data_CSF
#

_chem_comp.id                                   CSF
_chem_comp.name                                 "CYTIDINE-5'-MONOPHOSPHATE-3-FLUORO-N-ACETYL-NEURAMINIC ACID"
_chem_comp.type                                 "RNA LINKING"
_chem_comp.pdbx_type                            ATOMN
_chem_comp.formula                              "C20 H30 F N4 O16 P"
_chem_comp.mon_nstd_parent_comp_id              C
_chem_comp.pdbx_synonyms                        CMP-3FNEUAC
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2003-12-04
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       632.442
_chem_comp.one_letter_code                      C
_chem_comp.three_letter_code                    CSF
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  N
_chem_comp.pdbx_ideal_coordinates_details       ?
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       ?
_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
CSF  C5A     C5A   C  0  1  N  N  R  22.128  -5.514  11.468  -0.501  -1.002   4.162  C5A     CSF   1  
CSF  C4A     C4A   C  0  1  N  N  R  22.005  -4.016  11.206  -1.862  -1.356   3.552  C4A     CSF   2  
CSF  C2A     C2A   C  0  1  N  N  S  20.752  -3.803  13.492  -1.574   0.675   2.135  C2A     CSF   3  
CSF  O6A     O6A   O  0  1  N  N  N  21.531  -4.968  13.845  -0.384   1.021   2.841  O6A     CSF   4  
CSF  C6A     C6A   C  0  1  N  N  R  22.472  -5.670  12.982   0.305  -0.188   3.148  C6A     CSF   5  
CSF  C3A     C3A   C  0  1  N  N  R  20.939  -3.255  12.057  -2.533  -0.066   3.068  C3A     CSF   6  
CSF  O4A     O4A   O  0  1  N  N  N  21.682  -3.890   9.804  -2.681  -1.986   4.539  O4A     CSF   7  
CSF  N5A     N5A   N  0  1  N  N  N  23.114  -6.222  10.755   0.223  -2.232   4.491  N5A     CSF   8  
CSF  C7A     C7A   C  0  1  N  N  R  22.363  -7.031  13.677   1.678   0.143   3.736  C7A     CSF   9  
CSF  C8A     C8A   C  0  1  N  N  R  22.653  -7.190  15.150   1.499   0.954   5.022  C8A     CSF  10  
CSF  C9A     C9A   C  0  1  N  N  N  22.735  -8.635  15.676   2.863   1.175   5.679  C9A     CSF  11  
CSF  O9A     O9A   O  0  1  N  N  N  22.997  -8.659  17.056   2.696   1.932   6.880  O9A     CSF  12  
CSF  O8A     O8A   O  0  1  N  N  N  23.915  -6.633  15.565   0.911   2.218   4.709  O8A     CSF  13  
CSF  O7A     O7A   O  0  1  N  N  N  21.056  -7.596  13.365   2.375  -1.068   4.031  O7A     CSF  14  
CSF  C1A     C1A   C  0  1  N  N  N  19.771  -3.135  14.370  -2.238   1.929   1.627  C1A     CSF  15  
CSF  OBA     OBA   O  0  1  N  N  N  19.340  -1.877  14.094  -3.378   1.847   0.923  OBA     CSF  16  
CSF  OAA     OAA   O  0  1  N  N  N  19.343  -3.747  15.302  -1.744   3.009   1.854  OAA     CSF  17  
CSF  O1A     O1A   O  0  1  N  N  N  21.820  -2.911  13.997  -1.242  -0.165   1.028  O1A     CSF  18  
CSF  O2A     O2A   O  0  1  N  N  N  24.350  -2.909  13.223   0.883   1.189   0.898  O2A     CSF  19  
CSF  N1      N1    N  0  1  N  N  N  24.519   2.408  13.595   0.152  -0.817  -6.180  N1      CSF  20  
CSF  C2      C2    C  0  1  N  N  N  24.449   3.495  12.635  -0.714   0.211  -6.188  C2      CSF  21  
CSF  N3      N3    N  0  1  N  N  N  25.500   3.557  11.621  -1.710   0.264  -7.071  N3      CSF  22  
CSF  C4      C4    C  0  1  N  N  N  26.530   2.614  11.565  -1.880  -0.705  -7.959  C4      CSF  23  
CSF  C5      C5    C  0  1  N  N  N  26.607   1.476  12.559  -0.992  -1.801  -7.973  C5      CSF  24  
CSF  C6      C6    C  0  1  N  N  N  25.593   1.441  13.517   0.018  -1.837  -7.073  C6      CSF  25  
CSF  "C3'"   C3*   C  0  1  N  N  S  21.794   0.562  14.634   2.719   0.529  -3.879  "C3'"   CSF  26  
CSF  "C2'"   C2*   C  0  1  N  N  R  21.999   2.000  14.241   2.100   0.442  -5.299  "C2'"   CSF  27  
CSF  "C1'"   C1*   C  0  1  N  N  R  23.411   2.334  14.684   1.241  -0.844  -5.201  "C1'"   CSF  28  
CSF  "O4'"   O4*   O  0  1  N  N  N  23.748   1.360  15.703   0.718  -0.798  -3.856  "O4'"   CSF  29  
CSF  "C4'"   C4*   C  0  1  N  N  R  22.643   0.450  15.913   1.779  -0.327  -3.008  "C4'"   CSF  30  
CSF  PA      PA    P  0  1  N  N  R  23.416  -2.715  14.360  -0.243   0.675   0.087  PA      CSF  31  
CSF  "O5'"   O5*   O  0  1  N  N  N  23.955  -1.364  14.939   0.325  -0.277  -1.078  "O5'"   CSF  32  
CSF  "C5'"   C5*   C  0  1  N  N  N  23.226  -0.887  16.093   1.201   0.523  -1.875  "C5'"   CSF  33  
CSF  "O3'"   O3*   O  0  1  N  N  N  20.431   0.286  14.998   4.042  -0.009  -3.877  "O3'"   CSF  34  
CSF  "O2'"   O2*   O  0  1  N  N  N  21.135   2.905  14.947   3.118   0.301  -6.290  "O2'"   CSF  35  
CSF  N4      N4    N  0  1  N  N  N  27.437   2.726  10.635  -2.915  -0.643  -8.863  N4      CSF  36  
CSF  O2      O2    O  0  1  N  N  N  23.521   4.387  12.645  -0.579   1.116  -5.381  O2      CSF  37  
CSF  O3A     O3A   O  0  1  N  N  N  23.812  -3.618  15.332  -1.038   1.911  -0.569  O3A     CSF  38  
CSF  C10     C10   C  0  1  N  N  N  23.054  -7.477  10.270   0.081  -2.792   5.709  C10     CSF  39  
CSF  O10     O10   O  0  1  N  N  N  22.051  -8.177  10.425  -0.646  -2.278   6.532  O10     CSF  40  
CSF  C11     C11   C  0  1  N  N  N  24.261  -8.009   9.528   0.826  -4.057   6.048  C11     CSF  41  
CSF  F3A     F3A   F  0  1  N  N  N  19.690  -3.497  11.573  -2.839   0.743   4.168  F3A     CSF  42  
CSF  H5A     H5A   H  0  1  N  N  N  21.159  -5.951  11.131  -0.649  -0.412   5.067  H5A     CSF  43  
CSF  H4A     H4A   H  0  1  N  N  N  22.968  -3.540  11.502  -1.720  -2.032   2.709  H4A     CSF  44  
CSF  H6A     H6A   H  0  1  N  N  N  23.528  -5.324  12.896   0.433  -0.773   2.237  H6A     CSF  45  
CSF  H3A     H3A   H  0  1  N  N  N  21.306  -2.202  12.029  -3.449  -0.311   2.530  H3A     CSF  46  
CSF  H4      H4    H  0  1  N  N  N  21.605  -2.957   9.640  -3.524  -2.191   4.113  H4      CSF  47  
CSF  H3      H3    H  0  1  N  N  N  24.001  -5.757  10.561   0.805  -2.643   3.833  H3      CSF  48  
CSF  H7A     H7A   H  0  1  N  N  N  23.237  -7.576  13.251   2.251   0.726   3.016  H7A     CSF  49  
CSF  H8A     H8A   H  0  1  N  N  N  21.767  -6.654  15.565   0.849   0.410   5.707  H8A     CSF  50  
CSF  H9A1    1H9A  H  0  0  N  N  N  21.817  -9.216  15.422   3.513   1.718   4.994  H9A1    CSF  51  
CSF  H9A2    2H9A  H  0  0  N  N  N  23.481  -9.236  15.106   3.311   0.210   5.918  H9A2    CSF  52  
CSF  H9A     H9A   H  0  1  N  N  N  23.047  -9.550  17.380   3.576   2.048   7.262  H9A     CSF  53  
CSF  H2      H2    H  0  1  N  N  N  24.097  -6.733  16.491   1.516   2.666   4.102  H2      CSF  54  
CSF  H1      H1    H  0  1  N  N  N  20.988  -8.439  13.796   1.962  -1.444   4.820  H1      CSF  55  
CSF  HBA     HBA   H  0  1  N  N  N  18.708  -1.447  14.659  -3.804   2.652   0.598  HBA     CSF  56  
CSF  H7      H7    H  0  1  N  N  N  27.382   0.692  12.584  -1.117  -2.599  -8.690  H7      CSF  57  
CSF  H6      H6    H  0  1  N  N  N  25.642   0.613  14.244   0.711  -2.665  -7.064  H6      CSF  58  
CSF  "H3'"   H3*   H  0  1  N  N  N  22.056  -0.134  13.804   2.728   1.561  -3.529  "H3'"   CSF  59  
CSF  "H2'"   H2*   H  0  1  N  N  N  21.797   2.110  13.149   1.475   1.311  -5.506  "H2'"   CSF  60  
CSF  "H1'"   H1*   H  0  1  N  N  N  23.393   3.388  15.045   1.860  -1.730  -5.341  "H1'"   CSF  61  
CSF  "H4'"   H4*   H  0  1  N  N  N  22.007   0.667  16.803   2.326  -1.173  -2.594  "H4'"   CSF  62  
CSF  "H5'"   1H5*  H  0  1  N  N  N  23.868  -0.916  17.003   0.645   1.360  -2.297  "H5'"   CSF  63  
CSF  "H5''"  2H5*  H  0  0  N  N  N  22.442  -1.620  16.393   2.013   0.901  -1.255  "H5''"  CSF  64  
CSF  "HO3'"  H3T   H  0  0  N  Y  N  20.301  -0.621  15.246   4.565   0.531  -4.484  "HO3'"  CSF  65  
CSF  H8      H8    H  0  1  N  N  N  21.264   3.812  14.698   3.614   1.131  -6.302  H8      CSF  66  
CSF  H41     1H4   H  0  1  N  N  N  28.188   2.037  10.594  -3.524   0.111  -8.851  H41     CSF  67  
CSF  H42     2H4   H  0  1  N  N  N  27.847   3.658  10.686  -3.037  -1.354  -9.511  H42     CSF  68  
CSF  H5      H5    H  0  1  N  N  N  24.731  -3.505  15.541  -1.762   1.534  -1.088  H5      CSF  69  
CSF  H111    1H11  H  0  0  N  N  N  24.211  -9.048   9.126   0.587  -4.358   7.068  H111    CSF  70  
CSF  H112    2H11  H  0  0  N  N  N  24.519  -7.308   8.699   0.532  -4.848   5.358  H112    CSF  71  
CSF  H113    3H11  H  0  0  N  N  N  25.162  -7.910  10.177   1.899  -3.881   5.962  H113    CSF  72  
#   #
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
CSF  C5A    C4A     SING  N  N   1  
CSF  C5A    C6A     SING  N  N   2  
CSF  C5A    N5A     SING  N  N   3  
CSF  C5A    H5A     SING  N  N   4  
CSF  C4A    C3A     SING  N  N   5  
CSF  C4A    O4A     SING  N  N   6  
CSF  C4A    H4A     SING  N  N   7  
CSF  C2A    O6A     SING  N  N   8  
CSF  C2A    C3A     SING  N  N   9  
CSF  C2A    C1A     SING  N  N  10  
CSF  C2A    O1A     SING  N  N  11  
CSF  O6A    C6A     SING  N  N  12  
CSF  C6A    C7A     SING  N  N  13  
CSF  C6A    H6A     SING  N  N  14  
CSF  C3A    F3A     SING  N  N  15  
CSF  C3A    H3A     SING  N  N  16  
CSF  O4A    H4      SING  N  N  17  
CSF  N5A    C10     SING  N  N  18  
CSF  N5A    H3      SING  N  N  19  
CSF  C7A    C8A     SING  N  N  20  
CSF  C7A    O7A     SING  N  N  21  
CSF  C7A    H7A     SING  N  N  22  
CSF  C8A    C9A     SING  N  N  23  
CSF  C8A    O8A     SING  N  N  24  
CSF  C8A    H8A     SING  N  N  25  
CSF  C9A    O9A     SING  N  N  26  
CSF  C9A    H9A1    SING  N  N  27  
CSF  C9A    H9A2    SING  N  N  28  
CSF  O9A    H9A     SING  N  N  29  
CSF  O8A    H2      SING  N  N  30  
CSF  O7A    H1      SING  N  N  31  
CSF  C1A    OBA     SING  N  N  32  
CSF  C1A    OAA     DOUB  N  N  33  
CSF  OBA    HBA     SING  N  N  34  
CSF  O1A    PA      SING  N  N  35  
CSF  O2A    PA      DOUB  N  N  36  
CSF  N1     C2      SING  N  N  37  
CSF  N1     C6      SING  N  N  38  
CSF  N1     "C1'"   SING  N  N  39  
CSF  C2     N3      SING  N  N  40  
CSF  C2     O2      DOUB  N  N  41  
CSF  N3     C4      DOUB  N  N  42  
CSF  C4     C5      SING  N  N  43  
