data_5C0
# 
_chem_comp.id                                    5C0 
_chem_comp.name                                  "(2E)-3-[(6S,9R)-4-(cyclopropylamino)-6,7,8,9-tetrahydro-5H-6,9-epiminocyclohepta[d]pyrimidin-10-yl]-1-(2-hydroxyphenyl)prop-2-en-1-one" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 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                     2015-09-04 
_chem_comp.pdbx_modified_date                    2016-09-09 
_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                        362.425 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5C0 
_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        5DKH 
_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 
5C0 C4  C1  C 0 1 Y N N -15.109 38.755 8.565  2.540  -0.371 -0.183 C4  5C0 1  
5C0 C5  C2  C 0 1 N N N -14.749 37.695 7.551  2.457  -1.201 1.068  C5  5C0 2  
5C0 C6  C3  C 0 1 N N S -13.855 36.605 8.136  1.366  -2.265 0.940  C6  5C0 3  
5C0 N1  N1  N 0 1 Y N N -14.766 39.737 10.757 1.730  0.260  -2.280 N1  5C0 4  
5C0 C7  C4  C 0 1 N N N -14.610 35.748 9.160  1.787  -3.341 -0.079 C7  5C0 5  
5C0 C8  C5  C 0 1 N N N -14.332 36.413 10.544 1.158  -2.894 -1.416 C8  5C0 6  
5C0 N2  N2  N 0 1 Y N N -16.391 40.700 9.262  3.606  1.300  -1.440 N2  5C0 7  
5C0 C9  C6  C 0 1 N N R -13.446 37.632 10.237 0.512  -1.521 -1.093 C9  5C0 8  
5C0 C10 C7  C 0 1 Y N N -14.463 38.790 9.860  1.627  -0.502 -1.203 C10 5C0 9  
5C0 C11 C8  C 0 1 Y N N -15.705 40.623 10.407 2.706  1.140  -2.389 C11 5C0 10 
5C0 C12 C9  C 0 1 N N N -11.523 37.382 8.702  -0.978 -1.227 0.976  C12 5C0 11 
5C0 N3  N3  N 0 1 N N N -12.819 37.227 8.969  0.168  -1.625 0.348  N3  5C0 12 
5C0 C13 C10 C 0 1 N N N -10.836 36.907 7.625  -1.974 -0.655 0.265  C13 5C0 13 
5C0 C14 C11 C 0 1 N N N -9.374  36.879 7.650  -3.160 -0.243 0.915  C14 5C0 14 
5C0 C15 C12 C 0 1 Y N N -8.576  36.510 6.429  -4.250 0.382  0.138  C15 5C0 15 
5C0 O1  O1  O 0 1 N N N -8.743  37.176 8.699  -3.283 -0.403 2.117  O1  5C0 16 
5C0 C20 C13 C 0 1 Y N N -7.171  36.594 6.488  -5.427 0.792  0.779  C20 5C0 17 
5C0 O   O2  O 0 1 N N N -6.541  37.113 7.597  -5.570 0.617  2.117  O   5C0 18 
5C0 C19 C14 C 0 1 Y N N -6.396  36.182 5.396  -6.443 1.377  0.040  C19 5C0 19 
5C0 C18 C15 C 0 1 Y N N -7.010  35.738 4.228  -6.295 1.555  -1.322 C18 5C0 20 
5C0 C17 C16 C 0 1 Y N N -8.381  35.698 4.143  -5.134 1.150  -1.959 C17 5C0 21 
5C0 C16 C17 C 0 1 Y N N -9.164  36.059 5.233  -4.111 0.573  -1.238 C16 5C0 22 
5C0 C3  C18 C 0 1 Y N N -16.116 39.765 8.328  3.562  0.570  -0.329 C3  5C0 23 
5C0 N   N4  N 0 1 N N N -16.851 39.797 7.199  4.513  0.740  0.665  N   5C0 24 
5C0 C2  C19 C 0 1 N N N -17.893 40.784 6.943  5.579  1.731  0.497  C2  5C0 25 
