data_MFO
#

_chem_comp.id                                   MFO
_chem_comp.name                                 "[(2~{R},3~{S},5~{R})-5-[2-azanyl-8-[ethanoyl(naphthalen-2-yl)amino]-6-oxidanylidene-3~{H}-purin-9-yl]-3-oxidanyl-oxolan-2-yl]methyl dihydrogen phosphate"
_chem_comp.type                                 "DNA linking"
_chem_comp.pdbx_type                            ATOMN
_chem_comp.formula                              "C22 H23 N6 O8 P"
_chem_comp.mon_nstd_parent_comp_id              DG
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2016-04-06
_chem_comp.pdbx_modified_date                   2019-05-07
_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                       530.427
_chem_comp.one_letter_code                      G
_chem_comp.three_letter_code                    MFO
_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       5G33
_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
MFO  C6     C1   C  0  1  N  N  N  24.559  54.356  -28.776   0.394  -4.217  -0.064  C6     MFO   1  
MFO  C5     C2   C  0  1  Y  N  N  23.754  55.443  -29.363   0.655  -2.812   0.259  C5     MFO   2  
MFO  C4     C3   C  0  1  Y  N  N  22.979  56.302  -28.432  -0.253  -1.858  -0.182  C4     MFO   3  
MFO  C8     C4   C  0  1  Y  N  N  22.694  56.917  -30.440   1.379  -0.877   0.926  C8     MFO   4  
MFO  N4     N1   N  0  1  N  N  N  22.216  57.631  -31.501   2.167   0.102   1.520  N4     MFO   5  
MFO  C2     C5   C  0  1  N  N  N  23.825  55.025  -26.651  -1.543  -3.585  -1.168  C2     MFO   6  
MFO  C21    C6   C  0  1  Y  N  N  25.402  55.476  -34.447   6.541  -0.276  -0.538  C21    MFO   7  
MFO  C10    C7   C  0  1  N  N  N  19.901  58.267  -31.372   0.834  -0.184   3.584  C10    MFO   8  
MFO  C9     C8   C  0  1  N  N  N  21.358  58.631  -31.280   1.905   0.505   2.779  C9     MFO   9  
MFO  C12    C9   C  0  1  Y  N  N  22.614  57.252  -32.797   3.232   0.670   0.810  C12    MFO  10  
MFO  C20    C10  C  0  1  Y  N  N  25.801  55.076  -35.721   7.557   0.310  -1.228  C20    MFO  11  
MFO  N3     N2   N  0  1  N  N  N  23.058  56.042  -27.110  -1.349  -2.268  -0.896  N3     MFO  12  
MFO  C15    C11  C  0  1  Y  N  N  23.393  56.457  -35.352   5.325   1.835  -0.600  C15    MFO  13  
MFO  C14    C12  C  0  1  Y  N  N  22.197  57.145  -35.175   4.185   2.589  -0.272  C14    MFO  14  
MFO  C13    C13  C  0  1  Y  N  N  21.805  57.537  -33.897   3.166   2.012   0.418  C13    MFO  15  
MFO  N1     N3   N  0  1  N  N  N  24.544  54.211  -27.445  -0.707  -4.520  -0.768  N1     MFO  16  
MFO  C19    C14  C  0  1  Y  N  N  24.992  55.371  -36.815   7.483   1.647  -1.614  C19    MFO  17  
MFO  C18    C15  C  0  1  Y  N  N  23.792  56.059  -36.629   6.394   2.405  -1.312  C18    MFO  18  
