data_PYN
# 
_chem_comp.id                                    PYN 
_chem_comp.name                                  3-PYRROLIDIN-1-YL-N-[6-(3-PYRROLIDIN-1-YL-PROPIONYLAMINO)-ACRIDIN-3-YL]-PROPIONAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C27 H33 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-02-27 
_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                        459.583 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PYN 
_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        1L1H 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
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 
PYN C    C    C 0 1 Y N N 16.326 15.548 5.183  -2.518 -0.199 -1.087  C    PYN 1  
PYN C1   C1   C 0 1 Y N N 17.213 16.228 6.145  -1.094 -0.247 -0.738  C1   PYN 2  
PYN C2   C2   C 0 1 Y N N 15.002 15.358 5.510  -3.466 0.029  -0.086  C2   PYN 3  
PYN C3   C3   C 0 1 Y N N 14.541 15.834 6.725  -3.007 0.204  1.221   C3   PYN 4  
PYN C4   C4   C 0 1 Y N N 15.495 16.459 7.647  -1.568 0.143  1.498   C4   PYN 5  
PYN C5   C5   C 0 1 Y N N 14.980 16.995 8.850  -1.131 0.327  2.824   C5   PYN 6  
PYN C6   C6   C 0 1 Y N N 13.640 16.909 9.163  -2.051 0.545  3.816   C6   PYN 7  
PYN C7   C7   C 0 1 Y N N 12.746 16.174 8.306  -3.424 0.602  3.542   C7   PYN 8  
PYN C8   C8   C 0 1 Y N N 13.215 15.666 7.122  -3.903 0.437  2.284   C8   PYN 9  
PYN C9   C9   C 0 1 Y N N 16.857 15.098 3.981  -2.904 -0.385 -2.430  C9   PYN 10 
PYN C10  C10  C 0 1 Y N N 18.197 15.261 3.693  -1.958 -0.605 -3.377  C10  PYN 11 
PYN C11  C11  C 0 1 Y N N 19.033 16.070 4.535  -0.596 -0.653 -3.052  C11  PYN 12 
PYN C12  C12  C 0 1 Y N N 18.562 16.495 5.765  -0.159 -0.479 -1.765  C12  PYN 13 
PYN N    N    N 0 1 Y N N 16.784 16.595 7.353  -0.696 -0.076 0.518   N    PYN 14 
PYN N13  N13  N 0 1 N N N 13.051 17.534 10.308 -1.609 0.721  5.128   N13  PYN 15 
PYN C14  C14  C 0 1 N N N 13.758 18.189 11.295 -0.538 0.036  5.576   C14  PYN 16 
PYN C15  C15  C 0 1 N N N 12.841 18.745 12.403 0.012  0.315  6.951   C15  PYN 17 
PYN C16  C16  C 0 1 N N N 13.660 19.554 13.374 1.222  -0.585 7.207   C16  PYN 18 
PYN O14  O14  O 0 1 N N N 14.968 18.325 11.312 -0.015 -0.799 4.871   O14  PYN 19 
PYN N1   N1   N 0 1 N N N 20.351 16.422 4.064  0.338  -0.883 -4.064  N1   PYN 20 
PYN C17  C17  C 0 1 N N N 21.310 17.191 4.679  0.123  -0.397 -5.302  C17  PYN 21 
PYN C18  C18  C 0 1 N N N 22.225 17.992 3.736  1.067  -0.748 -6.424  C18  PYN 22 
PYN C19  C19  C 0 1 N N N 23.470 18.417 4.526  0.599  -0.072 -7.714  C19  PYN 23 
PYN O1   O1   O 0 1 N N N 21.443 17.267 5.880  -0.828 0.322  -5.514  O1   PYN 24 
PYN C21  C21  C 0 1 N N N 11.872 18.926 15.149 2.917  -1.209 8.729   C21  PYN 25 
PYN N22  N22  N 0 1 N N N 13.232 19.559 14.775 1.760  -0.313 8.547   N22  PYN 26 
PYN C23  C23  C 0 1 N N N 13.222 20.995 15.419 2.243  1.083  8.536   C23  PYN 27 
PYN C24  C24  C 0 1 N N N 11.473 19.634 16.449 4.169  -0.317 8.861   C24  PYN 28 
PYN C25  C25  C 0 1 N N N 12.403 20.782 16.708 3.582  1.044  9.314   C25  PYN 29 
PYN C26  C26  C 0 1 N N N 25.518 19.844 4.294  1.014  0.264  -10.014 C26  PYN 30 
PYN N27  N27  N 0 1 N N N 24.603 18.777 3.598  1.519  -0.415 -8.807  N27  PYN 31 
PYN C28  C28  C 0 1 N N N 24.038 19.508 2.319  2.832  0.165  -8.455  C28  PYN 32 
PYN C29  C29  C 0 1 N N N 25.916 20.787 3.148  2.081  1.296  -10.438 C29  PYN 33 
