data_53M
# 
_chem_comp.id                                    53M 
_chem_comp.name                                  "(2R,4S,4aS)-4',6'-dihydroxy-2,4-dimethyl-8-nitro-1,2,4,4a-tetrahydro-2'H,6H-spiro[1,4-oxazino[4,3-a]quinoline-5,5'-pyrimidin]-2'-one" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H18 N4 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-07-22 
_chem_comp.pdbx_modified_date                    2015-12-11 
_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                        374.348 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     53M 
_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        5CDO 
_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 
53M C2   C1  C 0  1 N N S 44.058 -45.687 66.179 -1.068 0.676  -0.575 C2   53M 1  
53M C3   C2  C 0  1 N N S 44.875 -44.429 66.029 -2.449 1.245  -0.241 C3   53M 2  
53M C5   C3  C 0  1 N N N 44.610 -43.426 67.115 -3.489 0.660  -1.199 C5   53M 3  
53M O6   O1  O 0  1 N N N 44.483 -43.736 64.855 -2.413 2.668  -0.383 O6   53M 4  
53M C7   C4  C 0  1 N N R 45.012 -44.401 63.739 -1.440 3.310  0.445  C7   53M 5  
53M C9   C5  C 0  1 N N N 44.609 -43.651 62.496 -1.460 4.817  0.183  C9   53M 6  
53M C10  C6  C 0  1 N N N 44.351 -45.761 63.663 -0.049 2.754  0.123  C10  53M 7  
53M N11  N1  N 0  1 N N N 44.302 -46.444 64.962 -0.060 1.295  0.289  N11  53M 8  
53M C12  C7  C 0  1 Y N N 44.253 -47.866 65.011 1.210  0.743  0.150  C12  53M 9  
53M C13  C8  C 0  1 Y N N 44.407 -48.625 63.868 2.302  1.502  0.574  C13  53M 10 
53M C14  C9  C 0  1 Y N N 44.393 -49.995 63.912 3.582  1.002  0.468  C14  53M 11 
53M C15  C10 C 0  1 Y N N 44.236 -50.611 65.123 3.790  -0.258 -0.061 C15  53M 12 
53M C16  C11 C 0  1 Y N N 44.096 -49.903 66.286 2.714  -1.012 -0.485 C16  53M 13 
53M C17  C12 C 0  1 Y N N 44.119 -48.530 66.214 1.424  -0.516 -0.385 C17  53M 14 
53M C18  C13 C 0  1 N N N 43.945 -47.810 67.494 0.290  -1.379 -0.880 C18  53M 15 
53M C19  C14 C 0  1 N N N 44.476 -46.411 67.450 -1.057 -0.837 -0.335 C19  53M 16 
53M C20  C15 C 0  1 N N N 45.936 -46.526 67.731 -1.157 -1.114 1.138  C20  53M 17 
53M O21  O2  O 0  1 N N N 46.704 -46.847 66.660 -0.216 -0.620 1.961  O21  53M 18 
53M N22  N2  N 0  1 N N N 46.441 -46.372 68.912 -2.128 -1.816 1.640  N22  53M 19 
53M C23  C16 C 0  1 N N N 45.587 -46.058 69.943 -3.098 -2.337 0.873  C23  53M 20 
53M O24  O3  O 0  1 N N N 45.947 -46.266 71.094 -3.984 -2.989 1.397  O24  53M 21 
53M N25  N3  N 0  1 N N N 44.354 -45.501 69.743 -3.118 -2.157 -0.456 N25  53M 22 
53M C26  C17 C 0  1 N N N 43.835 -45.674 68.576 -2.201 -1.473 -1.072 C26  53M 23 
53M O27  O4  O 0  1 N N N 42.619 -45.162 68.275 -2.278 -1.329 -2.405 O27  53M 24 
53M N28  N4  N 1  1 N N N 44.236 -52.046 65.148 5.164  -0.798 -0.173 N28  53M 25 
53M O29  O5  O 0  1 N N N 44.055 -52.621 64.069 5.345  -1.908 -0.639 O29  53M 26 
53M O30  O6  O -1 1 N N N 44.474 -52.578 66.237 6.112  -0.132 0.201  O30  53M 27 
53M H2   H1  H 0  1 N N N 42.993 -45.422 66.250 -0.831 0.882  -1.618 H2   53M 28 
53M H3   H2  H 0  1 N N N 45.946 -44.680 66.003 -2.712 0.985  0.785  H3   53M 29 
53M H51  H3  H 0  1 N N N 44.881 -43.859 68.089 -3.799 -0.322 -0.844 H51  53M 30 
53M H52  H4  H 0  1 N N N 45.212 -42.523 66.935 -4.354 1.321  -1.243 H52  53M 31 
53M H53  H5  H 0  1 N N N 43.543 -43.161 67.116 -3.053 0.566  -2.194 H53  53M 32 
53M H7   H6  H 0  1 N N N 46.106 -44.504 63.794 -1.673 3.120  1.493  H7   53M 33 
53M H91  H7  H 0  1 N N N 45.067 -42.651 62.506 -2.450 5.212  0.412  H91  53M 34 
53M H92  H8  H 0  1 N N N 44.951 -44.203 61.608 -0.719 5.306  0.814  H92  53M 35 
53M H93  H9  H 0  1 N N N 43.514 -43.552 62.467 -1.227 5.006  -0.865 H93  53M 36 
53M H102 H10 H 0  0 N N N 43.322 -45.632 63.295 0.211  2.997  -0.907 H102 53M 37 
53M H103 H11 H 0  0 N N N 44.917 -46.388 62.958 0.685  3.193  0.799  H103 53M 38 
53M H13  H12 H 0  1 N N N 44.541 -48.128 62.918 2.143  2.486  0.988  H13  53M 39 
53M H14  H13 H 0  1 N N N 44.504 -50.576 63.009 4.422  1.595  0.798  H14  53M 40 
53M H16  H14 H 0  1 N N N 43.971 -50.408 67.232 2.879  -1.996 -0.898 H16  53M 41 
53M H182 H15 H 0  0 N N N 42.872 -47.771 67.732 0.278  -1.371 -1.969 H182 53M 42 
53M H183 H16 H 0  0 N N N 44.476 -48.363 68.283 0.432  -2.401 -0.526 H183 53M 43 
53M H21  H17 H 0  1 N N N 47.610 -46.928 66.933 -0.310 -0.816 2.903  H21  53M 44 
53M H27  H18 H 0  1 N N N 42.274 -44.700 69.030 -3.026 -1.751 -2.850 H27  53M 45 
# 
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 
53M C9  C7   SING N N 1  
53M C10 C7   SING N N 2  
53M C10 N11  SING N N 3  
53M C7  O6   SING N N 4  
53M C13 C14  DOUB Y N 5  
53M C13 C12  SING Y N 6  
53M C14 C15  SING Y N 7  
53M O29 N28  DOUB N N 8  
53M O6  C3   SING N N 9  
53M N11 C12  SING N N 10 
53M N11 C2   SING N N 11 
53M C12 C17  DOUB Y N 12 
53M C15 N28  SING N N 13 
53M C15 C16  DOUB Y N 14 
53M N28 O30  SING N N 15 
53M C3  C2   SING N N 16 
53M C3  C5   SING N N 17 
53M C2  C19  SING N N 18 
53M C17 C16  SING Y N 19 
53M C17 C18  SING N N 20 
53M O21 C20  SING N N 21 
53M C19 C18  SING N N 22 
53M C19 C20  SING N N 23 
53M C19 C26  SING N N 24 
53M C20 N22  DOUB N N 25 
53M O27 C26  SING N N 26 
53M C26 N25  DOUB N N 27 
53M N22 C23  SING N N 28 
53M N25 C23  SING N N 29 
53M C23 O24  DOUB N N 30 
53M C2  H2   SING N N 31 
53M C3  H3   SING N N 32 
53M C5  H51  SING N N 33 
53M C5  H52  SING N N 34 
53M C5  H53  SING N N 35 
53M C7  H7   SING N N 36 
53M C9  H91  SING N N 37 
53M C9  H92  SING N N 38 
53M C9  H93  SING N N 39 
53M C10 H102 SING N N 40 
53M C10 H103 SING N N 41 
53M C13 H13  SING N N 42 
53M C14 H14  SING N N 43 
53M C16 H16  SING N N 44 
53M C18 H182 SING N N 45 
53M C18 H183 SING N N 46 
53M O21 H21  SING N N 47 
53M O27 H27  SING N N 48 
# 
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 
53M SMILES           ACDLabs              12.01 "C21C4(Cc3c(N1CC(OC2C)C)ccc([N+]([O-])=O)c3)C(=NC(=O)N=C4O)O"                                                                                                           
53M InChI            InChI                1.03  "InChI=1S/C17H18N4O6/c1-8-7-20-12-4-3-11(21(25)26)5-10(12)6-17(13(20)9(2)27-8)14(22)18-16(24)19-15(17)23/h3-5,8-9,13H,6-7H2,1-2H3,(H2,18,19,22,23,24)/t8-,9+,13-/m1/s1" 
53M InChIKey         InChI                1.03  DJZPHYIXNUOVJU-VYUIOLGVSA-N                                                                                                                                             
53M SMILES_CANONICAL CACTVS               3.385 "C[C@@H]1CN2[C@H]([C@H](C)O1)C3(Cc4cc(ccc24)[N+]([O-])=O)C(=NC(=O)N=C3O)O"                                                                                              
53M SMILES           CACTVS               3.385 "C[CH]1CN2[CH]([CH](C)O1)C3(Cc4cc(ccc24)[N+]([O-])=O)C(=NC(=O)N=C3O)O"                                                                                                  
53M SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "C[C@@H]1CN2c3ccc(cc3CC4([C@H]2[C@@H](O1)C)C(=NC(=O)N=C4O)O)[N+](=O)[O-]"                                                                                               
53M SMILES           "OpenEye OEToolkits" 1.9.2 "CC1CN2c3ccc(cc3CC4(C2C(O1)C)C(=NC(=O)N=C4O)O)[N+](=O)[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 
53M "SYSTEMATIC NAME" ACDLabs              12.01 "(2R,4S,4aS)-4',6'-dihydroxy-2,4-dimethyl-8-nitro-1,2,4,4a-tetrahydro-2'H,6H-spiro[1,4-oxazino[4,3-a]quinoline-5,5'-pyrimidin]-2'-one"  
53M "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "(2R,4S,4aS)-2,4-dimethyl-8-nitro-4',6'-bis(oxidanyl)spiro[2,4,4a,6-tetrahydro-1H-[1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2'-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 
53M "Create component" 2015-07-22 RCSB 
53M "Initial release"  2015-12-16 RCSB 
# 
