data_003
# 
_chem_comp.id                                    003 
_chem_comp.name                                  5-METHYL-7-(2-METHYLPROPYL)-2-(NAPHTHALEN-1-YLMETHYL)-3-PYRIDIN-4-YL-2H-PYRAZOLO[3,4-D]PYRIMIDINE-4,6(5H,7H)-DIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H25 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-02-06 
_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                        439.509 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     003 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
003 C2   C2   C 0 1 Y N N 15.229 56.504 36.336 0.071  -2.140 -2.375 C2   003 1  
003 O11  O11  O 0 1 N N N 15.872 55.553 35.883 0.090  -1.324 -3.304 O11  003 2  
003 N3   N3   N 0 1 Y N N 15.347 56.832 37.680 0.374  -1.773 -1.041 N3   003 3  
003 C7   C7   C 0 1 N N N 16.244 56.066 38.574 0.724  -0.393 -0.720 C7   003 4  
003 C8   C8   C 0 1 N N N 17.632 56.714 38.844 2.235  -0.149 -0.826 C8   003 5  
003 C10  C10  C 0 1 N N N 18.576 56.443 37.657 2.774  -0.448 -2.226 C10  003 6  
003 C9   C9   C 0 1 N N N 18.283 56.135 40.116 2.620  1.265  -0.391 C9   003 7  
003 C4   C4   C 0 1 Y N N 14.636 57.891 38.181 0.337  -2.737 -0.032 C4   003 8  
003 N16  N16  N 0 1 Y N N 14.628 58.344 39.361 0.595  -2.551 1.268  N16  003 9  
003 N15  N15  N 0 1 Y N N 13.787 59.404 39.418 0.422  -3.776 1.799  N15  003 10 
003 C23  C23  C 0 1 N N N 13.574 60.201 40.652 0.622  -3.954 3.220  C23  003 11 
003 C24  C24  C 0 1 Y N N 14.177 61.615 40.365 1.875  -3.266 3.689  C24  003 12 
003 C29  C29  C 0 1 Y N N 15.574 61.787 40.020 1.865  -1.937 4.131  C29  003 13 
003 C30  C30  C 0 1 Y N N 16.491 60.678 39.950 0.684  -1.177 4.159  C30  003 14 
003 C31  C31  C 0 1 Y N N 17.854 60.879 39.603 0.699  0.145  4.604  C31  003 15 
003 C32  C32  C 0 1 Y N N 18.324 62.192 39.315 1.891  0.725  5.025  C32  003 16 
003 C33  C33  C 0 1 Y N N 17.437 63.304 39.377 3.074  -0.015 5.003  C33  003 17 
003 C28  C28  C 0 1 Y N N 16.071 63.112 39.727 3.078  -1.347 4.559  C28  003 18 
003 C27  C27  C 0 1 Y N N 15.198 64.232 39.783 4.259  -2.106 4.530  C27  003 19 
003 C26  C26  C 0 1 Y N N 13.829 64.056 40.129 4.244  -3.429 4.086  C26  003 20 
003 C25  C25  C 0 1 Y N N 13.322 62.761 40.417 3.051  -4.009 3.665  C25  003 21 
003 C14  C14  C 0 1 Y N N 13.224 59.615 38.219 0.065  -4.728 0.890  C14  003 22 
003 C17  C17  C 0 1 Y N N 12.214 60.722 37.880 -0.171 -6.110 1.237  C17  003 23 
003 C22  C22  C 0 1 Y N N 10.902 60.683 38.443 0.876  -7.023 1.210  C22  003 24 
003 C21  C21  C 0 1 Y N N 9.981  61.718 38.139 0.597  -8.337 1.551  C21  003 25 
003 N20  N20  N 0 1 Y N N 10.356 62.748 37.310 -0.628 -8.783 1.908  N20  003 26 
003 C19  C19  C 0 1 Y N N 11.609 62.812 36.753 -1.620 -7.865 1.922  C19  003 27 
003 C18  C18  C 0 1 Y N N 12.564 61.805 37.024 -1.446 -6.529 1.598  C18  003 28 
003 C5   C5   C 0 1 Y N N 13.722 58.699 37.372 0.004  -4.071 -0.312 C5   003 29 
