data_9P9
#

_chem_comp.id                                   9P9
_chem_comp.name                                 "1-{5-[(3S)-3-carboxy-4-fluoro-3-hydroxybutanoyl]-7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzo[g]pteridin-10(2H)-yl}-1-deoxy-5-O-phosphono-D-ribitol"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C22 H28 F N4 O13 P"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2018-06-20
_chem_comp.pdbx_modified_date                   2019-06-14
_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                       606.449
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    9P9
_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       6A36
_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
9P9  OBD  O1   O  0  1  N  N  N  -10.893  -22.006  -30.171  -8.608  -1.897   0.479  OBD  9P9   1  
9P9  PBB  P1   P  0  1  N  N  N  -11.304  -20.995  -31.184  -8.142  -0.589   1.294  PBB  9P9   2  
9P9  OBE  O2   O  0  1  N  N  N  -12.649  -21.153  -31.836  -8.743   0.615   0.679  OBE  9P9   3  
9P9  OBC  O3   O  0  1  N  N  N  -10.644  -19.643  -31.252  -8.627  -0.709   2.824  OBC  9P9   4  
9P9  OAX  O4   O  0  1  N  N  N  -10.294  -21.625  -32.381  -6.537  -0.471   1.247  OAX  9P9   5  
9P9  CAW  C1   C  0  1  N  N  N  -10.649  -22.685  -33.225  -5.808  -0.246   0.039  CAW  9P9   6  
9P9  CAV  C2   C  0  1  N  N  R  -10.159  -24.015  -32.641  -4.311  -0.187   0.350  CAV  9P9   7  
9P9  OAZ  O5   O  0  1  N  N  N  -10.865  -24.270  -31.398  -3.872  -1.462   0.825  OAZ  9P9   8  
9P9  CAU  C3   C  0  1  N  N  S  -10.476  -25.157  -33.594  -3.540   0.176  -0.920  CAU  9P9   9  
9P9  OBA  O6   O  0  1  N  N  N   -9.622  -25.116  -34.734  -3.978   1.451  -1.395  OBA  9P9  10  
9P9  CAT  C4   C  0  1  N  N  S  -10.331  -26.551  -32.935  -2.043   0.235  -0.609  CAT  9P9  11  
9P9  OAY  O7   O  0  1  N  N  N  -11.077  -27.460  -33.768  -1.604  -1.039  -0.134  OAY  9P9  12  
9P9  CAS  C5   C  0  1  N  N  N   -8.859  -27.002  -32.720  -1.272   0.599  -1.879  CAS  9P9  13  
9P9  NAG  N1   N  0  1  N  N  N   -8.798  -28.225  -31.799   0.162   0.656  -1.581  NAG  9P9  14  
9P9  CAD  C6   C  0  1  Y  N  N   -8.787  -28.093  -30.434   0.954  -0.493  -1.712  CAD  9P9  15  
9P9  CAC  C7   C  0  1  Y  N  N   -9.101  -26.868  -29.853   0.475  -1.606  -2.384  CAC  9P9  16  
9P9  CAB  C8   C  0  1  Y  N  N   -9.155  -26.679  -28.469   1.269  -2.733  -2.504  CAB  9P9  17  
9P9  CAP  C9   C  0  1  N  N  N   -9.449  -25.408  -27.911   0.749  -3.943  -3.236  CAP  9P9  18  
9P9  CAA  C10  C  0  1  Y  N  N   -8.929  -27.792  -27.660   2.539  -2.752  -1.957  CAA  9P9  19  
9P9  CAO  C11  C  0  1  N  N  N   -8.977  -27.668  -26.233   3.396  -3.984  -2.093  CAO  9P9  20  
9P9  CAF  C12  C  0  1  Y  N  N   -8.657  -29.039  -28.227   3.024  -1.644  -1.284  CAF  9P9  21  
9P9  CAE  C13  C  0  1  Y  N  N   -8.630  -29.227  -29.600   2.235  -0.514  -1.161  CAE  9P9  22  
