data_VDN
# 
_chem_comp.id                                    VDN 
_chem_comp.name                                  2-{2-ETHOXY-5-[(4-ETHYLPIPERAZIN-1-YL)SULFONYL]PHENYL}-5-METHYL-7-PROPYLIMIDAZO[5,1-F][1,2,4]TRIAZIN-4(1H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H32 N6 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "VARDENAFIL, LEVITRA" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-07-10 
_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                        488.603 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     VDN 
_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        1UHO 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
VDN C1   C1   C 0 1 N N N 5.649  65.412 87.021 -5.759 -0.180 2.537  C1   VDN 1  
VDN C2   C2   C 0 1 N N N 5.743  66.607 86.066 -4.840 0.193  1.373  C2   VDN 2  
VDN O3   O3   O 0 1 N N N 4.448  66.652 85.451 -3.477 0.019  1.766  O3   VDN 3  
VDN C4   C4   C 0 1 Y N N 4.008  67.563 84.512 -2.714 0.363  0.699  C4   VDN 4  
VDN C5   C5   C 0 1 Y N N 4.736  68.613 83.976 -3.312 0.785  -0.478 C5   VDN 5  
VDN C6   C6   C 0 1 Y N N 4.148  69.523 82.977 -2.534 1.135  -1.563 C6   VDN 6  
VDN C7   C7   C 0 1 Y N N 2.847  69.329 82.555 -1.152 1.074  -1.484 C7   VDN 7  
VDN C8   C8   C 0 1 Y N N 2.044  68.207 83.113 -0.540 0.664  -0.320 C8   VDN 8  
VDN C9   C9   C 0 1 Y N N 2.548  67.357 84.027 -1.315 0.306  0.786  C9   VDN 9  
VDN S10  S10  S 0 1 N N N 2.096  70.361 81.367 -0.173 1.525  -2.878 S10  VDN 10 
VDN O11  O11  O 0 1 N N N 2.700  70.039 80.092 -0.996 2.369  -3.671 O11  VDN 11 
VDN O12  O12  O 0 1 N N N 0.674  70.087 81.440 1.102  1.872  -2.358 O12  VDN 12 
VDN C13  C13  C 0 1 N N N 2.476  77.196 80.332 2.694  -2.940 -6.821 C13  VDN 13 
VDN N14  N14  N 0 1 N N N 2.396  71.942 81.781 0.065  0.155  -3.778 N14  VDN 14 
VDN C15  C15  C 0 1 N N N 1.175  72.726 82.109 1.225  -0.716 -3.540 C15  VDN 15 
VDN C16  C16  C 0 1 N N N 1.482  74.208 82.424 1.900  -1.007 -4.880 C16  VDN 16 
VDN N17  N17  N 0 1 N N N 2.190  74.844 81.289 0.923  -1.584 -5.810 N17  VDN 17 
VDN C18  C18  C 0 1 N N N 3.439  74.092 81.010 -0.065 -0.542 -6.109 C18  VDN 18 
VDN C19  C19  C 0 1 N N N 3.172  72.602 80.707 -0.873 -0.223 -4.847 C19  VDN 19 
VDN C20  C20  C 0 1 N N N 2.446  76.265 81.569 1.642  -1.856 -7.062 C20  VDN 20 
VDN C21  C21  C 0 1 Y N N 1.702  66.271 84.553 -0.667 -0.133 2.034  C21  VDN 21 
VDN N22  N22  N 0 1 Y N N 1.597  66.025 85.891 -1.199 -1.132 2.706  N22  VDN 22 
VDN C23  C23  C 0 1 Y N N 0.815  65.023 86.515 -0.655 -1.575 3.855  C23  VDN 23 
VDN C24  C24  C 0 1 Y N N 0.057  64.195 85.542 0.564  -0.928 4.357  C24  VDN 24 
VDN N25  N25  N 0 1 Y N N 0.217  64.508 84.151 1.101  0.118  3.631  N25  VDN 25 
VDN N26  N26  N 0 1 Y N N 0.997  65.498 83.691 0.462  0.510  2.450  N26  VDN 26 
VDN O27  O27  O 0 1 N N N 0.789  64.885 87.721 -1.161 -2.501 4.464  O27  VDN 27 
VDN C28  C28  C 0 1 Y N N -0.835 63.129 85.464 1.364  -1.101 5.440  C28  VDN 28 
VDN N29  N29  N 0 1 Y N N -1.203 62.803 84.110 2.347  -0.199 5.366  N29  VDN 29 
VDN C30  C30  C 0 1 Y N N -0.545 63.662 83.402 2.197  0.528  4.287  C30  VDN 30 
VDN C31  C31  C 0 1 N N N -1.383 62.372 86.669 1.177  -2.126 6.530  C31  VDN 31 