003 C6   C6   C 0 1 Y N N 13.620 58.311 35.947 -0.320 -4.555 -1.621 C6   003 30 
003 O13  O13  O 0 1 N N N 12.881 58.941 35.211 -0.606 -5.728 -1.838 O13  003 31 
003 N1   N1   N 0 1 Y N N 14.371 57.239 35.521 -0.262 -3.524 -2.591 N1   003 32 
003 C12  C12  C 0 1 N N N 14.267 56.869 34.104 -0.572 -3.887 -3.971 C12  003 33 
003 H7C1 1H7C H 0 0 N N N 16.376 55.029 38.186 0.367  -0.171 0.291  H7C1 003 34 
003 H7C2 2H7C H 0 0 N N N 15.729 55.851 39.539 0.188  0.265  -1.413 H7C2 003 35 
003 H8   H8   H 0 1 N N N 17.471 57.809 38.979 2.721  -0.849 -0.134 H8   003 36 
003 H101 1H10 H 0 0 N N N 18.138 56.779 36.688 2.392  0.258  -2.970 H101 003 37 
003 H102 2H10 H 0 0 N N N 18.659 55.355 37.428 3.868  -0.381 -2.237 H102 003 38 
003 H103 3H10 H 0 0 N N N 19.571 56.908 37.851 2.500  -1.460 -2.541 H103 003 39 
003 H9C1 1H9C H 0 0 N N N 18.352 55.023 40.070 2.212  2.023  -1.068 H9C1 003 40 
003 H9C2 2H9C H 0 0 N N N 17.609 56.228 40.999 3.709  1.381  -0.379 H9C2 003 41 
003 H9C3 3H9C H 0 0 N N N 19.278 56.599 40.310 2.251  1.476  0.618  H9C3 003 42 
003 H231 1H23 H 0 0 N N N 13.988 59.719 41.569 0.659  -5.030 3.428  H231 003 43 
003 H232 2H23 H 0 0 N N N 12.510 60.231 40.983 -0.262 -3.567 3.741  H232 003 44 
003 H25  H25  H 0 1 N N N 12.258 62.645 40.683 3.053  -5.040 3.321  H25  003 45 
003 H30  H30  H 0 1 N N N 16.142 59.654 40.167 -0.268 -1.595 3.838  H30  003 46 
003 H31  H31  H 0 1 N N N 18.544 60.020 39.557 -0.221 0.722  4.622  H31  003 47 
003 H32  H32  H 0 1 N N N 19.381 62.349 39.042 1.902  1.755  5.372  H32  003 48 
003 H33  H33  H 0 1 N N N 17.809 64.318 39.153 3.995  0.459  5.338  H33  003 49 
003 H27  H27  H 0 1 N N N 15.584 65.240 39.557 5.203  -1.673 4.855  H27  003 50 
003 H26  H26  H 0 1 N N N 13.156 64.929 40.174 5.164  -4.006 4.069  H26  003 51 
003 H22  H22  H 0 1 N N N 10.601 59.857 39.110 1.884  -6.732 0.935  H22  003 52 
003 H18  H18  H 0 1 N N N 13.569 61.863 36.573 -2.288 -5.845 1.628  H18  003 53 
003 H21  H21  H 0 1 N N N 8.959  61.722 38.553 1.379  -9.090 1.547  H21  003 54 
003 H19  H19  H 0 1 N N N 11.846 63.664 36.094 -2.596 -8.243 2.210  H19  003 55 
003 H121 1H12 H 0 0 N N N 14.002 55.789 34.029 0.348  -3.963 -4.555 H121 003 56 
003 H122 2H12 H 0 0 N N N 15.287 56.871 33.653 -1.217 -3.130 -4.425 H122 003 57 
003 H123 3H12 H 0 0 N N N 13.580 57.457 33.452 -1.089 -4.850 -4.001 H123 003 58 
# 
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 
003 C2  O11  DOUB N N 1  
003 C2  N3   SING Y N 2  
003 C2  N1   SING Y N 3  
003 N3  C7   SING N N 4  
003 N3  C4   SING Y N 5  
003 C7  C8   SING N N 6  
003 C7  H7C1 SING N N 7  
003 C7  H7C2 SING N N 8  
003 C8  C10  SING N N 9  
003 C8  C9   SING N N 10 
003 C8  H8   SING N N 11 
003 C10 H101 SING N N 12 
003 C10 H102 SING N N 13 
003 C10 H103 SING N N 14 
003 C9  H9C1 SING N N 15 
003 C9  H9C2 SING N N 16 
003 C9  H9C3 SING N N 17 
003 C4  N16  DOUB Y N 18 
003 C4  C5   SING Y N 19 
