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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014570

Secondary Accession Numbers

HMDB14570

Metabolite Identification

Common Name

Famciclovir

Description

Famciclovir, also known as famvir or BRL-42810, belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. Famciclovir is a drug which is used for the treatment of acute herpes zoster (shingles). also for the treatment or suppression of recurrent genital herpes in immunocompetent patients and treatment of recurrent mucocutaneous herpes simplex infections in hiv infected patients. Famciclovir is a very strong basic compound (based on its pKa).

Structure

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

HMDB0014570
     RDKit          3D
Famciclovir
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.1968   -3.9951   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -2.6023   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7229   -2.3261   -0.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788   -1.6255   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -0.3260    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    0.6599    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960    0.1520    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.0824    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -0.8994   -0.3356 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859   -1.1302   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3242   -0.8107   -2.4123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.3805   -1.6816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247    0.0716   -1.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3970    0.4350   -0.9050 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9897    0.3831    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8760    0.7876    1.4036 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7484   -0.0543    0.6301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -0.4281   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635    1.9609    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    2.6597    0.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6867    2.5173    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5773    3.4618   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2448    1.5321    0.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176   -4.1717   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886   -4.1496   -1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6449   -4.6688    0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.4682    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400   -0.0059   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.8447   -0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2999   -0.0380    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869    1.0125    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7002   -1.3473    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -1.9850    0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725   -1.4989   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    0.1087   -2.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8821    0.5431    1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5044    1.3399    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431    2.6368    0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    1.7586    2.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9920    4.1550    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353    4.0269   -1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4389    2.9465   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 18  9  1  0
 18 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END

426
  Mrv0541 02231214402D          

 23 24  0  0  0  0            999 V2000
    6.0423    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4005    1.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840    2.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7588    0.7258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -1.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -2.8509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.3619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.3619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370    0.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806   -0.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734   -0.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    0.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1442    0.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4985   -2.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -2.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4913    2.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2078    1.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7476    3.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4641    2.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 19  1  0  0  0  0
  2 14  1  0  0  0  0
  2 20  1  0  0  0  0
  3 19  2  0  0  0  0
  4 20  2  0  0  0  0
  5 12  1  0  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6 16  2  0  0  0  0
  6 17  1  0  0  0  0
  7 15  2  0  0  0  0
  7 21  1  0  0  0  0
  8 18  1  0  0  0  0
  8 21  2  0  0  0  0
  9 21  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014570

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)

> <INCHI_KEY>
GGXKWVWZWMLJEH-UHFFFAOYSA-N

> <FORMULA>
C14H19N5O4

> <MOLECULAR_WEIGHT>
321.3318

> <EXACT_MASS>
321.143704121

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
32.82547944138288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
-0.4836860169999998

