data_M54
# 
_chem_comp.id                                    M54 
_chem_comp.name                                  6-(3-aminopropyl)-4-(3-hydroxyphenyl)-9-(1H-pyrazol-4-yl)benzo[h]isoquinolin-1(2H)-one 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H22 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-09-18 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        410.468 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     M54 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2R0U 
_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 
M54 C    C    C 0 1 Y N N 19.878 -2.087 9.405  -3.673 -0.025 0.262  C    M54 1  
M54 C1   C1   C 0 1 Y N N 19.987 -3.372 10.119 -3.438 -1.365 0.599  C1   M54 2  
M54 C2   C2   C 0 1 Y N N 18.859 -3.952 10.816 -2.171 -1.852 0.682  C2   M54 3  
M54 C3   C3   C 0 1 Y N N 18.610 -1.397 9.363  -2.613 0.829  0.005  C3   M54 4  
M54 C4   C4   C 0 1 Y N N 17.455 -1.964 9.992  -1.305 0.345  0.084  C4   M54 5  
M54 C5   C5   C 0 1 Y N N 17.586 -3.268 10.739 -1.076 -1.011 0.427  C5   M54 6  
M54 C6   C6   C 0 1 Y N N 16.446 -3.858 11.382 0.245  -1.497 0.507  C6   M54 7  
M54 C7   C7   C 0 1 Y N N 15.196 -3.233 11.306 1.309  -0.694 0.262  C7   M54 8  
M54 C8   C8   C 0 1 Y N N 16.158 -1.331 9.940  -0.154 1.203  -0.176 C8   M54 9  
M54 C9   C9   C 0 1 Y N N 14.989 -1.959 10.617 1.139  0.655  -0.080 C9   M54 10 
M54 C10  C10  C 0 1 N N N 13.689 -1.315 10.565 2.284  1.537  -0.346 C10  M54 11 
M54 C11  C11  C 0 1 N N N 13.494 -0.098 9.954  2.059  2.836  -0.672 C11  M54 12 
M54 N    N    N 0 1 N N N 14.631 0.508  9.279  0.805  3.353  -0.761 N    M54 13 
M54 C12  C12  C 0 1 N N N 15.886 -0.049 9.216  -0.297 2.611  -0.534 C12  M54 14 
M54 O    O    O 0 1 N N N 16.778 0.595  8.561  -1.404 3.112  -0.624 O    M54 15 
M54 C13  C13  C 0 1 Y N N 21.074 -1.505 8.730  -5.065 0.481  0.173  C13  M54 16 
M54 C14  C14  C 0 1 Y N N 22.346 -2.116 8.684  -6.202 -0.243 0.392  C14  M54 17 
M54 N15  N15  N 0 1 Y N N 23.120 -1.229 7.973  -7.252 0.583  0.211  N15  M54 18 
M54 N16  N16  N 0 1 Y N N 22.353 -0.136 7.623  -6.760 1.849  -0.128 N16  M54 19 
M54 C17  C17  C 0 1 Y N N 21.088 -0.282 8.051  -5.455 1.796  -0.148 C17  M54 20 
M54 C18  C18  C 0 1 N N N 16.705 -5.199 12.110 0.479  -2.941 0.873  C18  M54 21 
M54 C19  C19  C 0 1 N N N 16.302 -5.192 13.542 0.385  -3.807 -0.384 C19  M54 22 
M54 C20  C20  C 0 1 N N N 16.906 -4.180 14.410 0.623  -5.272 -0.013 C20  M54 23 
M54 N21  N21  N 0 1 N N N 16.332 -4.433 15.753 0.533  -6.104 -1.220 N21  M54 24 
M54 C22  C22  C 0 1 Y N N 12.477 -1.966 11.232 3.668  1.014  -0.259 C22  M54 25 
M54 C23  C23  C 0 1 Y N N 11.321 -2.375 10.375 4.105  0.039  -1.156 C23  M54 26 
M54 C24  C24  C 0 1 Y N N 10.063 -3.310 12.342 6.256  0.033  -0.103 C24  M54 27 
M54 C25  C25  C 0 1 Y N N 11.193 -2.928 13.123 5.831  1.006  0.790  C25  M54 28 