CSF  C4     N4      SING  N  N  44  
CSF  C5     C6      DOUB  N  N  45  
CSF  C5     H7      SING  N  N  46  
CSF  C6     H6      SING  N  N  47  
CSF  "C3'"  "C2'"   SING  N  N  48  
CSF  "C3'"  "C4'"   SING  N  N  49  
CSF  "C3'"  "O3'"   SING  N  N  50  
CSF  "C3'"  "H3'"   SING  N  N  51  
CSF  "C2'"  "C1'"   SING  N  N  52  
CSF  "C2'"  "O2'"   SING  N  N  53  
CSF  "C2'"  "H2'"   SING  N  N  54  
CSF  "C1'"  "O4'"   SING  N  N  55  
CSF  "C1'"  "H1'"   SING  N  N  56  
CSF  "O4'"  "C4'"   SING  N  N  57  
CSF  "C4'"  "C5'"   SING  N  N  58  
CSF  "C4'"  "H4'"   SING  N  N  59  
CSF  PA     "O5'"   SING  N  N  60  
CSF  PA     O3A     SING  N  N  61  
CSF  "O5'"  "C5'"   SING  N  N  62  
CSF  "C5'"  "H5'"   SING  N  N  63  
CSF  "C5'"  "H5''"  SING  N  N  64  
CSF  "O3'"  "HO3'"  SING  N  N  65  
CSF  "O2'"  H8      SING  N  N  66  
CSF  N4     H41     SING  N  N  67  
CSF  N4     H42     SING  N  N  68  
CSF  O3A    H5      SING  N  N  69  
CSF  C10    O10     DOUB  N  N  70  
CSF  C10    C11     SING  N  N  71  
CSF  C11    H111    SING  N  N  72  
CSF  C11    H112    SING  N  N  73  
CSF  C11    H113    SING  N  N  74  
#   #
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
CSF  SMILES            ACDLabs               10.04  "FC3C(O)C(NC(=O)C)C(OC3(OP(=O)(O)OCC2OC(N1C(=O)N=C(N)C=C1)C(O)C2O)C(=O)O)C(O)C(O)CO"  
CSF  SMILES_CANONICAL  CACTVS                3.341  "CC(=O)N[C@@H]1[C@@H](O)[C@@H](F)[C@@](O[C@H]1[C@H](O)[C@H](O)CO)(O[P@@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=NC3=O)N)C(O)=O"  
CSF  SMILES            CACTVS                3.341  "CC(=O)N[CH]1[CH](O)[CH](F)[C](O[CH]1[CH](O)[CH](O)CO)(O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=NC3=O)N)C(O)=O"  
CSF  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "CC(=O)N[C@@H]1[C@H]([C@H](C(O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O[P@](=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=NC3=O)N)O)O)F)O"  
CSF  SMILES            "OpenEye OEToolkits"  1.5.0  "CC(=O)NC1C(C(C(OC1C(C(CO)O)O)(C(=O)O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=NC3=O)N)O)O)F)O"  
CSF  InChI             InChI                 1.03   "InChI=1S/C20H30FN4O16P/c1-6(27)23-10-13(31)16(21)20(18(33)34,40-15(10)11(29)7(28)4-26)41-42(36,37)38-5-8-12(30)14(32)17(39-8)25-3-2-9(22)24-19(25)35/h2-3,7-8,10-17,26,28-32H,4-5H2,1H3,(H,23,27)(H,33,34)(H,36,37)(H2,22,24,35)/t7-,8-,10-,11-,12-,13-,14-,15-,16-,17-,20-/m1/s1"  
CSF  InChIKey          InChI                 1.03   HNJLGUNKGJTPBF-JTKQZVQZSA-N  
#   #
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
CSF  "SYSTEMATIC NAME"  ACDLabs               10.04  "(2S,3R,4R,5R,6R)-5-(acetylamino)-2-{[(R)-{[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-3-fluoro-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)"  
CSF  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "(3R,4R,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-3-fluoro-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic 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
CSF  "Create component"   2003-12-04  RCSB  
CSF  "Modify descriptor"  2011-06-04  RCSB  
CSF  "Modify synonyms"    2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     CSF
_pdbx_chem_comp_synonyms.name        CMP-3FNEUAC
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
