Penciclovir,3TMS,isomer #3	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2573.5	Semi standard non polar	33892256
Penciclovir,3TMS,isomer #3	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2943.3	Standard non polar	33892256
Penciclovir,3TMS,isomer #3	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	3614.5	Standard polar	33892256
Penciclovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2604.2	Semi standard non polar	33892256
Penciclovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2850.7	Standard non polar	33892256
Penciclovir,3TMS,isomer #4	C[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	3653.6	Standard polar	33892256
Penciclovir,3TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	2722.8	Semi standard non polar	33892256
Penciclovir,3TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	2952.9	Standard non polar	33892256
Penciclovir,3TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	3613.1	Standard polar	33892256
Penciclovir,4TMS,isomer #1	C[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CO[Si](C)(C)C	2582.8	Semi standard non polar	33892256
Penciclovir,4TMS,isomer #1	C[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CO[Si](C)(C)C	2900.7	Standard non polar	33892256
Penciclovir,4TMS,isomer #1	C[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CO[Si](C)(C)C	3283.2	Standard polar	33892256
Penciclovir,4TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO[Si](C)(C)C)CO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2598.1	Semi standard non polar	33892256
Penciclovir,4TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO[Si](C)(C)C)CO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2808.0	Standard non polar	33892256
Penciclovir,4TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO[Si](C)(C)C)CO[Si](C)(C)C)C=N2)N1[Si](C)(C)C	3321.3	Standard polar	33892256
Penciclovir,4TMS,isomer #3	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2668.2	Semi standard non polar	33892256
Penciclovir,4TMS,isomer #3	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	2956.4	Standard non polar	33892256
Penciclovir,4TMS,isomer #3	C[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	3257.1	Standard polar	33892256
Penciclovir,5TMS,isomer #1	C[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CO[Si](C)(C)C	2670.3	Semi standard non polar	33892256
Penciclovir,5TMS,isomer #1	C[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CO[Si](C)(C)C	2921.9	Standard non polar	33892256
Penciclovir,5TMS,isomer #1	C[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CO[Si](C)(C)C	2985.1	Standard polar	33892256
Penciclovir,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N)=NC2=O	2874.5	Semi standard non polar	33892256
Penciclovir,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO)CO)C=N2	2986.8	Semi standard non polar	33892256
Penciclovir,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2	2943.9	Semi standard non polar	33892256
Penciclovir,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N)=NC2=O)CO[Si](C)(C)C(C)(C)C	3002.7	Semi standard non polar	33892256
Penciclovir,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO)CO[Si](C)(C)C(C)(C)C)C=N2	3030.8	Semi standard non polar	33892256
Penciclovir,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O	3025.1	Semi standard non polar	33892256
Penciclovir,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N(CCC(CO)CO)C=N2)[Si](C)(C)C(C)(C)C	3103.8	Semi standard non polar	33892256
Penciclovir,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C(C)(C)C	3132.9	Semi standard non polar	33892256
Penciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C=N2	3198.8	Semi standard non polar	33892256
Penciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C=N2	3459.0	Standard non polar	33892256
Penciclovir,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N(CCC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C=N2	3741.2	Standard polar	33892256
Penciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O)CO[Si](C)(C)C(C)(C)C	3172.4	Semi standard non polar	33892256
Penciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O)CO[Si](C)(C)C(C)(C)C	3388.6	Standard non polar	33892256
Penciclovir,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O)CO[Si](C)(C)C(C)(C)C	3792.4	Standard polar	33892256
Penciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3183.3	Semi standard non polar	33892256
Penciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3559.5	Standard non polar	33892256
Penciclovir,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3645.0	Standard polar	33892256
Penciclovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3204.7	Semi standard non polar	33892256
Penciclovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3479.7	Standard non polar	33892256
Penciclovir,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO)CO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3658.9	Standard polar	33892256
Penciclovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3307.8	Semi standard non polar	33892256
Penciclovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3532.4	Standard non polar	33892256
Penciclovir,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C(N(CCC(CO)CO)C=N2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3595.9	Standard polar	33892256
Penciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CO[Si](C)(C)C(C)(C)C	3345.3	Semi standard non polar	33892256
Penciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CO[Si](C)(C)C(C)(C)C	3717.5	Standard non polar	33892256