MFO  N2     N4   N  0  1  N  N  N  23.858  54.823  -25.319  -2.651  -3.954  -1.884  N2     MFO  19  
MFO  C17    C16  C  0  1  Y  N  N  23.810  56.559  -32.982   4.331  -0.100   0.499  C17    MFO  20  
MFO  C16    C17  C  0  1  Y  N  N  24.202  56.165  -34.258   5.400   0.475  -0.207  C16    MFO  21  
MFO  P      P1   P  0  1  N  N  N  23.995  60.717  -24.235  -6.232   1.201   0.267  P      MFO  22  
MFO  OP1    O1   O  0  1  N  Y  N  24.019  62.141  -23.741  -6.870   2.197  -0.623  OP1    MFO  23  
MFO  "O5'"  O2   O  0  1  N  N  N  22.888  60.505  -25.408  -4.639   1.432   0.276  "O5'"  MFO  24  
MFO  "C5'"  C18  C  0  1  N  N  N  21.872  59.491  -25.324  -3.848   1.451  -0.914  "C5'"  MFO  25  
MFO  "C4'"  C19  C  0  1  N  N  R  21.104  59.290  -26.636  -2.382   1.692  -0.548  "C4'"  MFO  26  
MFO  "C3'"  C20  C  0  1  N  N  S  20.311  57.993  -26.656  -1.521   1.803  -1.826  "C3'"  MFO  27  
MFO  "O3'"  O3   O  0  1  N  N  N  19.011  58.125  -26.081  -1.287   3.174  -2.155  "O3'"  MFO  28  
MFO  "C2'"  C21  C  0  1  N  N  N  20.217  57.621  -28.124  -0.196   1.104  -1.448  "C2'"  MFO  29  
MFO  "C1'"  C22  C  0  1  N  N  R  21.414  58.295  -28.756  -0.414   0.653   0.014  "C1'"  MFO  30  
MFO  "O4'"  O4   O  0  1  N  N  N  21.966  59.180  -27.771  -1.848   0.553   0.162  "O4'"  MFO  31  
MFO  N9     N5   N  0  1  Y  N  N  22.341  57.211  -29.184   0.215  -0.650   0.245  N9     MFO  32  
MFO  N7     N6   N  0  1  Y  N  N  23.533  55.876  -30.619   1.636  -2.160   0.932  N7     MFO  33  
MFO  O6     O5   O  0  1  N  N  N  25.235  53.611  -29.522   1.164  -5.093   0.296  O6     MFO  34  
MFO  OP2    O6   O  0  1  N  Y  N  23.831  59.712  -23.123  -6.808   1.371   1.761  OP2    MFO  35  
MFO  O11    O7   O  0  1  N  N  N  21.736  59.761  -31.006   2.532   1.423   3.264  O11    MFO  36  
MFO  O1     O8   O  0  1  N  Y  N  25.377  60.437  -24.958  -6.556  -0.282  -0.268  O1     MFO  37  
MFO  H1     H1   H  0  1  N  N  N  26.028  55.251  -33.596   6.610  -1.315  -0.249  H1     MFO  38  
MFO  H2     H2   H  0  1  N  N  N  19.287  59.154  -31.159   0.321  -0.914   2.957  H2     MFO  39  
MFO  H3     H3   H  0  1  N  N  N  19.678  57.901  -32.385   1.288  -0.691   4.435  H3     MFO  40  
MFO  H4     H4   H  0  1  N  N  N  19.673  57.479  -30.639   0.116   0.554   3.941  H4     MFO  41  
MFO  H5     H5   H  0  1  N  N  N  26.730  54.542  -35.858   8.433  -0.269  -1.480  H5     MFO  42  
MFO  H6     H6   H  0  1  N  N  N  22.545  56.606  -26.463  -1.992  -1.613  -1.210  H6     MFO  43  
MFO  H7     H7   H  0  1  N  N  N  21.574  57.375  -36.027   4.119   3.626  -0.567  H7     MFO  44  
MFO  H8     H8   H  0  1  N  N  N  20.872  58.063  -33.757   2.293   2.597   0.667  H8     MFO  45  
MFO  H9     H9   H  0  1  N  N  N  25.293  55.068  -37.807   8.303   2.089  -2.161  H9     MFO  46  