9P9  N    N2   N  0  1  N  N  N   -8.285  -30.373  -30.194   2.710   0.623  -0.486  N    9P9  23  
9P9  CBH  C14  C  0  1  N  N  N   -7.228  -31.062  -29.659   3.819   0.557   0.278  CBH  9P9  24  
9P9  OBI  O8   O  0  1  N  N  N   -6.731  -30.783  -28.554   4.237   1.555   0.828  OBI  9P9  25  
9P9  CBF  C15  C  0  1  N  N  N   -6.586  -32.199  -30.410   4.540  -0.756   0.448  CBF  9P9  26  
9P9  CBG  C16  C  0  1  N  N  S   -5.092  -31.965  -30.002   5.467  -0.674   1.662  CBG  9P9  27  
9P9  CBJ  C17  C  0  1  N  N  N   -4.069  -32.459  -31.033   4.631  -0.520   2.934  CBJ  9P9  28  
9P9  FBK  F1   F  0  1  N  N  N   -2.779  -32.147  -30.805   3.967   0.711   2.909  FBK  9P9  29  
9P9  CBL  C18  C  0  1  N  N  N   -4.853  -30.478  -29.526   6.290  -1.934   1.751  CBL  9P9  30  
9P9  OBN  O9   O  0  1  N  N  N   -5.001  -29.439  -30.288   5.880  -2.959   1.260  OBN  9P9  31  
9P9  OBM  O10  O  0  1  N  N  N   -4.534  -30.426  -28.310   7.477  -1.917   2.376  OBM  9P9  32  
9P9  OBO  O11  O  0  1  N  N  N   -4.891  -32.794  -28.857   6.335   0.452   1.523  OBO  9P9  33  
9P9  CA   C19  C  0  1  N  N  N   -8.991  -30.562  -31.475   2.001   1.838  -0.625  CA   9P9  34  
9P9  CAH  C20  C  0  1  N  N  N   -8.864  -29.456  -32.326   0.737   1.838  -1.177  CAH  9P9  35  
9P9  NAK  N3   N  0  1  N  N  N   -9.034  -29.591  -33.661   0.062   3.027  -1.313  NAK  9P9  36  
9P9  CAL  C21  C  0  1  N  N  N   -9.237  -30.825  -34.251   0.634   4.179  -0.915  CAL  9P9  37  
9P9  OAQ  O12  O  0  1  N  N  N   -9.379  -30.956  -35.469   0.023   5.222  -1.043  OAQ  9P9  38  
9P9  NAM  N4   N  0  1  N  N  N   -9.302  -31.945  -33.427   1.867   4.199  -0.378  NAM  9P9  39  
9P9  C    C22  C  0  1  N  N  N   -9.044  -31.829  -32.087   2.568   3.054  -0.211  C    9P9  40  
9P9  O    O13  O  0  1  N  N  N   -9.161  -32.869  -31.401   3.685   3.081   0.277  O    9P9  41  
9P9  H1   H1   H  0  1  N  N  N  -11.582  -22.652  -30.071  -8.250  -2.725   0.827  H1   9P9  42  
9P9  H2   H2   H  0  1  N  N  N  -11.204  -19.040  -31.727  -9.585  -0.784   2.928  H2   9P9  43  
9P9  H3   H3   H  0  1  N  N  N  -10.191  -22.532  -34.213  -6.002  -1.061  -0.659  H3   9P9  44  
9P9  H4   H4   H  0  1  N  N  N  -11.744  -22.715  -33.329  -6.124   0.697  -0.406  H4   9P9  45  
9P9  H5   H5   H  0  1  N  N  N   -9.074  -23.965  -32.469  -4.128   0.568   1.115  H5   9P9  46  
9P9  H6   H6   H  0  1  N  N  N  -10.685  -23.570  -30.782  -4.004  -2.183   0.195  H6   9P9  47  
9P9  H7   H7   H  0  1  N  N  N  -11.521  -25.048  -33.919  -3.722  -0.578  -1.685  H7   9P9  48  
9P9  H8   H8   H  0  1  N  N  N   -9.695  -24.267  -35.155  -3.846   2.172  -0.764  H8   9P9  49  
9P9  H9   H9   H  0  1  N  N  N  -10.809  -26.501  -31.945  -1.860   0.991   0.156  H9   9P9  50  
9P9  H10  H10  H  0  1  N  N  N  -11.022  -28.337  -33.408  -1.737  -1.760  -0.764  H10  9P9  51  
9P9  H11  H11  H  0  1  N  N  N   -8.414  -27.259  -33.693  -1.454  -0.156  -2.644  H11  9P9  52  
