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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-17 11:32:11 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005039

Secondary Accession Numbers

HMDB05039

Metabolite Identification

Common Name

Sildenafil

Description

Sildenafil is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. It was initially studied for use in hypertension (high blood pressure) and angina pectoris (a form of ischaemic cardiovascular disease). Phase I clinical trials under the direction of Ian Osterloh suggested that the drug had little effect on angina, but that it could induce marked penile erections; Sildenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. The molecular structure of sildenafil is similar to that of cGMP and acts as a competitive binding agent of PDE5 in the corpus cavernosum, resulting in more cGMP and better erections. Without sexual stimulation, and therefore lack of activation of the NO/cGMP system, sildenafil should not cause an erection. Other drugs that operate by the same mechanism include tadalafil (Cialis) and vardenafil (Levitra); Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. Viagra pills are blue and diamond-shaped with the words 'Pfizer' on one side, and 'VGR xx' (where xx stands for '25', '50' or '100', the dose of that pill in milligrams) on the other. Its primary competitors on the market are tadalafil (Cialis), and vardenafil (Levitra).

Structure

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

5212
  Mrv0541 02231214312D          

 33 36  0  0  0  0            999 V2000
    4.5080   -0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756   -1.4889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0571   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756   -0.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8318    0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6391    0.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8318   -2.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8954    1.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 16  1  0  0  0  0
  4 23  1  0  0  0  0
  4 32  1  0  0  0  0
  5 28  2  0  0  0  0
  6 12  1  0  0  0  0
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  8 21  1  0  0  0  0
  8 22  1  0  0  0  0
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 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
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 27 29  1  0  0  0  0
 29 31  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0005039
     RDKit          3D
Sildenafil
 63 66  0  0  0  0  0  0  0  0999 V2000
    5.6239    2.1712   -2.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458    1.0349   -1.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289    1.6977   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284    0.7282    0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0950    0.3068    1.9440 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -0.5736    2.6016 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6855   -1.2882    3.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912   -0.7606    1.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850   -1.5504    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -2.2964    3.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0902   -1.4617    1.3414 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -0.6512    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792   -0.6925   -0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -1.5120   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3066   -1.6568   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -2.7145   -0.4276 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.0139   -3.8952    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3414   -3.2895   -1.6084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165   -1.9547    0.6125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3413   -0.8623   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8972    0.4874    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.6668    1.8167 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081    1.8277    2.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8883   -0.5189    2.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -1.4061    1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167   -0.9188   -2.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -0.0932   -2.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    0.0292   -1.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625    0.8748   -2.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7491    1.6499   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    0.8941   -4.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732    0.0890    0.0200 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    0.0580    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088    1.9115   -3.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7135    2.3550   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4663    0.3811   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1551    0.4181   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411    2.2279    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829    2.4994   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   -2.3662    3.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -0.8675    4.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7660   -1.2748    4.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759   -2.1099    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4431   -0.9138    0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802   -0.8844   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5269    1.2385   -0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    0.7415    0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6531    1.8877    3.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    2.7685    1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4247    1.8469    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8287   -1.0378    2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3353   -0.2176    3.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1761   -0.7744    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686   -2.2415    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -1.0137   -2.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2192    0.7145   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
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 33  4  1  0
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 28 13  1  0
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 32 63  1  0
M  END

5212
  Mrv0541 02231214312D          

 33 36  0  0  0  0            999 V2000
    4.5080   -0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756   -1.4889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0571   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9370    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7949   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8318    0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8318   -2.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8954    1.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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 27 29  1  0  0  0  0
 29 31  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005039

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)

> <INCHI_KEY>
BNRNXUUZRGQAQC-UHFFFAOYSA-N

> <FORMULA>
C22H30N6O4S

> <MOLECULAR_WEIGHT>
474.576

> <EXACT_MASS>
474.204924168

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
51.177398593346254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
1.6464821276953228

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.271521788115507

> <JCHEM_PKA_STRONGEST_BASIC>
5.9693714214707825

> <JCHEM_POLAR_SURFACE_AREA>
109.13

> <JCHEM_REFRACTIVITY>
139.44050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
revatio