MFO  H10    H10  H  0  1  N  N  N  23.167  56.285  -37.480   6.351   3.440  -1.618  H10    MFO  47  
MFO  H11    H11  H  0  1  N  N  N  24.409  54.080  -24.939  -3.279  -3.280  -2.187  H11    MFO  48  
MFO  H12    H12  H  0  1  N  N  N  23.331  55.416  -24.710  -2.807  -4.890  -2.088  H12    MFO  49  
MFO  H13    H13  H  0  1  N  N  N  24.434  56.327  -32.132   4.375  -1.135   0.805  H13    MFO  50  
MFO  H14    H14  H  0  1  N  N  N  21.155  59.779  -24.541  -3.942   0.495  -1.428  H14    MFO  51  
MFO  H15    H15  H  0  1  N  N  N  22.351  58.539  -25.051  -4.196   2.251  -1.568  H15    MFO  52  
MFO  H16    H16  H  0  1  N  N  N  20.410  60.133  -26.770  -2.285   2.595   0.054  H16    MFO  53  
MFO  H17    H17  H  0  1  N  N  N  20.883  57.217  -26.127  -2.003   1.288  -2.657  H17    MFO  54  
MFO  H18    H18  H  0  1  N  N  N  19.092  58.358  -25.164  -0.751   3.302  -2.949  H18    MFO  55  
MFO  H19    H19  H  0  1  N  N  N  19.281  57.997  -28.562  -0.022   0.242  -2.091  H19    MFO  56  
MFO  H20    H20  H  0  1  N  N  N  20.270  56.530  -28.254   0.637   1.803  -1.514  H20    MFO  57  
MFO  H21    H21  H  0  1  N  N  N  21.084  58.865  -29.637  -0.013   1.396   0.704  H21    MFO  58  
MFO  H22    H22  H  0  1  N  N  N  23.771  60.167  -22.291  -7.764   1.245   1.831  H22    MFO  59  
MFO  H23    H23  H  0  1  N  N  N  25.916  61.218  -24.924  -6.169  -0.988   0.269  H23    MFO  60  
#   #
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
MFO  C19    C18    DOUB  Y  N   1  
MFO  C19    C20    SING  Y  N   2  
MFO  C18    C15    SING  Y  N   3  
MFO  C20    C21    DOUB  Y  N   4  
MFO  C15    C14    DOUB  Y  N   5  
MFO  C15    C16    SING  Y  N   6  
MFO  C14    C13    SING  Y  N   7  
MFO  C21    C16    SING  Y  N   8  
MFO  C16    C17    DOUB  Y  N   9  
MFO  C13    C12    DOUB  Y  N  10  
MFO  C17    C12    SING  Y  N  11  
MFO  C12    N4     SING  N  N  12  
MFO  N4     C9     SING  N  N  13  
MFO  N4     C8     SING  N  N  14  
MFO  C10    C9     SING  N  N  15  
MFO  C9     O11    DOUB  N  N  16  
MFO  N7     C8     DOUB  Y  N  17  
MFO  N7     C5     SING  Y  N  18  
MFO  C8     N9     SING  Y  N  19  
MFO  O6     C6     DOUB  N  N  20  
MFO  C5     C6     SING  N  N  21  
MFO  C5     C4     DOUB  Y  N  22  
MFO  N9     "C1'"  SING  N  N  23  
MFO  N9     C4     SING  Y  N  24  
MFO  C6     N1     SING  N  N  25  
MFO  "C1'"  "C2'"  SING  N  N  26  
MFO  "C1'"  "O4'"  SING  N  N  27  
MFO  C4     N3     SING  N  N  28  
MFO  "C2'"  "C3'"  SING  N  N  29  
MFO  "O4'"  "C4'"  SING  N  N  30  
MFO  N1     C2     DOUB  N  N  31  
MFO  N3     C2     SING  N  N  32  
MFO  "C3'"  "C4'"  SING  N  N  33  
MFO  "C3'"  "O3'"  SING  N  N  34  
MFO  C2     N2     SING  N  N  35  