003 N16 N15  SING Y N 20 
003 N15 C23  SING N N 21 
003 N15 C14  SING Y N 22 
003 C23 C24  SING N N 23 
003 C23 H231 SING N N 24 
003 C23 H232 SING N N 25 
003 C24 C29  SING Y N 26 
003 C24 C25  DOUB Y N 27 
003 C29 C30  SING Y N 28 
003 C29 C28  DOUB Y N 29 
003 C30 C31  DOUB Y N 30 
003 C30 H30  SING N N 31 
003 C31 C32  SING Y N 32 
003 C31 H31  SING N N 33 
003 C32 C33  DOUB Y N 34 
003 C32 H32  SING N N 35 
003 C33 C28  SING Y N 36 
003 C33 H33  SING N N 37 
003 C28 C27  SING Y N 38 
003 C27 C26  DOUB Y N 39 
003 C27 H27  SING N N 40 
003 C26 C25  SING Y N 41 
003 C26 H26  SING N N 42 
003 C25 H25  SING N N 43 
003 C14 C17  SING N N 44 
003 C14 C5   DOUB Y N 45 
003 C17 C22  SING Y N 46 
003 C17 C18  DOUB Y N 47 
003 C22 C21  DOUB Y N 48 
003 C22 H22  SING N N 49 
003 C21 N20  SING Y N 50 
003 C21 H21  SING N N 51 
003 N20 C19  DOUB Y N 52 
003 C19 C18  SING Y N 53 
003 C19 H19  SING N N 54 
003 C18 H18  SING N N 55 
003 C5  C6   SING Y N 56 
003 C6  O13  DOUB N N 57 
003 C6  N1   SING Y N 58 
003 N1  C12  SING N N 59 
003 C12 H121 SING N N 60 
003 C12 H122 SING N N 61 
003 C12 H123 SING N N 62 
# 
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 
003 SMILES           ACDLabs              10.04 O=C3c2c(c1ccncc1)n(nc2N(C(=O)N3C)CC(C)C)Cc5c4ccccc4ccc5                                                                                              
003 InChI            InChI                1.02b InChI=1/C26H25N5O2/c1-17(2)15-30-24-22(25(32)29(3)26(30)33)23(19-11-13-27-14-12-19)31(28-24)16-20-9-6-8-18-7-4-5-10-21(18)20/h4-14,17H,15-16H2,1-3H3 
003 InChIKey         InChI                1.02b NNZDBCPMOOEFTE-UHFFFAOYAZ                                                                                                                            
003 SMILES_CANONICAL CACTVS               3.341 CC(C)CN1C(=O)N(C)C(=O)c2c1nn(Cc3cccc4ccccc34)c2c5ccncc5                                                                                              
003 SMILES           CACTVS               3.341 CC(C)CN1C(=O)N(C)C(=O)c2c1nn(Cc3cccc4ccccc34)c2c5ccncc5                                                                                              
003 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)CN1c2c(c(n(n2)Cc3cccc4c3cccc4)c5ccncc5)C(=O)N(C1=O)C                                                                                            
003 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CN1c2c(c(n(n2)Cc3cccc4c3cccc4)c5ccncc5)C(=O)N(C1=O)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 
003 "SYSTEMATIC NAME" ACDLabs              10.04 5-methyl-7-(2-methylpropyl)-2-(naphthalen-1-ylmethyl)-3-pyridin-4-yl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione 
003 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-methyl-7-(2-methylpropyl)-2-(naphthalen-1-ylmethyl)-3-pyridin-4-yl-pyrazolo[4,3-e]pyrimidine-4,6-dione           
# 