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.700940442073367

> <JCHEM_PKA_STRONGEST_BASIC>
5.048475789934001

> <JCHEM_POLAR_SURFACE_AREA>
122.22

> <JCHEM_REFRACTIVITY>
81.53530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
famciclovir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014570
     RDKit          3D
Famciclovir
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.1968   -3.9951   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -2.6023   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7229   -2.3261   -0.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788   -1.6255   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -0.3260    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    0.6599    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960    0.1520    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.0824    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -0.8994   -0.3356 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859   -1.1302   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3242   -0.8107   -2.4123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.3805   -1.6816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247    0.0716   -1.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3970    0.4350   -0.9050 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9897    0.3831    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8760    0.7876    1.4036 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7484   -0.0543    0.6301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -0.4281   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635    1.9609    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    2.6597    0.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6867    2.5173    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5773    3.4618   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2448    1.5321    0.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176   -4.1717   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886   -4.1496   -1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6449   -4.6688    0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.4682    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400   -0.0059   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.8447   -0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2999   -0.0380    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869    1.0125    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7002   -1.3473    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -1.9850    0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725   -1.4989   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    0.1087   -2.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8821    0.5431    1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5044    1.3399    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431    2.6368    0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    1.7586    2.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9920    4.1550    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353    4.0269   -1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4389    2.9465   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 18  9  1  0
 18 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 426                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.279   3.012   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.814   2.184   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.743   3.841   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.350   1.355   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.365  -2.843   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.365  -5.322   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       6.574  -2.542   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.241  -4.852   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       3.907  -2.542   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.829   0.402   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.350  -1.062   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.844  -1.379   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.800   1.548   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.336   0.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -3.312   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.264  -4.082   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908  -4.852   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574  -5.622   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.250   4.159   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.321   2.501   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.241  -3.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.729   5.622   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.800   3.965   0.000  0.00  0.00           C+0
CONECT    1   13   19                                                       
CONECT    2   14   20                                                       
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   12   15   16                                                  
CONECT    6   16   17                                                       
CONECT    7   15   21                                                       
CONECT    8   18   21                                                       
CONECT    9   21                                                            
CONECT   10   11   13   14                                                  
CONECT   11   10   12                                                       
CONECT   12    5   11                                                       
CONECT   13    1   10                                                       
CONECT   14    2   10                                                       
CONECT   15    5    7   17                                                  
CONECT   16    5    6                                                       
CONECT   17    6   15   18                                                  
CONECT   18    8   17                                                       
CONECT   19    1    3   22                                                  
CONECT   20    2    4   23                                                  
CONECT   21    7    8    9                                                  
CONECT   22   19                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0014570
HETATM    1  C1  UNL     1      -2.197  -3.995  -0.781  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.531  -2.602  -0.310  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.723  -2.326  -0.016  1.00  0.00           O  
HETATM    4  O2  UNL     1      -1.579  -1.626  -0.191  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.987  -0.326   0.265  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.874   0.660   0.358  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.196   0.152   1.289  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.913  -1.082   0.923  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.652  -0.899  -0.336  1.00  0.00           N  
HETATM   10  C7  UNL     1       1.286  -1.130  -1.593  1.00  0.00           C  
HETATM   11  N2  UNL     1       2.324  -0.811  -2.412  1.00  0.00           N  
HETATM   12  C8  UNL     1       3.342  -0.380  -1.682  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.625   0.072  -1.943  1.00  0.00           C  
HETATM   14  N3  UNL     1       5.397   0.435  -0.905  1.00  0.00           N  
HETATM   15  C10 UNL     1       4.990   0.383   0.377  1.00  0.00           C  
HETATM   16  N4  UNL     1       5.876   0.788   1.404  1.00  0.00           N  
HETATM   17  N5  UNL     1       3.748  -0.054   0.630  1.00  0.00           N  
HETATM   18  C11 UNL     1       2.939  -0.428  -0.367  1.00  0.00           C  
HETATM   19  C12 UNL     1      -1.364   1.961   0.944  1.00  0.00           C  
HETATM   20  O3  UNL     1      -2.356   2.660   0.356  1.00  0.00           O  
HETATM   21  C13 UNL     1      -3.687   2.517   0.220  1.00  0.00           C  
HETATM   22  C14 UNL     1      -4.577   3.462  -0.534  1.00  0.00           C  
HETATM   23  O4  UNL     1      -4.245   1.532   0.752  1.00  0.00           O  
HETATM   24  H1  UNL     1      -1.118  -4.172  -0.761  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.689  -4.150  -1.740  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.645  -4.669   0.004  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.436  -0.468   1.257  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.740  -0.006  -0.525  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.391   0.845  -0.641  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.300  -0.038   2.285  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.887   1.012   1.509  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.700  -1.347   1.710  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.293  -1.985   0.860  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.372  -1.499  -1.985  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.940   0.109  -2.974  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.882   0.543   1.380  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.504   1.340   2.193  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.443   2.637   0.973  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.520   1.759   2.045  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.992   4.155   0.242  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.035   4.027  -1.294  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.439   2.947  -0.984  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   27   28
CONECT    6    7   19   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   18
CONECT   10   11   11   34
CONECT   11   12
CONECT   12   13   13   18
CONECT   13   14   35
CONECT   14   15   15
CONECT   15   16   17
CONECT   16   36   37
CONECT   17   18   18
CONECT   19   20   38   39
CONECT   20   21
CONECT   21   22   23   23
CONECT   22   40   41   42
END

HMDB0014570
     RDKit          3D
Famciclovir
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.1968   -3.9951   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -2.6023   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7229   -2.3261   -0.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788   -1.6255   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -0.3260    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    0.6599    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960    0.1520    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.0824    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -0.8994   -0.3356 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859   -1.1302   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3242   -0.8107   -2.4123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.3805   -1.6816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247    0.0716   -1.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3970    0.4350   -0.9050 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9897    0.3831    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8760    0.7876    1.4036 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7484   -0.0543    0.6301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -0.4281   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635    1.9609    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    2.6597    0.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6867    2.5173    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5773    3.4618   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2448    1.5321    0.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176   -4.1717   -0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886   -4.1496   -1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6449   -4.6688    0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.4682    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400   -0.0059   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.8447   -0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2999   -0.0380    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869    1.0125    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7002   -1.3473    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930   -1.9850    0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725   -1.4989   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    0.1087   -2.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8821    0.5431    1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5044    1.3399    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431    2.6368    0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    1.7586    2.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9920    4.1550    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353    4.0269   -1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4389    2.9465   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 18  9  1  0
 18 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(2-(2-Amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetate	ChEBI
9-[4-Acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine	ChEBI
Acetic acid 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl ester	ChEBI
BRL-42810	ChEBI
Famciclovirum	ChEBI
Famvir	ChEBI
FCV	ChEBI
2-(2-(2-Amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetic acid	Generator
Acetate 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl ester	Generator
9-(4-Acetoxy-3-(acetoxymethyl)but-1-yl)-2-aminopurine	HMDB

Chemical Formula

C₁₄H₁₉N₅O₄

Average Molecular Weight

321.3318

Monoisotopic Molecular Weight

321.143704121

IUPAC Name

2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate

Traditional Name

famciclovir

CAS Registry Number

104227-87-4

SMILES

CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O

InChI Identifier

InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)

InChI Key

GGXKWVWZWMLJEH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purines and purine derivatives

Alternative Parents

Substituents

Purine
Aminopyrimidine
Pyrimidine
Dicarboxylic acid or derivatives
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetate ester (CHEBI:4974 )
2-aminopurines (CHEBI:4974 )

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: HMDB0014570)
Membrane (HMDB: HMDB0014570)

Source

Exogenous

Exogenous (HMDB: HMDB0014570)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102 - 104 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.32 g/L	Not Available
LogP	0.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	168.417	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001040

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.32 g/L	ALOGPS
logP	0.13	ALOGPS
logP	-0.48	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.7	ChemAxon
pKa (Strongest Basic)	5.05	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	122.22 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	81.54 m³·mol⁻¹	ChemAxon
Polarizability	32.83 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]+	175.555	31661259
DarkChem	[M-H]-	173.419	31661259
DeepCCS	[M-2H]-	196.714	30932474
DeepCCS	[M+Na]+	172.221	30932474
AllCCS	[M+H]+	172.1	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	174.9	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	174.2	32859911
AllCCS	[M+HCOO]-	174.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.79 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2613 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.1 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1575.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	194.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	98.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	140.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	278.7 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	329.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	157.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	731.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	255.6 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	1142.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	363.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	208.5 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	172.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Famciclovir	CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O	3329.3	Standard polar	33892256
Famciclovir	CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O	2355.3	Standard non polar	33892256
Famciclovir	CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O	2704.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Famciclovir,1TMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C)N=C21)COC(C)=O	2706.3	Semi standard non polar	33892256
Famciclovir,1TMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C)N=C21)COC(C)=O	2697.2	Standard non polar	33892256
Famciclovir,1TMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C)N=C21)COC(C)=O	4556.9	Standard polar	33892256
Famciclovir,2TMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C21)COC(C)=O	2696.7	Semi standard non polar	33892256
Famciclovir,2TMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C21)COC(C)=O	2783.8	Standard non polar	33892256
Famciclovir,2TMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C21)COC(C)=O	4020.5	Standard polar	33892256
Famciclovir,1TBDMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O	2850.5	Semi standard non polar	33892256
Famciclovir,1TBDMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O	2922.4	Standard non polar	33892256
Famciclovir,1TBDMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O	4426.2	Standard polar	33892256
Famciclovir,2TBDMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O	3092.0	Semi standard non polar	33892256
Famciclovir,2TBDMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O	3245.2	Standard non polar	33892256
Famciclovir,2TBDMS,isomer #1	CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O	3978.4	Standard polar	33892256

Spectra

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 DB00426	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00426	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00426

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Famciclovir

METLIN ID

Not Available

PubChem Compound

3324

PDB ID

Not Available

ChEBI ID

4974

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

References

Rashidi MR, Smith JA, Clarke SE, Beedham C: In vitro oxidation of famciclovir and 6-deoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver. Drug Metab Dispos. 1997 Jul;25(7):805-13. [PubMed:9224775 ]
Al-Salmy HS: Inter-strain variability in aldehyde oxidase activity in the mouse. Comp Biochem Physiol C Toxicol Pharmacol. 2002 Jul;132(3):341-7. [PubMed:12161167 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

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

Showing metabocard for Famciclovir (HMDB0014570)

MOL for HMDB0014570 (Famciclovir)

3D MOL for HMDB0014570 (Famciclovir)

3D SDF for HMDB0014570 (Famciclovir)

3D-SDF for HMDB0014570 (Famciclovir)

PDB for HMDB0014570 (Famciclovir)

3D PDB for HMDB0014570 (Famciclovir)

SMILES for HMDB0014570 (Famciclovir)

INCHI for HMDB0014570 (Famciclovir)

Structure for HMDB0014570 (Famciclovir)

3D Structure for HMDB0014570 (Famciclovir)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References