Penciclovir,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CO[Si](C)(C)C(C)(C)C	3498.7	Standard polar	33892256
Penciclovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3361.8	Semi standard non polar	33892256
Penciclovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3639.4	Standard non polar	33892256
Penciclovir,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C(N(CCC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3521.4	Standard polar	33892256
Penciclovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3403.6	Semi standard non polar	33892256
Penciclovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3714.5	Standard non polar	33892256
Penciclovir,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(CO)CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O	3455.6	Standard polar	33892256
Penciclovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CO[Si](C)(C)C(C)(C)C	3557.5	Semi standard non polar	33892256
Penciclovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CO[Si](C)(C)C(C)(C)C	3823.4	Standard non polar	33892256
Penciclovir,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CO[Si](C)(C)C(C)(C)C	3346.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Penciclovir GC-MS (Non-derivatized) - 70eV, Positive	splash10-024r-4890000000-ed3881f9b07a40fef086	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penciclovir GC-MS (2 TMS) - 70eV, Positive	splash10-0089-4039000000-39d85efcb22394abeb78	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penciclovir 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 - Penciclovir LC-ESI-QFT , negative-QTOF	splash10-0udi-0190000000-ed1701b795cb216e6d66	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , negative-QTOF	splash10-0udi-0790000000-212e25de28163f343cac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , negative-QTOF	splash10-0udi-0910000000-3a8ca3a0b3701c27b51d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , negative-QTOF	splash10-0kai-0900000000-36122e670b73f1113fff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , negative-QTOF	splash10-053r-1900000000-bceccffce9861527c0c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , negative-QTOF	splash10-0api-3900000000-2322dab886ffdf508841	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , positive-QTOF	splash10-0udi-0490000000-0e41d127a3f6d343b9d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , positive-QTOF	splash10-0udi-0920000000-8e58b381a6b3d470746b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , positive-QTOF	splash10-0udi-0900000000-d498bce256e98e4cf88c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , positive-QTOF	splash10-0udi-0900000000-ae0beed2651e1125764f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , positive-QTOF	splash10-0udi-0900000000-19ad8b8788d0275996b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QFT , positive-QTOF	splash10-0udr-1900000000-5c4ec47a69c82954d428	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QQ , positive-QTOF	splash10-0f79-0390000000-2bec5fbdf1e72aa84bde	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QQ , positive-QTOF	splash10-0uei-1940000000-6e49677068b47b74940f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QQ , positive-QTOF	splash10-0udi-3900000000-cc1f9ce4e3ed563ded5c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QQ , positive-QTOF	splash10-0zfr-8900000000-326741cdbb592bb9d271	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-QQ , positive-QTOF	splash10-0f8c-7900000000-295551b253f3f85729c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir LC-ESI-IT , positive-QTOF	splash10-0udi-0900000000-44a1abcea55a53906b2a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penciclovir 10V, Positive-QTOF	splash10-0udi-0980000000-aaaff73f565024ce9cff	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penciclovir 10V, Positive-QTOF	splash10-0udr-0090000000-b771df12ed0fcbbee1ca	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penciclovir 20V, Positive-QTOF	splash10-0udr-1980000000-be68269fbcfeb1eda4f2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penciclovir 40V, Positive-QTOF	splash10-0udr-4900000000-54f7176cadc1b67a66dc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penciclovir 10V, Negative-QTOF	splash10-0udi-0090000000-b42cd4e9561cb4baa03a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penciclovir 20V, Negative-QTOF	splash10-0udi-0960000000-012e01c533768b510f86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penciclovir 40V, Negative-QTOF	splash10-0a4l-4900000000-8dda187de53e2d7eb1fb	2016-08-03	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 DB00299	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00299	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00299

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4563

KEGG Compound ID

C07417

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Penciclovir

METLIN ID

Not Available

PubChem Compound

4725

PDB ID

Not Available

ChEBI ID

7956

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

Showing metabocard for Penciclovir (HMDB0014444)

MOL for HMDB0014444 (Penciclovir)

3D MOL for HMDB0014444 (Penciclovir)

3D SDF for HMDB0014444 (Penciclovir)

3D-SDF for HMDB0014444 (Penciclovir)

PDB for HMDB0014444 (Penciclovir)

3D PDB for HMDB0014444 (Penciclovir)

SMILES for HMDB0014444 (Penciclovir)

INCHI for HMDB0014444 (Penciclovir)

Structure for HMDB0014444 (Penciclovir)

3D Structure for HMDB0014444 (Penciclovir)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra