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enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015000

Secondary Accession Numbers

HMDB15000

Metabolite Identification

Common Name

Vardenafil

Description

Vardenafil (Levitra) is an oral therapy for the treatment of erectile dysfunction. It is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Penile erection is a hemodynamic process initiated by the relaxation of smooth muscle in the corpus cavernosum and its associated arterioles. During sexual stimulation, nitric oxide is released from nerve endings and endothelial cells in the corpus cavernosum. Nitric oxide activates the enzyme guanylate cyclase resulting in increased synthesis of cyclic guanosine monophosphate (cGMP) in the smooth muscle cells of the corpus cavernosum. The cGMP in turn triggers smooth muscle relaxation, allowing increased blood flow into the penis, resulting in erection. The tissue concentration of cGMP is regulated by both the rates of synthesis and degradation via phosphodiesterases (PDEs). The most abundant PDE in the human corpus cavernosum is the cGMPspecific phosphodiesterase type 5 (PDE5); therefore, the inhibition of PDE5 enhances erectile function by increasing the amount of cGMP.

Structure

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

862
  Mrv0541 02231215032D          

 34 37  0  0  0  0            999 V2000
    5.2224   -0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7715   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  1  0  0  0  0
M  END

HMDB0015000
     RDKit          3D
Vardenafil
 66 69  0  0  0  0  0  0  0  0999 V2000
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M  END

862
  Mrv0541 02231215032D          

 34 37  0  0  0  0            999 V2000
    5.2224   -0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015000

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)

> <INCHI_KEY>
SECKRCOLJRRGGV-UHFFFAOYSA-N

> <FORMULA>
C23H32N6O4S

> <MOLECULAR_WEIGHT>
488.603

> <EXACT_MASS>
488.220574232

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
53.222173915473334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
1.3251205046367571

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.0073360900325

> <JCHEM_PKA_STRONGEST_BASIC>
6.207399200497821

> <JCHEM_POLAR_SURFACE_AREA>
109.13

> <JCHEM_REFRACTIVITY>
142.70970000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levitra

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015000
     RDKit          3D
Vardenafil
 66 69  0  0  0  0  0  0  0  0999 V2000
   -5.1792    3.4907    2.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    2.9571    2.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7259    1.5281    3.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4777    0.6276    2.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7885    0.2921    2.4962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452   -0.5227    1.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798   -1.1370    1.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8928   -0.6928    0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5634   -1.4142   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031   -2.0790   -0.8861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239   -1.3976   -0.8762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512   -0.6668   -0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922   -0.6539   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632    0.0475   -0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243    0.0314   -0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6050    0.9467   -0.1724 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4944    1.4910   -1.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    2.1449    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936    0.0792    1.0052 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -1.0879    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2855   -0.7564   -0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8130    0.5719   -0.2369 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1800    0.5933   -0.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7386    2.0007   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8359    0.8202    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4116    1.0030    1.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -0.7122   -2.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -1.4290   -2.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242   -1.3995   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872   -2.1226   -2.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5462   -2.8842   -3.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540   -3.6148   -4.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    0.0254    0.8117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9166    0.0284    1.3371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8475    3.0912    3.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    3.3039    1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1715    4.6088    2.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887    3.0137    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783    3.5921    3.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1541    1.4383    4.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.1814    3.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5005   -2.1156    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5165   -1.2504    0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1647   -0.4169    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    0.6467    0.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984   -1.6239    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4006   -1.7535    0.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719   -0.7998   -1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1238   -1.4730   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8448   -0.1033   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1901    0.3954   -1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4854    2.0041    0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2707    2.3508   -1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042    2.6947   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3179    0.0287    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3744    1.7569    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948    0.8529    2.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    2.0597    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -0.7454   -2.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929   -2.0341   -3.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339   -3.6385   -3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1739   -2.2324   -4.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011   -4.6261   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7319   -3.8199   -5.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -3.1055   -3.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9812    0.6102    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 15 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 12 33  1  0
 33 34  1  0
 34  4  1  0
 34  8  1  0
 29 13  1  0
 26 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
 14 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 28 60  1  0
 31 61  1  0
 31 62  1  0
 32 63  1  0
 32 64  1  0
 32 65  1  0
 33 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 862                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.748  -0.770   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.519  -2.104   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.978   0.564   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.083   2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.417  -4.620   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.415  -1.540   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.748  -3.080   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      17.751  -0.770   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      16.417   0.000   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      15.083  -2.310   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      20.107  -1.540   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.083  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.208  -0.301   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.751  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.687   1.163   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.208  -2.779   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.417  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.194   1.481   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.687  -4.243   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.672   2.944   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.083   3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.417   4.620   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   17                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   22   33                                                       
CONECT    5   29                                                            
CONECT    6    1   12   13                                                  
CONECT    7   14   15   16                                                  
CONECT    8    9   25   26                                                  
CONECT    9    8   23                                                       
CONECT   10   23   29                                                       
CONECT   11   25   28                                                       
CONECT   12    6   14                                                       
CONECT   13    6   15                                                       
CONECT   14    7   12                                                       
CONECT   15    7   13                                                       
CONECT   16    7   18                                                       
CONECT   17    1   19   20                                                  
CONECT   18   16                                                            
CONECT   19   17   21                                                       
CONECT   20   17   24                                                       
CONECT   21   19   22   23                                                  
CONECT   22    4   21   24                                                  
CONECT   23    9   10   21                                                  
CONECT   24   20   22                                                       
CONECT   25    8   11   27                                                  
CONECT   26    8   28   29                                                  
CONECT   27   25   30                                                       
CONECT   28   11   26   31                                                  
CONECT   29    5   10   26                                                  
CONECT   30   27   32                                                       
CONECT   31   28                                                            
CONECT   32   30                                                            
CONECT   33    4   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0015000
HETATM    1  C1  UNL     1      -5.179   3.491   2.774  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.787   2.957   2.848  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.726   1.528   3.316  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.478   0.628   2.400  1.00  0.00           C  
HETATM    5  N1  UNL     1      -5.789   0.292   2.496  1.00  0.00           N  
HETATM    6  C5  UNL     1      -6.045  -0.523   1.485  1.00  0.00           C  
HETATM    7  C6  UNL     1      -7.380  -1.137   1.208  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.893  -0.693   0.761  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.563  -1.414  -0.372  1.00  0.00           C  
HETATM   10  O1  UNL     1      -5.503  -2.079  -0.886  1.00  0.00           O  
HETATM   11  N2  UNL     1      -3.324  -1.398  -0.876  1.00  0.00           N  
HETATM   12  C9  UNL     1      -2.351  -0.667  -0.285  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.992  -0.654  -0.845  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.063   0.048  -0.329  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.324   0.031  -0.888  1.00  0.00           C  
HETATM   16  S1  UNL     1       2.605   0.947  -0.172  1.00  0.00           S  
HETATM   17  O2  UNL     1       3.494   1.491  -1.262  1.00  0.00           O  
HETATM   18  O3  UNL     1       1.994   2.145   0.513  1.00  0.00           O  
HETATM   19  N3  UNL     1       3.494   0.079   1.005  1.00  0.00           N  
HETATM   20  C13 UNL     1       4.154  -1.088   0.488  1.00  0.00           C  
HETATM   21  C14 UNL     1       5.285  -0.756  -0.452  1.00  0.00           C  
HETATM   22  N4  UNL     1       5.813   0.572  -0.237  1.00  0.00           N  
HETATM   23  C15 UNL     1       7.180   0.593  -0.775  1.00  0.00           C  
HETATM   24  C16 UNL     1       7.739   2.001  -0.548  1.00  0.00           C  
HETATM   25  C17 UNL     1       5.836   0.820   1.172  1.00  0.00           C  
HETATM   26  C18 UNL     1       4.412   1.003   1.640  1.00  0.00           C  
HETATM   27  C19 UNL     1       1.569  -0.712  -2.015  1.00  0.00           C  
HETATM   28  C20 UNL     1       0.528  -1.429  -2.558  1.00  0.00           C  
HETATM   29  C21 UNL     1      -0.724  -1.400  -1.985  1.00  0.00           C  
HETATM   30  O4  UNL     1      -1.787  -2.123  -2.528  1.00  0.00           O  
HETATM   31  C22 UNL     1      -1.546  -2.884  -3.679  1.00  0.00           C  
HETATM   32  C23 UNL     1      -2.754  -3.615  -4.170  1.00  0.00           C  
HETATM   33  N5  UNL     1      -2.691   0.025   0.812  1.00  0.00           N  
HETATM   34  N6  UNL     1      -3.917   0.028   1.337  1.00  0.00           N  
HETATM   35  H1  UNL     1      -5.848   3.091   3.541  1.00  0.00           H  
HETATM   36  H2  UNL     1      -5.575   3.304   1.740  1.00  0.00           H  
HETATM   37  H3  UNL     1      -5.172   4.609   2.878  1.00  0.00           H  
HETATM   38  H4  UNL     1      -3.289   3.014   1.841  1.00  0.00           H  
HETATM   39  H5  UNL     1      -3.178   3.592   3.514  1.00  0.00           H  
HETATM   40  H6  UNL     1      -4.154   1.438   4.337  1.00  0.00           H  
HETATM   41  H7  UNL     1      -2.676   1.181   3.342  1.00  0.00           H  
HETATM   42  H8  UNL     1      -7.500  -2.116   1.706  1.00  0.00           H  
HETATM   43  H9  UNL     1      -7.517  -1.250   0.103  1.00  0.00           H  
HETATM   44  H10 UNL     1      -8.165  -0.417   1.537  1.00  0.00           H  
HETATM   45  H11 UNL     1      -0.134   0.647   0.579  1.00  0.00           H  
HETATM   46  H12 UNL     1       4.598  -1.624   1.353  1.00  0.00           H  
HETATM   47  H13 UNL     1       3.401  -1.754   0.054  1.00  0.00           H  
HETATM   48  H14 UNL     1       4.972  -0.800  -1.523  1.00  0.00           H  
HETATM   49  H15 UNL     1       6.124  -1.473  -0.334  1.00  0.00           H  
HETATM   50  H16 UNL     1       7.845  -0.103  -0.244  1.00  0.00           H  
HETATM   51  H17 UNL     1       7.190   0.395  -1.851  1.00  0.00           H  
HETATM   52  H18 UNL     1       8.485   2.004   0.269  1.00  0.00           H  
HETATM   53  H19 UNL     1       8.271   2.351  -1.460  1.00  0.00           H  
HETATM   54  H20 UNL     1       6.904   2.695  -0.385  1.00  0.00           H  
HETATM   55  H21 UNL     1       6.318   0.029   1.763  1.00  0.00           H  
HETATM   56  H22 UNL     1       6.374   1.757   1.354  1.00  0.00           H  
HETATM   57  H23 UNL     1       4.395   0.853   2.736  1.00  0.00           H  
HETATM   58  H24 UNL     1       4.143   2.060   1.448  1.00  0.00           H  
HETATM   59  H25 UNL     1       2.560  -0.745  -2.482  1.00  0.00           H  
HETATM   60  H26 UNL     1       0.693  -2.034  -3.461  1.00  0.00           H  
HETATM   61  H27 UNL     1      -0.734  -3.639  -3.528  1.00  0.00           H  
HETATM   62  H28 UNL     1      -1.174  -2.232  -4.516  1.00  0.00           H  
HETATM   63  H29 UNL     1      -2.801  -4.626  -3.676  1.00  0.00           H  
HETATM   64  H30 UNL     1      -2.732  -3.820  -5.256  1.00  0.00           H  
HETATM   65  H31 UNL     1      -3.704  -3.106  -3.913  1.00  0.00           H  
HETATM   66  H32 UNL     1      -1.981   0.610   1.314  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5    5   34
CONECT    5    6
CONECT    6    7    8    8
CONECT    7   42   43   44
CONECT    8    9   34
CONECT    9   10   10   11
CONECT   11   12   12
CONECT   12   13   33
CONECT   13   14   14   29
CONECT   14   15   45
CONECT   15   16   27   27
CONECT   16   17   17   18   18
CONECT   16   19
CONECT   19   20   26
CONECT   20   21   46   47
CONECT   21   22   48   49
CONECT   22   23   25
CONECT   23   24   50   51
CONECT   24   52   53   54
CONECT   25   26   55   56
CONECT   26   57   58
CONECT   27   28   59
CONECT   28   29   29   60
CONECT   29   30
CONECT   30   31
CONECT   31   32   61   62
CONECT   32   63   64   65
CONECT   33   34   66
END

HMDB0015000
     RDKit          3D
Vardenafil
 66 69  0  0  0  0  0  0  0  0999 V2000
   -5.1792    3.4907    2.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    2.9571    2.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7259    1.5281    3.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4777    0.6276    2.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7885    0.2921    2.4962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452   -0.5227    1.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3798   -1.1370    1.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8928   -0.6928    0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5634   -1.4142   -0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031   -2.0790   -0.8861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239   -1.3976   -0.8762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512   -0.6668   -0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922   -0.6539   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632    0.0475   -0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243    0.0314   -0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6050    0.9467   -0.1724 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4944    1.4910   -1.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    2.1449    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936    0.0792    1.0052 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -1.0879    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2855   -0.7564   -0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8130    0.5719   -0.2369 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1800    0.5933   -0.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7386    2.0007   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8359    0.8202    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4116    1.0030    1.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -0.7122   -2.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -1.4290   -2.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242   -1.3995   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872   -2.1226   -2.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5462   -2.8842   -3.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540   -3.6148   -4.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    0.0254    0.8117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9166    0.0284    1.3371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8475    3.0912    3.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    3.3039    1.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1715    4.6088    2.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887    3.0137    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783    3.5921    3.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1541    1.4383    4.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.1814    3.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5005   -2.1156    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5165   -1.2504    0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1647   -0.4169    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    0.6467    0.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984   -1.6239    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4006   -1.7535    0.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719   -0.7998   -1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1238   -1.4730   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8448   -0.1033   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1901    0.3954   -1.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4854    2.0041    0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2707    2.3508   -1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042    2.6947   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3179    0.0287    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3744    1.7569    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948    0.8529    2.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    2.0597    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -0.7454   -2.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929   -2.0341   -3.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339   -3.6385   -3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1739   -2.2324   -4.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011   -4.6261   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7319   -3.8199   -5.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -3.1055   -3.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9812    0.6102    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 15 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 12 33  1  0
 33 34  1  0
 34  4  1  0
 34  8  1  0
 29 13  1  0
 26 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
 14 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 28 60  1  0
 31 61  1  0
 31 62  1  0
 32 63  1  0
 32 64  1  0
 32 65  1  0
 33 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-F][1,2,4]triazin-4(1H)-one	ChEBI
Levitra	ChEBI
2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulphonyl]phenyl}-5-methyl-7-propylimidazo[5,1-F][1,2,4]triazin-4(1H)-one	Generator
VDN	HMDB
Trihydrate, vardenafil hydrochloride	HMDB
Dihydrochloride, vardenafil	HMDB
Vardenafil hydrochloride	HMDB
Vardenafil hydrochloride anhydrous	HMDB
Vardenafil hydrochloride trihydrate	HMDB
Anhydrous, vardenafil hydrochloride	HMDB
Hydrochloride anhydrous, vardenafil	HMDB
Hydrochloride trihydrate, vardenafil	HMDB
Hydrochloride, vardenafil	HMDB
1-(((3-(3,4-Dihydro-5-methyl)-4-oxo-7-propylimidazo(5,1-F)-as-triazin-2-yl)-4-ethoxyphenyl)sulfonyl)-4-ethylpiperazine	HMDB
Vardenafil dihydrochloride	HMDB

Chemical Formula

C₂₃H₃₂N₆O₄S

Average Molecular Weight

488.603

Monoisotopic Molecular Weight

488.220574232

IUPAC Name

2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one

Traditional Name

levitra

CAS Registry Number

224785-90-4

SMILES

CCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1

InChI Identifier

InChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)

InChI Key

SECKRCOLJRRGGV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Phenoxy compound
Phenol ether
Alkyl aryl ether
N-alkylpiperazine
1,4-diazinane
N-substituted imidazole
Piperazine
Organosulfonic acid amide
Triazine
1,2,4-triazine
Heteroaromatic compound
Sulfonyl
Azole
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Imidazole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organonitrogen compound
Amine
Organooxygen compound
Organosulfur compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-alkylpiperazine (CHEBI:46295 )
imidazotriazine (CHEBI:46295 )
N-sulfonylpiperazine (CHEBI:46295 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015000)
Membrane (HMDB: HMDB0015000)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.32 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	225.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.33	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	6.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.71 m³·mol⁻¹	ChemAxon
Polarizability	53.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	211.273	31661259
DarkChem	[M-H]-	210.713	31661259
DeepCCS	[M+H]+	216.11	30932474
DeepCCS	[M-H]-	213.715	30932474
DeepCCS	[M-2H]-	246.698	30932474
DeepCCS	[M+Na]+	222.023	30932474
AllCCS	[M+H]+	212.5	32859911
AllCCS	[M+H-H2O]+	210.7	32859911
AllCCS	[M+NH4]+	214.2	32859911
AllCCS	[M+Na]+	214.7	32859911
AllCCS	[M-H]-	204.3	32859911
AllCCS	[M+Na-2H]-	205.5	32859911
AllCCS	[M+HCOO]-	206.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vardenafil	CCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1	5121.7	Standard polar	33892256
Vardenafil	CCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1	3809.6	Standard non polar	33892256
Vardenafil	CCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1	4262.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vardenafil,1TMS,isomer #1	CCCC1=NC(C)=C2C(=O)N=C(C3=CC(S(=O)(=O)N4CCN(CC)CC4)=CC=C3OCC)N([Si](C)(C)C)N12	4028.0	Semi standard non polar	33892256
Vardenafil,1TMS,isomer #1	CCCC1=NC(C)=C2C(=O)N=C(C3=CC(S(=O)(=O)N4CCN(CC)CC4)=CC=C3OCC)N([Si](C)(C)C)N12	3994.3	Standard non polar	33892256
Vardenafil,1TMS,isomer #1	CCCC1=NC(C)=C2C(=O)N=C(C3=CC(S(=O)(=O)N4CCN(CC)CC4)=CC=C3OCC)N([Si](C)(C)C)N12	5714.4	Standard polar	33892256
Vardenafil,1TBDMS,isomer #1	CCCC1=NC(C)=C2C(=O)N=C(C3=CC(S(=O)(=O)N4CCN(CC)CC4)=CC=C3OCC)N([Si](C)(C)C(C)(C)C)N12	4162.0	Semi standard non polar	33892256
Vardenafil,1TBDMS,isomer #1	CCCC1=NC(C)=C2C(=O)N=C(C3=CC(S(=O)(=O)N4CCN(CC)CC4)=CC=C3OCC)N([Si](C)(C)C(C)(C)C)N12	4264.0	Standard non polar	33892256
Vardenafil,1TBDMS,isomer #1	CCCC1=NC(C)=C2C(=O)N=C(C3=CC(S(=O)(=O)N4CCN(CC)CC4)=CC=C3OCC)N([Si](C)(C)C(C)(C)C)N12	5599.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vardenafil GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9304600000-78a6e2bde8e38b367f38	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vardenafil 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 - Vardenafil LC-ESI-QFT , negative-QTOF	splash10-000i-0040900000-a78a646244f2fb1f6276	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil , positive-QTOF	splash10-000f-0011900000-88f62b9a8f7aec917a41	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil , positive-QTOF	splash10-0002-0092000000-cf98ecae287c01370dbc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 35V, Negative-QTOF	splash10-052r-0000900000-9008f3921907d4675261	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 10V, Positive-QTOF	splash10-000i-0000900000-1fcc6df6cdb6126d7ef0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 40V, Positive-QTOF	splash10-055r-0091200000-d63a9cf854a198162e08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 10V, Negative-QTOF	splash10-000i-0000900000-93d391256ac331406fac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 40V, Positive-QTOF	splash10-0udi-1924200000-417e1644b94601dd7f35	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 20V, Positive-QTOF	splash10-000i-0000900000-b883d879992fbedff256	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 40V, Negative-QTOF	splash10-001i-0090200000-050ed3eecf1ffddad8e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 50V, Positive-QTOF	splash10-014i-0925000000-41aba03d13dfc7df8faf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 40V, Positive-QTOF	splash10-000i-0413900000-e1526827ae9f58ddf244	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 20V, Negative-QTOF	splash10-052r-0000900000-e5ff9d0dc7199d2f0c84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 10V, Negative-QTOF	splash10-000i-0000900000-e10263c8f866f8b725ea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 35V, Positive-QTOF	splash10-000i-3100900000-665b3066495254822a6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 30V, Positive-QTOF	splash10-000i-0000900000-3b1c3b5e3ebaf21ef591	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 20V, Negative-QTOF	splash10-000i-0000900000-99f18e7a2ea26f21682b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 40V, Negative-QTOF	splash10-055r-0091200000-74cac0a8c4e6f18b2567	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vardenafil 20V, Positive-QTOF	splash10-000i-0000900000-7205fafb37f359d4065d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vardenafil 10V, Positive-QTOF	splash10-000i-0002900000-c0cecdb93e99efbd369e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vardenafil 20V, Positive-QTOF	splash10-01w0-3536900000-89e4ca7c7d6e6e2e281e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vardenafil 40V, Positive-QTOF	splash10-02ai-5492100000-78d239c94528460e3603	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vardenafil 10V, Negative-QTOF	splash10-000i-0000900000-caa7e887e43db6fbbc44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vardenafil 20V, Negative-QTOF	splash10-0570-0412900000-c93873d3bd3336545c26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vardenafil 40V, Negative-QTOF	splash10-01ot-3900000000-b864d4adedbfa7b24b3b	2016-08-03	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 DB00862	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00862	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00862

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

99300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vardenafil

METLIN ID

Not Available

PubChem Compound

110634

PDB ID

Not Available

ChEBI ID

46295

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. Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:: PDE6H
Uniprot ID:: Q13956
Molecular weight:: 9074.36

References

Zhang XJ, Cahill KB, Elfenbein A, Arshavsky VY, Cote RH: Direct allosteric regulation between the GAF domain and catalytic domain of photoreceptor phosphodiesterase PDE6. J Biol Chem. 2008 Oct 31;283(44):29699-705. doi: 10.1074/jbc.M803948200. Epub 2008 Sep 8. [PubMed:18779324 ]

Enzyme Details

2. Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:: PDE6G
Uniprot ID:: P18545
Molecular weight:: 9643.09

References

Zhang XJ, Cahill KB, Elfenbein A, Arshavsky VY, Cote RH: Direct allosteric regulation between the GAF domain and catalytic domain of photoreceptor phosphodiesterase PDE6. J Biol Chem. 2008 Oct 31;283(44):29699-705. doi: 10.1074/jbc.M803948200. Epub 2008 Sep 8. [PubMed:18779324 ]

Enzyme Details

3. cGMP-specific 3',5'-cyclic phosphodiesterase

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP.
Gene Name:: PDE5A
Uniprot ID:: O76074
Molecular weight:: 99984.14

References

Blount MA, Zoraghi R, Ke H, Bessay EP, Corbin JD, Francis SH: A 46-amino acid segment in phosphodiesterase-5 GAF-B domain provides for high vardenafil potency over sildenafil and tadalafil and is involved in phosphodiesterase-5 dimerization. Mol Pharmacol. 2006 Nov;70(5):1822-31. Epub 2006 Aug 22. [PubMed:16926278 ]
Carrier S: Pharmacology of phosphodiesterase 5 inhibitors. Can J Urol. 2003 Feb;10 Suppl 1:12-6. [PubMed:12625845 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kim NN, Huang YH, Goldstein I, Bischoff E, Traish AM: Inhibition of cyclic GMP hydrolysis in human corpus cavernosum smooth muscle cells by vardenafil, a novel, selective phosphodiesterase type 5 inhibitor. Life Sci. 2001 Sep 28;69(19):2249-56. [PubMed:11669467 ]
Saenz de Tejada I, Angulo J, Cuevas P, Fernandez A, Moncada I, Allona A, Lledo E, Korschen HG, Niewohner U, Haning H, Pages E, Bischoff E: The phosphodiesterase inhibitory selectivity and the in vitro and in vivo potency of the new PDE5 inhibitor vardenafil. Int J Impot Res. 2001 Oct;13(5):282-90. [PubMed:11890515 ]
Scheen AJ: [Medication of the month. Vardenafil (Levitra)]. Rev Med Liege. 2003 Sep;58(9):576-9. [PubMed:14626653 ]
Sung BJ, Hwang KY, Jeon YH, Lee JI, Heo YS, Kim JH, Moon J, Yoon JM, Hyun YL, Kim E, Eum SJ, Park SY, Lee JO, Lee TG, Ro S, Cho JM: Structure of the catalytic domain of human phosphodiesterase 5 with bound drug molecules. Nature. 2003 Sep 4;425(6953):98-102. [PubMed:12955149 ]
Wang H, Ye M, Robinson H, Francis SH, Ke H: Conformational variations of both phosphodiesterase-5 and inhibitors provide the structural basis for the physiological effects of vardenafil and sildenafil. Mol Pharmacol. 2008 Jan;73(1):104-10. Epub 2007 Oct 24. [PubMed:17959709 ]
Zoraghi R, Francis SH, Corbin JD: Critical amino acids in phosphodiesterase-5 catalytic site that provide for high-affinity interaction with cyclic guanosine monophosphate and inhibitors. Biochemistry. 2007 Nov 27;46(47):13554-63. Epub 2007 Nov 3. [PubMed:17979301 ]

Enzyme Details

4. 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 ]

Enzyme Details

5. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

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 Vardenafil (HMDB0015000)

MOL for HMDB0015000 (Vardenafil)

3D MOL for HMDB0015000 (Vardenafil)

3D SDF for HMDB0015000 (Vardenafil)

3D-SDF for HMDB0015000 (Vardenafil)

PDB for HMDB0015000 (Vardenafil)

3D PDB for HMDB0015000 (Vardenafil)

SMILES for HMDB0015000 (Vardenafil)

INCHI for HMDB0015000 (Vardenafil)

Structure for HMDB0015000 (Vardenafil)

3D Structure for HMDB0015000 (Vardenafil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References