PYN C30  C30  C 0 1 N N N 25.425 20.160 1.846  3.376  0.749  -9.782  C30  PYN 34 
PYN H21  1H2  H 0 1 N N N 14.325 14.836 4.813  -4.520 0.069  -0.317  H21  PYN 35 
PYN H51  1H5  H 0 1 N N N 15.647 17.498 9.570  -0.077 0.292  3.059   H51  PYN 36 
PYN H71  1H7  H 0 1 N N N 11.687 15.998 8.560  -4.116 0.780  4.352   H71  PYN 37 
PYN H81  1H8  H 0 1 N N N 12.513 15.112 6.477  -4.966 0.485  2.098   H81  PYN 38 
PYN H91  1H9  H 0 1 N N N 16.204 14.603 3.243  -3.949 -0.353 -2.704  H91  PYN 39 
PYN H101 1H10 H 0 0 N N N 18.595 14.751 2.800  -2.261 -0.747 -4.403  H101 PYN 40 
PYN H121 1H12 H 0 0 N N N 19.252 17.039 6.433  0.896  -0.521 -1.539  H121 PYN 41 
PYN HN1  1HN  H 0 1 N N N 12.039 17.511 10.431 -2.073 1.335  5.718   HN1  PYN 42 
PYN H151 1H15 H 0 0 N N N 12.259 17.941 12.911 0.317  1.359  7.015   H151 PYN 43 
PYN H152 2H15 H 0 0 N N N 11.984 19.326 11.989 -0.755 0.113  7.698   H152 PYN 44 
PYN H161 1H16 H 0 0 N N N 13.737 20.604 13.007 0.918  -1.630 7.143   H161 PYN 45 
PYN H162 2H16 H 0 0 N N N 14.726 19.234 13.315 1.990  -0.383 6.460   H162 PYN 46 
PYN HN11 1HN1 H 0 0 N N N 20.652 16.073 3.154  1.141  -1.393 -3.875  HN11 PYN 47 
PYN H181 1H18 H 0 0 N N N 21.703 18.854 3.259  2.070  -0.403 -6.175  H181 PYN 48 
PYN H182 2H18 H 0 0 N N N 22.476 17.434 2.804  1.078  -1.829 -6.563  H182 PYN 49 
PYN H191 1H19 H 0 0 N N N 23.774 17.638 5.264  -0.403 -0.417 -7.962  H191 PYN 50 
PYN H192 2H19 H 0 0 N N N 23.243 19.245 5.238  0.588  1.008  -7.574  H192 PYN 51 
PYN H211 1H21 H 0 0 N N N 11.890 17.814 15.221 2.787  -1.802 9.635   H211 PYN 52 
PYN H212 2H21 H 0 0 N N N 11.104 18.983 14.343 3.017  -1.865 7.865   H212 PYN 53 
PYN H231 1H23 H 0 0 N N N 12.842 21.804 14.752 2.409  1.419  7.513   H231 PYN 54 
PYN H232 2H23 H 0 0 N N N 14.230 21.445 15.575 1.530  1.735  9.040   H232 PYN 55 
PYN H241 1H24 H 0 0 N N N 11.425 18.930 17.312 4.848  -0.715 9.615   H241 PYN 56 
PYN H242 2H24 H 0 0 N N N 10.405 19.953 16.442 4.674  -0.218 7.900   H242 PYN 57 
PYN H251 1H25 H 0 0 N N N 11.878 21.704 17.051 3.409  1.056  10.390  H251 PYN 58 
PYN H252 2H25 H 0 0 N N N 13.039 20.636 17.613 4.231  1.868  9.016   H252 PYN 59 
PYN H261 1H26 H 0 0 N N N 26.379 19.415 4.857  0.863  -0.461 -10.813 H261 PYN 60 
PYN H262 2H26 H 0 0 N N N 25.048 20.354 5.167  0.076  0.772  -9.789  H262 PYN 61 
PYN H281 1H28 H 0 0 N N N 23.175 20.199 2.467  2.712  0.955  -7.714  H281 PYN 62 
PYN H282 2H28 H 0 0 N N N 23.490 18.883 1.576  3.501  -0.609 -8.079  H282 PYN 63 
PYN H291 1H29 H 0 0 N N N 27.007 21.019 3.135  2.180  1.324  -11.523 H291 PYN 64 
PYN H292 2H29 H 0 0 N N N 25.547 21.829 3.295  1.839  2.284  -10.046 H292 PYN 65 
PYN H301 1H30 H 0 0 N N N 25.355 20.855 0.977  3.825  -0.031 -10.397 H301 PYN 66 
PYN H302 2H30 H 0 0 N N N 26.139 19.460 1.354  4.088  1.552  -9.593  H302 PYN 67 
# 
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 
PYN C   C1   DOUB Y N 1  
PYN C   C2   SING Y N 2  
PYN C   C9   SING Y N 3  
PYN C1  C12  SING Y N 4  
PYN C1  N    SING Y N 5  
PYN C2  C3   DOUB Y N 6  
PYN C2  H21  SING N N 7  
PYN C3  C4   SING Y N 8  
PYN C3  C8   SING Y N 9  
PYN C4  C5   SING Y N 10 
PYN C4  N    DOUB Y N 11 
PYN C5  C6   DOUB Y N 12 
PYN C5  H51  SING N N 13 
PYN C6  C7   SING Y N 14 
PYN C6  N13  SING N N 15 
PYN C7  C8   DOUB Y N 16 
PYN C7  H71  SING N N 17 
PYN C8  H81  SING N N 18 
PYN C9  C10  DOUB Y N 19 