9P9  H12  H12  H  0  1  N  N  N   -8.291  -26.177  -32.264  -1.606   1.571  -2.241  H12  9P9  53  
9P9  H13  H13  H  0  1  N  N  N   -9.312  -26.028  -30.498  -0.516  -1.594  -2.813  H13  9P9  54  
9P9  H14  H14  H  0  1  N  N  N  -10.537  -25.306  -27.783   1.009  -3.869  -4.292  H14  9P9  55  
9P9  H15  H15  H  0  1  N  N  N   -8.954  -25.314  -26.933   1.196  -4.843  -2.814  H15  9P9  56  
9P9  H16  H16  H  0  1  N  N  N   -9.084  -24.619  -28.584  -0.335  -3.992  -3.131  H16  9P9  57  
9P9  H17  H17  H  0  1  N  N  N  -10.003  -27.852  -25.883   3.988  -3.915  -3.006  H17  9P9  58  
9P9  H18  H18  H  0  1  N  N  N   -8.297  -28.404  -25.778   4.062  -4.060  -1.233  H18  9P9  59  
9P9  H19  H19  H  0  1  N  N  N   -8.667  -26.653  -25.943   2.759  -4.867  -2.139  H19  9P9  60  
9P9  H20  H20  H  0  1  N  N  N   -8.462  -29.880  -27.578   4.016  -1.662  -0.857  H20  9P9  61  
9P9  H21  H21  H  0  1  N  N  N   -6.734  -32.109  -31.496   3.812  -1.553   0.600  H21  9P9  62  
9P9  H22  H22  H  0  1  N  N  N   -6.956  -33.177  -30.069   5.128  -0.966  -0.445  H22  9P9  63  
9P9  H23  H23  H  0  1  N  N  N   -4.347  -32.033  -32.008   3.899  -1.326   2.987  H23  9P9  64  
9P9  H24  H24  H  0  1  N  N  N   -4.144  -33.556  -31.077   5.284  -0.564   3.806  H24  9P9  65  
9P9  H25  H25  H  0  1  N  N  N   -5.308  -30.552  -27.773   7.968  -2.750   2.408  H25  9P9  66  
9P9  H26  H26  H  0  1  N  N  N   -5.452  -32.499  -28.149   6.897   0.422   0.737  H26  9P9  67  
9P9  H27  H27  H  0  1  N  N  N   -9.012  -28.775  -34.238  -0.828   3.037  -1.698  H27  9P9  68  
9P9  H28  H28  H  0  1  N  N  N   -9.538  -32.836  -33.814   2.255   5.043  -0.098  H28  9P9  69  
#   #
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
9P9  OAQ  CAL  DOUB  N  N   1  
9P9  OBA  CAU  SING  N  N   2  
9P9  CAL  NAK  SING  N  N   3  
9P9  CAL  NAM  SING  N  N   4  
9P9  OAY  CAT  SING  N  N   5  
9P9  NAK  CAH  SING  N  N   6  
9P9  CAU  CAT  SING  N  N   7  
9P9  CAU  CAV  SING  N  N   8  
9P9  NAM  C    SING  N  N   9  
9P9  CAW  CAV  SING  N  N  10  
9P9  CAW  OAX  SING  N  N  11  
9P9  CAT  CAS  SING  N  N  12  
9P9  CAS  NAG  SING  N  N  13  
9P9  CAV  OAZ  SING  N  N  14  
9P9  OAX  PBB  SING  N  N  15  
9P9  CAH  NAG  SING  N  N  16  
9P9  CAH  CA   DOUB  N  N  17  
9P9  C    CA   SING  N  N  18  
9P9  C    O    DOUB  N  N  19  
9P9  OBE  PBB  DOUB  N  N  20  
9P9  NAG  CAD  SING  N  N  21  
9P9  CA   N    SING  N  N  22  
9P9  OBC  PBB  SING  N  N  23  
9P9  PBB  OBD  SING  N  N  24  
9P9  CBJ  FBK  SING  N  N  25  
9P9  CBJ  CBG  SING  N  N  26  
9P9  CAD  CAC  SING  Y  N  27  
9P9  CAD  CAE  DOUB  Y  N  28  
9P9  CBF  CBG  SING  N  N  29  
9P9  CBF  CBH  SING  N  N  30  
9P9  OBN  CBL  DOUB  N  N  31  
9P9  N    CBH  SING  N  N  32  
9P9  N    CAE  SING  N  N  33  
9P9  CBG  CBL  SING  N  N  34  
9P9  CBG  OBO  SING  N  N  35  
9P9  CAC  CAB  DOUB  Y  N  36  
9P9  CBH  OBI  DOUB  N  N  37  
9P9  CAE  CAF  SING  Y  N  38  
9P9  CBL  OBM  SING  N  N  39  