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005039
     RDKit          3D
Sildenafil
 63 66  0  0  0  0  0  0  0  0999 V2000
    5.6239    2.1712   -2.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458    1.0349   -1.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289    1.6977   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284    0.7282    0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0950    0.3068    1.9440 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -0.5736    2.6016 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6855   -1.2882    3.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912   -0.7606    1.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850   -1.5504    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -2.2964    3.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0902   -1.4617    1.3414 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -0.6512    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792   -0.6925   -0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -1.5120   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3066   -1.6568   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -2.7145   -0.4276 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.0139   -3.8952    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3414   -3.2895   -1.6084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165   -1.9547    0.6125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3413   -0.8623   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8972    0.4874    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.6668    1.8167 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081    1.8277    2.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8883   -0.5189    2.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -1.4061    1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167   -0.9188   -2.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -0.0932   -2.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    0.0292   -1.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625    0.8748   -2.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7491    1.6499   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    0.8941   -4.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732    0.0890    0.0200 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    0.0580    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088    1.9115   -3.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7135    2.3550   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758    3.1023   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663    0.3811   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1551    0.4181   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411    2.2279    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829    2.4994   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   -2.3662    3.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -0.8675    4.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7660   -1.2748    4.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759   -2.1099    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4431   -0.9138    0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802   -0.8844   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5269    1.2385   -0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    0.7415    0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6531    1.8877    3.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    2.7685    1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4247    1.8469    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8287   -1.0378    2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3353   -0.2176    3.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1761   -0.7744    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686   -2.2415    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -1.0137   -2.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5241    0.4766   -3.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    2.4693   -3.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256    2.2167   -3.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5609    0.9910   -5.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188   -0.1935   -4.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282    1.2294   -5.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    0.7145   -0.8074 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  1  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
 22 24  1  0
 24 25  1  0
 15 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 12 32  1  0
 32 33  1  0
 33  4  1  0
 33  8  2  0
 28 13  1  0
 25 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
 14 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 30 58  1  0
 30 59  1  0
 31 60  1  0
 31 61  1  0
 31 62  1  0
 32 63  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5212                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.415  -0.770   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.645   0.564   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.185  -2.104   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.750   2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      15.083  -4.620   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.081  -1.540   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.414  -3.080   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      15.083   0.000   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      17.874  -2.779   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      18.773  -1.540   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      13.750  -2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.747  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.417  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.416   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.082   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.874  -0.301   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.417  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.353   1.163   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.083  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.860   1.481   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.353  -4.243   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.338   2.944   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.750   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.083   4.620   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   16                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   23   32                                                       
CONECT    5   28                                                            
CONECT    6    1   12   13                                                  
CONECT    7   14   15   17                                                  
CONECT    8   21   22                                                       
CONECT    9   10   26   30                                                  
CONECT   10    9   25                                                       
CONECT   11   21   28                                                       
