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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:08:02 UTC

Update Date

2019-07-23 07:15:24 UTC

HMDB ID

HMDB0060932

Secondary Accession Numbers

HMDB60932

Metabolite Identification

Common Name

N-Desmethyl sildenafil (UK-103,320)

Description

N-Desmethyl sildenafil (UK-103 320) is a metabolite of sildenafil. Sildenafil citrate, sold as Viagra, Revatio and under various other trade names, is a drug used to treat erectile dysfunction and pulmonary arterial hypertension (PAH). It was originally developed by British scientists and then brought to market by the US-based pharmaceutical company Pfizer. It acts by inhibiting cGMP-specific phosphodiesterase type 5, an enzyme that promotes degradation of cGMP, which regulates blood flow in the penis. (Wikipedia)

Structure

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

5212
  Mrv0541 02271201062D          

 32 35  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
    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 22  1  0  0  0  0
  4 31  1  0  0  0  0
  5 27  2  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
  9 29  1  0  0  0  0
 10 24  2  0  0  0  0
 11 20  2  0  0  0  0
 11 27  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  2  0  0  0  0
 21 24  1  0  0  0  0
 21 25  2  0  0  0  0
 22 23  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0060932
     RDKit          3D
N-Desmethyl sildenafil (UK-103,320)
 60 63  0  0  0  0  0  0  0  0999 V2000
   -1.9826   -3.3500   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3472   -3.6548    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644   -2.5184    0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -1.3526    0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.0866   -0.6354 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030    0.0118   -1.3465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3190    0.6083   -2.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659    0.4810   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4036    1.5958   -1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155    2.3466   -2.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583    1.8271   -1.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813    1.0352   -0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    1.3740    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    0.6275    0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.0097    1.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.0151    2.4291 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.8225   -0.7080    3.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237    0.9061    3.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -1.1610    1.7198 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -2.1419    0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1207   -3.1665    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -2.4536   -0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9087   -1.6930    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1146   -0.7505    1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964    2.1549    0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7458    2.8999   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    2.5277   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968    3.2757   -1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918    4.4680   -1.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093    5.5538   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219   -0.0433    0.1511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986   -0.3429   -0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -2.5640   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3559   -3.0165    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -4.2935   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0300   -4.0506   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3246   -4.4876    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401   -2.1998    1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0774   -2.9090    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5522    1.6241   -1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512    0.7005   -3.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859   -0.0499   -2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131   -0.2772    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -1.6927    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269   -2.6815    1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6726   -3.5968    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -3.9350   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7816   -3.0976   -0.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360   -2.4188    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6955   -1.1154    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885   -0.5794    2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053    0.2465    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054    2.4074    1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    3.7961   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613    4.2515   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593    4.8090   -2.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    6.4321   -1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274    5.9766   -1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    5.1130    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -0.6866    0.8257 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
 23 24  1  0
 15 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 12 31  1  0
 31 32  1  0
 32  4  1  0
 32  8  2  0
 27 13  1  0
 24 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
 14 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
 31 60  1  0
M  END

5212
  Mrv0541 02271201062D          

 32 35  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
    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 22  1  0  0  0  0
  4 31  1  0  0  0  0
  5 27  2  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
  9 29  1  0  0  0  0
 10 24  2  0  0  0  0
 11 20  2  0  0  0  0
 11 27  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  2  0  0  0  0
 21 24  1  0  0  0  0
 21 25  2  0  0  0  0
 22 23  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060932

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H28N6O4S/c1-4-6-16-18-19(26(3)25-16)21(28)24-20(23-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,28)

> <INCHI_KEY>
UZTKBZXHEOVDRL-UHFFFAOYSA-N

> <FORMULA>
C21H28N6O4S

> <MOLECULAR_WEIGHT>
460.55

> <EXACT_MASS>
460.189274104

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
48.956690985003554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
0.9258672344071224