M54 C26  C26  C 0 1 Y N N 10.110 -3.005 10.931 5.395  -0.445 -1.074 C26  M54 29 
M54 C27  C27  C 0 1 Y N N 12.421 -2.298 12.630 4.538  1.499  0.715  C27  M54 30 
M54 O28  O28  O 0 1 N N N 11.156 -3.189 14.291 6.683  1.476  1.739  O28  M54 31 
M54 H1   H1   H 0 1 N N N 20.933 -3.894 10.122 -4.274 -2.020 0.797  H1   M54 32 
M54 H2   H2   H 0 1 N N N 18.964 -4.869 11.377 -2.007 -2.887 0.943  H2   M54 33 
M54 H3   H3   H 0 1 N N N 18.532 -0.448 8.854  -2.796 1.861  -0.256 H3   M54 34 
M54 H7   H7   H 0 1 N N N 14.349 -3.711 11.775 2.307  -1.101 0.333  H7   M54 35 
M54 H11  H11  H 0 1 N N N 12.531 0.390  9.975  2.905  3.479  -0.866 H11  M54 36 
M54 HN   HN   H 0 1 N N N 14.490 1.390  8.830  0.699  4.288  -0.997 HN   M54 37 
M54 H14  H14  H 0 1 N N N 22.643 -3.063 9.110  -6.251 -1.288 0.662  H14  M54 38 
M54 HN15 HN15 H 0 0 N N N 24.086 -1.356 7.746  -8.187 0.341  0.301  HN15 M54 39 
M54 H17  H17  H 0 1 N N N 20.261 0.397  7.903  -4.790 2.616  -0.377 H17  M54 40 
M54 H181 1H18 H 0 0 N N N 16.128 -5.982 11.597 1.469  -3.047 1.315  H181 M54 41 
M54 H182 2H18 H 0 0 N N N 17.790 -5.378 12.081 -0.276 -3.260 1.592  H182 M54 42 
M54 H191 1H19 H 0 0 N N N 15.215 -5.026 13.567 -0.605 -3.700 -0.826 H191 M54 43 
M54 H192 2H19 H 0 0 N N N 16.652 -6.155 13.941 1.140  -3.487 -1.103 H192 M54 44 
M54 H201 1H20 H 0 0 N N N 18.002 -4.277 14.425 1.613  -5.379 0.429  H201 M54 45 
M54 H202 2H20 H 0 0 N N N 16.695 -3.159 14.059 -0.132 -5.592 0.705  H202 M54 46 
M54 H211 1H21 H 0 0 N N N 17.070 -4.490 16.426 1.179  -5.786 -1.927 H211 M54 47 
M54 H212 2H21 H 0 0 N N N 15.715 -3.685 15.998 0.686  -7.077 -1.001 H212 M54 48 
M54 H23  H23  H 0 1 N N N 11.376 -2.202 9.310  3.435  -0.336 -1.915 H23  M54 49 
M54 H24  H24  H 0 1 N N N 9.211  -3.805 12.785 7.264  -0.350 -0.043 H24  M54 50 
M54 H26  H26  H 0 1 N N N 9.270  -3.235 10.293 5.732  -1.200 -1.768 H26  M54 51 
M54 H27  H27  H 0 1 N N N 13.250 -2.091 13.290 4.206  2.257  1.409  H27  M54 52 
M54 HO28 HO28 H 0 0 N N N 11.146 -4.132 14.405 7.202  2.242  1.457  HO28 M54 53 
# 
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 
M54 N16 N15  SING Y N 1  
M54 N16 C17  DOUB Y N 2  
M54 N15 C14  SING N N 3  
M54 C17 C13  SING N N 4  
M54 O   C12  DOUB Y N 5  
M54 C14 C13  DOUB Y N 6  
M54 C13 C    SING N N 7  
M54 C12 N    SING Y N 8  
M54 C12 C8   SING Y N 9  
M54 N   C11  SING Y N 10 
M54 C3  C    DOUB N N 11 
M54 C3  C4   SING Y N 12 
M54 C   C1   SING N N 13 
M54 C8  C4   DOUB Y N 14 
M54 C8  C9   SING Y N 15 
M54 C11 C10  DOUB Y N 16 
M54 C4  C5   SING N N 17 
M54 C1  C2   DOUB N N 18 
M54 C23 C26  DOUB N N 19 
M54 C23 C22  SING N N 20 
M54 C10 C9   SING N N 21 
M54 C10 C22  SING N N 22 
M54 C9  C7   DOUB N N 23 
M54 C5  C2   SING N N 24 
M54 C5  C6   DOUB N N 25 
M54 C26 C24  SING N N 26 