VDN C32  C32  C 0 1 N N N -0.544 63.806 81.886 3.105  1.650  3.856  C32  VDN 32 
VDN C33  C33  C 0 1 N N N 0.581  63.056 81.129 4.217  1.092  2.964  C33  VDN 33 
VDN C34  C34  C 0 1 N N N 0.200  61.591 80.911 5.140  2.232  2.526  C34  VDN 34 
VDN H11  1H1  H 0 1 N N N 5.336  64.458 86.536 -6.798 -0.048 2.237  H11  VDN 35 
VDN H12  2H1  H 0 1 N N N 6.656  65.377 87.499 -5.591 -1.221 2.813  H12  VDN 36 
VDN H13  3H1  H 0 1 N N N 4.799  65.463 87.741 -5.543 0.461  3.391  H13  VDN 37 
VDN H21  1H2  H 0 1 N N N 6.593  66.556 85.347 -5.008 1.234  1.097  H21  VDN 38 
VDN H22  2H2  H 0 1 N N N 6.056  67.561 86.551 -5.056 -0.448 0.519  H22  VDN 39 
VDN H5   H5   H 0 1 N N N 5.771  68.723 84.340 -4.389 0.835  -0.548 H5   VDN 40 
VDN H6   H6   H 0 1 N N N 4.696  70.371 82.534 -3.005 1.459  -2.479 H6   VDN 41 
VDN H8   H8   H 0 1 N N N 1.001  67.990 82.829 0.537  0.619  -0.263 H8   VDN 42 
VDN H131 1H13 H 0 0 N N N 1.531  77.087 79.750 3.228  -3.141 -7.750 H131 VDN 43 
VDN H132 2H13 H 0 0 N N N 2.670  78.273 80.544 3.400  -2.598 -6.064 H132 VDN 44 
VDN H133 3H13 H 0 0 N N N 3.213  76.816 79.587 2.205  -3.851 -6.477 H133 VDN 45 
VDN H151 1H15 H 0 0 N N N 0.606  72.250 82.942 1.930  -0.219 -2.874 H151 VDN 46 
VDN H152 2H15 H 0 0 N N N 0.415  72.639 81.298 0.889  -1.650 -3.088 H152 VDN 47 
VDN H161 1H16 H 0 0 N N N 2.046  74.321 83.380 2.718  -1.712 -4.730 H161 VDN 48 
VDN H162 2H16 H 0 0 N N N 0.562  74.771 82.706 2.293  -0.079 -5.295 H162 VDN 49 
VDN H181 1H18 H 0 0 N N N 4.173  74.208 81.841 -0.738 -0.894 -6.891 H181 VDN 50 
VDN H182 2H18 H 0 0 N N N 4.022  74.571 80.189 0.446  0.357  -6.449 H182 VDN 51 
VDN H191 1H19 H 0 0 N N N 2.677  72.475 79.716 -1.440 -1.103 -4.542 H191 VDN 52 
VDN H192 2H19 H 0 0 N N N 4.122  72.056 80.503 -1.555 0.602  -5.046 H192 VDN 53 
VDN H201 1H20 H 0 0 N N N 1.709  76.645 82.314 0.936  -2.197 -7.819 H201 VDN 54 
VDN H202 2H20 H 0 0 N N N 3.391  76.374 82.151 2.131  -0.944 -7.406 H202 VDN 55 
VDN H26  H26  H 0 1 N N N 1.646  65.105 83.009 0.822  1.242  1.926  H26  VDN 56 
VDN H311 1H31 H 0 0 N N N -1.841 63.130 87.347 0.559  -1.704 7.323  H311 VDN 57 
VDN H312 2H31 H 0 0 N N N -2.097 61.518 86.607 0.688  -3.009 6.118  H312 VDN 58 
VDN H313 3H31 H 0 0 N N N -0.504 62.017 87.256 2.149  -2.405 6.936  H313 VDN 59 
VDN H321 1H32 H 0 0 N N N -0.530 64.886 81.610 2.530  2.390  3.299  H321 VDN 60 
VDN H322 2H32 H 0 0 N N N -1.538 63.507 81.478 3.546  2.119  4.735  H322 VDN 61 
VDN H331 1H33 H 0 0 N N N 1.564  63.155 81.645 4.792  0.352  3.521  H331 VDN 62 
VDN H332 2H33 H 0 0 N N N 0.844  63.562 80.171 3.776  0.623  2.085  H332 VDN 63 
VDN H341 1H34 H 0 0 N N N -0.783 61.492 80.395 5.931  1.834  1.891  H341 VDN 64 
VDN H342 2H34 H 0 0 N N N 1.010  61.051 80.366 4.564  2.971  1.970  H342 VDN 65 
VDN H343 3H34 H 0 0 N N N -0.062 61.085 81.869 5.580  2.701  3.406  H343 VDN 66 
# 
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 
VDN C1  C2   SING N N 1  
VDN C1  H11  SING N N 2  
VDN C1  H12  SING N N 3  
VDN C1  H13  SING N N 4  
VDN C2  O3   SING N N 5  
VDN C2  H21  SING N N 6  
VDN C2  H22  SING N N 7  
VDN O3  C4   SING N N 8  
VDN C4  C5   DOUB Y N 9  
VDN C4  C9   SING Y N 10 
VDN C5  C6   SING Y N 11 
VDN C5  H5   SING N N 12 
VDN C6  C7   DOUB Y N 13 