9P9  CAB  CAP  SING  N  N  40  
9P9  CAB  CAA  SING  Y  N  41  
9P9  CAF  CAA  DOUB  Y  N  42  
9P9  CAA  CAO  SING  N  N  43  
9P9  OBD  H1   SING  N  N  44  
9P9  OBC  H2   SING  N  N  45  
9P9  CAW  H3   SING  N  N  46  
9P9  CAW  H4   SING  N  N  47  
9P9  CAV  H5   SING  N  N  48  
9P9  OAZ  H6   SING  N  N  49  
9P9  CAU  H7   SING  N  N  50  
9P9  OBA  H8   SING  N  N  51  
9P9  CAT  H9   SING  N  N  52  
9P9  OAY  H10  SING  N  N  53  
9P9  CAS  H11  SING  N  N  54  
9P9  CAS  H12  SING  N  N  55  
9P9  CAC  H13  SING  N  N  56  
9P9  CAP  H14  SING  N  N  57  
9P9  CAP  H15  SING  N  N  58  
9P9  CAP  H16  SING  N  N  59  
9P9  CAO  H17  SING  N  N  60  
9P9  CAO  H18  SING  N  N  61  
9P9  CAO  H19  SING  N  N  62  
9P9  CAF  H20  SING  N  N  63  
9P9  CBF  H21  SING  N  N  64  
9P9  CBF  H22  SING  N  N  65  
9P9  CBJ  H23  SING  N  N  66  
9P9  CBJ  H24  SING  N  N  67  
9P9  OBM  H25  SING  N  N  68  
9P9  OBO  H26  SING  N  N  69  
9P9  NAK  H27  SING  N  N  70  
9P9  NAM  H28  SING  N  N  71  
#   #
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
9P9  SMILES            ACDLabs               12.01  "OP(=O)(O)OCC(O)C(C(CN2c1cc(C)c(C)cc1N(C(=O)CC(C(O)=O)(O)CF)C3=C2NC(NC3=O)=O)O)O"  
9P9  InChI             InChI                 1.03   "InChI=1S/C22H28FN4O13P/c1-9-3-11-12(4-10(9)2)27(15(30)5-22(36,8-23)20(33)34)16-18(24-21(35)25-19(16)32)26(11)6-13(28)17(31)14(29)7-40-41(37,38)39/h3-4,13-14,17,28-29,31,36H,5-8H2,1-2H3,(H,33,34)(H2,37,38,39)(H2,24,25,32,35)/t13-,14+,17-,22+/m0/s1"  
9P9  InChIKey          InChI                 1.03   OPWYTCBSKCFWKS-TYGMBGIGSA-N  
9P9  SMILES_CANONICAL  CACTVS                3.385  "Cc1cc2N(C[C@H](O)[C@H](O)[C@H](O)CO[P](O)(O)=O)C3=C(N(C(=O)C[C@@](O)(CF)C(O)=O)c2cc1C)C(=O)NC(=O)N3"  
9P9  SMILES            CACTVS                3.385  "Cc1cc2N(C[CH](O)[CH](O)[CH](O)CO[P](O)(O)=O)C3=C(N(C(=O)C[C](O)(CF)C(O)=O)c2cc1C)C(=O)NC(=O)N3"  
9P9  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.6  "Cc1cc2c(cc1C)N(C3=C(N2C[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)O)NC(=O)NC3=O)C(=O)C[C@@](CF)(C(=O)O)O"  
9P9  SMILES            "OpenEye OEToolkits"  2.0.6  "Cc1cc2c(cc1C)N(C3=C(N2CC(C(C(COP(=O)(O)O)O)O)O)NC(=O)NC3=O)C(=O)CC(CF)(C(=O)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
9P9  "SYSTEMATIC NAME"  ACDLabs               12.01  "1-{5-[(3S)-3-carboxy-4-fluoro-3-hydroxybutanoyl]-7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzo[g]pteridin-10(2H)-yl}-1-deoxy-5-O-phosphono-D-ribitol"  
9P9  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.6  "(2~{S})-4-[7,8-dimethyl-2,4-bis(oxidanylidene)-10-[(2~{S},3~{S},4~{R})-2,3,4-tris(oxidanyl)-5-phosphonooxy-pentyl]-1~{H}-benzo[g]pteridin-5-yl]-2-(fluoranylmethyl)-2-oxidanyl-4-oxidanylidene-butanoic acid"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
9P9  "Create component"  2018-06-20  PDBJ  
9P9  "Modify name"       2018-07-23  PDBJ  
9P9  "Initial release"   2019-06-19  RCSB  
##