M54 C22 C27  DOUB Y N 27 
M54 C7  C6   SING N N 28 
M54 C6  C18  SING Y N 29 
M54 C18 C19  SING N N 30 
M54 C24 C25  DOUB Y N 31 
M54 C27 C25  SING Y N 32 
M54 C25 O28  SING Y N 33 
M54 C19 C20  SING N N 34 
M54 C20 N21  SING N N 35 
M54 C1  H1   SING N N 36 
M54 C2  H2   SING N N 37 
M54 C3  H3   SING N N 38 
M54 C7  H7   SING N N 39 
M54 C11 H11  SING N N 40 
M54 N   HN   SING N N 41 
M54 C14 H14  SING N N 42 
M54 N15 HN15 SING N N 43 
M54 C17 H17  SING N N 44 
M54 C18 H181 SING N N 45 
M54 C18 H182 SING Y N 46 
M54 C19 H191 SING Y N 47 
M54 C19 H192 SING Y N 48 
M54 C20 H201 SING N N 49 
M54 C20 H202 SING Y N 50 
M54 N21 H211 SING N N 51 
M54 N21 H212 SING N N 52 
M54 C23 H23  SING Y N 53 
M54 C24 H24  SING N N 54 
M54 C26 H26  SING Y N 55 
M54 C27 H27  SING N N 56 
M54 O28 HO28 SING N N 57 
# 
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 
M54 SMILES           ACDLabs              10.04 O=C5c3c2c(ccc(c1cnnc1)c2)c(cc3C(c4cccc(O)c4)=CN5)CCCN                                                                                                                            
M54 InChI            InChI                1.02b InChI=1/C25H22N4O2/c26-8-2-4-17-11-22-23(16-3-1-5-19(30)9-16)14-27-25(31)24(22)21-10-15(6-7-20(17)21)18-12-28-29-13-18/h1,3,5-7,9-14,30H,2,4,8,26H2,(H,27,31)(H,28,29)/f/h27-28H 
M54 InChIKey         InChI                1.02b BUSJQQYKXHYDNN-VEORKLDJCJ                                                                                                                                                        
M54 SMILES_CANONICAL CACTVS               3.341 NCCCc1cc2C(=CNC(=O)c2c3cc(ccc13)c4c[nH]nc4)c5cccc(O)c5                                                                                                                           
M54 SMILES           CACTVS               3.341 NCCCc1cc2C(=CNC(=O)c2c3cc(ccc13)c4c[nH]nc4)c5cccc(O)c5                                                                                                                           
M54 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)O)C2=CNC(=O)c3c2cc(c4c3cc(cc4)c5c[nH]nc5)CCCN                                                                                                                         
M54 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)O)C2=CNC(=O)c3c2cc(c4c3cc(cc4)c5c[nH]nc5)CCCN                                                                                                                         
# 
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 
M54 "SYSTEMATIC NAME" ACDLabs              10.04 6-(3-aminopropyl)-4-(3-hydroxyphenyl)-9-(1H-pyrazol-4-yl)benzo[h]isoquinolin-1(2H)-one 
M54 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-(3-aminopropyl)-4-(3-hydroxyphenyl)-9-(1H-pyrazol-4-yl)-2H-benzo[h]isoquinolin-1-one 
# 