CONECT   12    6   14                                                       
CONECT   13    6   15                                                       
CONECT   14    7   12                                                       
CONECT   15    7   13                                                       
CONECT   16    1   18   20                                                  
CONECT   17    7                                                            
CONECT   18   16   19                                                       
CONECT   19   18   21   23                                                  
CONECT   20   16   24                                                       
CONECT   21    8   11   19                                                  
CONECT   22    8   25   26                                                  
CONECT   23    4   19   24                                                  
CONECT   24   20   23                                                       
CONECT   25   10   22   27                                                  
CONECT   26    9   22   28                                                  
CONECT   27   25   29                                                       
CONECT   28    5   11   26                                                  
CONECT   29   27   31                                                       
CONECT   30    9                                                            
CONECT   31   29                                                            
CONECT   32    4   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0005039
HETATM    1  C1  UNL     1       5.624   2.171  -2.422  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.246   1.035  -1.476  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.829   1.698  -0.180  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.428   0.728   0.853  1.00  0.00           C  
HETATM    5  N1  UNL     1       5.095   0.307   1.944  1.00  0.00           N  
HETATM    6  N2  UNL     1       4.359  -0.574   2.602  1.00  0.00           N  
HETATM    7  C5  UNL     1       4.685  -1.288   3.839  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.191  -0.761   1.971  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.085  -1.550   2.222  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.053  -2.296   3.229  1.00  0.00           O  
HETATM   11  N3  UNL     1       1.090  -1.462   1.341  1.00  0.00           N  
HETATM   12  C8  UNL     1       1.106  -0.651   0.232  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.079  -0.692  -0.624  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.142  -1.512  -0.259  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.307  -1.657  -0.954  1.00  0.00           C  
HETATM   16  S1  UNL     1      -3.603  -2.715  -0.428  1.00  0.00           S  
HETATM   17  O2  UNL     1      -3.014  -3.895   0.313  1.00  0.00           O  
HETATM   18  O3  UNL     1      -4.341  -3.289  -1.608  1.00  0.00           O  
HETATM   19  N4  UNL     1      -4.716  -1.955   0.612  1.00  0.00           N  
HETATM   20  C12 UNL     1      -5.341  -0.862  -0.082  1.00  0.00           C  
HETATM   21  C13 UNL     1      -4.897   0.487   0.428  1.00  0.00           C  
HETATM   22  N5  UNL     1      -5.193   0.667   1.817  1.00  0.00           N  
HETATM   23  C14 UNL     1      -4.508   1.828   2.346  1.00  0.00           C  
HETATM   24  C15 UNL     1      -4.888  -0.519   2.584  1.00  0.00           C  
HETATM   25  C16 UNL     1      -3.995  -1.406   1.753  1.00  0.00           C  
HETATM   26  C17 UNL     1      -2.417  -0.919  -2.113  1.00  0.00           C  
HETATM   27  C18 UNL     1      -1.395  -0.093  -2.519  1.00  0.00           C  
HETATM   28  C19 UNL     1      -0.212   0.029  -1.778  1.00  0.00           C  
HETATM   29  O4  UNL     1       0.762   0.875  -2.250  1.00  0.00           O  
HETATM   30  C20 UNL     1       0.749   1.650  -3.394  1.00  0.00           C  
HETATM   31  C21 UNL     1       0.611   0.894  -4.685  1.00  0.00           C  
HETATM   32  N6  UNL     1       2.173   0.089   0.020  1.00  0.00           N  
HETATM   33  C22 UNL     1       3.230   0.058   0.868  1.00  0.00           C  
HETATM   34  H1  UNL     1       5.409   1.912  -3.484  1.00  0.00           H  
HETATM   35  H2  UNL     1       6.713   2.355  -2.330  1.00  0.00           H  
HETATM   36  H3  UNL     1       5.076   3.102  -2.187  1.00  0.00           H  
HETATM   37  H4  UNL     1       4.466   0.381  -1.891  1.00  0.00           H  
HETATM   38  H5  UNL     1       6.155   0.418  -1.331  1.00  0.00           H  
HETATM   39  H6  UNL     1       5.741   2.228   0.207  1.00  0.00           H  
HETATM   40  H7  UNL     1       4.083   2.499  -0.348  1.00  0.00           H  
HETATM   41  H8  UNL     1       4.369  -2.366   3.736  1.00  0.00           H  
HETATM   42  H9  UNL     1       4.091  -0.868   4.675  1.00  0.00           H  
HETATM   43  H10 UNL     1       5.766  -1.275   4.026  1.00  0.00           H  
HETATM   44  H11 UNL     1      -1.076  -2.110   0.663  1.00  0.00           H  
HETATM   45  H12 UNL     1      -6.443  -0.914   0.102  1.00  0.00           H  
HETATM   46  H13 UNL     1      -5.180  -0.884  -1.169  1.00  0.00           H  
HETATM   47  H14 UNL     1      -5.527   1.238  -0.128  1.00  0.00           H  
HETATM   48  H15 UNL     1      -3.859   0.741   0.182  1.00  0.00           H  
HETATM   49  H16 UNL     1      -4.653   1.888   3.444  1.00  0.00           H  
HETATM   50  H17 UNL     1      -4.965   2.769   1.941  1.00  0.00           H  
HETATM   51  H18 UNL     1      -3.425   1.847   2.056  1.00  0.00           H  
HETATM   52  H19 UNL     1      -5.829  -1.038   2.886  1.00  0.00           H  
HETATM   53  H20 UNL     1      -4.335  -0.218   3.504  1.00  0.00           H  
HETATM   54  H21 UNL     1      -3.176  -0.774   1.356  1.00  0.00           H  
HETATM   55  H22 UNL     1      -3.569  -2.242   2.347  1.00  0.00           H  
HETATM   56  H23 UNL     1      -3.344  -1.014  -2.698  1.00  0.00           H  
HETATM   57  H24 UNL     1      -1.524   0.477  -3.443  1.00  0.00           H  
HETATM   58  H25 UNL     1      -0.030   2.469  -3.352  1.00  0.00           H  
HETATM   59  H26 UNL     1       1.726   2.217  -3.417  1.00  0.00           H  
HETATM   60  H27 UNL     1       1.561   0.991  -5.289  1.00  0.00           H  
HETATM   61  H28 UNL     1       0.519  -0.193  -4.485  1.00  0.00           H  
HETATM   62  H29 UNL     1      -0.228   1.229  -5.303  1.00  0.00           H  
HETATM   63  H30 UNL     1       2.219   0.715  -0.807  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   37   38
CONECT    3    4   39   40
CONECT    4    5    5   33
CONECT    5    6
CONECT    6    7    8
CONECT    7   41   42   43
CONECT    8    9   33   33
CONECT    9   10   10   11
CONECT   11   12   12
CONECT   12   13   32
CONECT   13   14   14   28
CONECT   14   15   44
CONECT   15   16   26   26
CONECT   16   17   17   18   18
CONECT   16   19
CONECT   19   20   25
CONECT   20   21   45   46
CONECT   21   22   47   48
CONECT   22   23   24
CONECT   23   49   50   51
CONECT   24   25   52   53
CONECT   25   54   55
CONECT   26   27   56
CONECT   27   28   28   57
CONECT   28   29
CONECT   29   30
CONECT   30   31   58   59
CONECT   31   60   61   62
CONECT   32   33   63
END