PYN C9  H91  SING N N 20 
PYN C10 C11  SING Y N 21 
PYN C10 H101 SING N N 22 
PYN C11 C12  DOUB Y N 23 
PYN C11 N1   SING N N 24 
PYN C12 H121 SING N N 25 
PYN N13 C14  SING N N 26 
PYN N13 HN1  SING N N 27 
PYN C14 C15  SING N N 28 
PYN C14 O14  DOUB N N 29 
PYN C15 C16  SING N N 30 
PYN C15 H151 SING N N 31 
PYN C15 H152 SING N N 32 
PYN C16 N22  SING N N 33 
PYN C16 H161 SING N N 34 
PYN C16 H162 SING N N 35 
PYN N1  C17  SING N N 36 
PYN N1  HN11 SING N N 37 
PYN C17 C18  SING N N 38 
PYN C17 O1   DOUB N N 39 
PYN C18 C19  SING N N 40 
PYN C18 H181 SING N N 41 
PYN C18 H182 SING N N 42 
PYN C19 N27  SING N N 43 
PYN C19 H191 SING N N 44 
PYN C19 H192 SING N N 45 
PYN C21 N22  SING N N 46 
PYN C21 C24  SING N N 47 
PYN C21 H211 SING N N 48 
PYN C21 H212 SING N N 49 
PYN N22 C23  SING N N 50 
PYN C23 C25  SING N N 51 
PYN C23 H231 SING N N 52 
PYN C23 H232 SING N N 53 
PYN C24 C25  SING N N 54 
PYN C24 H241 SING N N 55 
PYN C24 H242 SING N N 56 
PYN C25 H251 SING N N 57 
PYN C25 H252 SING N N 58 
PYN C26 N27  SING N N 59 
PYN C26 C29  SING N N 60 
PYN C26 H261 SING N N 61 
PYN C26 H262 SING N N 62 
PYN N27 C28  SING N N 63 
PYN C28 C30  SING N N 64 
PYN C28 H281 SING N N 65 
PYN C28 H282 SING N N 66 
PYN C29 C30  SING N N 67 
PYN C29 H291 SING N N 68 
PYN C29 H292 SING N N 69 
PYN C30 H301 SING N N 70 
PYN C30 H302 SING N N 71 
# 
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 
PYN SMILES           ACDLabs              10.04 O=C(Nc4cc3nc2cc(NC(=O)CCN1CCCC1)ccc2cc3cc4)CCN5CCCC5                                                                                                                                
PYN InChI            InChI                1.02b InChI=1/C27H33N5O2/c33-26(9-15-31-11-1-2-12-31)28-22-7-5-20-17-21-6-8-23(19-25(21)30-24(20)18-22)29-27(34)10-16-32-13-3-4-14-32/h5-8,17-19H,1-4,9-16H2,(H,28,33)(H,29,34)/f/h28-29H 
PYN InChIKey         InChI                1.02b WQSTTZVZUNIDBE-LKHHGCNMCX                                                                                                                                                           
PYN SMILES_CANONICAL CACTVS               3.341 O=C(CCN1CCCC1)Nc2ccc3cc4ccc(NC(=O)CCN5CCCC5)cc4nc3c2                                                                                                                                
PYN SMILES           CACTVS               3.341 O=C(CCN1CCCC1)Nc2ccc3cc4ccc(NC(=O)CCN5CCCC5)cc4nc3c2                                                                                                                                
PYN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc2c1cc3ccc(cc3n2)NC(=O)CCN4CCCC4)NC(=O)CCN5CCCC5                                                                                                                              
PYN SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc2c1cc3ccc(cc3n2)NC(=O)CCN4CCCC4)NC(=O)CCN5CCCC5                                                                                                                              
# 
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 
PYN "SYSTEMATIC NAME" ACDLabs              10.04 "N,N'-acridine-3,6-diylbis(3-pyrrolidin-1-ylpropanamide)"                        
PYN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-pyrrolidin-1-yl-N-[6-(3-pyrrolidin-1-ylpropanoylamino)acridin-3-yl]propanamide 
# 