MFO  "C4'"  "C5'"  SING  N  N  36  
MFO  "O5'"  "C5'"  SING  N  N  37  
MFO  "O5'"  P      SING  N  N  38  
MFO  P      OP1    DOUB  N  N  39  
MFO  P      OP2    SING  N  N  40  
MFO  P      O1     SING  N  N  41  
MFO  C21    H1     SING  N  N  42  
MFO  C10    H2     SING  N  N  43  
MFO  C10    H3     SING  N  N  44  
MFO  C10    H4     SING  N  N  45  
MFO  C20    H5     SING  N  N  46  
MFO  N3     H6     SING  N  N  47  
MFO  C14    H7     SING  N  N  48  
MFO  C13    H8     SING  N  N  49  
MFO  C19    H9     SING  N  N  50  
MFO  C18    H10    SING  N  N  51  
MFO  N2     H11    SING  N  N  52  
MFO  N2     H12    SING  N  N  53  
MFO  C17    H13    SING  N  N  54  
MFO  "C5'"  H14    SING  N  N  55  
MFO  "C5'"  H15    SING  N  N  56  
MFO  "C4'"  H16    SING  N  N  57  
MFO  "C3'"  H17    SING  N  N  58  
MFO  "O3'"  H18    SING  N  N  59  
MFO  "C2'"  H19    SING  N  N  60  
MFO  "C2'"  H20    SING  N  N  61  
MFO  "C1'"  H21    SING  N  N  62  
MFO  OP2    H22    SING  N  N  63  
MFO  O1     H23    SING  N  N  64  
#   #
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
MFO  InChI             InChI                 1.03   "InChI=1S/C22H23N6O8P/c1-11(29)27(14-7-6-12-4-2-3-5-13(12)8-14)22-24-18-19(25-21(23)26-20(18)31)28(22)17-9-15(30)16(36-17)10-35-37(32,33)34/h2-8,15-17,30H,9-10H2,1H3,(H2,32,33,34)(H3,23,25,26,31)/t15-,16+,17+/m0/s1"  
MFO  InChIKey          InChI                 1.03   AEEKNUIQRYLODW-GVDBMIGSSA-N  
MFO  SMILES_CANONICAL  CACTVS                3.385  "CC(=O)N(c1ccc2ccccc2c1)c3nc4C(=O)N=C(N)Nc4n3[C@H]5C[C@H](O)[C@@H](CO[P](O)(O)=O)O5"  
MFO  SMILES            CACTVS                3.385  "CC(=O)N(c1ccc2ccccc2c1)c3nc4C(=O)N=C(N)Nc4n3[CH]5C[CH](O)[CH](CO[P](O)(O)=O)O5"  
MFO  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.5  "CC(=O)N(c1ccc2ccccc2c1)c3nc4c(n3[C@H]5C[C@@H]([C@H](O5)COP(=O)(O)O)O)NC(=NC4=O)N"  
MFO  SMILES            "OpenEye OEToolkits"  2.0.5  "CC(=O)N(c1ccc2ccccc2c1)c3nc4c(n3C5CC(C(O5)COP(=O)(O)O)O)NC(=NC4=O)N"  
#
_pdbx_chem_comp_identifier.comp_id          MFO
_pdbx_chem_comp_identifier.type             "SYSTEMATIC NAME"
_pdbx_chem_comp_identifier.program          "OpenEye OEToolkits"
_pdbx_chem_comp_identifier.program_version  2.0.5
_pdbx_chem_comp_identifier.identifier       "[(2~{R},3~{S},5~{R})-5-[2-azanyl-8-[ethanoyl(naphthalen-2-yl)amino]-6-oxidanylidene-3~{H}-purin-9-yl]-3-oxidanyl-oxolan-2-yl]methyl dihydrogen phosphate"
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
MFO  "Create component"        2016-04-06  EBI   
MFO  "Other modification"      2016-04-21  EBI   
MFO  "Other modification"      2016-04-22  EBI   
MFO  "Initial release"         2016-06-01  RCSB  
MFO  "Other modification"      2016-06-02  RCSB  
MFO  "Modify one letter code"  2019-05-07  EBI   
##