5C0 C1  C20 C 0 1 N N N -18.120 41.218 5.549  6.880  1.506  1.269  C1  5C0 26 
5C0 C   C21 C 0 1 N N N -17.492 42.142 6.524  5.917  2.616  1.699  C   5C0 27 
5C0 H1  H1  H 0 1 N N N -14.220 38.173 6.714  3.416  -1.689 1.238  H1  5C0 28 
5C0 H2  H2  H 0 1 N N N -15.676 37.231 7.182  2.229  -0.554 1.914  H2  5C0 29 
5C0 H3  H3  H 0 1 N N N -13.423 35.979 7.341  1.135  -2.704 1.910  H3  5C0 30 
5C0 H4  H4  H 0 1 N N N -15.688 35.749 8.942  2.873  -3.376 -0.165 H4  5C0 31 
5C0 H5  H5  H 0 1 N N N -14.235 34.714 9.148  1.397  -4.315 0.216  H5  5C0 32 
5C0 H6  H6  H 0 1 N N N -15.274 36.730 11.015 1.926  -2.784 -2.181 H6  5C0 33 
5C0 H7  H7  H 0 1 N N N -13.807 35.712 11.210 0.400  -3.608 -1.739 H7  5C0 34 
5C0 H8  H8  H 0 1 N N N -12.751 37.903 11.045 -0.350 -1.296 -1.722 H8  5C0 35 
5C0 H9  H9  H 0 1 N N N -15.940 41.375 11.146 2.766  1.750  -3.279 H9  5C0 36 
5C0 H10 H10 H 0 1 N N N -10.951 37.949 9.422  -1.087 -1.369 2.041  H10 5C0 37 
5C0 H11 H11 H 0 1 N N N -11.370 36.552 6.756  -1.865 -0.513 -0.800 H11 5C0 38 
5C0 H12 H12 H 0 1 N N N -7.181  37.269 8.282  -5.257 1.363  2.647  H12 5C0 39 
5C0 H13 H13 H 0 1 N N N -5.318  36.209 5.460  -7.352 1.695  0.530  H13 5C0 40 
5C0 H14 H14 H 0 1 N N N -6.408  35.425 3.388  -7.090 2.011  -1.893 H14 5C0 41 
5C0 H15 H15 H 0 1 N N N -8.853  35.384 3.224  -5.028 1.293  -3.024 H15 5C0 42 
5C0 H16 H16 H 0 1 N N N -10.240 35.992 5.161  -3.207 0.259  -1.739 H16 5C0 43 
5C0 H17 H17 H 0 1 N N N -17.299 38.905 7.140  4.472  0.203  1.472  H17 5C0 44 
5C0 H18 H18 H 0 1 N N N -18.789 40.722 7.579  5.653  2.179  -0.494 H18 5C0 45 
5C0 H19 H19 H 0 1 N N N -19.143 41.407 5.191  6.943  0.621  1.903  H19 5C0 46 
5C0 H20 H20 H 0 1 N N N -17.520 40.787 4.734  7.810  1.806  0.787  H20 5C0 47 
5C0 H21 H21 H 0 1 N N N -16.426 42.397 6.432  6.214  3.645  1.498  H21 5C0 48 
5C0 H22 H22 H 0 1 N N N -18.049 43.018 6.890  5.346  2.460  2.614  H22 5C0 49 
# 
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 
5C0 C17 C18 DOUB Y N 1  
5C0 C17 C16 SING Y N 2  
5C0 C18 C19 SING Y N 3  
5C0 C16 C15 DOUB Y N 4  
5C0 C19 C20 DOUB Y N 5  
5C0 C1  C   SING N N 6  
5C0 C1  C2  SING N N 7  
5C0 C15 C20 SING Y N 8  
5C0 C15 C14 SING N N 9  
5C0 C20 O   SING N N 10 
5C0 C   C2  SING N N 11 
5C0 C2  N   SING N N 12 
5C0 N   C3  SING N N 13 
5C0 C5  C6  SING N N 14 
5C0 C5  C4  SING N N 15 
5C0 C13 C14 SING N N 16 
5C0 C13 C12 DOUB N E 17 
5C0 C14 O1  DOUB N N 18 
5C0 C6  N3  SING N N 19 
5C0 C6  C7  SING N N 20 
5C0 C3  C4  DOUB Y N 21 
5C0 C3  N2  SING Y N 22 
5C0 C4  C10 SING Y N 23 
5C0 C12 N3  SING N N 24 
5C0 N3  C9  SING N N 25 
5C0 C7  C8  SING N N 26 
5C0 N2  C11 DOUB Y N 27 
5C0 C10 C9  SING N N 28 
5C0 C10 N1  DOUB Y N 29 
5C0 C9  C8  SING N N 30 
5C0 C11 N1  SING Y N 31 
5C0 C5  H1  SING N N 32 
5C0 C5  H2  SING N N 33 
5C0 C6  H3  SING N N 34 
5C0 C7  H4  SING N N 35 
5C0 C7  H5  SING N N 36 
5C0 C8  H6  SING N N 37 
5C0 C8  H7  SING N N 38 
5C0 C9  H8  SING N N 39 
5C0 C11 H9  SING N N 40 
5C0 C12 H10 SING N N 41 
5C0 C13 H11 SING N N 42 
5C0 O   H12 SING N N 43 
5C0 C19 H13 SING N N 44 
5C0 C18 H14 SING N N 45 
5C0 C17 H15 SING N N 46 
5C0 C16 H16 SING N N 47 
5C0 N   H17 SING N N 48 
5C0 C2  H18 SING N N 49 
5C0 C1  H19 SING N N 50 
5C0 C1  H20 SING N N 51 
5C0 C   H21 SING N N 52 
5C0 C   H22 SING N N 53 
# 
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 
5C0 SMILES           ACDLabs              12.01 "c31c(ncnc1NC2CC2)C4CCC(C3)N4[C@H]=CC(=O)c5c(O)cccc5"                                                                                                                            
5C0 InChI            InChI                1.03  "InChI=1S/C21H22N4O2/c26-18-4-2-1-3-15(18)19(27)9-10-25-14-7-8-17(25)20-16(11-14)21(23-12-22-20)24-13-5-6-13/h1-4,9-10,12-14,17,26H,5-8,11H2,(H,22,23,24)/b10-9+/t14-,17+/m0/s1" 
5C0 InChIKey         InChI                1.03  RQOKOKQQGKYASH-FPBOJHQQSA-N                                                                                                                                                      
5C0 SMILES_CANONICAL CACTVS               3.385 "Oc1ccccc1C(=O)\C=C\N2[C@H]3CC[C@@H]2c4ncnc(NC5CC5)c4C3"                                                                                                                         
5C0 SMILES           CACTVS               3.385 "Oc1ccccc1C(=O)C=CN2[CH]3CC[CH]2c4ncnc(NC5CC5)c4C3"                                                                                                                              
5C0 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1ccc(c(c1)C(=O)/C=C/N2[C@H]3CC[C@@H]2c4c(c(ncn4)NC5CC5)C3)O"                                                                                                                   
5C0 SMILES           "OpenEye OEToolkits" 1.9.2 "c1ccc(c(c1)C(=O)C=CN2C3CCC2c4c(c(ncn4)NC5CC5)C3)O"                                                                                                                              
# 
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 
5C0 "SYSTEMATIC NAME" ACDLabs 12.01 "(2E)-3-[(6S,9R)-4-(cyclopropylamino)-6,7,8,9-tetrahydro-5H-6,9-epiminocyclohepta[d]pyrimidin-10-yl]-1-(2-hydroxyphenyl)prop-2-en-1-one" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
5C0 "Create component" 2015-09-04 EBI  
5C0 "Initial release"  2016-09-14 RCSB 
# 