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.508904808055715

> <JCHEM_PKA_STRONGEST_BASIC>
6.902752959193913

> <JCHEM_POLAR_SURFACE_AREA>
117.92000000000002

> <JCHEM_REFRACTIVITY>
134.1458

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060932
     RDKit          3D
N-Desmethyl sildenafil (UK-103,320)
 60 63  0  0  0  0  0  0  0  0999 V2000
   -1.9826   -3.3500   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3472   -3.6548    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644   -2.5184    0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -1.3526    0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.0866   -0.6354 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030    0.0118   -1.3465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3190    0.6083   -2.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659    0.4810   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4036    1.5958   -1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155    2.3466   -2.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583    1.8271   -1.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813    1.0352   -0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    1.3740    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    0.6275    0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.0097    1.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.0151    2.4291 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.8225   -0.7080    3.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237    0.9061    3.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -1.1610    1.7198 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -2.1419    0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1207   -3.1665    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -2.4536   -0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9087   -1.6930    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1146   -0.7505    1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964    2.1549    0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7458    2.8999   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    2.5277   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968    3.2757   -1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918    4.4680   -1.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093    5.5538   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219   -0.0433    0.1511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986   -0.3429   -0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -2.5640   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3559   -3.0165    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -4.2935   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0300   -4.0506   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3246   -4.4876    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401   -2.1998    1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0774   -2.9090    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5522    1.6241   -1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512    0.7005   -3.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859   -0.0499   -2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131   -0.2772    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -1.6927    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269   -2.6815    1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6726   -3.5968    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -3.9350   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7816   -3.0976   -0.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360   -2.4188    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6955   -1.1154    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885   -0.5794    2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053    0.2465    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054    2.4074    1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    3.7961   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613    4.2515   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593    4.8090   -2.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    6.4321   -1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274    5.9766   -1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    5.1130    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -0.6866    0.8257 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
 23 24  1  0
 15 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 12 31  1  0
 31 32  1  0
 32  4  1  0
 32  8  2  0
 27 13  1  0
 24 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
 14 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
 31 60  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5212                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-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      11.082  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.750  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.417  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.874  -0.301   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.417  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.353   1.163   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.083  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.860   1.481   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.353  -4.243   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.338   2.944   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.750   3.850   0.000  0.00  0.00           C+0
HETATM   32  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   22   31                                                       
CONECT    5   27                                                            
CONECT    6    1   12   13                                                  
CONECT    7   14   15                                                       
CONECT    8   20   21                                                       
CONECT    9   10   25   29                                                  
CONECT   10    9   24                                                       
CONECT   11   20   27                                                       
CONECT   12    6   14                                                       
CONECT   13    6   15                                                       
CONECT   14    7   12                                                       
CONECT   15    7   13                                                       
