data_66A
# 
_chem_comp.id                                    66A 
_chem_comp.name                                  "7-[cis-3-(azetidin-1-ylmethyl)cyclobutyl]-5-[3-(benzyloxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H29 N5 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2016-02-03 
_chem_comp.pdbx_modified_date                    2016-04-01 
_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                        439.552 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     66A 
_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        5HZN 
_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 
66A C10 C1  C 0 1 Y N N 19.525 1.484  11.974 -0.843 -1.547 -0.748 C10 66A 1  
66A C11 C2  C 0 1 Y N N 20.023 2.776  12.123 -1.730 -0.632 -0.185 C11 66A 2  
66A C12 C3  C 0 1 Y N N 19.896 3.657  11.051 -3.016 -0.521 -0.687 C12 66A 3  
66A C13 C4  C 0 1 Y N N 19.323 3.252  9.856  -3.419 -1.321 -1.748 C13 66A 4  
66A C14 C5  C 0 1 Y N N 18.893 1.944  9.694  -2.539 -2.230 -2.307 C14 66A 5  
66A C15 C6  C 0 1 Y N N 19.030 1.056  10.750 -1.253 -2.342 -1.817 C15 66A 6  
66A C19 C7  C 0 1 Y N N 18.712 7.914  11.799 -6.013 2.777  -0.415 C19 66A 7  
66A C20 C8  C 0 1 Y N N 18.899 9.215  12.249 -6.761 3.728  0.254  C20 66A 8  
66A C21 C9  C 0 1 Y N N 20.023 9.918  11.820 -7.503 3.368  1.363  C21 66A 9  
66A C22 C10 C 0 1 Y N N 20.949 9.337  10.949 -7.497 2.057  1.803  C22 66A 10 
66A C27 C11 C 0 1 N N N 23.800 -1.132 15.940 4.551  1.587  0.689  C27 66A 11 
66A C31 C12 C 0 1 N N N 26.277 -2.055 14.197 5.089  4.727  -1.318 C31 66A 12 
66A C32 C13 C 0 1 N N N 27.677 -1.454 14.033 6.400  5.341  -0.804 C32 66A 13 
66A C33 C14 C 0 1 N N N 27.462 -0.533 15.237 6.195  4.369  0.366  C33 66A 14 
66A N24 N1  N 0 1 N N N 16.667 -0.501 12.151 -0.366 -4.692 -0.246 N24 66A 15 
66A C29 C15 C 0 1 N N N 24.961 -0.253 15.463 4.230  2.969  0.116  C29 66A 16 
66A C26 C16 C 0 1 N N N 22.510 -0.432 16.366 3.405  0.981  1.515  C26 66A 17 
66A C28 C17 C 0 1 N N N 23.017 -1.967 14.919 4.335  0.438  -0.310 C28 66A 18 
66A C25 C18 C 0 1 N N N 21.718 -1.358 15.441 3.754  -0.368 0.864  C25 66A 19 
66A N30 N2  N 0 1 N N N 26.131 -1.137 15.341 5.421  3.512  -0.551 N30 66A 20 
66A C06 C19 C 0 1 Y N N 17.508 -1.076 13.043 0.880  -4.269 0.181  C06 66A 21 
66A N05 N3  N 0 1 Y N N 17.070 -2.189 13.645 1.787  -5.144 0.607  N05 66A 22 
66A C04 C20 C 0 1 Y N N 17.794 -2.870 14.544 2.978  -4.744 1.014  C04 66A 23 
66A C07 C21 C 0 1 Y N N 18.786 -0.688 13.381 1.220  -2.910 0.170  C07 66A 24 
66A C02 C22 C 0 1 Y N N 19.532 -1.303 14.257 2.499  -2.530 0.613  C02 66A 25 
66A N03 N4  N 0 1 Y N N 19.021 -2.486 14.892 3.338  -3.479 1.026  N03 66A 26 
66A N01 N5  N 0 1 Y N N 20.745 -0.775 14.474 2.581  -1.168 0.504  N01 66A 27 
66A C08 C23 C 0 1 Y N N 19.675 0.446  12.996 0.535  -1.670 -0.216 C08 66A 28 
66A C09 C24 C 0 1 Y N N 20.880 0.326  13.668 1.411  -0.660 0.010  C09 66A 29 
66A O16 O1  O 0 1 N N N 20.297 4.961  11.143 -3.885 0.369  -0.141 O16 66A 30 
66A C17 C25 C 0 1 N N N 19.427 5.903  10.462 -5.195 0.430  -0.708 C17 66A 31 
66A C18 C26 C 0 1 Y N N 19.638 7.331  10.930 -6.011 1.466  0.021  C18 66A 32 
66A C23 C27 C 0 1 Y N N 20.753 8.035  10.496 -6.749 1.107  1.134  C23 66A 33 
66A H1  H1  H 0 1 N N N 20.494 3.086  13.044 -1.416 -0.010 0.640  H1  66A 34 
66A H2  H2  H 0 1 N N N 19.211 3.959  9.047  -4.422 -1.234 -2.138 H2  66A 35 
66A H3  H3  H 0 1 N N N 18.458 1.622  8.760  -2.857 -2.850 -3.132 H3  66A 36 
66A H4  H4  H 0 1 N N N 18.749 0.022  10.619 -0.568 -3.052 -2.256 H4  66A 37 
66A H5  H5  H 0 1 N N N 17.848 7.352  12.122 -5.433 3.059  -1.282 H5  66A 38 
66A H6  H6  H 0 1 N N N 18.186 9.673  12.919 -6.766 4.752  -0.090 H6  66A 39 
66A H7  H7  H 0 1 N N N 20.181 10.929 12.166 -8.088 4.110  1.886  H7  66A 40 
66A H8  H8  H 0 1 N N N 21.815 9.897  10.628 -8.077 1.776  2.670  H8  66A 41 
66A H9  H9  H 0 1 N N N 24.148 -1.785 16.754 5.518  1.552  1.192  H9  66A 42 
66A H10 H10 H 0 1 N N N 25.589 -1.867 13.359 4.199  5.240  -0.955 H10 66A 43 
66A H11 H11 H 0 1 N N N 26.258 -3.124 14.454 5.076  4.570  -2.396 H11 66A 44 
66A H12 H12 H 0 1 N N N 28.491 -2.181 14.170 7.269  5.119  -1.423 H12 66A 45 
66A H13 H13 H 0 1 N N N 27.821 -0.917 13.084 6.322  6.393  -0.529 H13 66A 46 
66A H14 H14 H 0 1 N N N 28.126 -0.726 16.092 7.120  3.908  0.715  H14 66A 47 
66A H15 H15 H 0 1 N N N 27.466 0.542  15.005 5.599  4.786  1.178  H15 66A 48 
66A H16 H16 H 0 1 N N N 15.823 -1.035 12.095 -1.017 -4.044 -0.558 H16 66A 49 
66A H17 H17 H 0 1 N N N 16.453 0.430  12.447 -0.589 -5.635 -0.233 H17 66A 50 
66A H18 H18 H 0 1 N N N 25.161 0.543  16.195 3.417  2.882  -0.606 H18 66A 51 
66A H19 H19 H 0 1 N N N 24.721 0.197  14.488 3.929  3.636  0.923  H19 66A 52 
66A H20 H20 H 0 1 N N N 22.461 0.631  16.089 3.580  1.006  2.590  H20 66A 53 
66A H21 H21 H 0 1 N N N 22.267 -0.545 17.433 2.420  1.358  1.238  H21 66A 54 
66A H22 H22 H 0 1 N N N 23.098 -3.054 15.068 3.605  0.666  -1.086 H22 66A 55 
66A H23 H23 H 0 1 N N N 23.240 -1.723 13.870 5.262  0.025  -0.707 H23 66A 56 
66A H24 H24 H 0 1 N N N 21.203 -2.109 16.058 4.503  -0.937 1.415  H24 66A 57 
66A H26 H26 H 0 1 N N N 17.371 -3.754 14.998 3.686  -5.487 1.353  H26 66A 58 
66A H27 H27 H 0 1 N N N 21.745 0.966  13.576 1.214  0.387  -0.171 H27 66A 59 
66A H28 H28 H 0 1 N N N 18.381 5.620  10.654 -5.123 0.700  -1.762 H28 66A 60 
66A H29 H29 H 0 1 N N N 19.629 5.852  9.382  -5.677 -0.544 -0.615 H29 66A 61 
66A H30 H30 H 0 1 N N N 21.458 7.579  9.817  -6.741 0.084  1.480  H30 66A 62 
# 
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 
66A C14 C13 DOUB Y N 1  
66A C14 C15 SING Y N 2  
66A C13 C12 SING Y N 3  
66A C17 C18 SING N N 4  
66A C17 O16 SING N N 5  
66A C23 C18 DOUB Y N 6  
66A C23 C22 SING Y N 7  
66A C15 C10 DOUB Y N 8  
66A C18 C19 SING Y N 9  
66A C22 C21 DOUB Y N 10 
66A C12 O16 SING N N 11 
66A C12 C11 DOUB Y N 12 
66A C19 C20 DOUB Y N 13 
66A C21 C20 SING Y N 14 
66A C10 C11 SING Y N 15 
66A C10 C08 SING N N 16 
66A N24 C06 SING N N 17 
66A C08 C07 SING Y N 18 
66A C08 C09 DOUB Y N 19 
66A C06 C07 DOUB Y N 20 
66A C06 N05 SING Y N 21 
66A C07 C02 SING Y N 22 
66A N05 C04 DOUB Y N 23 
66A C09 N01 SING Y N 24 
66A C32 C31 SING N N 25 
66A C32 C33 SING N N 26 
66A C31 N30 SING N N 27 
66A C02 N01 SING Y N 28 
66A C02 N03 DOUB Y N 29 
66A N01 C25 SING N N 30 
66A C04 N03 SING Y N 31 
66A C28 C25 SING N N 32 
66A C28 C27 SING N N 33 
66A C33 N30 SING N N 34 
66A N30 C29 SING N N 35 
66A C25 C26 SING N N 36 
66A C29 C27 SING N N 37 
66A C27 C26 SING N N 38 
66A C11 H1  SING N N 39 
66A C13 H2  SING N N 40 
66A C14 H3  SING N N 41 
66A C15 H4  SING N N 42 
66A C19 H5  SING N N 43 
66A C20 H6  SING N N 44 
66A C21 H7  SING N N 45 
66A C22 H8  SING N N 46 
66A C27 H9  SING N N 47 
66A C31 H10 SING N N 48 
66A C31 H11 SING N N 49 
66A C32 H12 SING N N 50 
66A C32 H13 SING N N 51 
66A C33 H14 SING N N 52 
66A C33 H15 SING N N 53 
66A N24 H16 SING N N 54 
66A N24 H17 SING N N 55 
66A C29 H18 SING N N 56 
66A C29 H19 SING N N 57 
66A C26 H20 SING N N 58 
66A C26 H21 SING N N 59 
66A C28 H22 SING N N 60 
66A C28 H23 SING N N 61 
66A C25 H24 SING N N 62 
66A C04 H26 SING N N 63 
66A C09 H27 SING N N 64 
66A C17 H28 SING N N 65 
66A C17 H29 SING N N 66 
66A C23 H30 SING N N 67 
# 
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 
66A SMILES           ACDLabs              12.01 "c2(cc(OCc1ccccc1)ccc2)c6c3c(N)ncnc3n(C5CC(CN4CCC4)C5)c6"                                                                                                                                         
66A InChI            InChI                1.03  "InChI=1S/C27H29N5O/c28-26-25-24(21-8-4-9-23(14-21)33-17-19-6-2-1-3-7-19)16-32(27(25)30-18-29-26)22-12-20(13-22)15-31-10-5-11-31/h1-4,6-9,14,16,18,20,22H,5,10-13,15,17H2,(H2,28,29,30)/t20-,22+" 
66A InChIKey         InChI                1.03  AECDBHGVIIRMOI-GRGXKFILSA-N                                                                                                                                                                       
66A SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n(cc(c3cccc(OCc4ccccc4)c3)c12)[C@@H]5C[C@@H](C5)CN6CCC6"                                                                                                                                 
66A SMILES           CACTVS               3.385 "Nc1ncnc2n(cc(c3cccc(OCc4ccccc4)c3)c12)[CH]5C[CH](C5)CN6CCC6"                                                                                                                                     
66A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.4 "c1ccc(cc1)COc2cccc(c2)c3cn(c4c3c(ncn4)N)C5CC(C5)CN6CCC6"                                                                                                                                         
66A SMILES           "OpenEye OEToolkits" 2.0.4 "c1ccc(cc1)COc2cccc(c2)c3cn(c4c3c(ncn4)N)C5CC(C5)CN6CCC6"                                                                                                                                         
# 
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 
66A "SYSTEMATIC NAME" ACDLabs              12.01 "7-[cis-3-(azetidin-1-ylmethyl)cyclobutyl]-5-[3-(benzyloxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine" 
66A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.4 "7-[3-(azetidin-1-ylmethyl)cyclobutyl]-5-(3-phenylmethoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine"       
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
66A "Create component" 2016-02-03 EBI  
66A "Initial release"  2016-04-06 RCSB 
# 