VDN C6  H6   SING N N 14 
VDN C7  C8   SING Y N 15 
VDN C7  S10  SING N N 16 
VDN C8  C9   DOUB Y N 17 
VDN C8  H8   SING N N 18 
VDN C9  C21  SING N N 19 
VDN S10 O11  DOUB N N 20 
VDN S10 O12  DOUB N N 21 
VDN S10 N14  SING N N 22 
VDN C13 C20  SING N N 23 
VDN C13 H131 SING N N 24 
VDN C13 H132 SING N N 25 
VDN C13 H133 SING N N 26 
VDN N14 C15  SING N N 27 
VDN N14 C19  SING N N 28 
VDN C15 C16  SING N N 29 
VDN C15 H151 SING N N 30 
VDN C15 H152 SING N N 31 
VDN C16 N17  SING N N 32 
VDN C16 H161 SING N N 33 
VDN C16 H162 SING N N 34 
VDN N17 C18  SING N N 35 
VDN N17 C20  SING N N 36 
VDN C18 C19  SING N N 37 
VDN C18 H181 SING N N 38 
VDN C18 H182 SING N N 39 
VDN C19 H191 SING N N 40 
VDN C19 H192 SING N N 41 
VDN C20 H201 SING N N 42 
VDN C20 H202 SING N N 43 
VDN C21 N22  DOUB Y N 44 
VDN C21 N26  SING Y N 45 
VDN N22 C23  SING Y N 46 
VDN C23 C24  SING Y N 47 
VDN C23 O27  DOUB N N 48 
VDN C24 N25  SING Y N 49 
VDN C24 C28  DOUB Y N 50 
VDN N25 N26  SING Y N 51 
VDN N25 C30  SING Y N 52 
VDN N26 H26  SING N N 53 
VDN C28 N29  SING Y N 54 
VDN C28 C31  SING N N 55 
VDN N29 C30  DOUB Y N 56 
VDN C30 C32  SING N N 57 
VDN C31 H311 SING N N 58 
VDN C31 H312 SING N N 59 
VDN C31 H313 SING N N 60 
VDN C32 C33  SING N N 61 
VDN C32 H321 SING N N 62 
VDN C32 H322 SING N N 63 
VDN C33 C34  SING N N 64 
VDN C33 H331 SING N N 65 
VDN C33 H332 SING N N 66 
VDN C34 H341 SING N N 67 
VDN C34 H342 SING N N 68 
VDN C34 H343 SING N N 69 
# 
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 
VDN SMILES           ACDLabs              10.04 O=C2N=C(Nn1c(nc(c12)C)CCC)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC)CC4                                                                                                                  
VDN InChI            InChI                1.02b InChI=1/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)/f/h26H 
VDN InChIKey         InChI                1.02b SECKRCOLJRRGGV-HXTKINSTCG                                                                                                                                                     
VDN SMILES_CANONICAL CACTVS               3.341 CCCc1nc(C)c2n1NC(=NC2=O)c3cc(ccc3OCC)[S](=O)(=O)N4CCN(CC)CC4                                                                                                                  
VDN SMILES           CACTVS               3.341 CCCc1nc(C)c2n1NC(=NC2=O)c3cc(ccc3OCC)[S](=O)(=O)N4CCN(CC)CC4                                                                                                                  
VDN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCc1nc(c2n1NC(=NC2=O)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC4)CC)C                                                                                                                    
VDN SMILES           "OpenEye OEToolkits" 1.5.0 CCCc1nc(c2n1NC(=NC2=O)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC4)CC)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 
VDN "SYSTEMATIC NAME" ACDLabs              10.04 2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one 
VDN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonyl-phenyl]-5-methyl-7-propyl-1H-imidazo[5,1-f][1,2,4]triazin-4-one  
# 