HMDB0005039
     RDKit          3D
Sildenafil
 63 66  0  0  0  0  0  0  0  0999 V2000
    5.6239    2.1712   -2.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458    1.0349   -1.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8289    1.6977   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284    0.7282    0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0950    0.3068    1.9440 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -0.5736    2.6016 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6855   -1.2882    3.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912   -0.7606    1.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850   -1.5504    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -2.2964    3.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0902   -1.4617    1.3414 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -0.6512    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0792   -0.6925   -0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -1.5120   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3066   -1.6568   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -2.7145   -0.4276 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.0139   -3.8952    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3414   -3.2895   -1.6084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165   -1.9547    0.6125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3413   -0.8623   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8972    0.4874    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.6668    1.8167 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081    1.8277    2.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8883   -0.5189    2.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -1.4061    1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167   -0.9188   -2.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -0.0932   -2.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    0.0292   -1.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625    0.8748   -2.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7491    1.6499   -3.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    0.8941   -4.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732    0.0890    0.0200 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301    0.0580    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088    1.9115   -3.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7135    2.3550   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758    3.1023   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663    0.3811   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1551    0.4181   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411    2.2279    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829    2.4994   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   -2.3662    3.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -0.8675    4.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7660   -1.2748    4.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759   -2.1099    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4431   -0.9138    0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802   -0.8844   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5269    1.2385   -0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    0.7415    0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6531    1.8877    3.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9647    2.7685    1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4247    1.8469    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8287   -1.0378    2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3353   -0.2176    3.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1761   -0.7744    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686   -2.2415    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -1.0137   -2.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5241    0.4766   -3.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    2.4693   -3.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256    2.2167   -3.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5609    0.9910   -5.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188   -0.1935   -4.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282    1.2294   -5.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192    0.7145   -0.8074 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  1  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
 22 24  1  0
 24 25  1  0
 15 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 12 32  1  0
 32 33  1  0
 33  4  1  0
 33  8  2  0
 28 13  1  0
 25 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
 14 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 30 58  1  0
 30 59  1  0
 31 60  1  0
 31 61  1  0
 31 62  1  0
 32 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine	ChEBI
Aphrodil	Kegg
1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazine	Generator
Caverta	HMDB
Revatio	HMDB
Sildenafil citrate	HMDB
Viagra	HMDB
Desmethyl sildenafil	HMDB
Hydroxyhomosildenafil	HMDB
1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrate	HMDB
Lactate, sildenafil	HMDB
NCX-911	HMDB
Nitrate, sildenafil	HMDB
Acetildenafil	HMDB
Sildenafil nitrate	HMDB
NCX 911	HMDB
Homosildenafil	HMDB
Citrate, sildenafil	HMDB
Sildenafil, desmethyl	HMDB
Desmethylsildenafil	HMDB
Sildenafil lactate	HMDB

Chemical Formula

C₂₂H₃₀N₆O₄S

Average Molecular Weight

474.576

Monoisotopic Molecular Weight

474.204924168

IUPAC Name

5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one

Traditional Name

revatio

CAS Registry Number

139755-83-2

SMILES

CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1

InChI Identifier

InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)

InChI Key

BNRNXUUZRGQAQC-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
Pyrazolopyrimidine
Benzenesulfonyl group
Phenoxy compound
Phenol ether
Alkyl aryl ether
Pyrimidone
N-methylpiperazine
N-alkylpiperazine
Piperazine
Pyrimidine
Organosulfonic acid amide
1,4-diazinane
Pyrazole
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Azole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Lactam
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:9139 )
piperazines (CHEBI:9139 )
pyrazolopyrimidine (CHEBI:9139 )

Ontology

Not Available

Liver (HMDB: HMDB0005039)

Tissue

Muscle tissue

Smooth muscle (HMDB: HMDB0005039)
Smooth muscle (HMDB: HMDB0005039)

Source

Exogenous

Exogenous (HMDB: HMDB0005039)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005039)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	212.7	30932474
[M+H]+	Not Available	210.825	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000882

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	2.35	ALOGPS
logP	1.65	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	5.97	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	6	ChemAxon
Refractivity	139.44 m³·mol⁻¹	ChemAxon
Polarizability	51.18 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]+	208.635	31661259
DarkChem	[M-H]-	207.097	31661259
DeepCCS	[M+H]+	211.155	30932474
DeepCCS	[M-H]-	208.76	30932474
DeepCCS	[M-2H]-	241.749	30932474
DeepCCS	[M+Na]+	217.068	30932474
AllCCS	[M+H]+	209.5	32859911
AllCCS	[M+H-H2O]+	207.5	32859911
AllCCS	[M+NH4]+	211.4	32859911
AllCCS	[M+Na]+	211.9	32859911
AllCCS	[M-H]-	205.0	32859911
AllCCS	[M+Na-2H]-	206.1	32859911
AllCCS	[M+HCOO]-	207.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sildenafil	CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1	5075.6	Standard polar	33892256
Sildenafil	CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1	3724.7	Standard non polar	33892256
Sildenafil	CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1	4112.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sildenafil,1TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN(C)CC3)=CC=C1OCC)=NC2=O	3859.8	Semi standard non polar	33892256
Sildenafil,1TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN(C)CC3)=CC=C1OCC)=NC2=O	3901.2	Standard non polar	33892256
Sildenafil,1TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN(C)CC3)=CC=C1OCC)=NC2=O	5427.6	Standard polar	33892256
Sildenafil,1TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN(C)CC3)=CC=C1OCC)=NC2=O	3980.5	Semi standard non polar	33892256
Sildenafil,1TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN(C)CC3)=CC=C1OCC)=NC2=O	4171.5	Standard non polar	33892256
Sildenafil,1TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN(C)CC3)=CC=C1OCC)=NC2=O	5372.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sildenafil GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-9004300000-55c87eff7b6ad40ea3d5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sildenafil 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 - Sildenafil LC-ESI-qTof , Positive-QTOF	splash10-0059-2494500000-e3f8387aee5a0463363c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sildenafil LC-ESI-qTof , Positive-QTOF	splash10-05s0-3892000000-aa19715309275e16a6c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sildenafil , positive-QTOF	splash10-0059-2494500000-e3f8387aee5a0463363c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sildenafil , positive-QTOF	splash10-05s0-3892000000-aa19715309275e16a6c0	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 10V, Positive-QTOF	splash10-004i-0002900000-b281f59f40caaba85ac9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 20V, Positive-QTOF	splash10-004i-4436900000-0c5804e76b9d495c76d6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 40V, Positive-QTOF	splash10-0459-6292000000-5a32bfcdda2067978be9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 10V, Negative-QTOF	splash10-00di-0001900000-51b4957d0b3d25c41773	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 20V, Negative-QTOF	splash10-01vk-0302900000-86c63c2fd17f7c5b7d6f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 40V, Negative-QTOF	splash10-03dj-8916100000-e941afc576d544ed32a7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 10V, Positive-QTOF	splash10-004i-0000900000-c92b21b6524ea5040313	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 20V, Positive-QTOF	splash10-004i-0000900000-06d94f4626e8bee6e389	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 40V, Positive-QTOF	splash10-006t-9101300000-ef50cfadb7bd34e88187	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 10V, Negative-QTOF	splash10-00di-0000900000-1617a2dfdf2b96a0cd2c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 20V, Negative-QTOF	splash10-0002-0010900000-744efa093f1de0f36d62	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sildenafil 40V, Negative-QTOF	splash10-003r-0272900000-aa5d9fef9c0fb52ad923	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Liver
Smooth Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00203

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023606

KNApSAcK ID

Not Available

Chemspider ID

5023

KEGG Compound ID

C07259

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sildenafil

METLIN ID

Not Available

PubChem Compound

5212

PDB ID

Not Available

ChEBI ID

9139

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Dunn, Peter James; Wood, Albert Shaw. Process for preparation of Sildenafil by cyclization. Eur. Pat. Appl. (1997), 18 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kekilli M, Beyazit Y, Purnak T, Dogan S, Atalar E: Acute myocardial infarction after sildenafil citrate ingestion. Ann Pharmacother. 2005 Jul-Aug;39(7-8):1362-4. Epub 2005 May 24. [PubMed:15914518 ]
Kim NN, Goldstein I, Moreland RB, Traish AM: Alpha-adrenergic receptor blockade by phentolamine increases the efficacy of vasodilators in penile corpus cavernosum. Int J Impot Res. 2000 Mar;12 Suppl 1:S26-36. [PubMed:10845762 ]
Warrington JS, Shader RI, von Moltke LL, Greenblatt DJ: In vitro biotransformation of sildenafil (Viagra): identification of human cytochromes and potential drug interactions. Drug Metab Dispos. 2000 Apr;28(4):392-7. [PubMed:10725306 ]
Chua R, Keogh A, Miyashita M: Novel use of sildenafil in the treatment of portopulmonary hypertension. J Heart Lung Transplant. 2005 Apr;24(4):498-500. [PubMed:15797756 ]
Fekete F, Fabian E: [Effectiveness and adverse effects of sildenafil in erectile dysfunction]. Orv Hetil. 2000 Jan 16;141(3):115-8. [PubMed:10693332 ]
Blount MA, Beasley A, Zoraghi R, Sekhar KR, Bessay EP, Francis SH, Corbin JD: Binding of tritiated sildenafil, tadalafil, or vardenafil to the phosphodiesterase-5 catalytic site displays potency, specificity, heterogeneity, and cGMP stimulation. Mol Pharmacol. 2004 Jul;66(1):144-52. [PubMed:15213306 ]

Enzymes

Enzyme Details

1. cGMP-dependent 3',5'-cyclic phosphodiesterase

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
Gene Name:: PDE2A
Uniprot ID:: O00408
Molecular weight:: 105145.485

Enzyme Details

2. 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

Enzyme Details

3. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

4. Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides cAMP and cGMP. Catalyzes the hydrolysis of both cAMP and cGMP to 5'-AMP and 5'-GMP, respectively.
Gene Name:: PDE11A
Uniprot ID:: Q9HCR9
Molecular weight:: 55699.16

Showing metabocard for Sildenafil (HMDB0005039)

MOL for HMDB0005039 (Sildenafil)

3D MOL for HMDB0005039 (Sildenafil)

3D SDF for HMDB0005039 (Sildenafil)

3D-SDF for HMDB0005039 (Sildenafil)

PDB for HMDB0005039 (Sildenafil)

3D PDB for HMDB0005039 (Sildenafil)

SMILES for HMDB0005039 (Sildenafil)

INCHI for HMDB0005039 (Sildenafil)

Structure for HMDB0005039 (Sildenafil)

3D Structure for HMDB0005039 (Sildenafil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes