data_VIA
# 
_chem_comp.id                                    VIA 
_chem_comp.name                                  5-{2-ETHOXY-5-[(4-METHYLPIPERAZIN-1-YL)SULFONYL]PHENYL}-1-METHYL-3-PROPYL-1H,6H,7H-PYRAZOLO[4,3-D]PYRIMIDIN-7-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H30 N6 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "SILDENAFIL, VIAGRA" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-05-07 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        474.576 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     VIA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1UDT 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
VIA C34  C34  C 0 1 N N N -0.132 61.467 80.120 2.732  2.531  5.972  C34  VIA 1  
VIA C33  C33  C 0 1 N N N -0.169 61.792 81.589 1.592  1.545  5.707  C33  VIA 2  
VIA C32  C32  C 0 1 N N N -1.261 62.864 81.927 0.475  2.252  4.937  C32  VIA 3  
VIA C30  C30  C 0 1 Y N N -1.114 63.031 83.405 -0.647 1.281  4.677  C30  VIA 4  
VIA N29  N29  N 0 1 Y N N -1.798 62.280 84.370 -1.669 1.071  5.462  N29  VIA 5  
VIA N28  N28  N 0 1 Y N N -1.414 62.696 85.612 -2.504 0.102  4.891  N28  VIA 6  
VIA C31  C31  C 0 1 N N N -1.948 62.111 86.845 -3.752 -0.406 5.466  C31  VIA 7  
VIA C24  C24  C 0 1 Y N N -0.495 63.700 85.440 -1.949 -0.284 3.703  C24  VIA 8  
VIA C23  C23  C 0 1 Y N N 0.260  64.519 86.346 -2.317 -1.207 2.697  C23  VIA 9  
VIA O27  O27  O 0 1 N N N 0.180  64.422 87.549 -3.337 -1.866 2.797  O27  VIA 10 
VIA N22  N22  N 0 1 Y N N 1.125  65.474 85.816 -1.510 -1.339 1.621  N22  VIA 11 
VIA C21  C21  C 0 1 Y N N 1.308  65.684 84.442 -0.367 -0.594 1.518  C21  VIA 12 
VIA N26  N26  N 0 1 Y N N 0.597  64.907 83.520 -0.014 0.264  2.444  N26  VIA 13 
VIA C25  C25  C 0 1 Y N N -0.293 63.928 84.046 -0.771 0.455  3.543  C25  VIA 14 
VIA C9   C9   C 0 1 Y N N 2.223  66.702 84.058 0.493  -0.762 0.331  C9   VIA 15 
VIA C8   C8   C 0 1 Y N N 1.731  67.655 83.084 -0.077 -0.919 -0.933 C8   VIA 16 
VIA C7   C7   C 0 1 Y N N 2.568  68.758 82.617 0.732  -1.076 -2.038 C7   VIA 17 
VIA C6   C6   C 0 1 Y N N 3.952  68.860 83.180 2.110  -1.078 -1.899 C6   VIA 18 
VIA C5   C5   C 0 1 Y N N 4.466  67.911 84.162 2.687  -0.924 -0.654 C5   VIA 19 
VIA C4   C4   C 0 1 Y N N 3.609  66.806 84.633 1.887  -0.759 0.466  C4   VIA 20 
VIA O3   O3   O 0 1 N N N 4.019  65.830 85.620 2.453  -0.607 1.690  O3   VIA 21 
VIA C2   C2   C 0 1 N N N 5.304  65.803 86.273 3.869  -0.661 1.501  C2   VIA 22 
VIA C1   C1   C 0 1 N N N 5.234  64.623 87.228 4.571  -0.495 2.850  C1   VIA 23 
VIA S10  S10  S 0 1 N N N 2.023  69.831 81.561 0.010  -1.275 -3.633 S10  VIA 24 
VIA O11  O11  O 0 1 N N N 2.313  69.600 80.294 0.996  -1.923 -4.424 O11  VIA 25 
VIA O12  O12  O 0 1 N N N 0.712  69.861 81.611 -1.307 -1.756 -3.403 O12  VIA 26 
VIA N14  N14  N 0 1 N N N 2.690  71.159 82.127 -0.170 0.235  -4.286 N14  VIA 27 
VIA C19  C19  C 0 1 N N N 1.724  72.087 82.963 0.897  0.844  -5.096 C19  VIA 28 
VIA C18  C18  C 0 1 N N N 0.820  73.057 82.178 0.276  1.378  -6.391 C18  VIA 29 
VIA N17  N17  N 0 1 N N N 1.426  73.686 80.956 -0.808 2.311  -6.067 N17  VIA 30 
VIA C20  C20  C 0 1 N N N 1.557  75.156 81.201 -1.340 2.801  -7.346 C20  VIA 31 
VIA C16  C16  C 0 1 N N N 2.752  73.145 80.416 -1.881 1.535  -5.435 C16  VIA 32 
VIA C15  C15  C 0 1 N N N 3.539  72.092 81.285 -1.405 1.009  -4.081 C15  VIA 33 
VIA H341 1H34 H 0 0 N N N 0.001  62.388 79.506 3.528  2.027  6.520  H341 VIA 34 
VIA H342 2H34 H 0 0 N N N 0.645  60.704 79.880 3.121  2.899  5.023  H342 VIA 35 
VIA H343 3H34 H 0 0 N N N -1.136 61.152 79.750 2.359  3.368  6.561  H343 VIA 36 
VIA H331 1H33 H 0 0 N N N 0.835  62.107 81.959 1.966  0.708  5.117  H331 VIA 37 
VIA H332 2H33 H 0 0 N N N -0.302 60.871 82.204 1.203  1.176  6.656  H332 VIA 38 
VIA H321 1H32 H 0 0 N N N -2.291 62.605 81.587 0.101  3.089  5.527  H321 VIA 39 
VIA H322 2H32 H 0 0 N N N -1.185 63.809 81.341 0.864  2.621  3.988  H322 VIA 40 
VIA H311 1H31 H 0 0 N N N -1.780 61.010 86.794 -4.586 0.205  5.123  H311 VIA 41 
VIA H312 2H31 H 0 0 N N N -1.634 62.451 87.860 -3.904 -1.438 5.149  H312 VIA 42 
VIA H313 3H31 H 0 0 N N N -3.060 62.184 86.796 -3.694 -0.365 6.554  H313 VIA 43 
VIA H22  H22  H 0 1 N N N 1.654  66.051 86.470 -1.742 -1.966 0.918  H22  VIA 44 
VIA H8   H8   H 0 1 N N N 0.706  67.539 82.693 -1.151 -0.919 -1.045 H8   VIA 45 
VIA H6   H6   H 0 1 N N N 4.624  69.672 82.856 2.736  -1.202 -2.770 H6   VIA 46 
VIA H5   H5   H 0 1 N N N 5.494  68.028 84.545 3.762  -0.927 -0.554 H5   VIA 47 
VIA H21  1H2  H 0 1 N N N 5.582  66.765 86.763 4.141  -1.622 1.065  H21  VIA 48 
VIA H22A 2H2  H 0 0 N N N 6.168  65.764 85.569 4.176  0.141  0.830  H22A VIA 49 
VIA H11  1H1  H 0 1 N N N 4.956  63.661 86.738 5.650  -0.536 2.705  H11  VIA 50 
VIA H12  2H1  H 0 1 N N N 6.228  64.602 87.733 4.299  0.465  3.286  H12  VIA 51 
VIA H13  3H1  H 0 1 N N N 4.370  64.662 87.932 4.263  -1.298 3.520  H13  VIA 52 
VIA H191 1H19 H 0 0 N N N 2.319  72.660 83.712 1.355  1.664  -4.543 H191 VIA 53 
VIA H192 2H19 H 0 0 N N N 1.095  71.457 83.634 1.651  0.094  -5.333 H192 VIA 54 
VIA H181 1H18 H 0 0 N N N 0.437  73.851 82.860 1.039  1.896  -6.972 H181 VIA 55 
VIA H182 2H18 H 0 0 N N N -0.134 72.547 81.906 -0.121 0.547  -6.973 H182 VIA 56 
VIA H201 1H20 H 0 0 N N N 2.127  75.387 82.131 -2.153 3.501  -7.158 H201 VIA 57 
VIA H202 2H20 H 0 0 N N N 2.007  75.623 80.294 -0.548 3.304  -7.900 H202 VIA 58 
VIA H203 3H20 H 0 0 N N N 0.591  75.630 81.494 -1.713 1.959  -7.930 H203 VIA 59 
VIA H161 1H16 H 0 0 N N N 3.427  74.002 80.184 -2.754 2.172  -5.291 H161 VIA 60 
VIA H162 2H16 H 0 0 N N N 2.585  72.723 79.398 -2.146 0.694  -6.075 H162 VIA 61 
VIA H151 1H15 H 0 0 N N N 4.222  71.498 80.634 -2.172 0.369  -3.645 H151 VIA 62 
VIA H152 2H15 H 0 0 N N N 4.283  72.614 81.931 -1.200 1.845  -3.413 H152 VIA 63 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
VIA C34 C33  SING N N 1  
VIA C34 H341 SING N N 2  
VIA C34 H342 SING N N 3  
VIA C34 H343 SING N N 4  
VIA C33 C32  SING N N 5  
VIA C33 H331 SING N N 6  
VIA C33 H332 SING N N 7  
VIA C32 C30  SING N N 8  
VIA C32 H321 SING N N 9  
VIA C32 H322 SING N N 10 
VIA C30 N29  DOUB Y N 11 
VIA C30 C25  SING Y N 12 
VIA N29 N28  SING Y N 13 
VIA N28 C31  SING N N 14 
VIA N28 C24  SING Y N 15 
VIA C31 H311 SING N N 16 
VIA C31 H312 SING N N 17 
VIA C31 H313 SING N N 18 
VIA C24 C23  SING Y N 19 
VIA C24 C25  DOUB Y N 20 
VIA C23 O27  DOUB N N 21 
VIA C23 N22  SING Y N 22 
VIA N22 C21  SING Y N 23 
VIA N22 H22  SING N N 24 
VIA C21 N26  DOUB Y N 25 
VIA C21 C9   SING N N 26 
VIA N26 C25  SING Y N 27 
VIA C9  C8   DOUB Y N 28 
VIA C9  C4   SING Y N 29 
VIA C8  C7   SING Y N 30 
VIA C8  H8   SING N N 31 
VIA C7  C6   DOUB Y N 32 
VIA C7  S10  SING N N 33 
VIA C6  C5   SING Y N 34 
VIA C6  H6   SING N N 35 
VIA C5  C4   DOUB Y N 36 
VIA C5  H5   SING N N 37 
VIA C4  O3   SING N N 38 
VIA O3  C2   SING N N 39 
VIA C2  C1   SING N N 40 
VIA C2  H21  SING N N 41 
VIA C2  H22A SING N N 42 
VIA C1  H11  SING N N 43 
VIA C1  H12  SING N N 44 
VIA C1  H13  SING N N 45 
VIA S10 O11  DOUB N N 46 
VIA S10 O12  DOUB N N 47 
VIA S10 N14  SING N N 48 
VIA N14 C19  SING N N 49 
VIA N14 C15  SING N N 50 
VIA C19 C18  SING N N 51 
VIA C19 H191 SING N N 52 
VIA C19 H192 SING N N 53 
VIA C18 N17  SING N N 54 
VIA C18 H181 SING N N 55 
VIA C18 H182 SING N N 56 
VIA N17 C20  SING N N 57 
VIA N17 C16  SING N N 58 
VIA C20 H201 SING N N 59 
VIA C20 H202 SING N N 60 
VIA C20 H203 SING N N 61 
VIA C16 C15  SING N N 62 
VIA C16 H161 SING N N 63 
VIA C16 H162 SING N N 64 
VIA C15 H151 SING N N 65 
VIA C15 H152 SING N N 66 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
VIA SMILES           ACDLabs              10.04 O=S(=O)(N1CCN(C)CC1)c4cc(C2=Nc3c(C(=O)N2)n(nc3CCC)C)c(OCC)cc4                                                                                                             
VIA InChI            InChI                1.02b InChI=1/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)/f/h24H 
VIA InChIKey         InChI                1.02b BNRNXUUZRGQAQC-LQFNOIFHCL                                                                                                                                                 
VIA SMILES_CANONICAL CACTVS               3.341 CCCc1nn(C)c2C(=O)NC(=Nc12)c3cc(ccc3OCC)[S](=O)(=O)N4CCN(C)CC4                                                                                                             
VIA SMILES           CACTVS               3.341 CCCc1nn(C)c2C(=O)NC(=Nc12)c3cc(ccc3OCC)[S](=O)(=O)N4CCN(C)CC4                                                                                                             
VIA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCc1c2c(n(n1)C)C(=O)NC(=N2)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC4)C                                                                                                             
VIA SMILES           "OpenEye OEToolkits" 1.5.0 CCCc1c2c(n(n1)C)C(=O)NC(=N2)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC4)C                                                                                                             
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
VIA "SYSTEMATIC NAME" ACDLabs              10.04 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 
VIA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-1-methyl-3-propyl-6H-pyrazolo[5,4-e]pyrimidin-7-one              
# 