CONECT   16    1   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   20   22                                                  
CONECT   19   16   23                                                       
CONECT   20    8   11   18                                                  
CONECT   21    8   24   25                                                  
CONECT   22    4   18   23                                                  
CONECT   23   19   22                                                       
CONECT   24   10   21   26                                                  
CONECT   25    9   21   27                                                  
CONECT   26   24   28                                                       
CONECT   27    5   11   25                                                  
CONECT   28   26   30                                                       
CONECT   29    9                                                            
CONECT   30   28                                                            
CONECT   31    4   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0060932
HETATM    1  C1  UNL     1      -1.983  -3.350  -0.212  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.347  -3.655   0.307  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.064  -2.518   0.949  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.291  -1.353   0.069  1.00  0.00           C  
HETATM    5  N1  UNL     1      -5.433  -1.087  -0.635  1.00  0.00           N  
HETATM    6  N2  UNL     1      -5.303   0.012  -1.347  1.00  0.00           N  
HETATM    7  C5  UNL     1      -6.319   0.608  -2.225  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.066   0.481  -1.114  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.404   1.596  -1.582  1.00  0.00           C  
HETATM   10  O1  UNL     1      -4.015   2.347  -2.388  1.00  0.00           O  
HETATM   11  N3  UNL     1      -2.158   1.827  -1.166  1.00  0.00           N  
HETATM   12  C8  UNL     1      -1.481   1.035  -0.301  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.111   1.374   0.105  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.641   0.628   0.974  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.944   1.010   1.329  1.00  0.00           C  
HETATM   16  S1  UNL     1       2.826   0.015   2.429  1.00  0.00           S  
HETATM   17  O2  UNL     1       1.823  -0.708   3.319  1.00  0.00           O  
HETATM   18  O3  UNL     1       3.624   0.906   3.335  1.00  0.00           O  
HETATM   19  N4  UNL     1       3.812  -1.161   1.720  1.00  0.00           N  
HETATM   20  C12 UNL     1       3.173  -2.142   0.930  1.00  0.00           C  
HETATM   21  C13 UNL     1       4.121  -3.167   0.385  1.00  0.00           C  
HETATM   22  N5  UNL     1       5.121  -2.454  -0.398  1.00  0.00           N  
HETATM   23  C14 UNL     1       5.909  -1.693   0.550  1.00  0.00           C  
HETATM   24  C15 UNL     1       5.115  -0.751   1.373  1.00  0.00           C  
HETATM   25  C16 UNL     1       2.496   2.155   0.805  1.00  0.00           C  
HETATM   26  C17 UNL     1       1.746   2.900  -0.063  1.00  0.00           C  
HETATM   27  C18 UNL     1       0.464   2.528  -0.414  1.00  0.00           C  
HETATM   28  O4  UNL     1      -0.297   3.276  -1.289  1.00  0.00           O  
HETATM   29  C19 UNL     1       0.092   4.468  -1.919  1.00  0.00           C  
HETATM   30  C20 UNL     1       0.409   5.554  -0.916  1.00  0.00           C  
HETATM   31  N6  UNL     1      -2.122  -0.043   0.151  1.00  0.00           N  
HETATM   32  C21 UNL     1      -3.399  -0.343  -0.233  1.00  0.00           C  
HETATM   33  H1  UNL     1      -1.970  -2.564  -0.976  1.00  0.00           H  
HETATM   34  H2  UNL     1      -1.356  -3.017   0.639  1.00  0.00           H  
HETATM   35  H3  UNL     1      -1.485  -4.294  -0.590  1.00  0.00           H  
HETATM   36  H4  UNL     1      -4.030  -4.051  -0.492  1.00  0.00           H  
HETATM   37  H5  UNL     1      -3.325  -4.488   1.071  1.00  0.00           H  
HETATM   38  H6  UNL     1      -3.540  -2.200   1.881  1.00  0.00           H  
HETATM   39  H7  UNL     1      -5.077  -2.909   1.247  1.00  0.00           H  
HETATM   40  H8  UNL     1      -6.552   1.624  -1.852  1.00  0.00           H  
HETATM   41  H9  UNL     1      -5.851   0.700  -3.227  1.00  0.00           H  
HETATM   42  H10 UNL     1      -7.186  -0.050  -2.250  1.00  0.00           H  
HETATM   43  H11 UNL     1       0.213  -0.277   1.392  1.00  0.00           H  
HETATM   44  H12 UNL     1       2.562  -1.693   0.104  1.00  0.00           H  
HETATM   45  H13 UNL     1       2.427  -2.682   1.581  1.00  0.00           H  
HETATM   46  H14 UNL     1       4.673  -3.597   1.258  1.00  0.00           H  
HETATM   47  H15 UNL     1       3.596  -3.935  -0.202  1.00  0.00           H  
HETATM   48  H16 UNL     1       5.782  -3.098  -0.885  1.00  0.00           H  
HETATM   49  H17 UNL     1       6.436  -2.419   1.233  1.00  0.00           H  
HETATM   50  H18 UNL     1       6.696  -1.115   0.016  1.00  0.00           H  
HETATM   51  H19 UNL     1       5.688  -0.579   2.332  1.00  0.00           H  
HETATM   52  H20 UNL     1       5.105   0.246   0.862  1.00  0.00           H  
HETATM   53  H21 UNL     1       3.505   2.407   1.109  1.00  0.00           H  
HETATM   54  H22 UNL     1       2.191   3.796  -0.471  1.00  0.00           H  
HETATM   55  H23 UNL     1       0.961   4.252  -2.577  1.00  0.00           H  
HETATM   56  H24 UNL     1      -0.759   4.809  -2.550  1.00  0.00           H  
HETATM   57  H25 UNL     1      -0.282   6.432  -1.040  1.00  0.00           H  
HETATM   58  H26 UNL     1       1.427   5.977  -1.074  1.00  0.00           H  
HETATM   59  H27 UNL     1       0.287   5.113   0.107  1.00  0.00           H  
HETATM   60  H28 UNL     1      -1.656  -0.687   0.826  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   36   37
CONECT    3    4   38   39
CONECT    4    5    5   32
CONECT    5    6
CONECT    6    7    8
CONECT    7   40   41   42
CONECT    8    9   32   32
CONECT    9   10   10   11
CONECT   11   12   12
CONECT   12   13   31
CONECT   13   14   14   27
CONECT   14   15   43
CONECT   15   16   25   25
CONECT   16   17   17   18   18
CONECT   16   19
CONECT   19   20   24
CONECT   20   21   44   45
CONECT   21   22   46   47
CONECT   22   23   48
CONECT   23   24   49   50
CONECT   24   51   52
CONECT   25   26   53
CONECT   26   27   27   54
CONECT   27   28
CONECT   28   29
CONECT   29   30   55   56
CONECT   30   57   58   59
CONECT   31   32   60
END

HMDB0060932
     RDKit          3D
N-Desmethyl sildenafil (UK-103,320)
 60 63  0  0  0  0  0  0  0  0999 V2000
   -1.9826   -3.3500   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3472   -3.6548    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644   -2.5184    0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -1.3526    0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.0866   -0.6354 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030    0.0118   -1.3465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3190    0.6083   -2.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659    0.4810   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4036    1.5958   -1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155    2.3466   -2.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583    1.8271   -1.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813    1.0352   -0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    1.3740    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    0.6275    0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.0097    1.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.0151    2.4291 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.8225   -0.7080    3.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237    0.9061    3.3353 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -1.1610    1.7198 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -2.1419    0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1207   -3.1665    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -2.4536   -0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9087   -1.6930    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1146   -0.7505    1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964    2.1549    0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7458    2.8999   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    2.5277   -0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968    3.2757   -1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918    4.4680   -1.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093    5.5538   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219   -0.0433    0.1511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986   -0.3429   -0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -2.5640   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3559   -3.0165    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -4.2935   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0300   -4.0506   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3246   -4.4876    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401   -2.1998    1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0774   -2.9090    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5522    1.6241   -1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512    0.7005   -3.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859   -0.0499   -2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131   -0.2772    1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -1.6927    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269   -2.6815    1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6726   -3.5968    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -3.9350   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7816   -3.0976   -0.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360   -2.4188    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6955   -1.1154    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885   -0.5794    2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053    0.2465    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054    2.4074    1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    3.7961   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613    4.2515   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593    4.8090   -2.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    6.4321   -1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274    5.9766   -1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    5.1130    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559   -0.6866    0.8257 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
 23 24  1  0
 15 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 12 31  1  0
 31 32  1  0
 32  4  1  0
 32  8  2  0
 27 13  1  0
 24 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
 14 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  0
 30 58  1  0
 30 59  1  0
 31 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citrate, sildenafil	HMDB
Desmethyl sildenafil	HMDB
Sildenafil lactate	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
Revatio	HMDB
Viagra	HMDB
Acetildenafil	HMDB
Sildenafil citrate	HMDB
Sildenafil, desmethyl	HMDB
Hydroxyhomosildenafil	HMDB
NCX 911	HMDB
Homosildenafil	HMDB
Sildenafil	HMDB
Sildenafil nitrate	HMDB
5-[2-Ethoxy-5-(piperazine-1-sulphonyl)phenyl]-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-D]pyrimidin-7-one	Generator

Chemical Formula

C₂₁H₂₈N₆O₄S

Average Molecular Weight

460.55

Monoisotopic Molecular Weight

460.189274104

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1

InChI Identifier

InChI=1S/C21H28N6O4S/c1-4-6-16-18-19(26(3)25-16)21(28)24-20(23-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,28)

InChI Key

UZTKBZXHEOVDRL-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
Pyrimidine
1,4-diazinane
Organosulfonic acid amide
Piperazine
Sulfonyl
Azole
Organosulfonic acid or derivatives
Vinylogous amide
Pyrazole
Organic sulfonic acid or derivatives
Heteroaromatic compound
Secondary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Secondary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic oxide
Organic nitrogen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060932)

Organ

Kidney (HMDB: HMDB0060932)
Liver (HMDB: HMDB0060932)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060932)

Cellular substructure

Cytoplasm (HMDB: HMDB0060932)

Source

Endogenous

Endogenous (HMDB: HMDB0060932)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	1.78	ALOGPS
logP	0.93	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.51	ChemAxon
pKa (Strongest Basic)	6.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.15 m³·mol⁻¹	ChemAxon
Polarizability	48.96 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]+	205.065	31661259
DarkChem	[M-H]-	202.632	31661259
DeepCCS	[M+H]+	205.792	30932474
DeepCCS	[M-H]-	203.396	30932474
DeepCCS	[M-2H]-	236.497	30932474
DeepCCS	[M+Na]+	211.794	30932474
AllCCS	[M+H]+	205.9	32859911
AllCCS	[M+H-H2O]+	203.8	32859911
AllCCS	[M+NH4]+	207.9	32859911
AllCCS	[M+Na]+	208.5	32859911
AllCCS	[M-H]-	201.3	32859911
AllCCS	[M+Na-2H]-	202.1	32859911
AllCCS	[M+HCOO]-	203.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl sildenafil (UK-103,320)	CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1	4911.4	Standard polar	33892256
N-Desmethyl sildenafil (UK-103,320)	CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1	3798.9	Standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320)	CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1	4209.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O	3810.6	Semi standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O	3842.0	Standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O	5788.9	Standard polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2	CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O	4007.4	Semi standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2	CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O	3940.5	Standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2	CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O	5666.6	Standard polar	33892256
N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O	3994.3	Semi standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O	4063.9	Standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O	5282.9	Standard polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O	3930.5	Semi standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O	4112.9	Standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O	5655.7	Standard polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2	CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O	4178.3	Semi standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2	CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O	4178.3	Standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2	CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O	5709.4	Standard polar	33892256
N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O	4276.6	Semi standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O	4550.5	Standard non polar	33892256
N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1	CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O	5266.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) GC-MS (Non-derivatized) - 70eV, Positive	splash10-06su-9003200000-8c16e5a5f7c9fd1beeec	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 10V, Positive-QTOF	splash10-03di-0002900000-f0e3e78187afd93a4841	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 20V, Positive-QTOF	splash10-03dr-3235900000-dd447bbc8e39fc99d123	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 40V, Positive-QTOF	splash10-014u-5092100000-0b6e7602ec4d55ff9d63	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 10V, Negative-QTOF	splash10-0a4i-0000900000-f84c25238b265817528b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 20V, Negative-QTOF	splash10-053s-0303900000-1fb03e95cc836e9368b4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 40V, Negative-QTOF	splash10-0002-9716200000-b08598b77f5c8dcf3abf	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6426858

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-Desmethyl sildenafil (UK-103,320) (HMDB0060932)

MOL for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

3D MOL for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

3D SDF for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

3D-SDF for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

PDB for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

3D PDB for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

SMILES for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

INCHI for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

Structure for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

3D Structure for HMDB0060932 (N-Desmethyl sildenafil (UK-103,320))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra